Large selection of Longboat Key Sarasota Vacation Rentals, book your property Direct and Save!
Many rental properties to choose from, including private Homes, Cottages or Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities that will make your Florida visit the perfect getaway.
Sea Grape Inn #4- BEACHFRONT Property
Longboat Key Apartment 
4.7 Star Review
*Need to stay less than the minimum required nights? Please call the office at 941-383-2105. Also, Returning Guests or those requesting a 4 week stay or longer, please call the office for a promo code discount.*
BEACHVIEW Condo- 1st Floor, 2 BDRMS/2 BATH, Sleeps 4: 1-King Bed, 1-Queen.
A first floor 2 bedroom 2 bath condo that offers a view o.......read more
2 Bedrooms
- Sleeps 4
Apartment in Longboat Key
Sea Grape Inn #5- BEACHFRONT Property
Longboat Key Apartment 5.0 Star Review
*Need to stay less than the minimum required nights? Please call the office at 941-383-2105. Also, Returning Guests or those requesting a 4 week stay or longer, please call the office for a promo code discount.*
BEACHVIEW Condo- 2nd Floor, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper.
Beautifully remodeled and upgraded; .......read more
2 Bedrooms
- Sleeps 6
Apartment in Longboat Key
Sea Grape Inn #7 - BEACHFRONT Property
Longboat Key Apartment 4.9 Star Review
*Need to stay less than the minimum required nights? Please call the office at 941-383-2105. Also, Returning Guests or those requesting a 4 week stay or longer, please call the office for a promo code discount.*
BEACHVIEW Condo- 2nd Floor, 2 BDRMS/2 BATH, Sleeps 4: 1-King Bed, 2-Twin Beds.
Situated in this idyllic resort comprised of eight un.......read more
2 Bedrooms
- Sleeps 4
Apartment in Longboat Key
Standalone Unit at Little Gull Resort. Amazing Sarasota Bay View! Walk to Beach.
Longboat Key Condo 4.0 Star Review
In the middle of April, the Florida weather is warm, the ocean is cool and blue, and the beach is all yours. We are pleased to offer our beautiful 4-bedroom, second-story timeshare for week 16 of 2018 (April 21st to the 28th). Unit #16 at Little Gull Cottages has spectacular, unencumbered views of the Sarasota Bay and is only a five minute walk t.......read more
4 Bedrooms
- Sleeps 8
Condo in Longboat Key
Luxury Condo located on Beachfront Property
Longboat Key Condo
We just purchased this condo and it will be ready for Rental in December 2022 . The condo is situated in one of the most beautiful Beachfront Properties in Longboat Key. The lush landscape along with the ammenities that Beachplace has to offer makes you feel like you are staying in paradise........read more
2 Bedrooms
- Sleeps 6
Condo in Longboat Key
Longboat key paradise townhome with an attached double deep garage.
Longboat Key Vacation Rental 4.5 Star Review
This beautiful townhouse house built in the style of the west coast, has been furnished recently with skilful whimsical, bohemian style in the warm colors of pinks and blues. The house is spread over three levels on the first floor and will welcome you with beautiful and soft sofas (bed) positioned towards a veranda terrace directly overlooking th.......read more
2 Bedrooms
- Sleeps 7
Vacation Rental Home in Longboat Key
LBK Getaway
Longboat Key Condo
Welcome to Paradise at LBK Getaway! Great opportunity to stay at an exquisite 2-bedroom, 2-bathroom villa style home in the coveted north end of Longboat Key. Just feet away from the crystal blue gulf water and beautiful pristine sandy beaches. Spend the day catching a wide variety of fish on the fishing piers or building sand castles in the sand. .......read more
Studio
- Sleeps 5
Condo in Longboat Key
On the Beach - 1 week rental Long Boat Key ( Sarasota barrier Island )
Longboat Key Condo
June 29 thru July 6 this is week 26 ONLY Week 26 & 27- UNIT 402 are both available, discount if you book both weeks
3 PM Saturday
Enjoy partial views of the Gulf from a two-bedroom apartment with accommodation for up to six guests. This includes a king size bed in the master bedroom, two twin beds in the guest bedroom and a.......read more
2 Bedrooms
- Sleeps 6
Condo in Longboat Key
On the beach, Sun set and Sunrise view, Gulf front condo, Monthly rental
Longboat Key Condo 5.0 Star Review
The view is amazing! The condo overlooks the pristine white sand beach and has a beautiful Gulf view. This second floor gulf front condo has a heated pool and a tennis court. This remodeled condo is furnished to an exceptional contemporary standard, with travertine flooring throughout, new beds, furniture and appliances (bluetooth wireless Bose box.......read more
2 Bedrooms
- Sleeps 6
Condo in Longboat Key
Luxurious Beachfront Villa with Private Pool
Longboat Key Condo 4.9 Star Review
This three-bedroom, three-bathroom unit is 2,200 square feet and steps from the Gulf of Mexico. Guests will enjoy a secluded beach, heated community pool, private balconies, community hot tub and secure access. The unit is recently renovated and located across the street from a public park, a convenience store, two restaurants and a bicycle shop. .......read more
3 Bedrooms
- Sleeps 8
Condo in Longboat Key