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 $345 per night (USD)
VRBO
Beach Castle Resort, 2nd Floor, Updated, Private Beach, Heated Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your ideal getaway at Beach Castle Resort, Unit 16 on Longboat Key! This charming second-floor condo offers a ...
From $345 per night (USD)
VRBO
From $269 per night (USD)
VRBO
Cozy 1-bedroom townhome in charming Longboat Key with AC, WiFi
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Discover the beauty of Longboat Key from this superb 1-bedroom townhome. With a pleasant living room and 2 sofa beds, ou ...
From $269 per night (USD)
VRBO
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VRBO
Tennis Beach Resort - Club Longboat
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Updated top-floor 2 Bedroom + Den with a pullout sleeper with stunning water views from nearly every room. Enjoy the pri ...
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VRBO
From $688 per night (USD)
Expedia
Beautiful pool home in the historic village of Longboat Key | Close to beach - Longboat Oasis
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Longboat Oasis! Professionally managed by Gulf Coast Vacation Rentals, this beautifully designed private pool ...
From $688 per night (USD)
Expedia
From $148 per night (USD)
VRBO
2/2 Condo, Beach/Pools/Fitness/Tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Seaplace Condominium G6-306 by FVC: Your Island Oasis Awaits Welcome to your island oasis! This beautifully updated, br ...
From $148 per night (USD)
VRBO
From $310 per night (USD)
Expedia
Panoramic Gulf Views That Take Your Breath Away – 2BR Beachfront Condo by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your beachfront escape! This stunning two-bedroom, two-bathroom condo sits right on the pristine shores of th ...
From $310 per night (USD)
Expedia
From $223 per night (USD)
VRBO
Turtle Walk - Walk to Gorgeous Beach! WALK to 12 different Restaurants!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Private BEACH Access! *Designer Renovation* Single level, 4 min walk to Bright White Quartz Sand, Welcome to UPGRADED BE ...
From $223 per night (USD)
VRBO
From $210 per night (USD)
Expedia
Beachplace 11-302 by FGC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
2 Bedroom and 2 Bath condo located in the resort community of Beachplace. Faces the golf course with limited Gulf view ...
From $210 per night (USD)
Expedia
From $438 per night (USD)
VRBO
2 Br/2Ba Gulf Front Condo w/ private beach access, on Long Boat Key, Florida
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover the beauty of Longboat Key from this 2-bedroom condo. Beautiful, 2 Br/2Ba renovated Gulf Front Condo with gorge ...
From $438 per night (USD)
VRBO
From $368 per night (USD)
Expedia
Beach Bliss: Open Sept 13th & 14th!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in e ...
From $368 per night (USD)
Expedia
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VRBO
Coastal Serenity Sea Twig 102-Beachfront Condo w Private Lanai & Pool by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to Sea Twig, an inviting beachfront condo nestled on the serene shores of Longboat Key. This exclusive retreat of ...
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VRBO
From $268 per night (USD)
Expedia
Charming Longboat Key Bungalow minutes from beaches, restaurants, parks
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Looking for an “island style getaway” this is it! Public beaches minutes away or head next-door to the beautiful Duran ...
From $268 per night (USD)
Expedia
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VRBO
2/2 Condo, Beach/Pools/Fitness/Tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Professionally managed and offered by FL Vacation Connection. This is a wonderful unit at Seaplace that has been attrac ...
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VRBO
From $257 per night (USD)
Expedia
2/2 Bay Front Condo, Pool, Private Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Proudly offered by FL Vacation Connection, your gorgeous resort-like getaway awaits in this tastefully designed 2BR resi ...
From $257 per night (USD)
Expedia
From $238 per night (USD)
VRBO
Grand Bay 3 BR / 3 BA Condo on LBK by FVC
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
A plethora of top notch amenities await you at Grand Bay. There is so much to enjoy, that you will have a hard time deci ...
From $238 per night (USD)
VRBO
From $255 per night (USD)
Expedia
2/2 Direct Beachfront Condo, Pool, Fitness, Tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A beachfront condominium managed by Florida Vacation Connection is located on the world-renowned Longboat Key and only m ...
From $255 per night (USD)
Expedia
From $218 per night (USD)
VRBO
2/2 Condo BEACH VIEW, Pool, Fitness, Tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Offered by FL Vacation Connection, this lovely 6th floor unit at Beachplace is ready for you to enjoy. Feel free to pla ...
From $218 per night (USD)
VRBO
From $626 per night (USD)
Expedia
2/2 Direct Beachfront Condo, Pool, Fitness, Tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachplace Beachfront Escape | Completely Renovated Welcome to your perfect getaway at Beachplace, a completely renov ...
From $626 per night (USD)
Expedia
From $282 per night (USD)
VRBO
2/2 Condo BEACH VIEW, Pool, Fitness, Tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Offered by FL Vacation Connection, this lovely 5th floor unit at Beachplace is ready for you to enjoy. Feel free to pla ...
From $282 per night (USD)
VRBO
From $193 per night (USD)
Expedia
2/2 Bay Front Condo, Pool, Private Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FL Vacation Connection welcomes you to this amazing waterfront top-floor condo on Sarasota Bay! Professionally remodeled ...
From $193 per night (USD)
Expedia
From $395 per night (USD)
VRBO
2/2 Coner Condo LBK, Beach, Pool, Fitness, Tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Professionally managed and offered by FL Vacation Connection. Guest will enjoy this corner unit that was renovated in 2 ...
From $395 per night (USD)
VRBO
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Expedia
2/2 Bay Front Condo, Pool, Private Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FL Vacation Connection proudly presents Buttonwood Cove - Set on 5 beautifully landscaped acres, spanning from Gulf to B ...
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Expedia
From $470 per night (USD)
VRBO
2/2 Condo BEACH VIEW, Pool, Fitness, Tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Florida Vacation Connection offers this well-maintained and comfortable two-bedroom, two-bathroom condo at the highly so ...
From $470 per night (USD)
VRBO
From $239 per night (USD)
Expedia
2/2 Direct Beachfront Condo, Pool, Fitness, Tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A luxurious beachfront condominium managed by Florida Vacation Connection is located on the world-renowned Longboat Key ...
From $239 per night (USD)
Expedia
From $387 per night (USD)
VRBO
2/2 Beachplace Condo, Beach, Pool, Fitness, Tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Florida Vacation Connection offers this well-maintained and comfortable two-bedroom, two-bathroom condo at the highly so ...
From $387 per night (USD)
VRBO
From $323 per night (USD)
Expedia
2/2 Direct Beachfront Condo, Pool, Fitness, Tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This beachfront condominium professionally managed by Florida Vacation Connection is located on the world-renowned Longb ...
From $323 per night (USD)
Expedia
From $415 per night (USD)
VRBO
1/1 Waterview Condo, Pool, Private Beach Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Your Longboat Key Retreat with Sleepy Lagoon Views by FVC Experience the pinnacle of coastal living in this beautifully ...
From $415 per night (USD)
VRBO
From $172 per night (USD)
Expedia
2/2 Beachplace Condo, Beach, Pool, Fitness, Tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to this updated 2 bedroom condo at Beachplace managed by Florida Vacation Connection. FVC is pleased to offer ...
From $172 per night (USD)
Expedia
From $744 per night (USD)
VRBO
Bayview Paradise by FVC
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Bayview Paradise managed by Florida Vacation Connection. This spacious 4 bedroom/ 3 full baths private pool ...
From $744 per night (USD)
VRBO
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Expedia
2/2 Corner Beachfront Condo, Pool, Fitness, Tennis
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
This beachfront condominium professionally managed by Florida Vacation Connection is located on the world-renowned Longb ...
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Expedia
From $165 per night (USD)
VRBO
Beachfront 2 BR / 2 BA At Players Club By FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Players Club is a beachfront property located at the south end of Longboat Key. It is well known as an active tennis co ...
From $165 per night (USD)
VRBO
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Expedia
Mark III Beachfront Condo by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Wonderful location on Longboat Key. Located mid-Key, just a short distance north of Publix, right on the beach. Longboat ...
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Expedia
From $406 per night (USD)
VRBO
4/3 Canal Front Condo, Private Pool, Dock
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Escape to Casa Blanca, a relaxing canal-front retreat professionally managed by Florida Vacation Connection. Casa Blanc ...
From $406 per night (USD)
VRBO
From $383 per night (USD)
Expedia
3/3 Luxury Beach View, Pool, Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Sanctuary B202 by FVC, your idyllic retreat nestled in the heart of Longboat Key. This stunning 3-bedroom, 3- ...
From $383 per night (USD)
Expedia
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VRBO
3/2 Beachfront, Pools/Fitness/Tennis
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Penthouse Paradise on Longboat Key – Beachfront Luxury Steps from the St. Regis Experience unparalleled coastal eleganc ...
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VRBO
From $273 per night (USD)
Expedia
Direct Beachfront 2BR / 2 BA, Pool, Washer/Dryer
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FL Vacation Connection presents Salty Acres - a small, picturesque, beachfront community on Longboat Key. This unit h ...
From $273 per night (USD)
Expedia
From $421 per night (USD)
VRBO
Pool, Dock & Close to Beach– Florida Fun Starts Here: Marbury Lane LBK by RVA
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to your perfect getaway on Longboat Key, FL! This stunning three-story vacation home is a dream come true for fa ...
From $421 per night (USD)
VRBO
From $381 per night (USD)
VRBO
NEW Penthouse on the Bay - 2BR Condo Steps to Heated Pools, Tennis & Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience the tranquility of Sarasota Bay from this beautifully updated 4th-floor penthouse condo in Longboat Key. With ...
From $381 per night (USD)
VRBO
From $117 per night (USD)
VRBO
2/2 Canal front condo, Pool, Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This 2-bedroom, 2-bath condo offers stunning bayfront views and is located in the desirable Longboat Harbour community. ...
From $117 per night (USD)
VRBO
From $882 per night (USD)
Expedia
Luxury on the Sand – Large Oceanfront Condo La Playa #202D by RVA
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Experience the coastal charm of Longboat Key at our newest addition: La Playa, Unit 202D. This oceanfront getaway offers ...
From $882 per night (USD)
Expedia
From $600 per night (USD)
VRBO
Direct Beachfront Condo Birds eye view
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Imagine waking up to breathtaking views of the Gulf and the Sarasota skyline - every single room boasts this incredible ...
From $600 per night (USD)
VRBO
From $273 per night (USD)
Expedia
Partial Beach View 2 Bedroom Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful unit on the 5th floor with lake/pool view and partial Gulf. Beautifully appointed 2 bedroom, 2 bath unit with ...
From $273 per night (USD)
Expedia
From $314 per night (USD)
VRBO
Gulf Views & Cozy Comfort w Large Lanai Tern's Nest #22 Condo by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to paradise in this stunning Longboat Key condo, where every day starts with incredible water views and ends with ...
From $314 per night (USD)
VRBO
From $358 per night (USD)
VRBO
Charming 2-bedroom condo steps from Beach, Library and Grocery on Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Get ready to relax in this marvelous 2-bedroom condo in Longboat Key. This cozy retreat features 1 king bed and 2 queen ...
From $358 per night (USD)
VRBO
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VRBO
Gorgeous Beachside Condo in superior Longboat Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Amazing Direct Beach views from your balcony, living room, kitchen, dining room and bedroom in this Islands West Condo. ...
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VRBO
From $495 per night (USD)
Expedia
Unit #313 Sand Cay Beach Resort Pool View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Just like Longboat Key’s original tourists, residents and visitors alike enjoy the beaches and weather — but today’s isl ...
From $495 per night (USD)
Expedia
From $532 per night (USD)
VRBO
Longboat Key near St Armands Beachside Sanctuary 2BR/2BA w/Full Kitchen
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to your peaceful beachside + tropical retreat, nestled in desirable South Longboat Key on 31 acres of private bea ...
From $532 per night (USD)
VRBO
From $310 per night (USD)
Expedia
Beach front newly renovated 2.5 bedroom condo with private beach access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Luxury Longboat Key Condo – Fully Renovated (Dec 2024) & Steps from the beach (private access). Welcome to Sea Pines Co ...
From $310 per night (USD)
Expedia
From $213 per night (USD)
VRBO
3/2 Bay View Condo, Pool, Kayaks
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to this exquisite top-floor, 3 bedroom, 2 bath, end-unit condo at Bay Harbour by FVC. Newly furnished in 2022 an ...
From $213 per night (USD)
VRBO
From $590 per night (USD)
Expedia
4-bedroom house on Longboat Key with beach only 150 yards away.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Make yourself at home in this large recently remodeled 4-bedroom 3 bathroom Longboat Key retreat with 1 king bed and 3 q ...
From $590 per night (USD)
Expedia
From $406 per night (USD)
VRBO
Beachplace 8-601 by FGC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience Coastal Elegance at Beachplace Penthouse Welcome to your dream beachfront retreat, where coastal living meet ...
From $406 per night (USD)
VRBO
From $386 per night (USD)
Expedia
Newly Renovated Beach Castle #21, Just steps from Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to your dream getaway at Beach Castle Resort Unit 21! This fully renovated and newly furnished ground-floor beac ...
From $386 per night (USD)
Expedia
From $239 per night (USD)
VRBO
Charming Longboat Key 3-bedroom house with 3 min walk to beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover the best of Longboat Key and Sarasota from our cozy 3 bedroom rental. Just down the road is beautiful St. Arman ...
From $239 per night (USD)
VRBO
From $200 per night (USD)
Expedia
Waterfront with Dock, Beach Close!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
BEACH, BOAT, BIKE, FISH, KAYAK, TV/SPORTS, ENTERTAINMENT, FOOD, RELAX & ENJOY! Nestled between the highly sought after A ...
From $200 per night (USD)
Expedia
From $262 per night (USD)
VRBO
Steps from the Sand – Luxury Beach Condo with Pool Access!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Leave the snow behind and soak up the sun! This stunningly renovated 2-bedroom, 2-bathroom condo has everything you need ...
From $262 per night (USD)
VRBO
From $538 per night (USD)
Expedia
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Beach on Longboat Key: Gulf-Front Luxury with Stunning Views and Modern Comforts" Escape to paradise at The Beach o ...
From $538 per night (USD)
Expedia
From $293 per night (USD)
VRBO
Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Your home away from home in Longboat Key. This adorable condo is equipped with all the essentials for a comfortable stay ...
From $293 per night (USD)
VRBO
From $446 per night (USD)
Expedia
Charming 1-bedroom, beachfront condo in marvelous Longboat Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Consider this condo your home away from home while you visit Longboat Key. This fantastic rental offers 1 cozy bedroom, ...
From $446 per night (USD)
Expedia
From $446 per night (USD)
VRBO
Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to the beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Your home away from home in Longboat Key with 1 bedroom. This lovely condo offers WiFi, AC, heating, a washing machine, ...
From $446 per night (USD)
VRBO
From $156 per night (USD)
Expedia
2/2 Bay Front Condo, Pool, Private Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Fairway Bay Fifth-Floor Retreat: Unparalleled Sarasota Bay Views Offered by Florida Vacation Connections Experience ...
From $156 per night (USD)
Expedia
From $398 per night (USD)
VRBO
Gorgeous townhouse in desirable Cedar's East Tennis Resort!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
You will pinch yourself that you are staying on such a gorgeous island in a beautiful townhome! Every morning you will l ...
From $398 per night (USD)
VRBO
From $770 per night (USD)
Expedia
3-bedroom, 3 bath condo in beautiful Longboat Key. Beachfront views w/ pool.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Unit #221S - Spacious & Upgraded 3-Bedroom Beachfront Condo on Longboat Key Experience the perfect blend of comfort and ...
From $770 per night (USD)
Expedia
From $189 per night (USD)
VRBO
Gulf of Mexico Direct Gulf View Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your perfect Gulf Coast getaway! This stunning 2-bedroom, 2-bathroom condo offers breathtaking, direct views ...
From $189 per night (USD)
VRBO
From $142 per night (USD)
Expedia
Longboat Key waterfront condo-a short walk to the beach & bay!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Relax at this delightfully peaceful waterfront condo on the beautiful island of Longboat Key. A short 5-minute walk to o ...
From $142 per night (USD)
Expedia
From $375 per night (USD)
VRBO
Beachfront Escape – Private Balcony, Gulf Views, No Street to Cross, Watch the Sunset from Your Balcony
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Beachfront Condo – No Street to Cross, Just Steps to the Sand Enjoy panoramic Gulf and sunset views from your private co ...
From $375 per night (USD)
VRBO
From $279 per night (USD)
Expedia
Beach place in Longboat Key.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your dream getaway! Our beautifully appointed 2-bedroom, 2- bath condo offers the perfect balance of comfort, ...
From $279 per night (USD)
Expedia
From $355 per night (USD)
VRBO
Ground floor 2/2! Glass Lanai! Sleeps 5!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Enjoy all Longboat Key has to offer from Harbor Villa Club! Beautiful 2/2 directly on the bay! Gorgeous views off the pa ...
From $355 per night (USD)
VRBO
From $372 per night (USD)
Expedia
Beachplace 9-302 by FGC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachfront renting at its finest: relax, unwind, and enjoy the magnificent views of the pristine white sandy beach and t ...
From $372 per night (USD)
Expedia
From $458 per night (USD)
VRBO
Beachplace 8-603 by FGC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience Coastal Elegance at Beachplace Penthouse Welcome to Your Dream Beachfront Retreat! Discover the perfect ble ...
From $458 per night (USD)
VRBO
From $178 per night (USD)
Expedia
RENOVATED 2/2 w/ VIEW, Beach/Pools/Fitness/Tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to paradise in this newly renovated 2-bedroom, 2-bathroom beachfront condo at Seaplace on Longboat Key, managed b ...
From $178 per night (USD)
Expedia
From $541 per night (USD)
VRBO
Beach Condo with Quiet, Private Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Relax with your loved ones at this quiet, 2-bedroom beachfront condo at the Beach Castle Resort on Longboat Key. This se ...
From $541 per night (USD)
VRBO
From $210 per night (USD)
Expedia
2 Bedroom townhome Seaplace by FGC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This home located in the sought after Seaplace community has a very personal feel to it and the beach is steps away from ...
From $210 per night (USD)
Expedia
From $312 per night (USD)
VRBO
Full Beach View 2 Bedroom Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
** Welcome to our beachfront Longboat Key condo! If you’re looking for a special two-bedroom, two-bathroom retreat wit ...
From $312 per night (USD)
VRBO
From $360 per night (USD)
Expedia
The Pierre 507 by FGC
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
2 bedroom + Den and 3 bathrooms with views of the Beach of Longboat Key. Prestigious entrance to the Pierre through the ...
From $360 per night (USD)
Expedia
From $215 per night (USD)
VRBO
Beachplace 3 - 302 by FGC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Exquisite beach and Gulf view unit on the 3rd floor of building 3. Beautifully appointed 2 bedroom, 2 bath unit with m ...
From $215 per night (USD)
VRBO
From $267 per night (USD)
Expedia
Beachplace 3 - 503 by FGC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful beachfront unit on the 5th floor with pool view and partial Gulf. Beautifully appointed 2 bedroom, 2 bath uni ...
From $267 per night (USD)
Expedia
From $255 per night (USD)
VRBO
Beachplace 4 - 304 by FGC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful beachview unit on the 3rd floor with lake view and Gulf views. Beautifully appointed 2 bedroom, 2 bath unit w ...
From $255 per night (USD)
VRBO
From $458 per night (USD)
Expedia
The Village Bungalow of Long Beach in Longboat Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Consider this duplex-bungalow your home away from home while you visit Longboat Key. The duplex-bungalow set up offers i ...
From $458 per night (USD)
Expedia
From $266 per night (USD)
VRBO
Waterfront 2BR 2BA Pool - 10 min walk to Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A spacious first-floor 2-bedroom, 2-bathroom condo with direct pool access and stunning bayfront views. Located just a 1 ...
From $266 per night (USD)
VRBO
From $320 per night (USD)
VRBO
Sunset and Beach view unit 402
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
There are no ratings and reviews because this is my new property. However, I am a Premier Host with a 5-star rating and ...
From $320 per night (USD)
VRBO
From $254 per night (USD)
VRBO
Suzie's Beach House, Longboat Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located in Country Club Shores close to St. Armands Circle and downtown Sarasota, this quiet, three bedroom home offers ...
From $254 per night (USD)
VRBO
From $254 per night (USD)
Expedia
2/2 Bay Front Condo, Pool, Private Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Luxury Waterfront Retreat at Grand Bay – Unit 626, Longboat Key Experience the ultimate in coastal elegance at this s ...
From $254 per night (USD)
Expedia
From $307 per night (USD)
VRBO
3/2 Beachplace Condo, Beach, Pool, Fitness, Tennis
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beachplace 3-Bedroom Condo – Longboat Key Welcome to your perfect Florida retreat at Beachplace on Longboat Key! Prof ...
From $307 per night (USD)
VRBO
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Expedia
Waterfront 2-Bedroom Retreat in Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Welcome to this stunning 2-bedroom, 2-bath residence on Longboat Key. - Expansive water views from the livi ...
Click For Pricing
Expedia
From $366 per night (USD)
VRBO
Charming 2-bedroom condo with WiFi and AC in beautiful Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience Longboat Key like a local in this 2-bedroom condo. This lovely property features 2 queen beds, AC, WiFi, heat ...
From $366 per night (USD)
VRBO
From $261 per night (USD)
Expedia
Longboat Key tennis resort minutes to beach - Ospreys Nest
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Welcome to your perfect coastal escape in the heart of Cedars East on Longboat Key, Florida! Professionally managed by G ...
From $261 per night (USD)
Expedia
From $309 per night (USD)
VRBO
LBK Dreamin' Beach Bungalow
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Highlights/Resort Style Amenities: - 5 minute walk to beautiful white sand beach and numerous restaurants - On-site Te ...
From $309 per night (USD)
VRBO
From $330 per night (USD)
Expedia
Gulf-Front Grandeur in Longboat Key – Luxurious & Spacious Condo #102 by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Gulf-Front Elegance on Longboat Key – 2 Bed, 2 Bath Beachfront Condo Welcome to your private slice of paradise on the e ...
From $330 per night (USD)
Expedia
From $493 per night (USD)
VRBO
Charming 2-bedroom condo in fabulous Longboat Key-2027 SNOW BIRDS season OPEN
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
NOW AVAILABLE FOR SNOWBIRD SEASON. DECEMBER 2026 AND JANUARY THROUGH APRIL 30TH 2027. ONE MONTH MINUM LEASE. Nested in L ...
From $493 per night (USD)
VRBO
From $449 per night (USD)
Expedia
The Sea Is Calling Open Mon, $225/nt + Fees!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This sublime oceanfront condo is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Lo ...
From $449 per night (USD)
Expedia
From $283 per night (USD)
VRBO
Luxury Beachfront Retreat on Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Welcome to Your Luxury Beachfront Retreat on Longboat Key! - Spacious 2-story home with 2 bedrooms and 2 ba ...
From $283 per night (USD)
VRBO
From $580 per night (USD)
VRBO
Private Heated Pool & Hot Tub Retreat - Longboat Key Coastal Living
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Looking for a 3 month renter for January, February, and March or atleast January 2027. Experience elevated island livin ...
From $580 per night (USD)
VRBO
From $745 per night (USD)
VRBO
Charming 2-bedroom condo with AC, fitness room in wonderful Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Located in Longboat Key, this condo is a dream. Guests will feel right at home with 2 bedrooms featuring 1 king bed and ...
From $745 per night (USD)
VRBO
From $444 per night (USD)
Expedia
Beachfront Bliss on Longboat Key- Steps to the sand
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Step out your door and onto the sand—this beachfront gem on Longboat Key is the perfect escape for couples or solo trave ...
From $444 per night (USD)
Expedia
From $435 per night (USD)
VRBO
Gorgeous 2 Bedroom 2 Bath Fairway Bay Condo located in Bay Isles on Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A completely renovated newly furnished 2 bedrooms . 2 bath condo located at Fairway Bay in the Bay Isles Community. Thi ...
From $435 per night (USD)
VRBO
From $306 per night (USD)
Expedia
3/2.5 Private Pool, Dock, Walk to Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Pink Pelican – A Bright Key West-Style Retreat on Longboat Key Professionally Managed by Florida Vacation Connection ...
From $306 per night (USD)
Expedia
From $240 per night (USD)
VRBO
Beachfront Condo On Longboat Key - First Floor
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Direct waterfront on Longboat Key. Unobstructed views of the Gulf of Mexico. This first-floor beachfront condo has every ...
From $240 per night (USD)
VRBO
From $178 per night (USD)
Expedia
2/2 Bay Front Condo, Pool, Private Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Buttonwood Cove 204B | Longboat Key, Florida Bayfront Beauty with Gulf Access – Your Ideal Island Retreat Welcome to Un ...
From $178 per night (USD)
Expedia
From $1167 per night (USD)
VRBO
Upscale Canal Home – Private Pool & Boat Dock: Hideaway Bay in LBK by RVA
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Escape to paradise at Hideaway Bay, a luxurious 4-bedroom, 5-bathroom canal-front home nestled in the exclusive Longboat ...
From $1167 per night (USD)
VRBO
From $326 per night (USD)
Expedia
Enjoy endless gulf views from this welcoming oceanfront condo on Longboat Key - Pearl On The Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Pearl On The Key, your coastal sanctuary Professionally Managed by Gulf Coast Vacation Rentals, at Privateer, ...
From $326 per night (USD)
Expedia

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Results: 761 Rentals