Skip to content

Longboat Key, Sarasota Vacation Rentals

Book Your Longboat Key Sarasota Vacation Rentals Directly Online Here and Save!

Browse Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer in Longboat Key Sarasota, Florida.

We have partnered with a major provider for Vacation Rentals by Owner, directly through Florida Vacation Rental Homes. There are many home rentals to choose from, and we now have the selection and value to offer our visitors going to Florida.


Longboat Key Condo

Beach Castle Resort #2 - Longboat Key Condo

Beach Castle #2: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6. Between the azure blue of the Southwest Florida skies, and the turquoise Gulf of Mexico waters sits Beach Castle Resort on Longboat Key. A true beach-to-bay community, Beach Castle rests on one of the narrowest points of this prestigious island, allowing the community to extend from the Gulf side to the bay side – a quality few of the privilege t....

2 Bedrooms 2 Baths - Sleeps 6
Longboat Key, FL

View Rental

Longboat Key Condo

Club Longboat Key Condo #415 - Longboat Key Condo

Spacious Club Longboat Key steps to the sand, private beach paradise! Pools, Gym, Tennis, Sunsets!. Looking for beachfront paradise ? It doesn't get better than Club Longboat . This spacious condo comfortably sleeps 6 within 2 separate bedrooms and a queen pullout sofa. This newly remodeled condo is beautifully updated with coastal feel , including a new kitchen with white cabinetry, Quartz Countertops and breakfast bar leading to the spacious ....

3 Bedrooms 2 Baths - Sleeps 6
Longboat Key, FL

View Rental

Longboat Key Condo

Longboat Key 25 - Longboat Key Condo

2BR/2BA condo with breathtaking gulf views at Longboat Terrace. Longboat Key 25. Breathtaking Direct Gulf views from this second floor condo at Longboat Terrace. This two bedroom, two bath has everything you need to make this your home away from home. Both the master and guest suites have their own private baths and balconies. Enjoy the morning paper at the breakfast nook or entertain in the great room. This beachfront communit....

2 Bedrooms 2 Baths - Sleeps 6
Longboat Key, FL

View Rental

Longboat Key Condo

Club Longboat - Longboat Key Condo

3rd floor end unit Oceanfront Condo on Longboat Key..Sunset Views!. 3 bedroom, 2 full bath 3rd Floor (Top Floor) 1500+ sq./ft of living space Bedrooms (Sleeps 6): Bedroom #1 King Size bed, en suite bathroom Bedroom #2 2 Twins Bedroom #3 Full size pullout couch, office & laundry Over-sized couch in living room Covered Parking Space Elevator Full size washing machine and dryer in unit (Bedroom 3) Patio Balcony facin....

3 Bedrooms 2 Baths - Sleeps 6
Longboat Key, FL

View Rental

Longboat Key Condo

Turtle Crawl Inn Condo 401 - Longboat Key Condo

Amazing Panoramic Gulf View and The Most Beautiful Sunset.. GULF FRONT - ON THE SAND SPECTACULAR GULF VIEWS AND SUNSET VISTAS! The Turtle Crawl Inn encompass all that is hallmark to a Gulf front vacation. Many others on the island claim to be Gulf front, but actually include a view only from a certain vantage point. Recently upgraded with all new furniture, 55'' smart 4-K TV, 24" smart TV in the bedro....

1 Bedrooms 1 Baths - Sleeps 6
Longboat Key, FL

View Rental

Longboat Key Apartment

Islander Club - On the beach - Longboat Key Apartment

Islander Club - Waterfront- Amazing vacation 2bdr/2bathroom apartment. Wonderful 2 bedroom 2 bath apartment directly on the beach. This 3rd floor Islander Club condo is in perfect condition and has everything needed for an extended or winter stay. Master bedroom suite with king size bed has access to both balcony and oversized porch. Guest room has two full size beds and spacious closet. All rooms have access to big ....

2 Bedrooms 2 Baths - Sleeps 6
Longboat Key, FL

View Rental

Longboat Key Condo

Silver Sands #241 - Longboat Key Condo

Silver Sands #241: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4. RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary ch....

1 Bedrooms 1 Baths - Sleeps 4
Longboat Key, FL

View Rental

Longboat Key House

Endless Summer - Longboat Key House

Endless Summer: 3 BR / 3 BA House on Longboat Key by RVA, Sleeps 9. **For a limited time, 10% OFF any weekly or monthly stay thru 4/30/2020. Click on the specials link to the right for details.** RVA presents Endless Summer on the exclusive island known for its tasteful luxury and secluded vacations. This three-bedroom, three-bathroom vacation home sits in the popular community of Country Club Shores and is directl....

3 Bedrooms 3 Baths - Sleeps 9
Longboat Key, FL

View Rental

Longboat Key House

Longboat Key 51 - Longboat Key House

Spacious villa with private pool in Bay Isles of Longboat Key! Longboat Key 51. Nestled behind the gates of the prestigious Bay Isles of Longboat Key, this spacious 3 bedroom, 2.5 bath villa is a perfect seasonal getaway. Gorgeous views of the Habourside Course of the Longboat Key Club from the private swimming pool. This home offers many unique details such as vaulted ceilings, sky lights, plenty of storage, a large screened ....

3 Bedrooms 3 Baths - Sleeps 6
Longboat Key, FL

View Rental

Longboat Key Condo

Salty Acres #101 - Longboat Key Condo

Salty Acres #101: 2 BR/ 2 BA Condo on Longboat Key by RVA, Sleeps 4. RVA features Salty Acres, a lovely complex that is located directly on the azure waters of the Gulf of Mexico. A short boardwalk takes you past the pool and onto the sugary white sand of Longboat Key. This coastal decorated two-bedroom, two-bath condominium is very spacious with a private patio to sit and enjoy the beautiful sunsets. Modern decorat....

2 Bedrooms 2 Baths - Sleeps 4
Longboat Key, FL

View Rental

Longboat Key Condo

Beach Breeze - Longboat Key Condo

Beach Breeze: Stunning waterfront 2 BR / 2 BA condo.. Welcome to Beach Breeze! This immaculate 2-bedroom, 2-bath second-floor condo located in the highly sought-out community of Windward Bay has views of the Gulf in every direction! The community of Windward Bay is pristine. There is private deeded beach access just across the street, two public beach access, two marinas BBQ grills, 1/2 mile of walk....

2 Bedrooms 2 Baths - Sleeps 4
Longboat Key, FL

View Rental

Longboat Key Townhome

Cedars East #830 - Longboat Key Townhome

Cedars East #830: 2 BR / 2.5 BA Townhome on Longboat Key by RVA, Sleeps 4. RVA features Cedars Tennis Resort, a luxury vacation rental on Longboat Key where world-class facilities, magnificent beaches and tropical sunsets that are picture-perfect are daily occurrences. Guests enjoy an unforgettable Florida vacation in our spacious town homes that are perfect for families or couples. There is something to suit every mood a....

2 Bedrooms 3 Baths - Sleeps 4
Longboat Key, FL

View Rental

Longboat Key Condo

Longboat Key 54 - Longboat Key Condo

2BR/2BA condo located in Beach Harbor Club on Longboat Key. Longboat Key 54. Furnished, 2 bedrooms, 2 bath condo located in Beach Harbor Club on Longboat Key.  This ground floor unit is centrally located and minutes away from urban activities with in-unit washer and dryer.  The master bedroom features a queen bed, walk-in closet and ensuite bathroom; second bedroom features twin beds.  The spacious living and dining area....

2 Bedrooms 2 Baths - Sleeps 4
Longboat Key, FL

View Rental

Longboat Key Condo

Silver Sands #242 - Longboat Key Condo

Silver Sands #242: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4. RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary ch....

1 Bedrooms 1 Baths - Sleeps 4
Longboat Key, FL

View Rental

Longboat Key Condo

Sand Cay 312 - Longboat Key Condo

Unit #312 Sand Cay Beach Resort Pool and Garden View. Third floor,, with balcony and View of Gulf, unit. Must see! Open living room with vaulted ceilings. Light and brightly decorated with tropical beach theme. Beautiful, completely renovated kitchen and baths in 2009. Quaint, quiet, and the quality of a boutique resort, not the hassle, noise, the impersonal nature of a hotel. You will become part ....

2 Bedrooms 2 Baths - Sleeps 6
Longboat Key, FL

View Rental

Longboat Key Apartment

LaPlaya 104E-Prefectly located - Longboat Key Apartment

LaPlaya 104E-Prefectly located near the path to the beach, just steps from the pool.. 2 Bedroom & 1 bathroom, ground-floor condo just steps to the beach or sheltered pool. Fully furnished with everything you need for a relaxing island getaway on beautiful Longboat Key. Open floor plan, updated kitchen and bath with relaxing beach-style decor. Sleeps 4 with comfortable King-size bed in master bedroom and twins in the guest bedroo....

2 Bedrooms 1 Baths - Sleeps 4
Longboat Key, FL

View Rental

Longboat Key House

Longboat Key 29 - Longboat Key House

Luxury Rental home with private pool in Longboat Key. Longboat Key 29. Luxury Rental Home on Longboat Key. Newly built 4 bedroom, 4.5 bath single family home with a private attached guest suite. This home has many luxury details including a gourmet kitchen which is equipped with a wet bar and all WOLF appliances, SUBZERO refrigerator and wine cooler, Spanish porcelain tile floors, quartz counter tops, 10' ceilings, ....

4 Bedrooms 5 Baths - Sleeps 8
Longboat Key, FL

View Rental

Longboat Key Condo

Sand Cay 317 - Longboat Key Condo

Unit #317 Sand Cay Beach Resort Gulf Front 7 night minimum. No walls interrupt panoramic gulf views in this beautifully renovated condo. With soaring ceilings and tiled floors, the open plan offers views of sparkling blue gulf waters and sandy white beaches from the living room, dining room, den, kitchen, and master bedroom and bath! The well appointed kitchen features a center island with breakfast bar. ....

2 Bedrooms 2 Baths - Sleeps 6
Longboat Key, FL

View Rental

Longboat Key Condo

Beachcomber unit 603 - Longboat Key Condo

Beachcomber unit 603. Our building is located on the beach, this unit has an ISLAND view. Beach front units are available to reserve online up to ten (10) months in advance, however you may call or contact us directly for a reservation up to twelve (12) months in advance. Please note: We do not allow Sunday or holiday arrivals. Completely renovated 3 b....

3 Bedrooms 2 Baths - Sleeps 6
Longboat Key, FL

View Rental

Longboat Key Townhome

CEDARS EAST 840 - Longboat Key Townhome

Pet Friendly Townhome in Popular Cedars Resort. $1,000/WEEK SUMMER / FALL RENTAL RATE (plus tax and fees) - BAYSIDE TOWNHOUSE in Cedars East Tennis Resort. Spacious 2-bedroom, 2-1/2 bath turnkey furnished townhouse with gorgeous Bay views. Ground level parking garage with storage, 2nd level is living/dining and kitchen with all new stainless appliances and 1/2 bath with exterior screened balc....

2 Bedrooms 3 Baths - Sleeps 6
Longboat Key, FL

View Rental

Longboat Key Condo

Whitney Beach #315 - Longboat Key Condo

Whitney Beach #315: 2 BR / 2 BA Condo on Longboat Key by RVA, Sleeps 5. RVA invites you to experience the intimacy and warmth of northern Longboat Key at Whitney Beach. Located on a superb pristine beach with next door shopping at Whitney Beach Plaza, this property offers this two-bedroom, two-bathroom ground floor condo. Imagine spending your days lounging by the community pool, enjoying a game of tennis, or sipping m....

2 Bedrooms 2 Baths - Sleeps 5
Longboat Key, FL

View Rental

Longboat Key Condo

Silver Sands #240 - Longboat Key Condo

Silver Sands #240: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4. RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary ch....

1 Bedrooms 1 Baths - Sleeps 4
Longboat Key, FL

View Rental

Longboat Key Townhome

Cedars East #660 - Longboat Key Townhome

Cedars East #660: 2 BR / 2 BA Townhome on Longboat Key by RVA, Sleeps 6. RVA features Cedars Tennis Resort, a luxury vacation rental on Longboat Key where world-class facilities, magnificent beaches and tropical sunsets that are picture-perfect are daily occurrences. Guests enjoy an unforgettable Florida vacation in our spacious town homes that are perfect for families or couples. There is something to suit every mood a....

2 Bedrooms 2 Baths - Sleeps 6
Longboat Key, FL

View Rental

Longboat Key Condo

Covet II Condominium - Longboat Key Condo

ON the Beach, Covert II Condominium. On the Beach - Full view of the Gulf of Mexico. Fully furnished and equipped. Includes Long Distance phone service within the US, 2 TV's with cable service, Wi-Fi high speed internet, Screened Gulf front Lanai with table and chairs for a great dining view. second floor unit near the elevator. Coin operated washer / dryer available on each floor....

1 Bedrooms 1 Baths - Sleeps 4
Longboat Key, FL

View Rental

Scroll To Top