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 $490 per night (USD)
VRBO
Unit #312 Sand Cay Beach Resort Pool 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 $490 per night (USD)
VRBO
From $492 per night (USD)
Expedia
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 $492 per night (USD)
Expedia
From $533 per night (USD)
VRBO
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 $533 per night (USD)
VRBO
From $671 per night (USD)
Expedia
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 $671 per night (USD)
Expedia
From $543 per night (USD)
VRBO
Stunning -late summer sale 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 $543 per night (USD)
VRBO
From $812 per night (USD)
Expedia
1 of a kind home 13 steps to sand LATE SUMMER SALE
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 $812 per night (USD)
Expedia
From $478 per night (USD)
VRBO
3/2 Direct Beachfront Condo, Pool, Fitness, Tennis
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 $478 per night (USD)
VRBO
From $218 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 $218 per night (USD)
VRBO
From $412 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 $412 per night (USD)
VRBO
From $593 per night (USD)
Expedia
End-of-summer sale ready for a luxury 5-floor penthouse 60 ft from water,
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 $593 per night (USD)
Expedia
From $601 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 $601 per night (USD)
VRBO
From $213 per night (USD)
Expedia
Canal front home on Longboat Key -Just Steps to the Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Newly renovated and spacious canal-front home in beautiful Longboat Key with deeded beach access just steps down the str ...
From $213 per night (USD)
Expedia
From $302 per night (USD)
VRBO
Peaceful Condo – Cedars East #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 $302 per night (USD)
VRBO
From $375 per night (USD)
Expedia
1BR Beach Getaway – Silver Sands #254 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 $375 per night (USD)
Expedia
From $420 per night (USD)
VRBO
Gulf Views – Silver Sands #250, 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 $420 per night (USD)
VRBO
From $216 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 $216 per night (USD)
VRBO
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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. ...
Click For Pricing
VRBO
From $497 per night (USD)
Expedia
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 $497 per night (USD)
Expedia
From $423 per night (USD)
VRBO
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 $423 per night (USD)
VRBO
From $332 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 $332 per night (USD)
VRBO
From $517 per night (USD)
VRBO
BOOK NOW - BEAUTIFUL HOME NEAR BEACHES
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
ISLAND PARADISE!!! Enjoy this spectacular home in a beautiful, very quiet, Longboat Key neighborhood. Enjoy the nearby p ...
From $517 per night (USD)
VRBO
From $416 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 $416 per night (USD)
VRBO
From $207 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 $207 per night (USD)
VRBO
From $254 per night (USD)
Expedia
2/2 Beachplace Condo, Beach, Pool, Fitness, Tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Proudly offered by FL Vacation Connection, this property is ideal for professionals working remotely! Beautifully furn ...
From $254 per night (USD)
Expedia
From $195 per night (USD)
VRBO
2/2 Condo LBK, Pool, Fitness, Tennis
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 $195 per night (USD)
VRBO
From $206 per night (USD)
Expedia
2/2 RENOVTED Condo, Beach, Pool, Fitness, Tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Professionally managed by FL Vacation Connection, this spacious unit is furnished with comfortable seating in the living ...
From $206 per night (USD)
Expedia
From $566 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 $566 per night (USD)
VRBO
From $369 per night (USD)
Expedia
Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Direct beachfront access with a private beach area. Guests enjoy stunning sea views from a screened-in balcony patio and ...
From $369 per night (USD)
Expedia
From $818 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 $818 per night (USD)
VRBO
From $348 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 $348 per night (USD)
Expedia
From $705 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 $705 per night (USD)
VRBO
From $588 per night (USD)
Expedia
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 $588 per night (USD)
Expedia
From $562 per night (USD)
VRBO
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 $562 per night (USD)
VRBO
From $186 per night (USD)
Expedia
PAMS ISLAND RETREAT NEW HOUSE BOOK NOW LOW RATES
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
HOUSE HOLDS 8 GUESTS KITCHEN HAS NEW APPLIANCES FULLY EQUIPPED WITH UTENSILS DINING ROOM 4 BEDROOMS ROKU TV WITH FREE ...
From $186 per night (USD)
Expedia
From $761 per night (USD)
VRBO
Luxurious beachfront house on exclusive LONGBOAT KEY. Directly on the beach!
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 $761 per night (USD)
VRBO
From $394 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 $394 per night (USD)
VRBO
From $399 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 $399 per night (USD)
VRBO
From $415 per night (USD)
VRBO
Historic Longbeach Village Cottage - Private Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
'Sunny Side Up' is a restored beach cottage built in the 1950's located on the north end of Longboat Key in historic ...
From $415 per night (USD)
VRBO
From $392 per night (USD)
VRBO
Wonderful Canal Front Condo! See Manatees Right From Your Doorstep!Cabana #10
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Unit 10 at Cabana Beach Club, a beautifully renovated, exceptionally private bayfront condo located on iconic ...
From $392 per night (USD)
VRBO
From $347 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 $347 per night (USD)
Expedia
From $897 per night (USD)
VRBO
LaPlaya 205D! Spectacular views!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beachfront 3-Bedroom, 2-Bath townhouse located directly on the Gulf in the center of Longboat Key, just minutes north of ...
From $897 per night (USD)
VRBO
From $657 per night (USD)
Expedia
LaPlaya 108B-Dream views of the Gulf.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachfront 2 Bedroom, 2 Bath townhouse, directly on the beach, in the center of beautiful Longboat Key, an island just ...
From $657 per night (USD)
Expedia
From $434 per night (USD)
VRBO
LaPlaya 202E-Catch the gentle Gulf breezes on your private balcony!
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 $434 per night (USD)
VRBO
From $456 per night (USD)
Expedia
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 $456 per night (USD)
Expedia
From $610 per night (USD)
VRBO
LaPlaya 104A- Gulf front! Walk right from your lanai onto the private beach.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachfront 2 Bedroom, 2 Bath condo, directly on the beach, in the center of beautiful Longboat Key, an island just a fe ...
From $610 per night (USD)
VRBO
From $615 per night (USD)
Expedia
LaPlaya 106A-Beach front!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachfront 2 Bedroom, 2 Bath condo, directly on the beach, in the center of beautiful Longboat Key, an island just a fe ...
From $615 per night (USD)
Expedia
From $611 per night (USD)
VRBO
LaPlaya 107A-Soak up the sun or float in the warm Gulf waters.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachfront 2 Bedroom, 2 Bath condo, directly on the beach, in the center of beautiful Longboat Key, an island just a fe ...
From $611 per night (USD)
VRBO
From $615 per night (USD)
Expedia
LaPlaya 109A-Enjoy the balmy breezes in this corner end unit right on the beach.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachfront 2 Bedroom, 2 Bath condo, directly on the beach, in the center of beautiful Longboat Key, an island just a fe ...
From $615 per night (USD)
Expedia
From $669 per night (USD)
VRBO
LaPlaya 105B-Relax on the balcony and watch the dolphins swim by!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachfront 2 Bedroom, 2 Bath townhouse, directly on the beach in the center of beautiful Longboat Key, an island just a ...
From $669 per night (USD)
VRBO
From $906 per night (USD)
Expedia
LaPlaya 204D-Beach-lovers paradise!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beachfront 3-Bedroom, 2-Bath townhouse located directly on the Gulf in the center of Longboat Key, just minutes north of ...
From $906 per night (USD)
Expedia
From $459 per night (USD)
VRBO
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 $459 per night (USD)
VRBO
From $590 per night (USD)
Expedia
LaPlaya 103A- Enjoy the peaceful, beach just a shell's throw from your door.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachfront 2 Bedroom, 2 Bath condo, directly on the beach, in the center of beautiful Longboat Key, an island just a fe ...
From $590 per night (USD)
Expedia
From $664 per night (USD)
VRBO
LaPlaya 102B-Directly on the beach with the warm Gulf waters waiting!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachfront 2 Bedroom, 2 Bath townhouse, directly on the beach. Full view of the water, walk out to the sand. LaPlaya C ...
From $664 per night (USD)
VRBO
From $912 per night (USD)
Expedia
LaPlaya 206C-Gorgeous vistas of the Gulf!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beachfront 3-Bedroom, 2-Bath townhouse located directly on the Gulf in the center of Longboat Key, just minutes north of ...
From $912 per night (USD)
Expedia
From $462 per night (USD)
VRBO
LaPlaya 104E-Prefectly located near the path to the beach.
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 $462 per night (USD)
VRBO
From $615 per night (USD)
Expedia
LaPlaya 101A - Step out to the beach. Light and bright end unit.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachfront 2 Bedroom, 2 Bath condo, directly on the beach, in the center of beautiful Longboat Key, an island just a fe ...
From $615 per night (USD)
Expedia
From $462 per night (USD)
VRBO
LaPlaya 102E-Tropical garden view near 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 $462 per night (USD)
VRBO
From $897 per night (USD)
Expedia
LaPlaya 201C-Breathtaking Gulf panorama from this corner end unit.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beachfront 3-Bedroom, 2-Bath townhouse located directly on the beach in the center of Longboat Key, just minutes north o ...
From $897 per night (USD)
Expedia
From $228 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 $228 per night (USD)
VRBO
From $267 per night (USD)
Expedia
GULF FRONT, 1ST FLOOR, 2 Bedroom 2 Bath private gem!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Paradise found! Gorgeous. Two bedroom, two full bathrooms. Open concept. Leather couches, luxurious bathrooms. Master ...
From $267 per night (USD)
Expedia
From $595 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 $595 per night (USD)
VRBO
From $394 per night (USD)
Expedia
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 $394 per night (USD)
Expedia
From $328 per night (USD)
VRBO
OCEANFRONT STAY! 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 $328 per night (USD)
VRBO
From $268 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 $268 per night (USD)
Expedia
From $365 per night (USD)
VRBO
Upscale Oceanfront – Club Longboat #334 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 $365 per night (USD)
VRBO
From $387 per night (USD)
VRBO
waterfront bungalow north end LBK-2 minute walk to beach (weekly availability)
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Nicely updated 1 bedroom/1 bath on Greer Bay, North LBK. The largest beach on the island is just a short walk and the ba ...
From $387 per night (USD)
VRBO
From $297 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 $297 per night (USD)
VRBO
From $312 per night (USD)
Expedia
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 $312 per night (USD)
Expedia
From $696 per night (USD)
VRBO
Heated Pool, Dock, Putting Green, Close to Beach!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Decked Out on Marbury is a beautifully updated two-story home on a deep-water canal in the heart of Longboat Key. Boasti ...
From $696 per night (USD)
VRBO
$3 BEDROOM PENTHOUSE \CRUISE SHIP\ VIEWS w/DOUBLE BALCONY at Beachplace!$
From $596 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 $596 per night (USD)
VRBO
From $349 per night (USD)
VRBO
4 BR / 4 BA Beachfront Home by FVC
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
A beachfront home that will delight, professionally managed and offered by FL Vacation Connection. A full home-length s ...
From $349 per night (USD)
VRBO
From $167 per night (USD)
Expedia
Limited Time Deal 45% Discount - Best Value on LBK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
New to market! Introductory pricing. Premium dates available. Pet friendly single family home located in the quiet res ...
From $167 per night (USD)
Expedia
From $241 per night (USD)
VRBO
2/2 Bay Front Condo, Pool, Private Beach Access
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 $241 per night (USD)
VRBO
From $637 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 $637 per night (USD)
VRBO
From $332 per night (USD)
VRBO
Play all Day Cedars #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 $332 per night (USD)
VRBO
From $365 per night (USD)
Expedia
Luxury Gulf-Front Condo on Longboat Key with Breathtaking Sunsets
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Luxury Gulf-Front Condo on Longboat Key with Breathtaking Sunsets – Portobello Unit #204 Wake up to sweeping Gulf of Me ...
From $365 per night (USD)
Expedia
From $516 per night (USD)
VRBO
Stunning 2 BR Condo views of the Gulf and Lake
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Spacious 2 bedroom condo in Beachplace gated complex. King in Primary bedroom. Come enjoy your time at the Beach. Thi ...
From $516 per night (USD)
VRBO
From $319 per night (USD)
Expedia
Penthouse level with Beach View 2 Bedroom Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Penthouse unit on the top floor of building 3 at Beachplace. Top floor units enjoy a double balcony with access from t ...
From $319 per night (USD)
Expedia
From $310 per night (USD)
VRBO
Partial Beach View 3 Bedroom Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful partial beachview unit on the 2nd floor with lake view and Beach View. Hard to find beautifully appointed 3 be ...
From $310 per night (USD)
VRBO
From $257 per night (USD)
Expedia
Studio by the Sea | Beach, Pool & Sunset Vibes
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Ready for sun-soaked days and barefoot evenings? Gulf Tides is your summer escape—where the pace slows down, the sky str ...
From $257 per night (USD)
Expedia
From $357 per night (USD)
VRBO
Salty Air & Sandy Toes | Gulfside 1BR Retreat
Bedrooms:
2
Bathrooms:
1
Sleeps:
6
Where flip-flops are the dress code and your toughest decision is beach or pool first—this cheerful one-bedroom, two-bat ...
From $357 per night (USD)
VRBO
From $322 per night (USD)
Expedia
Bayside Comfort | 2BR Condo with Beach Access & Resort Amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Experience the best of Longboat Key in this inviting two-bedroom condo, located just steps across the street from the Gu ...
From $322 per night (USD)
Expedia
From $672 per night (USD)
VRBO
Gulf Front 2BR Retreat | Unmatched Views & Iconic Sunsets
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Experience classic Gulf Coast living with this beautifully updated two-bedroom, two-bath condo on Longboat Key. Perfectl ...
From $672 per night (USD)
VRBO
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Expedia
Gulfside Escape at Sea Twig #103- Relax & Unwind Steps to Sand & Pool by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
RVA features an intimate beachfront condominium property on the Gulf of Mexico. The quiet beach can be reached by charmi ...
Click For Pricing
Expedia
From $166 per night (USD)
VRBO
Bikini Top Cottage in the historic village of Longboat Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Bikini Top Cottage sweet spot for couples. Tiny Home in a Cozy Island village. The bungalow is on an alley way that ...
From $166 per night (USD)
VRBO
From $322 per night (USD)
Expedia
Cedars East Getaway–Tennis & Gulf Breezes 507/RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Recently Renovated Luxury Condo at Cedars East – Prime Longboat Key Location Welcome to Cedars 507, a beautifully newly ...
From $322 per night (USD)
Expedia
From $561 per night (USD)
VRBO
Waterfront Oasis: Private Heated Pool, Fire Pit & Gourmet Kitchen - Near Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
**2-Week Minimum Stay Required** Escape to this beautifully renovated waterfront retreat on Longboat Key. This spacious ...
From $561 per night (USD)
VRBO
From $495 per night (USD)
Expedia
Unit #308 Sand Cay Beach Resort Pool View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Bright and sunny; 3rd floor condo: Partial view to beach from private patio. Condo has Cathedral ceilings for spacious ...
From $495 per night (USD)
Expedia
From $495 per night (USD)
VRBO
Unit #210 Sand Cay Beach Resort Pool View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Second floor, poolside. Directly over pool. This unit has had numerous upgrades this year including a complete kitchen ...
From $495 per night (USD)
VRBO
Click For Pricing
Expedia
3/2 Canal Front Condo, Private Pool, Dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Coconut Place, a spectacular canalfront retreat professionally managed by Florida Vacation Connection. This b ...
Click For Pricing
Expedia
From $313 per night (USD)
VRBO
Cozy private beach condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Relax with the whole family at this peaceful place to stay steps away from the legendary longboat key private beach! Enj ...
From $313 per night (USD)
VRBO
From $287 per night (USD)
VRBO
Steps from the Water with Spectacular Bay Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Wake up every morning and have coffee from your front patio, just a few feet away from the Sarasota Bay. Play a round of ...
From $287 per night (USD)
VRBO
From $295 per night (USD)
VRBO
Waterfront Longboat Key Retreat With Dream Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Start your days waking up to waterfront views and end your days watching the sunset on the Gulf of Mexico from your priv ...
From $295 per night (USD)
VRBO
From $316 per night (USD)
Expedia
1BR Gulfside Cottage Charming, Quiet, and Warmer Than Your Forecast
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Step onto the porch, take a deep breath, and let the salty sea air remind you—you’re officially on beach time. Whether i ...
From $316 per night (USD)
Expedia
From $404 per night (USD)
VRBO
Salt Air, Sunlight, and Old Florida Flair
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Step into a simpler time with this cozy Cape Cod-style cottage, where beach vacations feel timeless and the pace is set ...
From $404 per night (USD)
VRBO
From $601 per night (USD)
Expedia
2BR Cottage Bayside Time for Relaxation
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape the daily hustle and embrace tranquility at this charming cottage with breathtaking bay views. The spacious main ...
From $601 per night (USD)
Expedia
From $310 per night (USD)
VRBO
Throwback Charm Meets Beach Bliss 1BR Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Step back in time to the golden days of beach vacations—think breezy porches, tiki huts, and palm-fringed paths that lea ...
From $310 per night (USD)
VRBO
From $364 per night (USD)
Expedia
2BR Cottage Bayside Close to the Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Little Gull Cottage, where Cape Cod charm meets Longboat Key's natural beauty. This cozy retreat features a s ...
From $364 per night (USD)
Expedia
Click For Pricing
VRBO
1BR Gulf Breezes & Old Florida Charm
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Kick off your shoes and settle into the easy rhythm of coastal living. Start your mornings with a stroll along the soft ...
Click For Pricing
VRBO
From $391 per night (USD)
Expedia
Your Vacation Reset: Gulf Breezes + Good Vibes
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Experience the charm of this cottage, featuring a generously sized main bedroom with a king bed, providing a comfortable ...
From $391 per night (USD)
Expedia

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Results: 761 Rentals