Longboat Key, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Longboat Key, Florida on RentalSaver.com!

Longboat Key Rentals

From $494 per night (USD)
VRBO
Unit #102 Sand Cay Beach Resort Gulf Front
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
First floor Gulf Front. Extended bedrooms. Recently redecorated. Private and very near Gulf. The kitchen is elegant ...
From $494 per night (USD)
VRBO
From $390 per night (USD)
Expedia
Unit #312 Sand Cay Beach Resort Pool and Garden View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Third floor,, with balcony and View of Gulf, unit. Must see! Open living room with vaulted ceilings. Light and brightl ...
From $390 per night (USD)
Expedia
From $436 per night (USD)
VRBO
Unit #305 Sand Cay Beach Resort Gulf View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Light and elegant, third floor with high ceiling and Bay windows, non-smoking unit. Open kitchen, newly renovated baths, ...
From $436 per night (USD)
VRBO
From $483 per night (USD)
Expedia
Unit #317 Sand Cay Beach Resort Gulf Front 7 night minimum
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
No walls interrupt panoramic gulf views in this beautifully renovated condo. With soaring ceilings and tiled floors, th ...
From $483 per night (USD)
Expedia
From $594 per night (USD)
VRBO
Direct Beachfront Gulf with Amazing Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
LongBoat Key wins Conde Nast Traveler Award _______________________________________ **Our unit has its own Full sized ...
From $594 per night (USD)
VRBO
From $344 per night (USD)
Expedia
Flash sale late, August/September 50 ft from sand, Private Island 125 +review
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. There is a full ki ...
From $344 per night (USD)
Expedia
From $681 per night (USD)
VRBO
Major Upgrades 1 of a kind home right on the beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to the Zilli family Villa beach house on Longboat Key. After using this 2,000 sf home for their own family vacat ...
From $681 per night (USD)
VRBO
From $440 per night (USD)
Expedia
Renovated Beachplace 3 BR Beachfront by FVC
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beachplace Condo: A 3-Bedroom Modern Oasis on Longboat Key by FVC Step into the epitome of modern beachfront living wit ...
From $440 per night (USD)
Expedia
From $633 per night (USD)
VRBO
Bermuda-esque Island Hideaway! Steps to Sand!
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Remodeled main house plus cottage features 3 bed/2 bath + spacious 1/1. Firepit in private fenced yard filled with heavy ...
From $633 per night (USD)
VRBO
From $345 per night (USD)
Expedia
Fisherman's 3 Bedroom Island Village Hideaway! Steps to the Sand
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nestled amidst lush tropical foliage and a profusion of fruit-bearing trees, this charming 3-bedroom, 2-bathroom home gr ...
From $345 per night (USD)
Expedia
From $169 per night (USD)
VRBO
Bermuda-esque Island Guest House! Steps to the Sand!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover this charming cottage tucked away on a serene corner lot, nestled in the heart of Long Beach—a historic fishing ...
From $169 per night (USD)
VRBO
From $230 per night (USD)
VRBO
Longboat Key Cedars Beach House-Pet Friendly-2 Minute Walk To The Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
We understand that plans can change, and we want you to book your stay with peace of mind. That’s why we offer the most ...
From $230 per night (USD)
VRBO
From $313 per night (USD)
VRBO
Longboat Key Beachfront - Beautifully Updated with Prime Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Come enjoy this beautiful beachfront condo! Completely renovated and updated,, this condo is located at the desirable ...
From $313 per night (USD)
VRBO
From $263 per night (USD)
Expedia
Stunning Canal Condo - Walk to Beach - Sleeps 4
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
***HOME WITH CANAL VIEW/WALK TO THE BEACH*** Pleasant and quiet residential street in beautiful Longboat Key. This 2 be ...
From $263 per night (USD)
Expedia
From $495 per night (USD)
VRBO
Flash sale Sept 2-4/ 7-13, 5-floor penthouse 60 feet from water, 150+ reviews
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. It is part of the ...
From $495 per night (USD)
VRBO
From $216 per night (USD)
Expedia
Tree-lined home w/ amazing decor & screened porch - near beach/dining
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Treetops Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired d ...
From $216 per night (USD)
Expedia
From $560 per night (USD)
VRBO
Beachfront Villa on Serene Gulf of Mexico
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
LongBoat Key wins Conde Nast Traveler Award _______________________________________ **Unit has its own Full sized was ...
From $560 per night (USD)
VRBO
From $831 per night (USD)
Expedia
2 Villas, Pickleball, Htd Pool,Game Room,6BR/24ppl
Bedrooms:
4
Bathrooms:
6
Sleeps:
24
Summary: Whether you’re here for a week-long adventure, a weekend getaway or extended visit to paradise, the moment you ...
From $831 per night (USD)
Expedia
From $209 per night (USD)
VRBO
Relax in a Spacious Townhouse on Beautiful Longboat Key!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy paradise in a spacious 2 bedroom & 2-1/2 bathroom townhome. The property backs up to conservation land which can ...
From $209 per night (USD)
VRBO
From $318 per night (USD)
Expedia
Peaceful Cedars East Condo–Coastal Comfort & Tennis Fun Unit #803 by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to Paradise at Cedars East Tennis Resort by RVA Resort Vacations. Discover the ultimate Longboat Key getaway at ...
From $318 per night (USD)
Expedia
From $395 per night (USD)
VRBO
1-Bedroom Beach Getaway–Steps to Gulf at Silver Sands #254 Resort by RVA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the ame ...
From $395 per night (USD)
VRBO
From $452 per night (USD)
Expedia
Breathtaking Direct Gulf Views! Silver Sands Unit 259 - Longboat Key, by RVA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the ame ...
From $452 per night (USD)
Expedia
From $590 per night (USD)
VRBO
Crooked Coconut: Resort Pool & Spa, Dock, Kayaks
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Crooked Coconut by Anna Maria Life Vacation Rentals 12204 45th Avenue Dr. W, Bradenton, FL 34210 What You'll Love About ...
From $590 per night (USD)
VRBO
From $247 per night (USD)
VRBO
Updated Modern condo just 50 steps from the beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
SEAPLACE CONDOMINIUM - Bright and sunny condo 50 steps to beach. G-1 is building closest to beach. Seaplace is a resort ...
From $247 per night (USD)
VRBO
From $845 per night (USD)
VRBO
Newly remodeled beach house by Lido Beach and private pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Enjoy early morning beachcombing and breathtaking sunsets on Lido Beach. Unwind and breathe deep strolling along the one ...
From $845 per night (USD)
VRBO
From $229 per night (USD)
VRBO
Cozy condo in Cedars East
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Cozy Condo in Cedars East is a place for you to unwind and revive yourself. Only a 5 minute walk to the beach. Close to ...
From $229 per night (USD)
VRBO
From $346 per night (USD)
VRBO
1st Floor Beachfront Luxury–Ocean Views Included Club Longboat #516 by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
RVA invites you to experience the intimacy and warmth of northern Longboat Key at Club Longboat Beach and Tennis Resort. ...
From $346 per night (USD)
VRBO
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Expedia
Family Retreat to Personal Getaway Resort
Bedrooms:
1
Bathrooms:
0
Sleeps:
0
Beautiful 3rd floor view overlooking the Gulf of Mexico. The room has a queen sized murphy bed, balcony overlooking the ...
Click For Pricing
Expedia
From $263 per night (USD)
VRBO
Beachfront Condo with a Beautiful, Renovated Kitchen, Shared Pool, & Tennis
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Whitney Beach View 332 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $263 per night (USD)
VRBO
From $548 per night (USD)
VRBO
Beautiful Beach Island Home
Bedrooms:
3
Bathrooms:
3
Sleeps:
5
This stunning property is a large two-story home on Longboat Key with private deeded beach access, pool, hot tub, dock, ...
From $548 per night (USD)
VRBO
From $397 per night (USD)
VRBO
Beachcomber unit 504
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Beachcomber is a jewel on the luxurious island of Longboat Key, located directly on the white sandy beach of the Gul ...
From $397 per night (USD)
VRBO
From $349 per night (USD)
Expedia
Dolphin’s Den: Seaside Escape w Rooftop Gulf Views & Private Beach by RVA
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Experience this peaceful beach vibe at the Dolphin's Den in Longboat Key located in a clean, quiet private cul-de-sac. J ...
From $349 per night (USD)
Expedia
From $428 per night (USD)
VRBO
Unit #309 great rates, 2 Bed 2 Bath, view of ocean, steps to the sandy beach.
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Located directly on the white sandy beach of the Gulf of Mexico. Sand Cay Beach Resort is a jewel on the luxurious isla ...
From $428 per night (USD)
VRBO
From $299 per night (USD)
VRBO
Beautiful private beach and backyard pool at our restored Old Florida house!
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Beach cottage on a double lot with fenced yard on Long Boat Key Barrier Island. This 3 bedroom two full bath 50s ranch w ...
From $299 per night (USD)
VRBO
From $470 per night (USD)
VRBO
BOOK NOW - BEAUTIFUL HOME, BEACH ACCESS!!
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
ISLAND PARADISE!!! Enjoy this spectacular home in a beautiful, very quiet, Longboat Key neighbourhood. Take a leisurely ...
From $470 per night (USD)
VRBO
From $402 per night (USD)
VRBO
Gorgeous Gulf views and a beachfront location!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
From the moment you walk in the door of this 2 1/2 bedroom, 2 bath beach front condo you will know you made the right ch ...
From $402 per night (USD)
VRBO
Click For Pricing
VRBO
4th of JULY - FREE BOAT SLIP! Last minute availability!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
4th of JULY - FREE BOAT SLIP! Last minute availability! Manatee sightings from this beautiful 2 bedroom/2bath condo (sl ...
Click For Pricing
VRBO
From $446 per night (USD)
VRBO
Renovated and bright corner beachfront unit in well appointed popular complex!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Step out to the newly tiled lanai to watch dolphin jump and enjoy amazing sunsets each night in this newly renovated, mo ...
From $446 per night (USD)
VRBO
From $194 per night (USD)
VRBO
Perfect cottage! Million dollar views
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Adorable beach cottage with million dollar views of Sarasota Bay out front and a canal out back. Gorgeous seating in bot ...
From $194 per night (USD)
VRBO
From $186 per night (USD)
Expedia
Beachplace 10-402 by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Proudly offered by FL Vacation Connection, this property is ideal for professionals working remotely! Beautifully furn ...
From $186 per night (USD)
Expedia
From $162 per night (USD)
VRBO
Beachplace building 4 unit 503 by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Offered by FL Vacation Connection, this fifth floor condo has views of the reflecting pond and fountain as well as a par ...
From $162 per night (USD)
VRBO
From $182 per night (USD)
Expedia
Updated 2 Bedroom Condo With Lanai Exit On Longboat Key By FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Professionally managed by FL Vacation Connection, this spacious unit is furnished with comfortable seating in the living ...
From $182 per night (USD)
Expedia
From $298 per night (USD)
VRBO
Secluded Bayside Gem with Spectacular Views!!!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Reservations for this property have to be in full week intervals Sat-Sat check in /out. During peak season Jan-April we ...
From $298 per night (USD)
VRBO
From $309 per night (USD)
Expedia
Luxury Condo -Breathtaking Front View Beach-PROMO -199 August -Septembe 2025
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Luxury Beachfront Condo with Breathtaking Views and Calm Serenity July 2025-199 per night PROMO-2025!!!! We have been ...
From $309 per night (USD)
Expedia
From $710 per night (USD)
VRBO
Longboat Key home on the canal and a 5 minute walk to the beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Updated single 4 BR 3 bath home in the popular Country Club Shores community of Longboat Key. Open concept main living ...
From $710 per night (USD)
VRBO
From $282 per night (USD)
Expedia
Beachcomber unit 507
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our building is located on the beach and this unit has a partial beach view. Beach front units are availabl ...
From $282 per night (USD)
Expedia
From $761 per night (USD)
VRBO
Waterfront Coastal 3 BR/3 BTH w/ Pool, 50ft. Boat Dock, Walk to Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Stunning, newly renovated 3BR/3BTH home on preferred southern end of Longboat Key. Luxury interior design features cozy, ...
From $761 per night (USD)
VRBO
From $505 per night (USD)
Expedia
ST. ARMANDS CIRCLE, 3 Bedroom 3 Bath, Heated Pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Beautiful completely renovated 3 bedroom 3 bath home. Ideally located steps (3-5 minute walk) from St Armand's Circle sh ...
From $505 per night (USD)
Expedia
From $494 per night (USD)
VRBO
Unit #218 Sand Cay Beach Resort Gulf Front
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy this breathtaking Gulf-front, sunny unit with spectacular beach and sunset views. Accommodation for up to 6 with 2 ...
From $494 per night (USD)
VRBO
From $479 per night (USD)
Expedia
Sea Grape Inn #3 - Beachfront Property
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
BEACH VIEW Condo- 1st Floor of Beach Front Property, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper. ...
From $479 per night (USD)
Expedia
From $138 per night (USD)
VRBO
COZY ISLAND RETREAT AS LOW AS 59.00 PER NIGHT
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
HOUSE HOLDS 8 GUESTS KITCHEN HAS UPDATED APPLIANCES FULLY EQUIPPED WITH UTENSILS DINING ROOM 4 BEDROOMS 3 BATHROOMS 2 WA ...
From $138 per night (USD)
VRBO
From $831 per night (USD)
VRBO
Available THANKSGIVING & CHRISTMAS! Luxurious beachfront house on exclusive LBK!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This exclusive beachfront house is located on the water's edge, directly on the Gulf of Mexico on sought after Longboat ...
From $831 per night (USD)
VRBO
From $447 per night (USD)
VRBO
Bay to Beach: Amazing Views of Gulf & Bay by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bay to Beach by Anna Maria Life Vacation Rentals 1407 Gulf, 101, Bradenton Beach, FL 34217 What You'll Love About This ...
From $447 per night (USD)
VRBO
From $420 per night (USD)
VRBO
Stunning Gulf views - Gorgeous, Spacious, Just 5 steps to the sand!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Just you and the Gulf! Enjoy breathtaking sunsets from this, 1,488 sq. ft., beautiful 2 bedroom, 2 bath direct Gulf walk ...
From $420 per night (USD)
VRBO
From $270 per night (USD)
VRBO
Longboat Key bliss. A perfect Retreat at Cabana Beach Club #9.Also available#8
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Discover Your Dream Escape at Cabana Beach Club Unit 9 on Longboat Key! Welcome to your newly remodeled Gulf-side retre ...
From $270 per night (USD)
VRBO
From $289 per night (USD)
VRBO
Historic Longbeach Village Cottage - Private Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
All repairs since hurricanes are now complete. 'Sunny Side Up' is a restored beach cottage built in the 1950's locat ...
From $289 per night (USD)
VRBO
From $309 per night (USD)
VRBO
Wonderful Canal Front Condo! See Manatees Right From Your Doorstep!Cabana #10
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Very private , renovated condo directly on the bay! See manatees right from your doorstep! This very well maintained, ...
From $309 per night (USD)
VRBO
From $411 per night (USD)
VRBO
2 Cottage Combo - Steps to the Sand & 478 Feet From Public Boat Ramp!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Two Charming Cottages for Two Couples – Perfect for a Longboat Key Getaway! Escape to Longboat Key with your favorite t ...
From $411 per night (USD)
VRBO
From $275 per night (USD)
VRBO
Spectacular water views plus everything you need!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to the beach-to-bay gated community of Longboat Harbour on world famous Longboat Key. Take the elevator to this ...
From $275 per night (USD)
VRBO
From $311 per night (USD)
Expedia
Island Living on Longboat Key 3 minute walk to the beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Longboat Key Island Fun in a newly updated beautiful property! Newly updated 3 story townhouse on beautiful Longboat Key ...
From $311 per night (USD)
Expedia
From $574 per night (USD)
VRBO
Beachplace Penthouse Gulf Front Paradise
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
PENTHOUSE, DOUBLE BALCONIES, breathtaking wide sweeping straight on views of the Gulf and Bay make our Beachplace condo ...
From $574 per night (USD)
VRBO
From $737 per night (USD)
Expedia
LaPlaya 205D January 2025 Discount!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beachfront 3 Bedroom, 2 Bath townhouse condo in the center of beautiful Longboat Key, an island just a few miles north o ...
From $737 per night (USD)
Expedia
From $533 per night (USD)
VRBO
LaPlaya 108B-Dream views of the Gulf.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachfront 2 Bedroom, 2 Bath townhouse condo in the center of beautiful Longboat Key, an island just a few miles north o ...
From $533 per night (USD)
VRBO
From $361 per night (USD)
Expedia
LaPlaya 202E-Catch the gentle Gulf breezes on your private balcony beneath the swaying palms.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
2 Bedroom & 1 bathroom, 2nd floor condo just steps to the beach or sheltered pool. Fully furnished with everything you n ...
From $361 per night (USD)
Expedia
From $352 per night (USD)
VRBO
LaPlaya 201E-Nestled in the palms. just steps from the pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
2 Bedroom & 1 bathroom, 2nd floor condo just steps to the beach or sheltered pool. Fully furnished with everything you ...
From $352 per night (USD)
VRBO
From $518 per night (USD)
Expedia
LaPlaya 104A- Gulf front! Walk right from your lanai onto the private beach.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachfront 2 Bedroom, 2Bath condo in the center of beautiful Longboat Key, an island just a few miles north of Sarasota. ...
From $518 per night (USD)
Expedia
From $488 per night (USD)
VRBO
LaPlaya 106A-Beach front!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachfront 2 Bedroom, 2Bath condo in the center of beautiful Longboat Key, an island just a few miles north of Sarasota. ...
From $488 per night (USD)
VRBO
From $473 per night (USD)
Expedia
LaPlaya 107A-Soak up the sun or float in the warm Gulf waters.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachfront 2 Bedroom, 2Bath condo in the center of beautiful Longboat Key, an island just a few miles north of Sarasota. ...
From $473 per night (USD)
Expedia
From $484 per night (USD)
VRBO
LaPlaya 109A-Enjoy the balmy breezes in this corner end unit right on the beach.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachfront 2 Bedroom, 2Bath condo in the center of beautiful Longboat Key, an island just a few miles north of Sarasota. ...
From $484 per night (USD)
VRBO
From $547 per night (USD)
Expedia
LaPlaya 105B-Relax on the balcony and watch the dolphins swim by and the pelicans dive!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachfront 2 Bedroom, 2 Bath townhouse condo in the center of beautiful Longboat Key, an island just a few miles north o ...
From $547 per night (USD)
Expedia
From $737 per night (USD)
VRBO
LaPlaya 204D-Beach-lovers paradise! 200 feet of private beach along the turquoise Gulf of Mexico.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beachfront 3 Bedroom, 2 Bath townhouse condo in the center of beautiful Longboat Key, an island just a few miles north o ...
From $737 per night (USD)
VRBO
From $354 per night (USD)
Expedia
LaPlaya 101E-Relax on your private lanai under the palms!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
2 Bedroom & 1 bathroom, groundfloor condo just steps to the beach or sheltered pool. Fully furnished with everything you ...
From $354 per night (USD)
Expedia
From $488 per night (USD)
VRBO
LaPlaya 103A-Time to relax! Enjoy the peaceful, private beach just a shell's throw from your door.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachfront 2 Bedroom, 2 Bath condo in the center of beautiful Longboat Key, an island just a few miles north of Sarasota ...
From $488 per night (USD)
VRBO
From $564 per night (USD)
Expedia
LaPlaya 102B-Directly on the beach with the warm Gulf waters waiting!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachfront 2 Bedroom, 2 Bath townhouse condo in the center of beautiful Longboat Key, an island just a few miles north o ...
From $564 per night (USD)
Expedia
From $775 per night (USD)
VRBO
LaPlaya 206C-Gorgeous vistas of the Gulf from this light and bright end unit with private access to the beach.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beachfront 3 Bedroom, 2 Bath townhouse condo in the center of beautiful Longboat Key, an island just a few miles north o ...
From $775 per night (USD)
VRBO
From $352 per night (USD)
Expedia
LaPlaya 104E-Prefectly located near the path to the beach, just steps from the pool.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
2 Bedroom & 1 bathroom, ground-floor condo just steps to the beach or sheltered pool. Fully furnished with everything yo ...
From $352 per night (USD)
Expedia
From $482 per night (USD)
VRBO
LaPlaya 101A - Step out to the beach from your screened lanai. Light and bright end unit.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachfront 2 Bedroom, 2 Bath condo in the center of beautiful Longboat Key, an island just a few miles north of Sarasota ...
From $482 per night (USD)
VRBO
From $351 per night (USD)
Expedia
LaPlaya 102E-Tropical garden view near the pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
2 Bedroom & 1 bathroom, groundfloor condo just steps to the beach or sheltered pool. Fully furnished with everything you ...
From $351 per night (USD)
Expedia
From $816 per night (USD)
VRBO
LaPlaya 201C-Breathtaking Gulf panorama from this corner end unit.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beachfront 3 Bedroom, 2 Bath townhouse condo in the center of beautiful Longboat Key, an island just a few miles north o ...
From $816 per night (USD)
VRBO
From $342 per night (USD)
Expedia
Heart of Bradenton Beach, on the Bay
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Relax on your balcony overlooking the bay, steps across the street to the beach. Walk to beach bars, restaurants and sho ...
From $342 per night (USD)
Expedia
From $208 per night (USD)
VRBO
Short walk to beach or take your boat from the canal / dock in your backyard!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This house offers the best of island living - a boat dock out back and deeded private access to the white sandy beaches ...
From $208 per night (USD)
VRBO
From $441 per night (USD)
Expedia
No hurricane damage inside! Gulf front, first floor, two bedroom. A hidden gem!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Paradise found! Gorgeous. Two bedroom, two full bathrooms. Open concept. Leather couches, luxurious bathrooms. Master ...
From $441 per night (USD)
Expedia
From $339 per night (USD)
VRBO
Cute canal front Cottage with dock & boat lift and pool ,short walk to the beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
What's better than your own private paradise? Come and enjoy this beautiful, recently remodeled, canal front 2 bedroom ...
From $339 per night (USD)
VRBO
From $682 per night (USD)
Expedia
Contemporary Coastal Retreat w Gourmet Kitchen & Stunning Gulf Views by RVA
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This exquisite Sea Grape Inn is just steps from the sandy beaches of Longboat Key and features a private infinity pool w ...
From $682 per night (USD)
Expedia
From $311 per night (USD)
VRBO
Island property on Longboat Key by the Beach! 3 minute walk to the beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Longboat Key Island Fun in a newly updated beautiful property! Newly updated 3 story townhouse on beautiful Longboat Key ...
From $311 per night (USD)
VRBO
From $326 per night (USD)
VRBO
Your Dream Vacation Awaits at Sea N Blue!OCEANFRONT WITH PANORAMIC GULF VIEWS!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Ready to swap the hustle and bustle for sun-soaked shores and gentle ocean breezes? Meet Sea N Blue, your ultimate vacat ...
From $326 per night (USD)
VRBO
From $170 per night (USD)
VRBO
Paradise awaits on LBK 2BR/2BA Updated Condo on the Bay with Water Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Meticulously maintained top (3rd) floor condominium located on Sarasota Bay. Private dock, pool, gym and water access. ...
From $170 per night (USD)
VRBO
From $275 per night (USD)
Expedia
Direct Bayfront LBK Condo, Private Beach, Near St Armands, Boat Slip
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to charming Buttonwood Bliss located in a beautiful, bayside community on Longboat Key. This two bedroom, two ba ...
From $275 per night (USD)
Expedia
From $375 per night (USD)
VRBO
Upscale Oceanfront Condo – Roomy & Refined: Club Longboat #334 by RVA
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Experience the intimacy and warmth of northern Longboat Key at Club Longboat Beach and Tennis Resort. This 3-bedroom/ 2 ...
From $375 per night (USD)
VRBO
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Expedia
Ground level, Bayview condo with Private beach parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Have your morning coffee with the dolphins and manatees in this one bedroom, one bath ,bay view unique unit. Enjoy Priva ...
Click For Pricing
Expedia
From $274 per night (USD)
VRBO
Completely Refurbished - Gorgeous Beachside Condo/Townhome on Longboat Key Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Experience the intimacy and warmth of northern Longboat Key at Club Longboat Beach and Tennis Resort. This 3-bedroom/ 2. ...
From $274 per night (USD)
VRBO
Click For Pricing
Expedia
Gorgeous Beachside Condo/Townhome on Longboat Key Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This is a very unique Condo/Townhome located in the beautiful Club Longboat Beach and Tennis Club. Only unit like this i ...
Click For Pricing
Expedia
From $221 per night (USD)
VRBO
Long Boat Key Vacation Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
3
This is a two bedroom, two bathroom open layout condo with an ally kitchen and views of both the gulf and the bay. The c ...
From $221 per night (USD)
VRBO
From $768 per night (USD)
Expedia
Amazing Canal Front 4 Bedrm Home, Heated Pool, Dock Putting Green Close to Beach
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Beautifully updated large home on a deep water canal with room for a boat. Resort-like setting with a heated pool, putti ...
From $768 per night (USD)
Expedia
From $348 per night (USD)
VRBO
Longboat Key beach house - 5 min walk to the beaches and top local restaurants
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Quiet beach house tucked away in the historic Longboat Village in walking distance to the beach and some of the top rest ...
From $348 per night (USD)
VRBO
$3 BEDROOM PENTHOUSE \CRUISE SHIP\ VIEWS w/DOUBLE BALCONY at Beachplace!$
From $674 per night (USD)
VRBO
3 BEDROOM PENTHOUSE \"CRUISE SHIP\" VIEWS w/DOUBLE BALCONY at Beachplace!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Full Wall-to-Wall renovation and re-imagined 3 Bedroom floor plan 2022! 6TH FLOOR PENTHOUSE "CRUISE SHIP" VIEWS WITH DOU ...
From $674 per night (USD)
VRBO
From $305 per night (USD)
VRBO
Direct beachfront private home by FVC
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Tropical Odyssey, a beachfront 4 bedroom home managed by Florida Vacation Connection provides a screened porch with enou ...
From $305 per night (USD)
VRBO
From $215 per night (USD)
Expedia
Buttonwood Cove 104B by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
You can't beat the view from this lovely and spacious 2 bedroom, 2 bath, first floor condo! Your private, enclosed lanai ...
From $215 per night (USD)
Expedia
From $582 per night (USD)
VRBO
The Promenade
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
2400Sq/Ft area, charming with 3 lovelly beds and 3 full baths..Condo full of ameneties, concierge, heated pool, privite ...
From $582 per night (USD)
VRBO
From $318 per night (USD)
Expedia
Play by Day, Unwind by Night - Cedars East #852 Pet-Friendly by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to Paradise at Cedars East Tennis Resort by RVA Resort Vacations. Discover the ultimate Longboat Key getaway at ...
From $318 per night (USD)
Expedia

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Results: 895 Rentals