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.

Vacation rentals in Longboat Key, FL

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
All 104 Rentals in Longboat Key
loading...
Sort by
From
$224
Per Night
1 / 23
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Enquiry
From
$153
Per Night
1 / 7
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (3) Make Enquiry
From
$192
Per Night
1 / 18
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Enquiry
From
$194
Per Night
1 / 8
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Parking
  • Washer
  • Dryer
  • Microwave
  • Stereo System
  • Satellite TV
  • Waterfront
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
We have a two bedroom, comfortably furnished condo unit overlooking the Gulf of Mexico. Our favorite room is the lanai - a screened in porch area with dining table and sitting area, especially the views as the sun sets over the Gulf. We are located on the north end of Longboat Key - more secluded... View all property information
Make Enquiry
5 of 5 stars Reviewed 13 August 2014
This place is AWESOME, we stayed in the 4 bedroom housebayview with the private pool. It was the perfect vacation. The only mishap was the AC in one of the small rooms stopped...
See all reviews
From
$174
Per Night
1 / 23
Payment Protection
3 Bedrooms, 3 Bathrooms, Sleeps 5
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Garage
  • Sauna
  • Refrigerator
  • Gym
  • TV
  • Hot Tub
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Secluded, elegant 3 Bedroom, 3.5 Bath condo, almost 3000 sq. ft with 700 sq ft covered wraparound terrace and 3 month minimum rental. Panoramic views of Sarasota bay, golf course, heated pools, hot tub and clubhouse; with workout room, saunas, Har-Tru Tennis courts, BBQ area, children's pool.... View all property information
Make Enquiry
5 of 5 stars Reviewed 21 November 2014
This is a beautiful condo with lovely furnishings and every resort amenity one could ask for. Lots of walk in closets, flat screens, Jacuzzi tub, large rooms and great views...
See all reviews
From
$1,598
Per Week
1 / 31
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Make Enquiry
Amenities & Details
  • Grill
  • Shared Outdoor Pool...
  • Patio
  • Garage
  • Number Of Bedrooms
  • Balcony
  • Satellite TV
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
The beautifully landscaped approach to this charming beach house provides a sense of peace and tranquilty. This is enhanced by the openness of the common rooms which provide ample space for your special vacation. Relax in the entertainment room with the large, flat screen TV. The ground floor... View all property information
Make Enquiry
From
$199
Per Night
1 / 29
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (3) Make Enquiry
Amenities & Details
  • Grill
  • Parking
  • Dryer
  • Refrigerator
  • Patio
  • Ceiling Fans
  • Dishwasher
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Welcome to your home away from home! Spread out in this beautifully remodeled 3 bedroom top floor unit, soaking in the water views and privacy of the small community of Longboat Landing. Whether you stay for a few nights, weeks, or months, there is plenty to see and do in between long bouts of... View all property information
Make Enquiry
5 of 5 stars Reviewed 13 July 2014
We rented this condo on a recent trip to Longboat Key. We chose this unit as we were able to take our boat with us on vacation and dock it at the condo. We utilized a public...
5 of 5 stars Reviewed 9 July 2014
Loved this rental for 7 days. Location has access to the bay, (manatees visited dock), and across the road with access to the beach for swimming was wonderful. Having a 3...
See all reviews
From
$4,416
Per Month
1 / 7
Payment Protection
1 Bedroom, 2 Bathrooms, Sleeps 4
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Guest Count
  • # Of Bathrooms
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Cute beach bungalow is the perfect compact pool home for those looking for a laid back feel in the quite Longboat Key Village. Just down the street to MarVista, and the Public boat ramp, and a short distance to the beach access this home is made for the water and beach enthusiast. Tastefully... View all property information
Make Enquiry
4 of 5 stars Reviewed 28 April 2014
I stayed here with my husband and daughter. The location was great as it is close to the bay and ocean. The neighborhood is quiet with nice neighbors. The peacocks in the...
See all reviews
From
$2,676
Per Week
1 / 24
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Refrigerator
  • Dryer
  • Parking
  • Balcony
  • Satellite TV
  • Terrace
  • Washer
  • Hot Tub
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Beachfront resort, set on beautiful white sand beaches that meet the turquoise waters of the Gulf of Mexico. Resort with golf courses, 6 restaurants, tennis courts, spa, and deep water marina. Studio unit with King bed, sofa sleeper, and full kitchen 'stove top only, no oven' Rate includes resort... View all property information
Make Enquiry
From
$122
Per Night
1 / 7
Payment Protection
Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Washer
  • DVD Player
  • Refrigerator
  • Satellite TV
  • Ceiling Fans
  • Parking
  • Grill
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Longboat Key Bargain on the beach. Our cozy get away on the beach is a favorite of many guests who enjoy the quiet beachfront. Just a simple beach hideaway for your next quiet stay at the beach. View all property information
Make Enquiry
5 of 5 stars Reviewed 24 July 2014
So close to the beach, exactly what I was looking for. The studio was cozy and clean, cutely furnished. We loved the outdoor shower and will definitely return again!
See all reviews
Get the List
From
$153
Per Night
1 / 7
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (5) Make Enquiry
Amenities & Details
  • Patio
  • Microwave
  • Air Conditioning
  • VCR
  • Dryer
  • Satellite TV
  • Washer
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Peaceful and quiet spot on the beach. Your one bedroom vacation home has a private beachfront patio and direct gulf views from the patio, lanai, and bedroom. A full kitchen so you can enjoy meals at sunset instead of fighting the crowd at restaurants. Las Hermanas is just one block from our... View all property information
Make Enquiry
5 of 5 stars Reviewed 10 December 2014
The owners were great, the place safe,clean,equipped,location perfect for walking to dine, shop and enjoy Longboat Key! We will be back!
5 of 5 stars Reviewed 28 September 2014
Don't let the word "Motel" detour you from checking out this fantastic property! There are 4 beautiful units right on the beach. Each is complete with full kitchen and there is a...
See all reviews
From
$182
Per Night
1 / 16
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (3) Make Enquiry
Amenities & Details
  • Fax
  • Washer
  • Dryer
  • Refrigerator
  • Dishwasher
  • Patio
  • Ceiling Fans
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
This one-bedroom, ground floor walk-out, has fantastic full gulf views and is only steps to the beach. It features a bright beach decor that will make your vacation in paradise truly memorable. The screened lanai is practically perched upon the sand! An added bonus is that it is a corner unit... View all property information
Make Enquiry
5 of 5 stars Reviewed 27 November 2014
Very clean appartment, well equipped kitchen for self catering, with all the kitchen utensils spotlessly clean, very good position on the beach. Quite and very peaceful. Would go...
5 of 5 stars Reviewed 13 June 2014
I am reluctant to review the property because it might be more difficult to get the weeks I want! My husband and I first went to this place 35 years ago when friends recommended...
See all reviews
From
$254
Per Night
1 / 9
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • TV
  • Satellite TV
  • Terrace
  • Microwave
  • Dishwasher
  • Waterfront
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Beautiful 2 bedroom condo for rent by owner on Sand Cay beach. Perfect for families, this vacation rental features flat screen TV's in every room, fine furnishings and everything you need to have an amazing vacation. Please read our reviews, you won't be dissapointed! The condo is unit 208 at the... View all property information
Make Enquiry
5 of 5 stars Reviewed 2 May 2014
We three enjoyed four days in late April. Kitchen has every spatula know to mankind, among other tools. Balcony table nicely shaded in the afternoon with sun lounger out in the...
See all reviews
From
$220
Per Night
1 / 17
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Terrace
  • Refrigerator
  • TV
  • Parking
  • Dryer
  • Grill
  • Ceiling Fans
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
About this property
This beautifully appointed spacious 1 BR/1BA is recently renovated and with new furniture, tile flooring, and kitchen upgrades. Enjoy the 180 degree view of the horizon over the beach and the Gulf of Mexico with incredible sunsets. SeaHorse Beach Resort consistently ranks at the top of the... View all property information
Make Enquiry
From
$227
Per Night
1 / 8
Payment Protection
Studio, 1 Bathroom, Sleeps 3
Details Make Enquiry
Amenities & Details
  • Playground
  • DVD Player
  • Hot Tub
  • Washer
  • Dryer
  • Microwave
  • TV
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Club Suite : Longboat Key Club complex located on the beach , with view of golf course : newly furnished / turn key suite ,fully equipped kitchen ,king bed and sleeper sofa ,new flat screen tv /dvd ,cable ,elevator , a/c, washer /dryer , private lanai deck for entertaining , private parking ,... View all property information
Make Enquiry
From
$215
Per Night
1 / 30
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Guest Count
  • Number Of Bedrooms
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This luxury, oceanfront end-unit condo is very bright and sunny, with 3 sides of floor to ceiling windows with beautiful water views (Sarasota Bay and Gulf of Mexico) from every room. Longboat Key is a beautiful barrier island that is 11 miles long, located between the counties of Sarasota and... View all property information
Make Enquiry
From
$4,410
Per Week
1 / 25
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Enquiry
Amenities & Details
  • Grill
  • Guest Count
  • Parking
  • Satellite TV
  • Shared Outdoor Pool...
  • Internet Access
  • # Of Bathrooms
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This gracious home, with a pool and a private entrance to the beach, offers a lovely location on Longboat Key for all that the area has to offer. There is a nice sense of space with an open living room, kitchen and dining area. There are also two sitting areas that adjoin the bedrooms. The... View all property information
Make Enquiry
From
$168
Per Night
1 / 17
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
Details Make Enquiry
Amenities & Details
  • Microwave
  • DVD Player
  • Terrace
  • Ceiling Fans
  • Dishwasher
  • Waterfront
  • Refrigerator
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Up to 4 person private accommodation in our deluxe studio Unit 222 with a beautiful Gulf view completely renovated, remodeled and refurbished in September 2014. With new furniture and stainless steel appliances. Face the sunset over the Mexican Gulf that you could enjoy every evening, having a cup... View all property information
Make Enquiry
From
$103
Per Night
1 / 20
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Grill
  • Shared Outdoor Pool...
  • Balcony
  • Guest Count
  • Parking
  • Internet Access
  • Terrace
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Lovely 1 bedroom 1 bath rental unit on the second floor. The master bedroom has a king bed and the sofa in the living room is a queen size sleeper sofa. This condo is freshly painted throughout, nicely furnished and has skylights in the ceiling for lots of light. This unit is located close to the... View all property information
Make Enquiry
From
$331
Per Night
1 / 11
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Waterfront
  • Satellite TV
  • DVD Player
  • Terrace
  • Washer
  • Refrigerator
  • Parking
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This deluxe beachfront unit was updated in 2012 with new living room furniture including a 55' flat screen television. Many upgrades fall 2010 include new flooring, kitchen appliances, beautiful kitchen counters and fresh interior paint. The perfect island getaway, located on the southern tip of... View all property information
Make Enquiry
From
$206
Per Night
1 / 6
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
Details Make Enquiry
Amenities & Details
  • Microwave
  • Washer
  • Dryer
  • Parking
  • Grill
  • Terrace
  • Dishwasher
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Beautifully furnished 1 bedroom/1 bath condo overlooking the Gulf of Mexico. Stroll for miles on the white sandy beaches of Beautiful Longboat Key or just relax and enjoy the sunsets View all property information
Make Enquiry
From
$216
Per Night
1 / 18
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Make Enquiry
Amenities & Details
  • Ceiling Fans
  • Microwave
  • Washer
  • TV
  • Dishwasher
  • Garage
  • DVD Player
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
A lovely pet and family friendly private home, located on a private deep water canal with direct access to Sarasota Bay and only a short walk (200 meters) away from the quiet white sand beach perfect for morning beach-combing and end of day amazing golden sunsets. Located in the prestigious yet... View all property information
Make Enquiry
From
$150
Per Night
1 / 23
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 3
Booking
Details Make Enquiry
Amenities & Details
  • Patio
  • Dishwasher
  • Washer
  • Refrigerator
  • DVD Player
  • Microwave
  • Grill
  • Garden
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
**LAST MINUTE SPECIAL** From $129/night, Ocean Front 1 bedroom with private balcony ~ NEW GULF FRONT CONDO # 225 ~ THE BEACH ON LONGBOAT KEY This beautiful brand new beach front condo features a modern motif, designer decor, beautifully landscaped, with sophisticated charm and a casual beach... View all property information
Make Enquiry
From
$3,718
Per Month
1 / 5
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Hot Tub
  • DVD Player
  • Ceiling Fans
  • Sauna
  • Safe
  • TV
  • Refrigerator
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Directly across the street from the beautiful Gulf of Mexico! Amenities in the unit include Fios internet, 2 flat screened TVs with cable. Windward Bay is a low-density complex offering protected under building parking, extra storage, deeded access to Longboat Key's pristine beach within a short... View all property information
Make Enquiry
From
$465
Per Night
1 / 1
Payment Protection
5 Bedrooms, 4 Bathrooms, Sleeps 12
Details Make Enquiry
Amenities & Details
  • # Of Bathrooms
  • Number Of Bedrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Our luxury vacation home will comfortably accomodate up to 12 guests and is located on a deepwater canal and has a dock suitable for a boat up to 30 feet in length. Beautiful Longboat Key beach is less than a 10 minute walk from the house and world-class shopping and dining at the famous St.... View all property information
Make Enquiry
From
$165
Per Night
1 / 6
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Microwave
  • TV
  • Grill
  • Refrigerator
  • Washer
  • Dishwasher
  • Ceiling Fans
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Welcome to Longboat Key! This 2 bedroom one bath ground floor condo offers a full kitchen, with open living and dining area. There is a enclosed patio opening to the community pool. Covert Condominiums are located on the northern part of Long Boat Key on Sarasota Bay. There is deeded beach access... View all property information
Make Enquiry
From
$2,963
Per Month
1 / 18
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Number Of Bedrooms
  • Guest Count
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Condo is located in Banyan Bay Club which consists of a total of only 44 units arranged in two floors. This condo is located at the Garden level. No stairs. The lanai at the rear of the unit opens onto a private Banyan and Palm tree-filled lawn with views of Sarasota Bay. The lanai contains a table... View all property information
Make Enquiry
From
$145
Per Night
1 / 19
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Enquiry
Amenities & Details
  • DVD Player
  • Hot Tub
  • Ceiling Fans
  • Gym
  • Dishwasher
  • Dryer
  • Washer
  • Playground
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
DESCRIPTION GULF FRONT-Magnificent views on LONGBOAT KEY Two (2) Bedroom, two (2) Bath Condo with direct and full water views (from Living Room, Dining Room, Kitchen, Master Bedroom and Screened Lanai). Comfortable and beautiful leather sofa in Living Room (opens to a comfortable queen bed). Very... View all property information
Make Enquiry
From
$81
Per Night
1 / 25
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Gym
  • Microwave
  • TV
  • Dryer
  • Ceiling Fans
  • Dishwasher
  • Sauna
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Beautiful view of Sarasota Bay with private beach access just across the street. Newly renovated open kitchen and breakfast bar with seating for three, upgraded stainless appliances, and quartz countertops. Entire unit is freshly painted and immaculate with new tile in kitchen and living area. New... View all property information
Make Enquiry
From
$261
Per Night
1 / 12
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (13) Make Enquiry
Amenities & Details
  • DVD Player
  • Dishwasher
  • Washer
  • Safe
  • Dryer
  • Patio
  • Microwave
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
La Playa is a small 21-unit resort property of privately-owned condominiums available exclusively for weekly rentals twelve-months per year. Located on spectacular Longboat Key, a short drive from Sarasota on the wide sand beaches of the Gulf of Mexico, La Playa offers privacy and direct beach... View all property information
Make Enquiry
5 of 5 stars Reviewed 14 December 2014
La Playa is a little gem, situated in the centre of beautiful Longboat Key. There is a beautiful private beach, and all the amenities needed for a perfect Gulfshore holiday...
4 of 5 stars Reviewed 11 August 2014
We were pleasantly surprised when we arrived at LaPlaya and entered our unit, which was very clean and nicely decorated. The staff was warm, friendly and very accommodating, too...
See all reviews
From
$194
Per Night
1 / 41
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Hot Tub
  • Gym
  • Microwave
  • Garage
  • Refrigerator
  • TV
  • Ceiling Fans
  • Safe
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Available for 3 MONTH MINIMUM rental with approval from condo association. Beautiful beach front condo located just 1.5 miles from St. Armand's Circle. Very upscale and beach feels very private. Pool, spa, and deck newly renovated. We have 24 hour, 7 days a week, guard gated community and... View all property information
Make Enquiry
From
$4,648
Per Month
1 / 23
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Parking
  • Dishwasher
  • Patio
  • Waterfront
  • Microwave
  • Dryer
  • Ceiling Fans
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Beautiful ground floor beachfront 3 bedroom 2 full bath condo on Longboat Key. Fully furnished kitchen, washer and dryer (in unit), dedicated parking for 1 car directly in front of unit, with additional guest parking. Master Bedroom has a king sized bed , en suite bathroom with two sinks, glass... View all property information
Make Enquiry
From
$539
Per Night
1 / 77
Payment Protection
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • TV
  • Ceiling Fans
  • Garage
  • Dishwasher
  • Refrigerator
  • Patio
  • Microwave
  • Gym
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This luxurious villa on gulf features a heated pool, 3 beautiful terraces, fully-equipped gourmet kitchen & outdoor BBQ grill, fine art & sculpture, high-speed internet, flat screen televisions, video & board games, bicycles, ping pong, & much more. Located near the historic town of Longboat at... View all property information
Make Enquiry
From
$168
Per Night
1 / 13
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Enquiry
Amenities & Details
  • # Of Bathrooms
  • Number Of Bedrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Doctor’s hidden home with gorgeous views: walk to Florida’s best secluded beaches. Longboat Key is a tropical paradise. Just bring your yacht, golf clubs, tennis rackets and relax. FREE Wi-Fi & Cable TV Our Venetian / Mediterranean Villa is nestled on the placid Longboat Key. With a short... View all property information
Make Enquiry
From
$227
Per Night
1 / 13
4 Bedrooms, 2 Bathrooms, Sleeps 10
Details Reviews (18) Make Enquiry
Amenities & Details
  • Ceiling Fans
  • Dishwasher
  • Dryer
  • TV
  • Microwave
  • Grill
  • Hot Tub
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
SEPT Specials: pay for 3 days, stay for 4! ++++++Rated ' EXCELLENT' digital badge on TripAdvisor and FlipKey++++++. This exclusive award recognizes outstanding vacation rentals based on reviews of past year so you can rent with confidence.... View all property information
Make Enquiry
5 of 5 stars Reviewed 18 October 2014
We just returned from our vacation at the Castle in the sky and are already talking about plans to return next year. Myself and 5 girlfriends decided to beach it for our informal...
5 of 5 stars Reviewed 26 May 2014
I rented this condo for three nights with family and friends. The condo is so comfortable with all the necessities needed to make your vacation as stress free as possible. My soon...
See all reviews
From
$5,810
Per Month
1 / 10
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Enquiry
Amenities & Details
  • Guest Count
  • # Of Bathrooms
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Spacious and beautiful 2 bedroom beach front property with spectular view of the gulf. Fully furnished with amenities that include pool and tennis courts. Conveniently located within walking minutes of shopping and shops. Within minutes of St. Armand's Circle. Premier location in Longboat... View all property information
Make Enquiry
From
$134
Per Night
1 / 6
Payment Protection
Studio, 1 Bathroom, Sleeps 4
Bookings
Details Make Enquiry
Amenities & Details
  • Parking
  • Dryer
  • DVD Player
  • Grill
  • Ceiling Fans
  • Deck
  • Refrigerator
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This is a gulf front studio apartment right on the beach! Sound of the surf will lull you to sleep at night. You'll love the quiet and privacy that a small beachfront complex offers. Recently updated interiors all have direct access to the beach and full gulf views . There are only 4 units here... View all property information
Make Enquiry
From
$221
Per Night
1 / 22
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Satellite TV
  • Refrigerator
  • Dryer
  • Terrace
  • Washer
  • Waterfront
  • Ceiling Fans
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
SEA PINES This rarely available premier oceanfront location has one of the best views on Longboat Key looking out over the low dunes to the Gulf of Mexico where you can see the dolphins play, and the most amazing sunsets you’ll see anywhere. Quiet and serene with magnificent views, yet only a ten... View all property information
Make Enquiry
From
$128
Per Night
1 / 29
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Gym
  • DVD Player
  • Refrigerator
  • Satellite TV
  • Ceiling Fans
  • TV
  • Sauna
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
WINDWARD BAY CLUB on beautiful LONGBOAT KEY. This warm and inviting large 2 bedroom 2 bath corner unit is almost paradise. Meticulously furnished with all the comforts of home. Light and bright, with a view of the bay and the Mangroves from the large and roomy lanai. A short walk to the lovely... View all property information
Make Enquiry
From
$415
Per Night
1 / 22
2 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Deck
  • Microwave
  • Refrigerator
  • Grill
  • Waterfront
  • Washer
  • DVD Player
  • Terrace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Set on a 30 acre private island a few hundred yards off North Longboat Key, this new water front home (completed in 2012) will provide an island vacation experience for you and your family like no other. The house has 2 bedrooms, an outside sleeping porch/bunk bed, along with 2 1/2 bathrooms and an... View all property information
Make Enquiry
From
$4,067
Per Month
1 / 14
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Microwave
  • Terrace
  • TV
  • Grill
  • Dryer
  • Pool Table
  • DVD Player
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Condo renovated 2 beds/2baths in Longboat key third floor..elevator, across from the beach...peaceful, beautiful! tennis, pool, bikes on the island, Publix, CVS, restaurants, shopping, café no pets, no smoking.... Minimum Stay : 1 Month View all property information
Make Enquiry
From
$232
Per Night
1 / 5
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Garage
  • Dishwasher
  • Hot Tub
  • Dryer
  • Ceiling Fans
  • TV
  • Washer
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This spectacular two bedroom condominium sits directly fronting on the Gulf in the middle of Long Boat Key. It was recently renovated from floor to ceiling and is beautifully decorated with warm, rich colors. The kitchen has stainless appliances, granite countertops and custom dark polished wood... View all property information
Make Enquiry
From
$115
Per Night
1 / 18
Payment Protection
Studio, 1 Bathroom, Sleeps 3
Booking
Details Make Enquiry
Amenities & Details
  • Parking
  • Microwave
  • Patio
  • Dishwasher
  • DVD Player
  • Garden
  • Washer
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
**LAST MINUTE SPECIAL** The STUDIO is available 12/10 to 12/16 from $99/night ~ NEW GULF FRONT CONDO # 103 ~ THE BEACH ON LONGBOAT KEY This complex is a two story building with only 15 condos, beautifully landscaped, with sophisticated charm and a casual beach atmosphere. The pictures of the... View all property information
Make Enquiry
From
$138
Per Night
1 / 22
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Make Enquiry
Amenities & Details
  • Number Of Bedrooms
  • Satellite TV
  • Air Conditioning
  • Internet Access
  • Terrace
  • Grill
  • # Of Bathrooms
  • Balcony
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Enjoy one of the best views of Sarasota Bay in the entire complex from this one bedroom, one bath second floor unit. Completely redecorated with new tile throughout, new furniture, and flat screen LCD TV's in both the living room and the bedroom, this end unit provides a higher degree of privacy... View all property information
Make Enquiry
From
$208
Per Night
1 / 30
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Washer
  • TV
  • DVD Player
  • Dishwasher
  • Parking
  • Microwave
  • Terrace
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Our condo has everything you will need for a relaxing vacation on the beach. The island of Longboat Key... ... is one of the most beautiful places in Florida. Longboat was voted the second most favored island in North America, according to a survey by a nationally recognized travel magazine.... View all property information
Make Enquiry
From
$128
Per Night
1 / 25
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Garage
  • Parking
  • Gym
  • Terrace
  • Grill
  • Balcony
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Will you be the lucky one to take advantage of this VERY RARE OPPORTUNITY to rent for the season at The Player's Club on Longboat Key. This gorgeous complex, featuring four mid-rise buildings facing the Gulf of Mexico, offers only a handful of rentals, most of which have been tenanted by the same... View all property information
Make Enquiry
From
$227
Per Night
1 / 25
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Grill
  • Internet Access
  • Parking
  • Shared Outdoor Pool...
  • # Of Bathrooms
  • Air Conditioning
  • Terrace
  • Gym
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This is a beach lover's paradise. It offers full Gulf of Mexico views from the wall of sliding glass doors in the main living space and the open porch – ideal for relaxing with your morning coffee and throughout the day to your front row seat for the famous west coast sunsets. Recently... View all property information
Make Enquiry
From
$3,486
Per Month
1 / 19
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Boat Available
  • Garage
  • Internet Access
  • Parking
  • Satellite TV
  • Ceiling Fans
  • Gym
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
The Shore is a Gulf-front complex located near the north end of the island, with exquisite views from everywhere on the property. If you treasure your time on the beach relaxing in the sun, you couldn't pick a better spot. Close your eyes and imagine the sound of the wind whispering through the... View all property information
Make Enquiry
From
$2,092
Per Month
1 / 23
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • # Of Bathrooms
  • Internet Access
  • Grill
  • Number Of Bedrooms
  • Ceiling Fans
  • Shared Outdoor Pool...
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Enjoy a relaxing holiday in this lovely two bedroom, two bath ground floor unit at popular Whitney Beach, nestled at the north end of Longboat Key. Located on the bay side of this sought-after resort complex, you'll find all sorts of amenities just outside your door, or across the street on the... View all property information
Make Enquiry
From
$185
Per Night
1 / 14
1 Bedroom, 1 Bathroom, Sleeps 3
Details Reviews (6) Make Enquiry
Amenities & Details
  • Microwave
  • TV
  • Ceiling Fans
  • Terrace
  • DVD Player
  • Dishwasher
  • Satellite TV
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
For more information on the condo, please see our website at http://www.SEAHORSE247.com NATURAL BEAUTY of Longboat Key RIGHT ON THE BEACH PANORAMIC 2ND FLOOR BALCONY VIEWS On beautiful tropically landscaped Longboat Key, Florida you will find the natural beauty, not miniature golf and go-cart... View all property information
Make Enquiry
5 of 5 stars Reviewed 9 August 2014
Everything was perfect for 2 people. Nice decor, room set-up and proximity to beach. Quiet, mostly private feel (except for renovations being done next door). easy to arrange the...
5 of 5 stars Reviewed 21 July 2014
My husband and I enjoyed everything about our stay in this beautiful condo. Not only did we have a nicely decorated room inside, but our view was amazing outside. We were able to...
See all reviews
Go to map view
Book Online(56)
Use filters to find the best results!

Suitability

  • Wheelchair access (13)
  • Elder access (50)
  • Suitable for children (10)
  • Pet friendly (8)
  • Smoking allowed (0)

Amenities

  • Air Conditioning (96)
  • Other outdoor space (92)
  • Internet (90)
  • Parking (80)
  • Grill (65)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Nearby cities
Beachfront condos and bayside villas – your vacation rental on Longboat Key

Imagine overlooking Sarasota Bay and relaxing in your own villa pool garden … or enjoying crimson sunsets from your Gulf front family vacation condo. Beach and bay rental homes deliver the best of all worlds with spacious living, exceptional kitchens and easy access to Longboat Key parks, shopping and upscale or relaxed dining selections. For fishing excursions or family vacations, select rentals offer flexibility and value for holidays at the beach.

Longboat Key - the upscale coastal vacation destination

This gorgeous Florida key combines serene seashore enjoyment with luxury shopping and dining choices. Families enjoy the many water sport activities from fishing, boating and kayaking to plucking perfect seashells along the shoreline. Couples and friends explore chic dining and shopping spots around St. Armand’s Circle. The aristocratic heritage of the St. Armand and Ringling families resonates through quiet gardens and plush Palm Beach-style shopping. Umbrella-draped cafes and handsome restaurants offer exceptional European fare and inventive coastal specialties. Work off that decadent dessert with a stroll around the circle for leather, jewelry, resort wear and art gallery browsing.

Cultural treasures along Sarasota Bay

Venture just across the bridge over Sarasota Bay for unrivalled cultural treats. The Ringling circus family bequeathed an elegant legacy of art and architecture. The estate includes the acclaimed John and Mable Ringling Museum of Art, the family’s winter Ca’ d’Zan mansion – a Venetian Gothic masterpiece - the Circus Museum and historic Asolo Repertory Theater. With elegant gardens and terraces spread over 20 bayside acres, the complex provides hours of enjoyment.

Waterfront dining

Beyond the eclectic mix of St. Armand Circle restaurants, you’ll want to sample excellent bay front restaurants. The Dry Dock is a favorite of locals and visitors alike, with waterside dining under coconut palms or indoor seating with the same exceptional views. Boasting ultra fresh grouper sandwiches, char-grilled burgers and a host of pasta and chicken selections, the Dry Dock grill is a casual dining treat. Diners arrive by car or boat to enjoy Mar Vista Dockside Restaurant and Pub in the historic village at the North end of the key. With quaint indoor or outdoor dining and spectacular views, try steamer pots of fresh seafood or exotic scallop and crab dishes that wash down quite well with islander mojitos, margaritas and other such flavorful concoctions. Land lovers can choose from the number of chicken, steak and pork dishes.

Visitor reviews aid vacation rental selection

You’ll have no trouble knowing what to expect, as you search for the just-right villa or condo rental. Our unbiased visitor reviews offer clear descriptions and candid evaluations, so you can feel confident in your choice.