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Large selection of Rentals, book your Longboat Key Sarasota Vacation Rental Home Here 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.

Rentals by Owner in Longboat Key Sarasota Florida.

We have partnered with a major provider for Vacation Rentals by Owner directly through Florida Vacation Rental Homes. With hundreds of Short Term Rentals to choose from, we now have the selection and value to offer our visitors searching for places to rent in Longboat Key Sarasota Florida.

Select from the following Rental Properties:

Sea Grape Inn #4- BEACHFRONT Property

Longboat Key Apartment Star 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 Star 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 Star 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 Star 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 Star 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 Star 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 Star 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



Awesome Winter Getaway-Four Winds Beach Resort condo on the Gulf of Mexico

Longboat Key Condo Star 4.7 Star Review

1 bedroom 1 bathroom full kitchen furnished condo at the beach. Offering 1, 2 or all 3 weeks beginning January 16 through February 6, 2021, check in and check out on each Saturday. All amenities included in room WIFI, cable TV, hot tub, heated pool, steps from the white sands of the Gulf of Mexico, tennis courts, shuffleboard, bicycles, grilling .......read more

1 Bedrooms - Sleeps 4
Condo in Longboat Key



Condo,private beach,kayak in bay

Longboat Key Condo

Enjoy your morning coffee while sitting on back patio watching the traffic of Sarasota Bay. Kayaks for use, private beach. Beautiful bike path that takes you to Bradenton or Sarasota. Sunsets are amazing. .......read more

1 Bedrooms - Sleeps 1
Condo in Longboat Key



2 bedroom 2 bath beach condo Rental

Longboat Key Condo

July 6 thru 13 Week 27- UNIT 402

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 queen size sleep sofa in the living room. Full Kitchen and washer and dryer in the uni.......read more

2 Bedrooms - Sleeps 6
Condo in Longboat Key



A couple’s retreat. Condo Nestled in quiet area. Walk to beach & shops.

Longboat Key Villa Star 5.0 Star Review

NEW LISTING!

Perfect place for a beach getaway! Newly remodeled charming 2 bed/ 1 bath condo located 5 min walk from beach, shops, restaurant, mini market, bike rental shop and more. Nestled in a quiet are, perfect to relax or work remotely. We offer Super Fast 600MBPS internet!

Centrally located in Longboat key, condo features a ful.......read more

2 Bedrooms
Villa in Longboat Key



NEW! Gulf Getaway w/ Porch + Direct Beach Access!

Longboat Key Condo Star 5.0 Star Review

Pack your sunscreen when you embrace a coastal retreat at this 1-bedroom, 1-bathroom vacation rental condo located in the Silver Sands Gulf Beach Resort. Boasting a fully equipped kitchen and nestled on the ground floor, this beach escape provides all of the essential comforts paired with convenience for a relaxing stay. Tee off at the green in the.......read more

1 Bedrooms - Sleeps 4
Condo in Longboat Key



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