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 $311 per night (USD)
VRBO
Waterfront, Spa/Pool, Private Paradise on Longboat Key!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Paradise at the Harbour Villa Club #114! Enjoy the "Captains Quarters" end unit which boasts over 1500 sf of ...
From $311 per night (USD)
VRBO
From $348 per night (USD)
Expedia
Pelican Harbour, Beach Club T2 Condo by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to paradise at this beautifully appointed 2-bedroom, 2-bath vacation rental on the bayside of Longboat Key, Flori ...
From $348 per night (USD)
Expedia
From $357 per night (USD)
VRBO
Gulffront Elegance | Renovated 1BR Condo w/ Direct Beach Access & Sunset Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Experience refined coastal living in this beautifully renovated ground-floor 1-bedroom condo on Longboat Key. E ...
From $357 per night (USD)
VRBO
From $609 per night (USD)
VRBO
Bright and Sunny Oceanfront Villa With Pool + Lanai | Hosts 6
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your private slice of paradise on the coveted Longboat Key. Nestled beachfront, this two-bedroom villa offe ...
From $609 per night (USD)
VRBO
From $240 per night (USD)
VRBO
Courtside Getaway – Cedars East #653 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 $240 per night (USD)
VRBO
From $336 per night (USD)
Expedia
Arts & Vines: LBK Pool Spa Dog Friendly by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This home requires a 28-night minimum stay. Arts and Vines by Anna Maria Life Vacation Rentals 6836 Pine St, Longboat K ...
From $336 per night (USD)
Expedia
From $235 per night (USD)
VRBO
Charming 2-bedroom condo in marvelous Longboat Key with WiFi, AC.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in Longboat Key, this condo is a dream. With 2 bedrooms featuring 1 king bed and 1 queen bed, guests will feel r ...
From $235 per night (USD)
VRBO
From $433 per night (USD)
VRBO
Beautifully renovated 3 bedroom ocean view condo on Longboat Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Located on the very end of the key, Three Seas is the perfect condo that sits directly off one of the most beautiful bea ...
From $433 per night (USD)
VRBO
From $278 per night (USD)
VRBO
SARASOTA LongBoat Key Florida Veranda Beach Club
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Veranda Beach Club on Longboat Key is all about the simple pleasures of a Florida vacation– Swimming, sunbathing on chai ...
From $278 per night (USD)
VRBO
From $363 per night (USD)
VRBO
Terrific Island Village Hideaway
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Tropical 3-bed, 2-bath ranch on large corner lot. Hurricane rebuild, all new! Kitchen features SS appliances including c ...
From $363 per night (USD)
VRBO
From $413 per night (USD)
VRBO
Luxury Coastal Escape in Longboat Key, Florida-Beachfront Condo for Rent!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience resort-style living in this beautifully updated sixth-floor condo at Promenade. The expansive open floor plan ...
From $413 per night (USD)
VRBO
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Expedia
Stunning, resort like, Longboat Key, 2-bedroom condo on Gulf beach, near stores!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover the beauty of Longboat Key from this elegant, resort like, 2-bedroom, 2-bath condo at the Islander Club located ...
Click For Pricing
Expedia
From $643 per night (USD)
VRBO
Whitney Beach at Longboat Key, 325 3 Bedroom Spacious Condo, First Floor
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover this 3-bedroom gem in Longboat Key. Wake up to the sound of waves and enjoy direct beach access just a few fe ...
From $643 per night (USD)
VRBO
From $259 per night (USD)
VRBO
Gulf front 2-bedroom condo with private beach central Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Consider this condo your home away from home while you visit Longboat Key. This adorable property features 2 bedrooms - ...
From $259 per night (USD)
VRBO
From $229 per night (USD)
VRBO
Quiet beach and sunset views in Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This spacious (1336 sq ft + balcony) condo offers breathtaking panoramic views of the beach, sunset, and Gulf of Mexico. ...
From $229 per night (USD)
VRBO
From $376 per night (USD)
Expedia
1901 Harbour Links Circle #1 by RVA
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located in Emerald Pointe, with deeded beach access to the private Bay Isles Beach Club on the Gulf of Mexico. With its ...
From $376 per night (USD)
Expedia
From $172 per night (USD)
VRBO
LBK Whitney Beach Retreat 1
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Highlights • Three-minute Walk to Whitney Beach • 1 Bedroom, 2 Bathroom • 1 King, 1 Queen sleeper sofa • Two heated comm ...
From $172 per night (USD)
VRBO
From $279 per night (USD)
Expedia
2-bedroom condo in beautiful Longboat Key with fitness room, AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This charming condo in Longboat Key is a fabulous choice for guests looking for a cozy retreat. With 2 bedrooms includin ...
From $279 per night (USD)
Expedia
From $270 per night (USD)
VRBO
No Longer Available! Spacious 2-BR/2 Bath Condo at Seaplace in Longboat Key, FL
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
3 month minimum stay Spacious (1257 sqft), 2nd floor, non-smoking, 2 bedroom/2 bathroom condo with screened lanai. The ...
From $270 per night (USD)
VRBO
From $145 per night (USD)
Expedia
2-bedroom, 1.5-bath townhome, Pool, Bay Access
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Sutton Place 577 – Old Florida Charm on Longboat Key Offered by Florida Vacation Connection, Sutton Place 577 invites y ...
From $145 per night (USD)
Expedia
Click For Pricing
VRBO
2/2 Canal front condo, Pool, Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Longboat Harbour D303 – Waterfront Getaway Welcome to Longboat Harbour D303, a bright and inviting 2-bedroom, 2-bath co ...
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VRBO
From $241 per night (USD)
Expedia
Bayfront Escape- Beach Harbor Club F202
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Bayfront Escape at Beach Harbor Club with Rooftop Deck for Stunning Sunsets, Dolphin & Manatee Watching Experience the ...
From $241 per night (USD)
Expedia
From $492 per night (USD)
VRBO
Peacock Place LBK - Gorgeous 3-bedroom house in Longboat Key
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Welcome to paradise! This tropical island retreat is located in a quiet residential area on the north end of Longboat ...
From $492 per night (USD)
VRBO
From $673 per night (USD)
Expedia
Canal-Front Charmer with Private Beach Access!
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
Escape to this beautiful 4-bedroom, 2-bath canal-front retreat on Longboat Key—perfect for families or groups seeking t ...
From $673 per night (USD)
Expedia
From $204 per night (USD)
VRBO
Wonderful Gulf and Sunset Views Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Privateer North 305, an exceptional beachfront condo located on the prestigious south end of Longboat Key, be ...
From $204 per night (USD)
VRBO
From $213 per night (USD)
VRBO
Charming 2-bedroom house in gorgeous Longboat Key
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This 2-bedroom house is perfect for your escape to Longboat Key. With 2 queen beds, nicely renovated bathroom, full kitc ...
From $213 per night (USD)
VRBO
From $212 per night (USD)
VRBO
Beach Villa on Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Your home away from home in Longboat Key with 2 bedrooms. This adorable villa features 1 king bed and 1 queen bed, perfe ...
From $212 per night (USD)
VRBO
From $316 per night (USD)
Expedia
HVC #203 - Spa/Pool - Private Paradise on LBK!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Looking for the ULTIMATE Beach getaway? This is it! Welcome to paradise at the Harbour Villa Club. 2 Bedrooms, 2 Bath ...
From $316 per night (USD)
Expedia
From $196 per night (USD)
VRBO
Stunning gulf front 6th floor Longboat Key Condo with endless views - Once Upon A Tide
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This magnificent Gulf front vacation retreat sits on the 6th floor of the prestigious Westchester of Longboat Key, while ...
From $196 per night (USD)
VRBO
From $518 per night (USD)
Expedia
Beachplace 8-305 by FGC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Property Newly Available - Fully Remodeled - Direct Beachfront Beautiful beachfront unit on the 3rd floor of building ...
From $518 per night (USD)
Expedia
From $309 per night (USD)
VRBO
Tarawitt Tides- 2B / 2B, Stunning and Close to the Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your coastal escape at 600 Tarawitt Drive on beautiful Longboat Key. This completely renovated 2-bedroom, 2-b ...
From $309 per night (USD)
VRBO
From $1193 per night (USD)
VRBO
Gulf View - An exceptional, 3 Bed/4 Bath Gulf-front retreat by The Bay and Key Collection
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Experience one of Longboat Key's most prestigious beachfront addresses at The Water Club. This is an exceptional luxury ...
From $1193 per night (USD)
VRBO
From $250 per night (USD)
VRBO
Lovely Gulf Front 2-bedroom condo with in charming Longboat Key. First floor.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Your cozy getaway awaits in Longboat Key at this pleasant condo. With two bedrooms featuring a king bed and a twin bed, ...
From $250 per night (USD)
VRBO
From $461 per night (USD)
Expedia
Beachplace Oasis on the south end of Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Newly renovated! Open and airy, seamless flooring runs throughout the unit with a mid-century modern design. Bright li ...
From $461 per night (USD)
Expedia
From $177 per night (USD)
VRBO
Beautifully renovated Longboat Key Villa brief walk to a private beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful villa- you can’t get closer to a private beach as this one is a short stroll from the unit. This lovely, spaci ...
From $177 per night (USD)
VRBO
From $223 per night (USD)
VRBO
Seaplace 2BR/2BA Condo On LBK, Beachfront, Bldg Closest To The Beach, Sleeps 4-6
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Completely renovated, ground floor 2BR/2BA unit in building closest to the beach. Sleeps 4. Garden views. Offered furnis ...
From $223 per night (USD)
VRBO
From $263 per night (USD)
VRBO
The Salt House 2 BR / 1.5 BA Canal Front Home by RVA
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Your Coastal Getaway on Longboat Key Welcome to your laid-back Florida escape! This charming canal-front home is the pe ...
From $263 per night (USD)
VRBO
From $359 per night (USD)
Expedia
Sunset at Banyan Bay|Gulf-Front Condo on Longboat Key Beach+Pool+Tennis |Sleep 8
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: Sunset at Banyan Bay is a 2nd-floor Gulf-front condo on Longboat Key — one of Florida's most serene and beauti ...
From $359 per night (USD)
Expedia
From $211 per night (USD)
VRBO
Dos Palmas | Canal-Front with Boat Dock on Longboat Key, Sleeps 4, by The Bay and Key Collection
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Dos Palmas, a peaceful Longboat Key home designed for guests looking to slow down, settle in, and enjoy Flori ...
From $211 per night (USD)
VRBO
From $463 per night (USD)
Expedia
Sea Club III #4 2B / 2B Direct Beachfront Condo by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sea Club III #4 – Direct Beachfront Vacation Rental on Longboat Key Wake up to breathtaking Gulf of Mexico views and th ...
From $463 per night (USD)
Expedia
From $432 per night (USD)
VRBO
Premium Gulf Coast condo awaits you in beautiful Longboat Key, Florida
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hello! We are the new owners of this lovely locale, which earned in 52 previous reviews, 4.9 stars out of 5. Thank for ...
From $432 per night (USD)
VRBO
From $421 per night (USD)
Expedia
Walk-Out Beachfront Condo | Sleeps 7 | Heated Pool | Old Florida Charm
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
This adorable Beach Front unit sleeps 7 in Cedars West where families, couples and friends have vacationed time after ti ...
From $421 per night (USD)
Expedia
From $695 per night (USD)
VRBO
Stunning Beachfront, Gulf-to-Bay Views, 3 Bedroom Corner Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to this beautiful beachfront condo on Longboat Key! This spacious 2,000-square-foot fourth story corner unit an ...
From $695 per night (USD)
VRBO
From $411 per night (USD)
Expedia
Gayle By The Gulf- 3 BR / 3.5 BA Private Home by RVA
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Gayle By The Gulf — Your Perfect Longboat Key Getaway Welcome to Gayle By The Gulf, a spacious and beautifully appointe ...
From $411 per night (USD)
Expedia
From $203 per night (USD)
VRBO
Perfect Beach View 2 Bedroom Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
NEW LISTING !!! 3-401 at Beachplace | Gulf-Front Luxury on Longboat Key Experience the pinnacle of coastal living in th ...
From $203 per night (USD)
VRBO
From $198 per night (USD)
Expedia
2 bedroom 2 bath Luxury Bayfront condo on Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Bayport 825, a beautifully updated two-bedroom, two-bathroom condo at Bayport Beach and Tennis Club on Longbo ...
From $198 per night (USD)
Expedia
From $232 per night (USD)
VRBO
Sutton Place #303A 2 BR / 2 BA Waterfront Condo by RVA
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sutton Place #303A Welcome to your perfect Florida getaway at 605 Sutton Place #303A! This beautifully located 2-bedroo ...
From $232 per night (USD)
VRBO
From $450 per night (USD)
Expedia
Beach view first floor Unit 104
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Vacation condo unit 104 is a one-bedroom, one-bath deluxe first-floor condo that allows you to walk out right to the bea ...
From $450 per night (USD)
Expedia
From $454 per night (USD)
VRBO
Beachfront I Private Deck I Pool I Villa 83
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape to coastal serenity at this private 1-bedroom, 1-bath villa located beach side on Longboat Key, Florida. Perfect ...
From $454 per night (USD)
VRBO
From $454 per night (USD)
Expedia
Beach view unit 303
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Enjoy the large living room area with a Queen Sleeper sofa, there`s plenty of room for 6 in this condo. Features of this ...
From $454 per night (USD)
Expedia
From $454 per night (USD)
VRBO
Beach view unit 302
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
We welcome you to this great one bedroom, one bath condo that can sleep up to 6 persons. It overlooks the awesome beache ...
From $454 per night (USD)
VRBO
From $454 per night (USD)
Expedia
Beach view unit 204
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
In vacation condo 204 you`ll enjoy a sweeping second floor view from your private balcony. Enjoy beautiful sunsets from ...
From $454 per night (USD)
Expedia
From $454 per night (USD)
VRBO
Beach view first floor Unit 102
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Vacation condo unit 102 is a one-bedroom, one-bath deluxe first-floor condo that allows you to walk out right to the bea ...
From $454 per night (USD)
VRBO
From $454 per night (USD)
Expedia
Beach view unit 103
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Nice large King Suite with ground floor walkout to the beach! Vacation condo 103 is a first-floor walk-out located on t ...
From $454 per night (USD)
Expedia
From $454 per night (USD)
VRBO
Beach view unit 502
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Vacation condo 502 is a 5th floor one bedroom, one bath vacation condo with a private balcony that overlooks the beach. ...
From $454 per night (USD)
VRBO
From $470 per night (USD)
Expedia
Turtle Crawl Villa 81
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your perfect beach vacation awaits in this 2-bedroom, 1 1/2-bath home located beach side on Longboat Key, Florida. Perf ...
From $470 per night (USD)
Expedia
From $593 per night (USD)
VRBO
Beach view unit 504
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Vacation condo 504 is a one bedroom condo on the fifth floor with a private balcony. It`s a great place to enjoy the sou ...
From $593 per night (USD)
VRBO
From $454 per night (USD)
Expedia
Beach view unit 404
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This cozy and modern apartment welcomes you for a perfect vacation. Condo 404 is a bright corner unit which offers a fan ...
From $454 per night (USD)
Expedia
From $386 per night (USD)
VRBO
Luxury at its best at Turtle Crawl Resort
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Enjoy the beauty of this fully equipped condo unit in the famous resort in Longboat Key, Florida. Walk the private beach ...
From $386 per night (USD)
VRBO
From $243 per night (USD)
Expedia
Lita Casita- 2 BR / 2 BA Private Home in Longboat Village by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your Longboat Key escape! Tucked away on a quiet residential street, this home offers the perfect setting to ...
From $243 per night (USD)
Expedia
From $297 per night (USD)
VRBO
Jungle Queen Paradise- 2 BR / 2 BA Canal Front Home by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your own slice of paradise on beautiful Longboat Key! This charming 2-bedroom, 2-bath canal-front home is the ...
From $297 per night (USD)
VRBO
From $382 per night (USD)
Expedia
2 bedroom 2 bath Luxury Beachfront condo on Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Islander Club 63S, a beautifully updated sixth-floor condo where breathtaking views of the Gulf of Mexico cre ...
From $382 per night (USD)
Expedia
From $193 per night (USD)
VRBO
Starfish Shore - Walk to Beach, Pool & Club by The Bay & Key Collection
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Starfish Shore, a charming 2-bedroom coastal retreat just a short walk from deeded Gulf beach access. Enjoy y ...
From $193 per night (USD)
VRBO
From $184 per night (USD)
VRBO
Starfish Sands - Walk to Beach, Pool & Club by The Bay & Key Collections
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to Longboat Key at Starfish Sands, a bright 2-bedroom, 2-bath coastal retreat just a short walk from deeded Gulf ...
From $184 per night (USD)
VRBO
From $312 per night (USD)
VRBO
Renovated 2/2 BEACH VIEW, Pool, Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Players Club 402, a beautifully renovated 2-bedroom, 2-bathroom beachfront condominium located on the pristin ...
From $312 per night (USD)
VRBO
From $274 per night (USD)
VRBO
Newly renovated two bedroom/two bathroom condo in LBK
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Gorgeous coastal renovation, waterfront location, deeded beach, pet friendly and more. Enjoy this new, fully renovated t ...
From $274 per night (USD)
VRBO
From $344 per night (USD)
VRBO
Longboat Key Modern Beach House Gem
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Discover the magic of Longboat Key! Relax and refresh at this spacious and Beautiful, newly renovated, unique and tranqu ...
From $344 per night (USD)
VRBO
From $436 per night (USD)
Expedia
Gulf-View Beachfront Condo – Unit 203 – Longboat Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Just renovated, everything is new. A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mex ...
From $436 per night (USD)
Expedia
From $559 per night (USD)
VRBO
Gr8 Vibes by Duncan Real Estate
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Gr8 Vibes at the Sea Club III Complex on beautiful Longboat Key! A beachfront escape directly on the Gulf of ...
From $559 per night (USD)
VRBO
Click For Pricing
VRBO
Gulf and Bay View Newly Renovated Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Totally renovated 2 Bedroom & 2 Bath 4th floor Condo in the Beachplace gated community with beautiful views of the Gulf ...
Click For Pricing
VRBO
From $248 per night (USD)
VRBO
2 bedroom 2 bath. Peaceful, Sunsets, White sands !! On the Gulf
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in Longboat Key, enjoy what this 2-bedroom cottage has to offer. The welcoming space features a king bed and a t ...
From $248 per night (USD)
VRBO
From $276 per night (USD)
VRBO
Longboat Key Waterfront Condo, Private Beach Access under 5 min walk to the sand
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Exceptional waterfront community with private beach access. Immaculate unit, fully furnished, open floor plan. Beautiful ...
From $276 per night (USD)
VRBO
From $302 per night (USD)
VRBO
2/2 RENOVATED Condo, Beach/Pools/Fitness/Tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Seaplace G6-405 by Florida Vacation Connection – Your Perfect Longboat Key Getaway Experience coastal comfor ...
From $302 per night (USD)
VRBO
From $252 per night (USD)
VRBO
Longboat Key - Bayport Beach & Tennis Club Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Longboat Key - Bayport Beach & Tennis Club condo. This 1,623 SQFT, 2 bedroom, 2 bathroom gives you the space, tranquili ...
From $252 per night (USD)
VRBO
From $313 per night (USD)
VRBO
The Blue Bungalow
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Keep it simple at this peaceful retreat. Walking distance to the island’s best restaurants, it is perfect for couples, a ...
From $313 per night (USD)
VRBO
From $412 per night (USD)
Expedia
Sunset and beach view from your balcony Unit 501
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Unit 501 is a stunning corner condo offering unobstructed views of the Gulf of Mexico and extra space thanks to its desi ...
From $412 per night (USD)
Expedia
From $309 per night (USD)
VRBO
Gulf & Greenbelt Views, No-Expense-Spared Remodel, Seaplace Oasis
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to paradise in this completely remodeled, no-expense-spared 2nd floor end-unit condo with no unit above at the ga ...
From $309 per night (USD)
VRBO
From $837 per night (USD)
Expedia
1001 Longboat Club Road by FGC
Bedrooms:
6
Bathrooms:
5
Sleeps:
12
Welcome to a residence where architectural grandeur meets modern luxury. Newly built in 2025, this fully furnished estat ...
From $837 per night (USD)
Expedia
From $230 per night (USD)
VRBO
Great Beach View 2 Bedroom Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful Beachplace beachfront unit on the 3rd floor spectacular Gulf and beach view. Has brand new windows and doors ...
From $230 per night (USD)
VRBO
From $490 per night (USD)
Expedia
Beachcomber unit 408
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
A Rare Gulf-Front Oasis!This unit offers ultimate relaxation on the gulf, located at The Beachcomber on Longboat Key, it ...
From $490 per night (USD)
Expedia
From $288 per night (USD)
VRBO
Beachview 2/2 condo, Pool, Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your Sunset Beach Retro Retreat by FVC, a fun, funky 2-bedroom, 2-bath condo on beautiful Longboat Key where ...
From $288 per night (USD)
VRBO
From $381 per night (USD)
Expedia
2/2 Bay Front Condo, Pool, Private Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your Longboat Key getaway at Buttonwood Cove 103C, a beautifully renovated 2-bedroom, 2-bath condo where comf ...
From $381 per night (USD)
Expedia
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VRBO
Renovated 2 Bed, 2 Bath, Beachfront w/ Gulf views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Arbomar 802 – Longboat Key Direct Gulf-Front | Newly Renovated 2-Bedroom Condo Welcome to Arbomar 802, an eighth-floor ...
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VRBO
From $656 per night (USD)
Expedia
Charming upper floor condo with Pool, Hot Tub, Tennis Courts and Fitness Center
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Luxury Longboat Key Retreat – Gulf & Bay Views, Private Beach Access, and Premier Resort Amenities. Welcome to your el ...
From $656 per night (USD)
Expedia
From $454 per night (USD)
VRBO
Oceanfront Condo with panoramic Gulf Views, Pool, Hot Tub and Fitness Center
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The Privateer – Gulf-Front Luxury with Panoramic Ocean Views and Resort-Style Amenities Welcome to The Privateer, one o ...
From $454 per night (USD)
VRBO
From $461 per night (USD)
Expedia
Beachplace 3 - 203 by FGC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful condo with pool and Gulf view. 2 bedroom, 2 bathrooms and very comfortable. Relax on your private balcony. ...
From $461 per night (USD)
Expedia
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VRBO
The Pierre 906 by FGC
Bedrooms:
3
Bathrooms:
3
Sleeps:
4
2 full bedrooms plus Den with pocket doors to make a 3rd bedroom with pullout. 3 Full Bathrooms. Amazing views of the ...
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VRBO
From $232 per night (USD)
Expedia
Partial Beach View 2 Bedroom Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful unit on the 3rd floor with pool view and partial Gulf. Beautifully appointed 2 bedroom, 2 bath unit with many ...
From $232 per night (USD)
Expedia
From $287 per night (USD)
VRBO
Beachplace 4 - 505 (3BR) by FGC
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful beachfront unit on the 5th floor with lake view and partial Gulf. Beautifully appointed 3 bedroom, 2 bath uni ...
From $287 per night (USD)
VRBO
From $298 per night (USD)
Expedia
Beautiful 2 BR Condo With Private Beach Access Sunset On The Gulf
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Sunset On The Gulf! Professionally managed by Gulf Coast Vacation Rentals. This gorgeous 2-bedroom, 2-bathroo ...
From $298 per night (USD)
Expedia
From $167 per night (USD)
VRBO
Longboat Key Paradise! Pool ~ Beach ~ Kayaking ~ Shopping
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Seasonal And Monthly Rental. Beautifully remodeled 1st floor Whitney Beach condo where you can enjoy the easy carefree ...
From $167 per night (USD)
VRBO
From $315 per night (USD)
Expedia
Charming 2-bedroom condo overlooking Sarasota Bay on Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to this brilliant condo in picturesque Longboat Key. This cozy retreat features 2 bedrooms with a king bed and fu ...
From $315 per night (USD)
Expedia
From $395 per night (USD)
VRBO
Luxe Waterfront Condo on Longboat Key - Beach Breeze
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Beach Breeze in Windward Bay, a stunning second-floor 2-bedroom, 2-bathroom condo perfectly situated along th ...
From $395 per night (USD)
VRBO
From $414 per night (USD)
Expedia
Longboat Harbor #107E Condo by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Relaxed Coastal Living at Longboat Harbour Welcome to your island retreat at Longboat Harbour, a gated waterfront commu ...
From $414 per night (USD)
Expedia
From $233 per night (USD)
VRBO
Enjoy the best of both beach and bay! 2 Bedroom, 2 Bathroom waterfront condo.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled in Longboat Key, this delightful condo boasts 2 bedrooms - one with a king bed, the other with two full beds an ...
From $233 per night (USD)
VRBO
From $526 per night (USD)
Expedia
2 Salty by Duncan Real Estate
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to 2 Salty at the Sea Club III complex on beautiful Longboat Key! A beachfront escape directly on the Gulf of Me ...
From $526 per night (USD)
Expedia
From $365 per night (USD)
VRBO
Renovated 3/3.5 Pool home, Private Beach Access
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Bayou Breeze Retreat is a newly furnished 3BR/3.5BA home in the exclusive gated Bay Isles community on Longboat Key. Fea ...
From $365 per night (USD)
VRBO
From $267 per night (USD)
Expedia
Casa Poinsetta- 2BR in a Quiet Coastal Neighborhood by RVA.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your island getaway at 6960 Poinsettia Avenue, a bright and breezy 2-bedroom, 2-bath home just a short stroll ...
From $267 per night (USD)
Expedia
From $267 per night (USD)
VRBO
Luxury Bayfront Condo | Stunning Views, Pools & Beach Across Street
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to Bay Dream Believer, your elegant bayfront retreat on beautiful Longboat Key, Florida. This stunning 2-bedroom ...
From $267 per night (USD)
VRBO
From $349 per night (USD)
Expedia
2/2 Gulf View condo at Beachplace on Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachplace 5-401 | Pond and Beach Views | Florida Vacation Connection Welcome to Beachplace 5-401, your serene getaway ...
From $349 per night (USD)
Expedia

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Results: 761 Rentals