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Longboat Key, Sarasota Vacation & Condo Rentals

Book Your Longboat Key Sarasota Florida Vacation Rental Homes Here and Save! Many to choose from!

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 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

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.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Longboat Key Condo Rental

Details

The Beach Fact Oar

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

Breathtaking Direct Gulf views from this second-floor condo at Longboat Terrace. Perfect for a small family or travel with friends, this two-bedroom, two-bath has everything you need to make this your home away from home. Looking for a perfect rest after a long day at the beach or after a few hours swimming at the pool both the master and guest s.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Longboat Key Condo Rental

Details

Club Longboat

REMOTE WORK WITH GULF OF MEXICO VIEW! BOOKING SUMMER AND FALL 2022!

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) P.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Longboat Key Condo Rental

Details

Islander Club - On the beach

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 .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Longboat Key Apartment Rental

Details

Silver Sands #241

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.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Longboat Key Condo Rental

Details

Endless Summer

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, desi.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 9 Longboat Key House Rental

Details

Salty Acres #101

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.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Longboat Key Condo Rental

Details

Beach Breeze

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.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Longboat Key Condo Rental

Details

Cedars East #830

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.......read more

2 Bedroom(s)
3 Bath(s) - Sleeps 4 Longboat Key Townhome Rental

Details

Sea Ya

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.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Longboat Key Condo Rental

Details

Silver Sands #242

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.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Longboat Key Condo Rental

Details

Sand Cay 312

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. Owner is constantly updating their unit. Quaint, quiet, and the quality of a boutique resort, not the hassle, noise, the impersonal.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Longboat Key Condo Rental

Details

Broadway Retreat

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, .......read more

4 Bedroom(s)
5 Bath(s) - Sleeps 8 Longboat Key House Rental

Details

Sand Cay 317

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. .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Longboat Key Condo Rental

Details

Beachcomber unit 603

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 s.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Longboat Key Condo Rental

Details

Whitney Beach #315

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.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 5 Longboat Key Condo Rental

Details

Silver Sands #240

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.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Longboat Key Condo Rental

Details

Silver Sands #238

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 ch.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 8 Longboat Key Condo Rental

Details

Sand Cay 305

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 imper.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Longboat Key Condo Rental

Details

Longboat arms

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 Longboat Key Condo Rental

Details

Sand Cay 218

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 n.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Longboat Key Condo Rental

Details

Island Paradise

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.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 8 Longboat Key House Rental

Details

Beach Castle Resort #26

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 impecca.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Longboat Key Condo Rental

Details

Longboat Key 20

A Rare, 2 Bedroom 2 Bath, Short-term, Rental Opportunity at Bayport Beach! - Longboat Key 20

Nestled in Longboat Key, this condo brings it all within your reach. Fans of nature and the outdoors will love being 10 minutes by car from Lido Beach and 37 minutes from Siesta Key Beach. You'll easily make the 10-minute drive to St. Armands Circle or the 9-minute drive to Coquina Beach. .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 100 Longboat Key Condo Rental

Details

Silver Sands #255

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 ch.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Longboat Key Condo Rental

Details

Silver Sands #258

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 ch.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Longboat Key Condo Rental

Details

The Shore #211

The Shore #211: 2 BR / 2 BA Condo on Longboat Key with RVA, Sleeps 4

RVA asks that you imagine the wonderful sunsets you can capture right from your own balcony at The Shore. Located directly on the shore of the Gulf of Mexico, you never have to travel far to enjoy the beach. Amenities include a heated pool, full service clubhouse and natural Florida landscape. This unit two-bedroom, two-bath unit offers beautiful v.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Longboat Key Condo Rental

Details

Beachcomber unit 305

Beachcomber unit 305

Our building is located on the beach, this unit has an ISLAND view. Pack your bags, invite your family and friends and come stay in paradise. Unit 305 in The Beachcomber Condominium offers up to 4 guests a stunning apartment on serene white sand beaches, with a heated Gulf-side pool and BBQ picnic areas. Plenty of conveniences like a laundry .......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 4 Longboat Key Condo Rental

Details

The Beach on Longboat Key #101

The Beach on Longboat Key #101: 1 BR + Den/2 BA Resort on Longboat Key by RVA

RVA features The Beach on Longboat Key. Savor warm Gulf breezes while resting lavishly in this Gulf-front condominium complex. New designs were created using South Beach flair, resulting in comfortably modern furnishings and decorations. Located directly on the beach, this resort features beautiful Gulf-front views, which means you are only steps f.......read more

1 Bedroom(s)
2 Bath(s) - Sleeps 6 Longboat Key Condo Rental

Details

Beachcomber unit 604

Beachcomber unit 604

Newly Renovated 2015: 2 bedroom; 2 bath sixth floor condo overlooking the Gulf of Mexico 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 requir.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Longboat Key Condo Rental

Details

Cedars East #850

Cedars East #850: 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.......read more

2 Bedroom(s)
3 Bath(s) - Sleeps 4 Longboat Key Townhome Rental

Details

Silver Sands #254

Silver Sands #254: 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.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Longboat Key Condo Rental

Details

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