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Longboat Key, Sarasota Vacation & Condo Rentals

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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. With hundreds of short term seasonal rentals in Longboat Key Sarasota to choose from, we now have the selection and value to offer our visitors going to Florida.

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 to carry. The buildings at Beach Castle are the color of sunshine and are accentuated by Bahama shutt.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

The Beach Fact Oar - Longboat Key Condo

The Beach Fact Oar: Breathtaking 2 BR / 2 BA second floor condo.

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 community features a large, heated swimming pool, fitness rooms, bicycle racks, and a clubhouse with a cater.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

Club Longboat - Longboat Key Condo

3rd floor corner condo facing Gulf of Mexico at Club Longboat on Longboat Key!

3 bedroom, 2 full bath 3rd Floor (Top Floor)-Southwest Corner 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 facing the Gulf of Mexico to watch beautiful sunsets Exercise room in clubhouse 8 HarTr.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

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 balcony. The apartment also has its own private terrace with a gulf view in addition to a balcony. .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Apartment Rentals

Vacation Home

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 chaise lounge and beach umbrella while breathing in the fresh salt-water air. Practice your golf game .......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

Endless Summer - Longboat Key House

Endless Summer: 3 BR / 3 BA House on Longboat Key by RVA, Sleeps 9

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 directly on a canal that leads to the Sarasota Bay. You'll enjoy the modern amenities of Endless Summer including updated kitchen, designer decorations and tiled floors throughout. There's even a computer available for guest use with w.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 9 House Rentals

Vacation Home

Beached Inn - Longboat Key House

Beached Inn: Prestigious 3 BR / 2.5 BA home with pool located in Bay Isles.

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 in lanai, and two car garage. Each bedroom is spacious and beautifully decorated. Bay Isles is a gat.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 6 House Rentals

Vacation Home

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 decorations in a elegant beach theme and picturesque location makes Unit 101 the ideal choice for a traveli.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

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 walking trails, two heated pools, lighted tennis courts, pickleball court, fitness center, locker rooms,.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

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 at Cedars Tennis Resort – a junior Olympic swimming pool, a fitness center, fishing pier, bicycle a.......read more

2 Bedroom(s)
3 Bath(s) - Sleeps 4 Townhome Rentals

Vacation Home

Sea Ya - Longboat Key Condo

Sea Ya: Furnished 2 BR / 2 BA ground floor condo located in Beach Harbor Club.

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 opens to a private outside patio.  If you enjoy an active lifestyle, then the Beach Harbor Club is.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

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 chaise lounge and beach umbrella while breathing in the fresh salt-water air. Practice your golf game .......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

Sand Cay 312 - Longboat Key Condo

Unit no. 312 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. Owner is constantly updating their unit. Quaint, quiet, and the quality of a boutique resort, not the hassle, noise, the impersonal nature of a hotel. You will become part of our Sand Cay family, and we will look forward to your re.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

LaPlaya 104E - 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 bedroom. Washer & dryer in the unit. Quiet, end-unit is just steps to the beach or pool from your palm-shad.......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 4 Apartment Rentals

Vacation Home

Broadway Retreat - Longboat Key House

Broadway Retreat: Luxurious 4 BR / 4.5 BA pool home with guest house.

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, custom PGT high impact doors and windows providing plenty of natural lighting and protection from th.......read more

4 Bedroom(s)
5 Bath(s) - Sleeps 8 House Rentals

Vacation Home

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. Cozy seating in the den with flat screen TV. More room to relax in the living room with bookshelve.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

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 and require a 7 night minimum stay. Completely renovated 3 bedroom, 2 bath. Come visit Longboat Key and enjoy our vacat.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

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 margaritas under one of the property palm huts scattered throughout the private beach. Unit #315 offe.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 5 Condo Rentals

Vacation Home

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 chaise lounge and beach umbrella while breathing in the fresh salt-water air. Practice your golf game .......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

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 at Cedars Tennis Resort – a junior Olympic swimming pool, a fitness center, fishing pier, bicycle a.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Townhome Rentals

Vacation Home

Silver Sands #245S - Longboat Key Condo

Silver Sands #245S: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6

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 chaise lounge and beach umbrella while breathing in the fresh salt-water air. Practice your golf game .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

Silver Sands #238 - Longboat Key Condo

Silver Sands #238: 3 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 8

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 chaise lounge and beach umbrella while breathing in the fresh salt-water air. Practice your golf game .......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 8 Condo Rentals

Vacation Home

LaPlaya 201C - Longboat Key Condo

LaPlaya 201C-Breathtaking Gulf panorama from this corner end unit.

Beachfront 3 Bedroom, 2 Bath townhouse condo in the center of beautiful Longboat Key, an island just a few miles north of Sarasota. LaPlaya Condominiums provides a private beach, sheltered pool with sundeck, and beachfront grills so you won’t miss a minute of the sunset. The unit has a fully equipped kitchen plus washer and dryer. All linens and beach towels are provided. Welcome to our island-style living. This spacious end unit is bright.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

Sand Cay 305 - Longboat Key Condo

Unit #305 Sand Cay Beach Resort Gulf View

Light and elegant, third floor with high ceiling and Bay windows, non-smoking unit. Open kitchen, newly renovated baths, new carpeting. Huge flat screen TV in den, sofa bed in living-room. New master-bedroom furniture with second flat-screen-TV. Balcony with great beach view.Quaint, quiet, and the quality of a boutique the hassle, noise, the impersonal nature of a hotel. You will become part of our Sand Cay family, and we will look forward to yo.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

Longboat arms - Longboat Key Condo

Wonderful End Condo With Full Awesome Bayview 1 Minute Walk To The Great Beach

This is a wonderful 2 bedroom+ 2 bathroom condo on Longboat key, on the third -End Level with awesome bay view. Watch Manatees, Dolphins and wildlife from almost any place in that condo. The perfect condo for your vacation or snowbirds. Rental minimum seasonal 2 months This condo is fully furnished and has cable TV & Internet. ................................................................................................read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

Sand Cay 218 - Longboat Key Condo

Unit #218 Sand Cay Beach Resort Gulf Front

Enjoy this breathtaking Gulf-front, sunny unit with spectacular beach and sunset views. Accommodation for up to 6 with 2 bedrooms, 2 bathrooms and queen sleeper sofa. The open floor plan of living room, dining room, kitchen and den offer full views of the sparkling turquoise water, blue sky and white sandy beach. The unit is newly re-decorated in natural, soothing tones of soft blues and tans that flow from the outside colors of the beach, water .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

LaPlaya 205D Spectacular Sunsets! - Longboat Key Apartment

LaPlaya 205D Spectacular Sunsets!

Beachfront 3 Bedroom, 2 Bath townhouse condo in the center of beautiful Longboat Key, an island just a few miles north of Sarasota. LaPlaya Condominiums provides a private beach, sheltered pool with sundeck, and beachfront grills so you won’t miss a minute of the sunset. The unit has a fully equipped kitchen plus washer and dryer. All linens and beach towels are provided. Welcome to our island-style living. This spacious unit is bright an.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Apartment Rentals

Vacation Home

Island Paradise - Longboat Key House

Island Paradise: 3 BR + Den / 2 BA House on Longboat Key by RVA, Sleeps 8

RVA features a relaxing, serene home beautifully furnished and ready for you to enjoy Longboat Key's sunshine. This home offers privacy un-matched with a tropical caged pool area offering a heated hot tub and pool. This large home seems to never end, around every corner there is comfortable spot to sit and read a book or watch your favorite show on one of the flat screen Trinitron televisions located throughout the home. With a short 10-15 minute.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 8 House Rentals

Vacation Home

Beach Castle Resort #26 - Longboat Key Condo

Beach Castle Resort #26: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4

Compliments of RVA, Beach Castle Resort expands from the bayside of Longboat Key to the Gulf – providing a place to launch your kayak and cast a line, a chance to spot exotic birds that stop here for our mild temperatures and to view a picture-perfect sunset over the Gulf of Mexico -- all courtesy of Mother Nature. The grounds here are impeccable – from the well-manicured vegetation to the vast palm trees that dot this serene Longboat Key .......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

Fanta Sea - Longboat Key Townhome

Fanta Sea: Modern beachfront townhouse on Longboat Key!

Welcome to Fanta Sea! Modern Beachfront townhome is available on Longboat Key. This 3 story home has been beautifully updated and comes turnkey furnished for your convenience. This 3 bedroom, 3 bath vacation home comfortably sleeps 6. The spacious master suite is on its own level (upper level) and features a comfy king-sized bed, 2 private balconies, skylights, barn doors, hardwood floors and plenty of storage space. The ensuite has a separate cl.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 4 Townhome Rentals

Vacation Home

Longboat Key 20 - Longboat Key Condo

2 Bedroom(s)
2 Bath(s) - Sleeps 100 Condo Rentals

Vacation Home

Silver Sands #255 - Longboat Key Condo

Silver Sands #255: 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 chaise lounge and beach umbrella while breathing in the fresh salt-water air. Practice your golf game .......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

Silver Sands #258 - Longboat Key Condo

Silver Sands #258: 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 chaise lounge and beach umbrella while breathing in the fresh salt-water air. Practice your golf game .......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

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