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Siesta Key Holiday Vacation with Pools

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    Travellers to Siesta Key are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    707 Matching Rentals in Siesta KeyView all 899 rentals
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    Midnight Cove #532 in Siesta Key, FL- Sun, Sand & Save1 / 24
    (39)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Jamaica Royale #92 on the #1 Beach in the USA!1 / 12
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Remodeled 2br 2ba with private patio, beautiful water views, walk to #1 beach1 / 45
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Children's Pool
    • DVD Player
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Patio
    • Sauna
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 19, 2019
    Loved the place! Loved the beach. It was just perfect for our family. Was worth every penny! Would love to go back.
    Reviewed January 21, 2019
    Perfect location. Walking distance to the beach and short drive to downtown Siesta Keys (there is also a trolly but I didn't get a chance to use it). Having access from the...
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    About this property
    This is a large, bright and clean 2 bedroom and 2 bath first floor Condo. Being first floor gives you extra entrance through patio or lobby. Also one of the few condos with a private patio with new furniture to enjoy the beautiful weather and view. Condo clean and bright and beautifully decorated....
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Siesta Breakers #603 in Siesta Key, FL- Sun, Sand & *Save*1 / 24
    (27)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • DVD Player
    • Air Conditioning
    • Porch
    • Ocean Views
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 3, 2019
    This Siesta Breakers condo was exactly as promised. Vic was very efficient and extremely thorough in sending all the information and access. He was easily accessible by phone if...
    Reviewed July 7, 2018
    Very nice condominium. Very clean, comfortable and spacious. Great location. I would like to rent there every year. I really love it. I used to visit Sarasota every year for...
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    About this property
    'All-In Price' 14% to 40% Discounted Rental Rates from $998 to $2,137 /Wk depending on the season (12% tax not included) & SAVINGS from $233 to $754 /Wk from the listed Siesta Breakers rental office rates. Full Week Rentals Only (Saturday to Saturday) Standard Occupancy: 4 Guests Maximum...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Beachfront Getaway in Siesta Key1 / 24
    (23)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Wi-Fi
    • Parking
    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 16, 2019
    We just Returned today from spending 4 nights at Seacrest Beach front getaway. It’s the Perfect Little Getaway! Dior, the owner is excellent to deal with. We booked this back in...
    Reviewed April 24, 2019
    Nice beachfront getaway only steps away from the white sand and ocean!! Clean !!! We enjoyed our stay!!
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    About this property
    This luxurious one story townhouse was newly renovated and has its own private access to the #1 beach in the US merely steps away from the front door. It boasts all the luxury you'd expect from a beach house! Modern kitchen, contemporary bathroom with walk in rain shower, luxurious bedroom and...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Midnight Cove #714 in Siesta Key, FL- Sun, Sand & Save1 / 24
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Ocean Views
    • Washer
    • DVD Player
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 7, 2019
    Booked this condo for my 2 boys (10 & 15) and myself. We pick a new beach every year and this year was Siesta Key. The condo was exactly as advertised! It was in my budget and...
    Reviewed March 10, 2019
    This was our third visit to Siesta Key in 3 years and ur second in a midnight cove condo.. We booked Vic's #714 condo for two weeks and the residence was exactly as billed...
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    About this property
    'All-In Price' 14% to 40% Discounted Rental Rates from $601 to $1,724 /Wk depending on the season (12% tax not included) & SAVINGS from $156 to $471 /Wk from the listed Midnight Cove rental office rates. Full Week Rentals Only (Saturday to Saturday) – Occupancy: 4 Guests (maximum) Arrival &...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Jamaica Royale #100-Peaceful Gulf Side Condo1 / 44
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Patio
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 12, 2019
    My first visit to the Gulf side of FL was a great surprise. Our condo owner was amazing. Rene has thought of everything imaginable to include her little piece of Heaven...
    Reviewed February 11, 2019
    Rene provided everything we could need for our stay in the condo and surprised us with much appreciated gifts on arrival. She was always available and pleasant to work with...
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    About this property
    Unlike many rental properties on Siesta Key, Unit #100 was recently renovated! This condo is a 2 bedroom, 2 bath garden view unit located in the quiet area of Jamaica Royale Condominiums! If you want peace and quiet, a relaxing environment to enjoy, this is the condo for you. Jamaica Royale is...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Washer
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We help make the most of your vacation by providing Free Admission to some of the area’s top attractions each and every day including a choice of a free, bike rental, free kayak rental, or free dolphin fun cruise! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Grill
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy an incredible sunset on Siesta Key's Crescent Beach and walk back to your private villa on Siesta Key in Polynesian Gardens. Plan your get-a-way at our two bedroom, two bath villa where you have a screened-in lanai looking into the grassy back yard with your own personal BBQ grill. The...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Siesta Key -  2bdrm on the beach - amazing views!!1 / 27
    (32)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Secure Parking
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 27, 2019
    Just finished up our week stay and couldn’t be more happy with this condo. It was beautifully decorated, clean and comfortable. The proximity to the beach could not be any...
    Reviewed June 22, 2019
    We just finished up our stay at this beautiful property. Heading home and already missing it! This condo is comfortably and tastefully furnished and has everything necessary...
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    About this property
    The condo benefits from its own private pool. The living room, master bedroom, and lanai (balcony) all have stunning ocean views. The lanai, with over $10,000 of new doors and windows, is furnished with a table and chairs to enable you to dine al fresco. There is also a comfortable couch to...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Quiet and Comfortable Condo Near Turtle Beach1 / 42
    (5)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 15, 2018
    We really enjoyed our stay at Dana Z's condo. It was close to all the amenities on Siesta Key. The condo was quiet and peaceful. The water front gave us many enjoyable evenings...
    Reviewed February 21, 2018
    Great place, but needs some attention to the bed in master bedroom also a updated tv in the living room. I would recommend this place for older adults.
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    About this property
    Cozy Cove is a small condominium complex of six total units, located on the south end of Siesta Key in Sarasota, Florida. The complex sits on the Gulf side of the Key along Blind Pass. The complex itself is on the inlet with a dock at the back of the property where you will often see fish jump and...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Cable/satellite TV
    • Patio
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Be the first to book this brand new completely remodeled unit right across the street from the Best Beach in the USA - Siesta Beach. You have a view of the gulf across the street from this beautifully and lovingly renovated condo with everything done with the most discriminating guest in mind....
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Fido Friendly, Saltwater Pool, Only 1 mile to SK Beach, Close to the Village, Sh1 / 38
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 31, 2018
    The house was beautiful and very spacious. Great proximity to the beach and town center, and the kids loved Glebe Park, which was located a short walk down the street. We are...
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    About this property
    On Siesta Key we offer a high-end gorgeous, Fido friendly with Prior Approval, Key West style 3 bedroom, 2.5 bath custom home. Desire a private saltwater heated pool while vacationing on Siesta Key? Then this vacation home will be your home away from home in tropical paradise…..just minutes from...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We help make the most of your vacation by providing Free Admission to some of the area’s top attractions each and every day including a choice of a free, bike rental, free kayak rental, or free dolphin fun cruise! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We help make the most of your vacation by providing Free Admission to some of the area’s top attractions each and every day including a choice of a free, bike rental, free kayak rental, or free dolphin fun cruise! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Bay Views - Private access to Beach. Enjoy Tennis, Heated Pools, Fishing1 / 50
    (12)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Grill
    • DVD Player
    • Washer
    • Sauna
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 28, 2017
    Beautiful beach and spacious condo with all amenities at your doorstep, enjoyed tennis , pool and exercise room and outdoor gas grill right across street yet still very private...
    Reviewed November 20, 2017
    We had a wonderful vacation stay in this condo. It was spacious, clean and had beautiful views of the waterway. We really enjoyed having our morning coffee watching the boats go...
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    About this property
    Gulf & Bay Club Bayside is a gated resort community is across the street from our private access to - Siesta Key Beach with the world renowned white sands - rated one of the top ten in the US! FREE High Speed Wireless Internet ! - just bring your Laptop. Watch the boats float by! Just steps from...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Gorgeous Direct gulf Front 2 Bedroom Condo on Siesta Keys... JUST REMODELLED1 / 58
    (17)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Housekeeping Included
    • Cable/satellite TV
    • Waterfront
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    This condo was absolutely perfect. Sweeping ocean front, and water views in every room. It was very comfortable, so clean, and had absolutely everything we needed - great...
    Reviewed July 22, 2019
    The beach and docks were amazing! We rented kayaks for the week and took them out 6 of the seven days we were there. There is a kayak rack to store your kayak right by the...
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    About this property
    Our Fisherman's Cove condo description Paradise awaits - GORGEOUS, totally renovated in 2017, two bedroom, beach front condo on the Gulf of Mexico with sunset views overlooking the and sunrise views of the lagoon, expansive water views from every window. Beach was restored so it is large...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Sandy Toes Siesta Key Florida  (6796)1 / 40
    (23)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    • Waterfront
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 9, 2018
    Everything was great. The condo was updated, clean and spacious. It had what we needed to really enjoy our week. It was a quick walk to the beach, restaurants and shops. We...
    Reviewed March 25, 2018
    We had so much fun. It was so nice that the kids had their own space , own TV, own bathroom. The beach is amazing. The owner provided beach towels, chairs and umbrellas. I...
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    About this property
    A spacious 2 bedroom 2 bath Townhouse, with a 2 car garage and extra guest parking. Stroll down a private road (about 300 yards) to the #1 Beach in the U,S. You are in the Resorts of Sara Sea and just a couple of blocks from restaurants, grocery, sports rentals and ice cream ! The Great room has...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Beachfront- Gulf View! 2 BR/BA Crescent Arms 603S, #1 Beach in the US.1 / 24
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Washer
    • Ocean Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 25, 2018
    Such a well appointed condo, with a fabulous location right on the beach.Easy walking distance to some great restaurants. Our owner was very attentive and answered all...
    Reviewed November 13, 2017
    We loved this condo. The beach was wonderful. Siesta Key Village was so close with great restaurants to choose from... Pavan was very nice to work with. What more can you ask...
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    About this property
    - Expansive, panoramic gulf view from every room of this 6th floor condo. -Crescent Arms is a quiet, beach front, high rise condominium building that is ideally located for maximum fun and relaxation. -Right on the beach with lounge chairs provided. As close as you can get to the Gulf without...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    WOW Factor Siesta Key Beach Gulf Front Condo in Siesta Dunes on #1 Beach in USA1 / 55
    (21)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Ocean Views
    • Housekeeping Included
    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 1, 2019
    Absolutely enjoyed the condo. Well maintained and stocked with everything you would need. The owner was very nice and always responded to my questions immediately. The pool and...
    Reviewed January 16, 2019
    This is a high class condominium resort ON THE BEACH of Sarasota's Siesta Key. The resort itself is first rate, plus it fills it's beachfront with chairs and chaise recliners...
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    About this property
    Our condo has 1,200 sq ft of living area, two bedrooms and two baths and sleeps 6. 2 twin size Aerobeds for the kids. It is in Building 5 Unit 202- 2nd floor - Elevator in building-laundry facility in building by elevator...just two doors away. The first picture on this website was taken from...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Siesta Key Beach Condo, 2Br/2Ba Direct Beach Front1 / 20
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Waterfront
    • Air Conditioning
    • Grill
    • Balcony
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 5, 2019
    The location and views were great. The shuttle is easy to catch and the beach is pristine. The condo itself was not very clean when we arrived. We found candy wrappers on the...
    Reviewed August 14, 2018
    This condo is right on the beach. If you are looking for a family friendly place this is it. We absolutely loved this place and the view ..OMG is AMAZING!!! The place was well...
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    About this property
    Description Details Features Inquires Similar Listings google-map-thumb Siesta Key Beach Condo, 2Br/2Ba Direct Beach Front USD 160 Per day 6312 Midnight Pass Rd., Siesta Key slider PreviousNext Property Description Relax in this beautiful fifth floor beach front Condo...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Hot Tub
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Vacation on Siesta Key in this newly built 4 bedroom custom pool & spa home just a 600 ft. away from Shell Beach. Across the street and down the small drive is the gulf. Shell Beach has a very small sandy beach. It's on Big Pass and looks out to Lido Key. Here the water has a current so little...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Beachy Chic Condo in Siesta Key - Waterfront - Free wifi - Sleeps 4 !1 / 30
    (21)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Patio
    • Waterfront
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 9, 2019
    Nice location and pool was great. Bedroom TV never worked the whole time. Owners are from Canada and my cell phone couldn't make international calls. Had to email and never got...
    Reviewed July 1, 2018
    Nothing negative to say here. Location was great, condo was spacious and had everything we needed. I would definitely book to stay here again!!
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    About this property
    Welcome to our Condo in Siesta Key ! Located on the inter-coastal Waterway and a short walk to the whitest sand and the # 1 beach in the USA. This 1 bedroom Condo is a great retreat for anyone looking for a beautiful Island getaway! Our condo is on the 2nd floor (sleeps 4) We are on Siesta...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We help make the most of your vacation by providing Free Admission to some of the area’s top attractions each and every day including a choice of a free, bike rental, free kayak rental, or free dolphin fun cruise! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
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    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New furnishings complete an already fabulous condo! Enjoy this newly painted, newly furnished adorable & quaint ground floor two bedroom, one bath condo with water views and all of the amenities you are looking for in a fun yet relaxing atmosphere. This particular unit is located only about 30...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We help make the most of your vacation by providing Free Admission to some of the area’s top attractions each and every day including a choice of a free, bike rental, free kayak rental, or free dolphin fun cruise! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    SIESTA KEY Gulf side 2 Bed 2 Bath at Jamaica Royale  #104!1 / 20
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 22, 2019
    All was great at the bill We had all we needed and were within a quick walk to the beachThe only thing I would change is the beach cart that is a little old and rundown...
    Reviewed May 29, 2019
    Great place by the beach. After we got our food and liquor supplies from the Publix down the road, we parked the car and didn't need to use it again. Everything we needed was...
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    About this property
    Jamaica Royale Condominiums are located directly on the Gulf of Mexico along the white sands of world-famous Siesta Key Beach in Sarasota, Florida. A barrier island on Florida’s West coast, considered the most beautiful of Florida’s barrier islands, Siesta Key’s beach boasts “the world’s finest...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Canal Home on Siesta Key w/ Pool, Wifi, Renovated 1950 Style Sarasota School of1 / 74
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed yesterday
    This is a large nice home. But it needs basic maintenance. Many light bulbs out, pool deck paint peeling, caulking painting needed, etc. In addition,not enough bath towels...
    Reviewed November 15, 2018
    This house is perfect for your Siesta getaway!Close to Village and #1 beaches great pool on the CanalI would defiantly stay here again!
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    About this property
    We help make the most of your vacation by providing Free Admission to some of the area’s top attractions each and every day including a choice of a free, bike rental, free kayak rental, or free dolphin fun cruise! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    Private Siesta Key House - Walk to Village & Beach - Heated Pool/Spa - No Stairs1 / 20
    (4)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 18, 2019
    We had such a great experience with this rental. The house was beautiful, perfect for a family with a small child (ours was about 15 months old). And you can't beat the location...
    Reviewed January 29, 2018
    I stayed over the winter holiday with my husband and other adult family.It was the perfect place to have a pleasant vacation. Close to all shops and downtown and also a short...
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    About this property
    Steps from the islands best restaurants, shops (in the Village area) and a short walk to the #1 beach in the USA! Great home with 2 car and 1 car private garages. Recently renovated including a screened in patio, hot tub and pool. Brand new appliances making this home a great place for monthly...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    LJ's 'Rustic Cottage'-- 2 Bedroom/ 2 Bath Steps From The Sand With Pool Access!!1 / 31
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 11, 2019
    pictures make it look bigger than it is. 4 plex was a little loud a couple nights. beds and pillows could use a upgradeOtherwise nice, comfortable place. Quality appliances...
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    About this property
    Beautiful 2 Bed, 2 bath vacation rental with a pool just steps from Siesta Beach Access! Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week office for your convenience and guest needs. There are four different units located on...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Siesta Key Townhouse across from Pristine Sands of Siesta Key 2B/2B sleeps 61 / 30
    (20)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    The condo is directly across the road from probably the best beach you will ever see. Additionally, there are all the beach accessories that you could possibly need provided...
    Reviewed July 15, 2019
    We enjoyed a 2 week stay in June , Michelle was easy and very pleasant to deal with and responded immediately to any questions .The property is as described and the photo images...
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    About this property
    “Pristine sand, blue skies - 'Number 1 Beach'” The Best Thing to Come Home to after a Day on the Beach Is... ...a vacation home as comfortable as your own home. Just a walk across the street to Siesta Key's world famous #1 Beach. This split-level townhouse, has 2 bedrooms (King in Master...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
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    • Wi-Fi
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    • Patio
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We help make the most of your vacation by providing Free Admission to some of the area’s top attractions each and every day including a choice of a free, bike rental, free kayak rental, or free dolphin fun cruise! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Honeymoon Suite - Gulf views - next to Siesta Key Beach1 / 20
    (6)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Waterfront
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 30, 2018
    The suite was lovely, and the bed was very comfortable. The grounds and pool were very well maintained. Great Beach access.
    Reviewed August 2, 2016
    Me and 2 friends booked this wonderful appoartment very short-term (the day before) and the owner Virginia was just amazing. She helped us with the booking, welcomed us...
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    About this property
    Gumbo Limbo Vacation Rentals: Honeymoon Suite, 60 steps to the BEACH. NEWLY REMODELED AND REFURBISHED. Spacious 1 bedroom / 2 full baths townhouse (850sq/ft) over 2 floors, with 1 King size bed, and a luxury Queen self inflating air bed for max. comfort. This townhouse also offers 2 balconies...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We help make the most of your vacation by providing Free Admission to some of the area’s top attractions each and every day including a choice of a free, bike rental, free kayak rental, or free dolphin fun cruise! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Balcony
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the most amazing #1 rated Siesta Key beach views on the Gulf of Mexico from the 15th floor of the Terrace Building in Siesta Key Village! Hands down, best location with the best views! This home away from home 2 bedroom 2 bath condo with almost 1,187 sq. ft. being almost 1/4 of the...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Luxury Villa, Sleeps 6 Comfortably Located on Siesta Key Beach, Sarasota Florida1 / 26
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 13, 2019
    The villa was great very clean and fully equipment with everything you would have at home. Great week would book next time.
    Reviewed August 26, 2018
    The house was spotlessly clean and up to date with tasteful decor. There were plenty of cleaning supplies, towels etc provided which made our stay with children very easy. In...
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    About this property
    This is a Luxurious Villa on Siesta Key Beach Florida on Crystal Sands - Experience why Siesta Key, Sarasota Florida has been rated the #1 beach in the USA (#5 in the world by TravelAdvisor) for so many years. Siesta Key is one of the only beaches in the world with 99% Pure Quartz powdery white...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Siesta Villa Palma1 / 33
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 7, 2016
    We had a great time at Villa Palma. The villa is very clean and it has everything you need for your stay. It is very close to the beach, we ended up only going to the beach. The...
    Reviewed August 10, 2016
    What a LOVELY place to stay!!! Sean was flexible, attentive and accommodating, and there was even fresh fruit, sparkling water and a personalized welcome sign waiting on the...
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    About this property
    The Property Villa Palma is a stand-alone single story villa located in the beautiful Polynesian Gardens community, on the beautiful barrier island of Siesta Key, Fl. Located less than 1/2 mile from the public beach access, the home is chic and hip in its mid-century modern beach cottage decor. The...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa1 / 38
    (12)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 15, 2019
    The house at Siesta Key was perfect for our family. There was plenty of space for everyone to spread out and enjoy the week. The pool and fishing dock worked wonders for the...
    Reviewed July 14, 2019
    The house was perfect for our large family! The Pool was a huge hit with the little ones on those cloudy/rainy days, well really the whole week. The walk to the beach is maybe 5...
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    About this property
    Excellent location at only 120 Yards To The Cool White Quartz Sand Of Siesta Beach! ?This Home Has Water Frontage, Pool, Hot Tub And BBQ Area Within A Screen Enclosure. There Is A Nice Sized Sunning Patio As Well With Views Down The Waterway. This Home Entertains Excellent Because The Pool Area Is...
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    Siesta Key, Florida 34242
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 13
    Beach Walk Townhouse1 / 16
    (5)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Reviewed July 22, 2018
    We had a great time. Very close to beach and within walking distance to many restaurants. The place was clean and as advertised.
    Reviewed May 20, 2018
    The space was great. Very close to Siesta Key Beach. The only thing is that it is a 3 floor duplex and it makes it kind of difficult bringing your stuff up the stairs.
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    About this property
    Spacious Beach Getaway (sleeps 6), Calle del Otoño unit D, a 3 bedroom / 2.5 baths townhouse of 2,000sq/feet which is located right next to Gumbo Limbo. It offers 1 king, 2 twins and 1 queen size bed, brand new carpeting (January 2016), a balcony with partial Gulf view and a heated pool. This...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Beach Across the Street, Partial Gulf Views, Wifi, Tennis Courts, Community Pool1 / 37
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 11, 2019
    This big, roomy condo is right across the street from Siesta Key beach! Owners had beach towels, coolers, an umbrella and chairs for beach use. Two balconies with different sun...
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    About this property
    We help make the most of your vacation by providing Free Admission to some of the area’s top attractions each and every day including a choice of a free, bike rental, free kayak rental, or free dolphin fun cruise! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Siesta Key Condo, Crescent Arms, unit 605 South1 / 24
    (19)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Ocean Views
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 29, 2019
    Of course we were impressed as we booked with Karen again. The condo was as clean as could be both times and Karen is terrific to deal with. The beach is visible from the...
    Reviewed July 6, 2018
    This was our second time coming to the specific condo and booking with Karen. After our first trip, we had to come back. The beach is incredible and the sand feels just like...
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    About this property
    Crescent Arms beach condo on Siesta Key. Completely updated condo with comfortable furniture and beds. Everything you need to relax and enjoy the beach setting. Split floor plan with each bedroom having a private full bath, tv and access to the lanai. Totally updated, comfortable furniture and...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Top Floor End Unit Directly Across the Street from Siesta Key public beach1 / 10
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    Reviewed February 16, 2018
    Very clean, great owner, super location, great value. My family with kids loved this space. Pool and clubhouse was nice as well.
    Reviewed July 14, 2017
    We loved our stay here, the owner was very nice and easy to work with. Her place was clean with lots of amenities. Great view of the beach and short walk to the white powdery sand.
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    About this property
    2 bedroom/2 bath top-floor end unit steps from the #1 beach in the County and #3 in the World (voted by Trip Advisor Feb. 2016). Sarasota County spent almost $30 million renovating all of the public facilities - new concession, bathrooms, SunDeck Restaurant, playground equipment and picnic...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discover Siesta Key at this three bedroom two bathroom vacation rental home located in the heart of Siesta Key tucked away in a quiet neighborhood. Hire one of the many free ride services on the key for a quick trip to visit Siesta Key village where you can find a multitude of restaurants,...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    $99 OCT SPECIAL! 3 min drive/15 min walk to Siesta Key! Super Clean!1 / 32
    (15)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 23, 2019
    Had a wonderful stay at this hidden gem. The location is off the main stream but is within walking distance of shopping and the beach. Sue thinks of everything you could...
    Reviewed April 16, 2019
    This was a really clean cute place… We appreciated the extra little nice cities in the kitchen to make her stay seamless. Sue was very kind. It was a clean and quiet place close...
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    About this property
    All newly done! New flooring (Nov 2018) since these photos. New bathroom tiles and floors. This spacious, 2 bedroom/2 bath has everything you need for a relaxing and fun vacation in Sarasota, just minutes to Siesta Key. Relax in comfort with all the amenities: - Fully equipped Kitchen with all...
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    Location Information
    Siesta Key, Florida 34231
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Crescent Arms 703S, Beachfront Penthouse, Gulf View from Every Room! 2BR-BA1 / 36
    (15)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
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    • Ocean Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 27, 2019
    Our stay at Crescent Arms 703S was terrific. The room came well furnished with beachy vibes and colors. Plenty of beach toys, ice chests, and rafts stocked in the condo was a...
    Reviewed July 7, 2019
    This is our 3rd year renting at Crescent Arms and with Pavan. The location of this condo is perfect. The bathrooms have been updated and the condo is very clean. Walking...
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    About this property
    -Accommodations: Condo, 2 Bedrooms + Convertible Bed, 2 Baths (Sleeps 4-6) -Expansive, panoramic gulf view from every room of this 7th (top) floor condo. -Crescent Arms is a quiet, beach front, high rise condominium building that is ideally located for maximum fun and relaxation. -Right on the...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Siesta Key, Heated pool, Gulf and Bay, Cute Siesta Key Condo, Gated1 / 24
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 27, 2019
    Condo was well stocked the location was perfect and the tenants around us were very friendly Nice pool Would stay again Thank you!!
    Reviewed April 9, 2018
    The Sea Club condo was fabulous!! The location, being on the inner coastal, watching the boats every day and night go by, was perfect. Loved to watch the others fishing off...
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    About this property
    Our condo has just been remodeled with granite counter tops, stainless steel appliances, dishwasher, cabinets, new tile, new bathroom, and new furniture. It is a second floor unit. We have included all the essentials for a family that likes to have the flexibility to make meals at 'home' or...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the global flair of Siesta Key, Villa Soleil! This beautiful, stand-alone villa has 3 bedrooms, 2 baths and boasts fine appointments throughout. It’s an eclectic and artistic mix of French and Asian décor met by coastal pops of color and high-quality design. It’s extravagant and comfortable....
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Sea Shell Condo-Right On Crescent Beach-Siesta Key1 / 24
    (10)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • Terrace
    • Wi-Fi
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    • Ocean Views
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 12, 2019
    Wow, what a fabulous beach and sunsets out of this world. One doesn't want this vacation to ever end. Every amenity in the condo you can think of. Roomy, clean, and...
    Reviewed April 17, 2018
    Clean, roomy, well-stocked with all kitchen amenities that you could think of. Master bedroom very roomy. Extra space for your bathroom essentials in medicine cabinet...
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    About this property
    If you are looking for the perfect spot for a family vacation, to escape the cold and snow, or a quiet romantic getaway this is the place for you. Recently updated throughout, this 2 bedroom 2 bath condo sleeps 6 comfortably all in real beds. Just outside your door is Crescent Beach, consistently...
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    Location Information
    Siesta Key, Florida 34243
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discover the beauty of Siesta Key at Siesta Villa Whispering Palms. Our recently renovated 3-bedroom, the 2-bathroom stand-alone villa is your new home-away-from-home. Featuring 1700 sqft of air-conditioned living space, an open floor plan, large living spaces, spacious bedrooms, and well-manicured...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    1
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