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We have partnered with a major provider for Vacation Rentals by Owner, directly through Vacation Places To Stay. There are many home rentals to choose from, and we now have the selection and value to offer our visitors going to Longboat Key, FL. Browse hundreds of Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer.
Cabana Beach Club #2: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6
Longboat Key Condo
- 
4.9 Star Review
RVA features Cabana Beach Club. With the majority of units located on the beach side of the exclusive Longboat Key island, including several overlooking the turquoise waters of the Gulf of Mexico, and a handful of others intimately nestled on the bayside, this condominium complex encompasses all the elements of a tropical paradise. The quiet ambian.......read more
2 Bedroom(s)
Sleeps 6
Condo
Cabana Beach Club #7: 2BR+Den / 2 BA Resort on Longboat Key by RVA, Sleeps 6
Longboat Key Condo
- 4.9 Star Review
RVA features Cabana Beach Club. With the majority of units located on the beach side of the exclusive Longboat Key island, including several overlooking the turquoise waters of the Gulf of Mexico, and a handful of others intimately nestled on the bayside, this condominium complex encompasses all the elements of a tropical paradise. The quiet ambian.......read more
2 Bedroom(s)
Sleeps 6
Condo
Silver Sands, Oceanfront - Gulf Beach Resort
Longboat Key Condo
55 steps away from the Gulf of Mexico Beach! Beautiful beach with the most amazing sunsets. Family friendly resort with super friendly staff. Plenty of lounge chairs and sun umbrellas, just bring your bathing suit and sunscreen. Special amenities include Pool, shuffle board and miniature golf course........read more
2 Bedroom(s)
Sleeps 6
Condo
Silver Sands #252: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4
Longboat Key Condo
- 4.6 Star Review
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
Studio
Sleeps 4
Condo
Silver Sands #241A: HOTEL / 1 BA Resort on Longboat Key by RVA, Sleeps 2
Longboat Key Apartment
- 4.5 Star Review
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
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 Bedroom(s)
Sleeps 6
Condo
Silver Sands #234: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4
Longboat Key Condo
- 4.6 Star Review
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
Studio
Sleeps 4
Condo
Beautiful Longboat Key RESORT 2 bed/2 bath, Sleeps 6,Granite/Stainless Kitchen
Longboat Key Hotel resort
Longboat Bay Club provides vacation accommodations that include recreation and pampered relaxation. Take advantage of the peace and privacy of a smaller property with the amenities of a larger resort. You will have plenty of room for relaxing in our 1600+ sq. ft. condominiums, each with a washer/dryer inside for your convenience. Our units also boa.......read more
2 Bedroom(s)
Sleeps 6
Hotel resort
Cedars East #810: 2 BR / 2.5 BA Townhome on Longboat Key by RVA, Sleeps 4
Longboat Key Private vacation home
- 5.0 Star Review
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 townhomes that are perfect for families or couples. There is something to suit every mood at.......read more
2 Bedroom(s)
Sleeps 7
Private vacation home
Inn on the Beach 2207
Longboat Key Condo
- 4.7 Star Review
Offered by FL Vacation Connection, this perfect island getaway is located on the southern tip of Longboat Key with a beautiful beach and pool area.
Our guests have access to the beautiful private beach, pool and hot tub area only. Resort amenities (golf, dining, tennis, room & maid service or fitness) are private and not includ.......read more
2 Bedroom(s)
Sleeps 4
Condo
Updated Beach Style Condo at Sand Cay with Great Ocean Views.
Longboat Key Condo
- 4.8 Star Review
Current COVID-19 situation:
The County restrictions include numerous cleaning and other requirements for your safety. Our own internal requirements meet or exceed what is required by the County/CDC. Please also note that our condo has its own separate entrance, there are no enclosed corridors or hallways to get to the unit, it is accessible by o.......read more
2 Bedroom(s)
Sleeps 6
Condo
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 Bedroom(s)
Sleeps 4
Apartment
Casa Del Mar: 3 BR / 2.5 BA Home on Longboat Key by RVA, Sleeps 6
Longboat Key Private vacation home
- 4.5 Star Review
Enjoy island-style vacations at the Casa del Mar Home. Located on the north end of the exclusive island of Longboat Key, this vacation home specializes in serenity with a natural ambiance. The Casa del Mar Home is a raised building, which allows for beautiful views of foliage and the canal. Some of the amenities you’ll enjoy are: comfortable furnis.......read more
3 Bedroom(s)
Sleeps 6
Private vacation home
Silver Sands #239: 2 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 6
Longboat Key Condo
- 4.8 Star Review
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
2 Bedroom(s)
Sleeps 6
Condo
Cedars East #519: 2 BR / 2.5 BA Townhome on Longboat Key by RVA, Sleeps 6
Longboat Key Private vacation home
- 5.0 Star Review
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)
Sleeps 6
Private vacation home
ANYDAY CHECK IN! BEAUTIFUL BAYFRONT VIEWS ON LONGBOAT KEY! Harbor Villa Club First Floor 2/2!
Longboat Key Condo
• Carefree check-in, go straight to your unit no office visit required.
• Fully Equipped Kitchen including microwave, stove, dishwasher, fridge, and coffee maker.
• Comfortable living room area
• Washer and Dryer Conveniently located in unit.
• Master bedroom with a king size bed and beautiful view of the bay!
• Spacious guest bedroo.......read more
2 Bedroom(s)
Sleeps 4
Condo
Silver Sands #255S: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6
Longboat Key Condo
- 4.6 Star Review
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
2 Bedroom(s)
Sleeps 6
Condo
Hidden Bay/Beach Paradise
Longboat Key Private vacation home
- 4.9 Star Review
Come stay for a month and discover this Hidden Beach/Bay 4 Bedroom Gem and enjoy all the amenities in your home away from home. Feed your outdoor appetite and enjoy the beautiful weather in this magnificently manicured tropical oasis. These spacious grounds are situated on 1.8 acres of land that also features a private, full-size, fenced tennis cou.......read more
4 Bedroom(s)
Private vacation home
Your Vacation Oasis Awaits on Beautiful Longboat Key!
Longboat Key Private vacation home
- 4.8 Star Review
3 Bed, 3 Bath recently renovated Beach house with large sun deck and heated pool surrounded by beautiful landscaping that will make you feel like you are at your own private resort! Upper level features an open floor plan with updated kitchen, master bedroom with renovated master bath, as well as second bedroom and bath. Lower level features a un.......read more
3 Bedroom(s)
Sleeps 6
Private vacation home
Gulf Front, luxury condominium in beautiful Long Boat Key, FL
Longboat Key Condo
- 5.0 Star Review
Prime location and luxury !!!! Enjoy spectacular sunsets and incredible water views of the Gulf of Mexico in this upscale, direct waterfront, luxury condo. This 3rd floor unit has incredible unobstructed views of the gulf---- direct views from living area and both bedrooms. Our condo boasts a full length, gulf front screened lanai with sliding door.......read more
2 Bedroom(s)
Sleeps 4
Condo
1000 Ft of private Gulf of Mexico Beach
Longboat Key Condo
1000 Feet of private beach in this one of a kind north end Whitney Beach 1st floor condo. This is the only condo with a large outdoor living room and tropical gardens. Relax on the outdoor sofa and indulge in a glass of wine and a grilled filet while the fire pit and lighted palms give you ambiance. This renovated unit is walking distance to all.......read more
Studio
Sleeps 4
Condo
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
Studio
Sleeps 1
Condo
PARADISE FOUND* PEACEFUL & ELEGANT UPDATED *CANAL HOME *WALK TO BEACH* NEW BIKES
Longboat Key Private vacation home
- 5.0 Star Review
*****ONLY ONE RENTAL PER MONTH, SO BOOK FAST TO SECURE YOUR SPOT****PLEASE PROVIDE DETAILED DESCRIPTION OF TRAVELERS WHEN REQUESTING A BOOKING ****CONTACT US FOR CANCELLATION TERMS
The Pineapple Cottage is a special oasis of tranquility and comfort. Surrounded by the palm trees that symbolize Florida, it is a private home nestled on a cana.......read more
3 Bedroom(s)
Sleeps 6
Private vacation home
Cedars East #607: 2 BR / 2 BA Townhome on Longboat Key by RVA, Sleeps 8
Longboat Key Private vacation home
- 5.0 Star Review
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)
Sleeps 8
Private vacation home
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 Bedroom(s)
Sleeps 8
Condo
Cedars East #528: 2 BR / 2.5 BA Townhome on Longboat Key by RVA, Sleeps 6
Longboat Key Private vacation home
- 5.0 Star Review
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)
Sleeps 6
Private vacation home
Longboat Key Club!! Direct Beachfront!!
Longboat Key Condo
- 4.7 Star Review
Enjoy your morning coffee on your spacious, open-air, Gulf view Balcony overlooking your included beach and swimming pool facilities at the Exclusive Resort at Longboat Key Club. This booking does not include use of private club facilities such as golf and tennis or restaurants, etc.. Condo has a maximum occupancy of five people, to include maxim.......read more
Studio
Condo
client said view crazy Aug sale arrive 26- leave 31 had cancellation
Longboat Key Condo
- 4.9 Star Review
This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. There is a full kitchen, living area with a queen size sleeper sofa, and a bedroom with two queen size beds. It is part of the Zilli Collection. Each with the Zilli touch of amazing view, decor, (not typical wicker furniture, silly beach artifact.......read more
Studio
Sleeps 6
Condo
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 Bedroom(s)
Sleeps 6
Apartment
Only requests for 9/12/22-11/12/22 time frame will be considered at this time!
Longboat Key Private vacation home
- 4.9 Star Review
At this time, We are unable to accept requests for next winter (Jan-April 2023) as we give right of first refusal to our current tenants. Please check back with us in June for that time frame. Our private waterfront residence is surrounded by the topical beauty of the Gulf of Mexico and Millar/Sarasota Bay. This updated Longboat Key beach/boater\.......read more
2 Bedroom(s)
Sleeps 5
Private vacation home
Find Affordable Longboat Key Hotels & Vacation Rentals
Plan your Longboat Key Florida Vacation here and get the best value possible for the trip! Find affordable Resort Hotels with oceanfront condo rentals, pool and much more. We have a great selection of 2,3 or 4 bedroom villas, condos or cottages that offer you the best available places to stay in Longboat Key, Florida. Our Vacation Rentals, including Pet Friendly Rentals, let you get the most from your vacation in Tampa Bay Area.
Vacation Rentals Nearby Tampa Bay Destinations
Find nearby vacation rentals and some of the Best Hotels with cheap rates in Longboat Key, FL for you visit to the area, all a short drive to Longboat Key, Florida. Spend quality time with your family and friends with cheap hotel rates you can afford, visit the nearby beaches for nightlife, entertainment and a wide variety of beach activities. Hundreds of properties to choose from, search for availability, photos, descriptions and best price.
Rentals in Longboat Key, FL
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