We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Siesta Key Vacation Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    $244 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Travellers to Siesta Key are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    All 538 Rentals in Siesta Key
    Sort by:
    Default
    Island House Beach Resort V351 / 17
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Large Studio. Walk to Village. Couple Getaway!1 / 25
    (1)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Island House Beach Resort 1N1 / 19
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    GULF FRONT - GROUND FLOOR UNIT!! This spectacular 2 bedrooms, 2 baths unit is 1300 sq. ft. as is located on Crescent Beach. This condo offers a view of palm trees, white sand and turquoise waters of the Gulf of Mexico.Fully equipped kitchen, all appliances. The unit has a king size bed and 2 twins....
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Island House Beach Resor 13N1 / 22
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Terrace
    • Parking
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Island House Beach Resort! Crescent Beach, Siesta Key Florida. This beautifully maintained complex is located on one of the best beaches in central Florida. This 3rd floor, 2 bedroom, 2 bath condo offers views of palm trees, white sand and the turquoise waters of the Gulf of Mexico. The view is...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Key West Suite next to Siesta Key Beach1 / 32
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Washer
    • Air Conditioning
    • Balcony
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 apartments to choose from: Key West Suite A relaxed beach experience. This cozy two bedrooms & den apartment, full 2 baths (1 King bed + 2 Twins + 1 Queen) 1,200 sq/ft. suite on second level with two private balconies and partial Gulf view from the den. This apartment is fully furnished and...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Stay on Siesta - Beach House Bungalows 21 / 12
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Balcony
    • Waterfront
    • Washer
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tastefully decorated in pastel colors, reflecting the relaxing ambiance of a Florida beach bungalow. As you gaze out the picture window the umbrella tables on the tropically landscaped patio come into view. The back of our bungalow is a private patio great for relaxing and taking in the sun. The...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    PRISTINE SIESTA KEY VILLAGE HOME1 / 28
    (5)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hidden behind a contemporary privacy wall, enter into our front yard oasis. The perfect setting for tanning, dining and entertaining alongside the waterfall feature. Extensive renos offering a stunning gourmet kitchen, updated bathrooms, flat screen tv's in bedrooms and the most appealing Lanai...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location! Location! Location! Walk out the door, across the street and onto the #1 ranked beaches in America! This beautiful condo sleeps up to 6 people and has been newly remodeled from top to bottom including brand new appliances,granite counters,bedrooms,flooring, as well as a new bathroom. The...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    • Secure Parking
    • Wi-Fi
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Siesta Dunes gated complex directly on the Gulf of Mexico. Beautiful complex with gated security. Parking next to the front door of this first floor garden unit with easy access to unit. Unit has everything you need for your stay. Washer and dryer in the unit for your use. Master suite with king...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Save time - get the best Siesta Key rentals sent straight to your email!
    Get the List
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Grill
    • Terrace
    • Patio
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casa Junonia! Our newly constructed luxury cottage has all the amenities your large group [up to 12!!!] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout the entire three-story building, an elevator to access each landing from the ground floor,...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Grill
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury hi-rise condo right on the beach. Enjoy amazing sunsets on the full lanai, with access from each bedroom. Take long walks on the beach. Location is close to shops and restaurants. Crystal Sands on Midnight Pass Rd is one of the most popular condos in Siesta Key. And our Crescent Beach is...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    La Contento Casa1 / 34
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Waterfront
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the completely remodeled, and newly furnished La Contento Casa! This lovely 3 bedroom, 2 bath home comfortably sleeps 6 in beds, with ultra deluxe rollaway beds for an extra 2. Enjoy the peacefulness of a large heated pool with beautiful and breathtaking views of the water via the...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Gorgeous  Condo Across from Siesta Key Beach1 / 40
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • DVD Player
    • Internet Access
    • Ocean Views
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gorgeous 2 bedroom condo across the street from #1 voted beach Siesta Key. We have everything for your home away from home. The beauty of Sarasota will get your attention on your first visit. Siesta Beach is one of the top ranked beaches in the world! Its fine quartz white sand has a silky,...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very cheerful, updated and professionally decorated 2 bedroom/2 bathroom, 1400+ sq. ft unit on 4th floor in elevator building. Ceramic tile throughout invites a cool and clean feel. King Bed in Master Bedroom. Two Twins in Guest Bedroom. Maximum of no more than 4 people. Spacious screened-in glass...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Island House Beach Resort V391 / 17
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Island House Beach Resort, Siesta key, Crescent Beach!New improvements in 2014! 60' tv and entertainment center ( netflix reaady), new ac unit, new dishwasher and ceiling fans in bedrooms. Professionally decorated in October 2011. This large 2 bedrooms, 2 bath unit is approx 1000 sq. ft. It has a...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Casa Van Lopik (Canal) – In Siesta Village just 1.5 blocks to the best beaches!1 / 54
    (19)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • Grill
    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    • Waterfront
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Van Lopik (c), our canal facing suite, is a large 3BR. Brought to you by Gertrude Rentals! Perfectly located 1.5 blocks away from the best beaches, shopping, dining and entertainment on the island. It was named for our father who was a ships captain and sailed the world for 30 years but...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    8 Bedrooms, 6 Bathrooms, Sleeps 24 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to The Big Kahuna! Our newly constructed luxury cottage (completion date of June 2017) has all the amenities your large group [up to 24!!!] can fathom. It also boasts the very BEST location, in the heart of Siesta Key Village, just behind Gilligan's and Lelu's Coffee Shop! Inside you’ll...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 24
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casa Ohana! Our newly constructed luxury cottage (completion date of June 2017) has all the amenities your large group [up to 12!!!] can fathom. The location is THE premier location in the heart of Siesta Key Village, just behind Gilligan's and Lelu's Coffee Shop! Inside you’ll enjoy...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    Our Tropical Island Home1 / 14
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Heated)
    • Balcony
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This wonderfully updated island vacation home has a spacious floor plan. There are tropical views from every window. The beautiful, heated private pool includes a spa and a waterfall. You can open the large patio doors to the screened in lanai that overlooks the pool and bring in the sound of...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • DVD Player
    • Wi-Fi
    • Porch
    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Turtle beach was just re-nourished in March 2016!! Come enjoy the great new beach at Fisherman's Cove! Leave your worries behind... If you're looking for a relaxing beachfront condo that's been totally remodeled you've come to the right place. (all new photos -just uploaded!) Our ground-level...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casita Morning Star! Our newly renovated luxury cottage (completion date of June 2017) has all the amenities your family [up to 10] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout gorgeous and decadent bathrooms, new appliances, new washers/dryers,...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    Siesta Key- Beach Chic Retreat,  Siesta Key 3 Bedroom 2 Bath Apartment1 / 40
    (15)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Outdoor Dining Area
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We offer a boutique style property with just 4 units. Close enough to the beach without the congestion of larger properties. Enjoy this newly renovated (2014) apartment, located less than a mile from beautiful Siesta Key Beach. We've fully remodeled in the 'Beach Chic' style, with a touch of...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casa Tegula! Our newly constructed luxury cottage has all the amenities your large group [up to 12!!!] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout the entire three-story building, an elevator to access each landing from the ground floor, gorgeous...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Grill
    • Central Heating
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Directly overlooking the gulf, this designer decorated unit is literally steps to Siesta Beach. This unit has 3 bedrooms each with a queen bed, and couch set up can accommodate 2 and 2 full baths. Open plan living and dining area with spectacular views of the beach. Full size kitchen with...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Private Garden
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to your own secluded tropical oasis. Lush island landscaping surrounding the property makes this home a unique and private setting. Private dock on protected cove 2 minutes from Sarasota Bay/ICW. Rent a boat at neighboring marina if you choose. Breathtaking large private pool, with numerous...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    Siesta Key - #1 Beach in USA1 / 20
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Ocean Views
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Children's Pool
    • DVD Player
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will feel like you have arrived in Paradise when you enter the lobby. The facility is more like a resort than a condominium. Unit has 2 bedroom, 2 baths, split plan. Both bedrooms and living room open to screened lanai facing the Gulf of Mexico. Perfect setting for 4 adults or for a family with...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Island House Beach Resort 16N1 / 15
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Terrace
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Island House Beach Resort! Newly remodeled!! Crescent Beach, Siesta Key Florida! This attractive complex is located on the widest part of one of the best beaches in central florida. This condo is 1300 sq. ft, non-carpeted and is located on the 4th floor. It is 2 bedrooms, 2 baths, King, 2 twins,...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa1 / 76
    (6)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 13
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely home is in Harbor Towers. Looking out to the marina and inter coastal waterway. Tennis courts and a heated pool, and just a five minute walk to the beach. We have lawn chairs, Umbrellas, coolers and all the toys for the beach. Contact me with any questions. We also have a two bedroom...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Island House Beach Resort V251 / 17
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Parking
    • Internet Access
    • Private Outdoor Pool (Heated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Island House Beach Resort - Siesta Key Florida, Crescent Beach - This large 2 bedrooms, 2 bath villa is appox. 1000 sq. ft. It has a large living area, dining area, fully equipped kitchen, all appliances, central ac/heat, covered parking, screened lanai, free wi-fi in unit! The unit is non-carpeted...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Island House Beach Resort 3N1 / 18
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Cable/satellite TV
    • Terrace
    • DVD Player
    • Parking
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Island House Beach Resort!! Crescent Beach, Siesta Key Florida! Direct Gulf Front - Panoramic Views. This beautifully mainained complex is located on the widest part of one of the best beaches in central florida. It is 1300 sq. ft, non carpeted, 2 bedrooms, 2 baths.King, 2 twins. The unit has a...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Patio
    • Balcony
    • Washer
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casa Stolida! Our newly constructed luxury cottage (completion date of June 2017) has all the amenities your large group [up to 12!!!] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout the entire three-story building, an elevator to access each landing...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    What a View!! 2/2 Cert. of Excellence Winner 20141 / 28
    (14)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • DVD Player
    • Grill
    • Waterfront
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Siesta Key, Sarasota upscale vacation rental unit with a direct view of the inter-coastal water. Lush, tropical landscaping in well maintained Bay Oaks. Breathtaking view of the inter-coastal with fully appointed fishing dock. Across the street from the beach and there are no beach charges on...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Island House Beach Resort 14S1 / 17
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Balcony
    • Internet Access
    • Parking
    • Terrace
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Island House Beach Resort! Crescent Beach, Siesta Key Florida. This beautifully maintained complex is located on the widest part of one of the best beaches in Florida. This condos offers a view of the palm trees, white sand and turquoise waters of the Gulf of Mexico. The view is picturesque and the...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Siesta Key - 2BR - Beachfront Condo on Crescent Beach - Heated Pool - Tennis Ct1 / 29
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Grill
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SIESTA BREAKERS - Siesta Key Beachfront Vacation Rental Condo on Crescent Beach (Two Bedroom Vacation Units for Rent)   Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FL   This gorgeous Siesta Key luxury beach view condo is directly on world famous Crescent Beach located...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Island House Beach Resort 5S1 / 17
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spectacular view on Crescent Beach, Siesta Key florida. This 3rd floor unit is located directly on the Gulf of Mexico. Enjoy panoramic views from living room, master bedroom, guest bedroom. This unit is 2 bedrooms, 2 bathrooms and is 1300 sq. ft. King, 2 twins, central heat/ac. It has a large...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    3BR/4BA TOWNHOUSE - POOL VIEW PARADISE - PRIVATE BEACH ACCESS1 / 38
    (1)Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Washer
    • Wi-Fi
    • DVD Player
    • Ocean Views
    • Waterfront
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    WELCOME TO PARADISE! -- BEST LOCATION on SIESTA KEY! MAY-OCT SPECIALS - 4 days min stay. 50-60% discount for longer stay. A very clean, cozy TH with a pool view, a few yards to Crescent beach. THIS IS NOT a typical DAILY RENTAL PLACE. There are TWO BEDROOMS upstairs and one bedroom on the...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 6
    Make Enquiry
    Island House Beach Resort V341 / 15
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Island House Beach Resort, Siesta Key Florida, Crescent Beach - This large 2 bedrooms, 2 bath villa is approx. 1000 sq. ft. It has a large living area, dining area, fully equipped kitchen, screened lanai, covered parking, central heat/air, 3 tvs, dvd, free wi-fi in unit, washer/dryer. It has a king...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    The Shells Villa - Next to Beach & Village1 / 41
    (66)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Patio
    • Waterfront
    • Air Conditioning
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Bedroom, 2.5 Bath Beach Villa (Sleeps 8-10) What makes us different than other homes you may be considering: · The Beach - The home is located on the ocean side of Beach Rd., so you just walk out your door and through our private access path. It’s literally 230 feet to Siesta Key Beach....
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to The Canopy Cottage! Nestled deep into a beautifully canopied tree neighborhood, this lovely 4 bedroom, 3 bathroom home features a heated pool and spa under a screened in lanai just a few minutes from Siesta Key's #1 Beach! Take a moment to breathe in the peace and serenity under the...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    • Grill
    • Patio
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to our Beach Get-away...where we invite you to relax, unwind and enjoy our casual Siesta Key way of life. Resting just yards from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach is our Tropical Siesta Key Inn. With no busy streets to cross, it's a...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Island House Beach Resort 4S1 / 18
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Parking
    • Terrace
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Island House Beach Resort - Crescent Beach, Siesta Key Florida. 2nd Floor unit, 2 bedrooms, 2 baths. This beautifully maintained complex is located on one of the best beaches in Florida. This condo offers a view of palm trees, white sand and the turquoise waters of the Gulf of Mexico. The view is...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Midnight Cove #532 in Siesta Key, FL- Sun, Sand & *Save 20% to 35% per Week*1 / 24
    (33)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Washer
    • Parking
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Stop clicking around the web, and endless window shopping for your next Siesta Key Vacation Property Rental, and take advantage of the super accommodation cost savings offered in “Every-Day Deals” and “Sell-Off Deals” with a Direct-with-Owner Reservation at Midnight Cove #532.' Sun, Sand &...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Island House Beach Resort! Crescent Beach, Siesta Key Florida. This beautifully maintained complex is located on the widest part of one of the best beaches in Florida. This condo offers a view of palm trees, white sand and the turquoise waters of the Gulf of Mexico. The view is picturesque and the...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take a look at this beautiful newly remodeled and redecorated unit! Ground floor 2/2 1400+ sq. ft. with slider glass enclosed lanai for a little more privacy. Open the sliders and still get the screened lanai effect and experience the cool tropical breeze from the Gulf of Mexico. Kitchen and baths...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Siesta Key Beachfront 3 Bedroom Home, Sarasota1 / 33
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Internet Access
    • Grill
    • DVD Player
    • Air Conditioning
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Description:Walk out the back door to the clean white sand of Siesta Key Beach. This home has private Siesta Key beach frontage on the prime section of beach, there are no homes between you and the beach. Nearly every room has a full view of the beach. The entire back of this house opens with...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
    Make Enquiry
    We like Blue,Siesta Blue! Cert.of Excellence 20141 / 46
    (30)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Patio
    • Grill
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Siesta Key, Sarasota upscale vacation rental unit within a few steps of the water or a gorgeous pool. Lush, tropical landscaping in well maintained Bay Oaks. Breathtaking views of the intercoastal with fully appointed fishing dock. Accross the street from the beach and there are no beach charges...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    4 Bd Waterfront Home w/Pool, Close to Siesta Beach1 / 37
    (8)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Cable/satellite TV
    • Parking
    • Patio
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Oh what a great feeling you get when you are looking out over the pool to the relaxing waters of the Grand Canal. This home is special with 188 ft. of canal wrapping the back of the home so you get to enjoy the views from three bedrooms, the kitchen, living and two dinning areas. Open all the...
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    Exceptional townhouse - Royal Palm Suite - with Gulf Views from all 3 balconies1 / 52
    (24)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Patio
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Royal Palm Suite (sleeps 6) is a 3 bedroom luxury townhouse of 1,850 sq/feet over 3 floors, 2 kings and 1 queen size bed, 3 balconies (each has a Gulf View), almost all rooms have a Gulf view, a kitchen with granite counter tops, master bathroom offers a bathtub with Gulf view and a bidet....
    View all property information
    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    List your property
    Owner log in