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 $328 per night (USD)
VRBO
2BR Cottage Bayside of Property, Full Resort Amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Longboat Key is a haven for wildlife lovers, where you might spot tortoises, egrets, wild parrots, and even the island's ...
From $328 per night (USD)
VRBO
From $391 per night (USD)
Expedia
2BR Swap Work Blues for Blue Skies at Little Gull
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This spacious retreat features a king bed in the main bedroom, ideal for recharging after a day of beach adventures. The ...
From $391 per night (USD)
Expedia
From $600 per night (USD)
VRBO
Your Home Away from Home: Little Gull 4BR Cottage
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Situated bayside with breathtaking views, this four-bedroom cottage is the ideal spot for your Florida beach getaway. Th ...
From $600 per night (USD)
VRBO
From $445 per night (USD)
Expedia
Relax and Recharge in this 1BR Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape to this charming bayside cottage, featuring a spacious main bedroom with a king bed and a living room with a fire ...
From $445 per night (USD)
Expedia
From $402 per night (USD)
VRBO
2BR Cottage Gulf Side of Property, Resort Amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Looking to relive the beach vacations of your childhood—minus the car fights and soggy bread? Welcome to your grown-up v ...
From $402 per night (USD)
VRBO
From $536 per night (USD)
Expedia
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 $536 per night (USD)
Expedia
From $149 per night (USD)
VRBO
Steps from the beach on Longboat Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Charming, one-of-a-kind property in a boutique-like setting with only 11 other units. There is a beautiful, heated pool ...
From $149 per night (USD)
VRBO
From $138 per night (USD)
VRBO
Waterfront Getaway Island Beach Villa at Longboat Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Relax or work remotely at our Waterfront Island Villa on LBK. Nestled 1 block from the beach & on Sarasota Bay, enjoy wa ...
From $138 per night (USD)
VRBO
From $301 per night (USD)
VRBO
Beachfront Bliss: 2/2 with Stunning Gulf Views!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Dolphin's Retreat, where you can experience the ultimate beachfront vacation! 🏡 Property Highlights: ✨ Bea ...
From $301 per night (USD)
VRBO
From $515 per night (USD)
Expedia
Relaxing Beachside Retreat on Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Newly Renovated!! Sunny southern exposure abounds from this charming 2 bedroom 2 bath get a way at Beachplace. This thi ...
From $515 per night (USD)
Expedia
From $235 per night (USD)
VRBO
Sutton Place with Private Beach, Pavilion with Grills/Showers, 2 Pools
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to paradise with this beautifully furnished 2-bedroom, 2-bathroom townhome on Longboat Key, Florida. With a beach ...
From $235 per night (USD)
VRBO
From $178 per night (USD)
VRBO
Gulf Beach front Club Longboat Beach & Tennis Assoc 2BDR 2BA Furn Condo Walk Out
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
RATE/AVAILABILITY NOTE: 30 DAY ASSOCIATION MINIMUM BOOKING average In season rental rates (Dec $175)/night (Jan-Apr) ...
From $178 per night (USD)
VRBO
From $308 per night (USD)
VRBO
2/2 Direct Beachfront Condo, Pool, Fitness, Tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachfront Bliss at Beachplace – Your Longboat Key Retreat Welcome to your dream coastal getaway, professionally manag ...
From $308 per night (USD)
VRBO
From $310 per night (USD)
VRBO
Seas The Day at Whitney Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to the Gulf Coast to an easy access first floor, 2 bedroom / 2 full bath condo. Beautifully decorated with a coa ...
From $310 per night (USD)
VRBO
From $263 per night (USD)
VRBO
Gorgeous Remodeled 2 Bedroom Longboat Key Condo with Stunning Bay Views!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful 2 bedroom/2 bath recently updated condo on Longboat Key looking over stunning Sarasota Bay. Top 3rd floor -wi ...
From $263 per night (USD)
VRBO
From $431 per night (USD)
VRBO
3bed/2bath Beachfront Condo on Longboat Key!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful 3bed/2bath Condo located on the 3rd floor of Tiffany Plaza with gorgeous views of the crystal blue waters of t ...
From $431 per night (USD)
VRBO
From $514 per night (USD)
VRBO
Whitney Beach 321 2brm beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Immerse yourself in refined luxury with this impeccably designed Whitney Beach #321. This condo offers spaciou ...
From $514 per night (USD)
VRBO
From $312 per night (USD)
Expedia
Whitney Beach 319 2brm beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Experience this ground floor 2 brm/2 bath Unit# 319 at the Whitney Beach III condo complex on Longboat Key. En ...
From $312 per night (USD)
Expedia
From $194 per night (USD)
VRBO
Beachfront Luxury Rental | Longboat Key Condo | Ground-Floor, King Bed
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Discover your Longboat Key beachfront luxury rental for a required one-month minimum stay. This completely ren ...
From $194 per night (USD)
VRBO
From $254 per night (USD)
Expedia
Beachplace 7 - 202 by FGC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful beachfront unit on the 2nd floor with lake view and partial Gulf. This is a beautifully appointed 2 bedroom, ...
From $254 per night (USD)
Expedia
From $284 per night (USD)
VRBO
Tropical Escape–Private Pool Home Near the Sand Hy Tee on Longboat Key by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Hy Tee, a charming coastal retreat nestled on Longboat Key, Florida. This beautiful vacation home promises a ...
From $284 per night (USD)
VRBO
From $357 per night (USD)
Expedia
Beachplace 9 - 501 by FGC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sought after beachfront unit on the 5th floor of building 9 and an end unit. 2 bedroom, 2 bath unit with stunning views ...
From $357 per night (USD)
Expedia
From $582 per night (USD)
VRBO
650 Norton - Longboat Key - Canal Home with private Pool - 3 Bedroom/ 2 Bath, maximum occupancy of 6 people. Distance to the Beach: 1 block
Bedrooms:
2
Bathrooms:
1
Sleeps:
6
650 Norton - Longboat Key - 3 Bedroom/ 2 Bath, maximum occupancy of 6 people. Canal Home - Private Pool - Distance to t ...
From $582 per night (USD)
VRBO
From $628 per night (USD)
VRBO
Longboat Key home rental w/ PRIVATE Pool & 1 minute to private beach access!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your dream rental home, perfectly positioned amid the Harbourside Course of the prestigious Longboat Key Club ...
From $628 per night (USD)
VRBO
From $422 per night (USD)
VRBO
Beach Castle Resort, 1st Floor, Pool, Walk to Beach/Bay
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to this tranquil resort on Longboat Key with heated pool, fully stocked kitchen and great local restaurants, park ...
From $422 per night (USD)
VRBO
From $534 per night (USD)
Expedia
Unit #101 Sand Cay, Gulf View, Steps to Beach, Recently Remodeled
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This privately located ground floor Gulf View unit was just remodeled with new paint and new luxury vinyl flooring. Well ...
From $534 per night (USD)
Expedia
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VRBO
Pura Vida 2 Bedroom Condo by RedAwning
Bedrooms:
2
Bathrooms:
2
Sleeps:
1
<p>Close to sailing, cycling, and more, this smoke-free condo brings it all within reach. Enjoy a short 5-minute walk to ...
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VRBO
From $184 per night (USD)
VRBO
Home away from home in LBK
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Relax with the whole family at this peaceful place to stay. The home offers an ample attached single car garage with sto ...
From $184 per night (USD)
VRBO
From $334 per night (USD)
VRBO
Beach Castle Resort, Pool, Private Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to It's A Shore Thing at the Beach Castle Resort, Unit 14! A tranquil oasis where the vibrant beachy theme and c ...
From $334 per night (USD)
VRBO
Click For Pricing
Expedia
Harbour Hideout: Condo on Longboat Key by RVA
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy elevated views that span the harbourside greens from the comfort of the 3BD/2BA villa residence positioned behind ...
Click For Pricing
Expedia
From $501 per night (USD)
VRBO
Beachfront Paradise on LBK - Steps to Sugar Sand, Gulf Waves and Magical Sunsets
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape to our stunning beach level oceanfront retreat on the Gulf of Mexico. Unwind amidst crystal clear waters, soft sa ...
From $501 per night (USD)
VRBO
From $238 per night (USD)
VRBO
2 bedroom/2bath private home in Longbeach Village on Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your vacation home! The elevated living space includes a master BR with en-suite bathroom and private balcony ...
From $238 per night (USD)
VRBO
From $77 per night (USD)
VRBO
Charming 2BR ground floor condo in Beach Harbor Club on Longboat Key - Sea Ya
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Sea Ya! Professionally managed by Gulf Coast Vacation Rentals. A condo in the desirable Beach Harbor Club on ...
From $77 per night (USD)
VRBO
From $312 per night (USD)
Expedia
Breathtaking beach views await from this 2BR 2nd floor condo on Longboat Key The Beach Fact Oar
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Breathtaking Direct Gulf views from this second-floor condo at Longboat Terrace. Perfect for a small family or travel wi ...
From $312 per night (USD)
Expedia
From $444 per night (USD)
VRBO
Gorgeous gulf views await from this 3/2 condo on Longboat Key - Snow On The Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This unit is located in the Islander Club, one of the best communities on the Gulf of Mexico. Professionally managed by ...
From $444 per night (USD)
VRBO
From $321 per night (USD)
Expedia
Waterfront, Spa/Pool, Private Paradise On Longboat Key!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
NOTE: BOOKING JANUARY or FEBRUARY? Please book whole months only NOT mid-month to mid-month. This time frame is a monthl ...
From $321 per night (USD)
Expedia
From $231 per night (USD)
VRBO
Condo- steps to the sand
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your beachfront paradise! Escape to the ultimate seaside getaway and create lasting memories at our stunning ...
From $231 per night (USD)
VRBO
From $381 per night (USD)
Expedia
Waves, White Sand & Private Beach at Club Longboat #312 Condo by RVA
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your very own slice of paradise on Longboat Key! #312 at Club Longboat Beach and Tennis Resort is a stunning ...
From $381 per night (USD)
Expedia
From $762 per night (USD)
VRBO
Beachfront 4th floor 4BR Longboat Key Condo With Stunning Gulf Views Paradise Sur Mer
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Experience the best of Longboat Key at Paradis Sur Mer, professionally managed by Gulf Coast Vacation Rentals. This stun ...
From $762 per night (USD)
VRBO
From $371 per night (USD)
VRBO
Gulf of Mexico Beach Front ....Walk out condo steps from the private beach!!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautiful main floor two plus bedroom condo with stunning views of the Gulf! Never miss a sunset, watch from the condo o ...
From $371 per night (USD)
VRBO
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VRBO
Gorgeous Beachside Condo in superior Longboat Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Great beach and Gulf views are breathtaking from your balcony, living room, kitchen and dining room of the Penthouse con ...
Click For Pricing
VRBO
From $277 per night (USD)
Expedia
Full Beach View 2 Bedroom Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Perfect beach view elevated walkdown level fully renovated 2 bedroom condo offers modern luxury. It is paradise within p ...
From $277 per night (USD)
Expedia
From $318 per night (USD)
VRBO
Longboat Key Beachfront Resort with Tennis by The Bay & Key Collection
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to a newly remodeled beachside condo featuring 3 bedrooms and 2 bathrooms, just steps from the soft, sandy shore. ...
From $318 per night (USD)
VRBO
From $248 per night (USD)
Expedia
Magnificent Oceanfront 2 BR Condo in Longboat Key - The Lookout
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to The Lookout! Professionally managed by Gulf Coast Vacation Rentals. This charming fourth-floor 2-bedroom, 2-b ...
From $248 per night (USD)
Expedia
From $708 per night (USD)
VRBO
One-of-a-Kind Villa in Beach Castle! Direct Views of the Bay, Walk to Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Escape to the pristine white sandy shores of Longboat Key and experience the epitome of waterfront luxury in this exquis ...
From $708 per night (USD)
VRBO
From $364 per night (USD)
VRBO
OceanVista Beachfront Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to the beauty of Southern Longboat Key with this stunning direct Gulf front vacation rental. From the moment you ...
From $364 per night (USD)
VRBO
From $234 per night (USD)
VRBO
Beach lovers dream
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our 1st floor beachside condominium, just steps from the beach on Longboat Key. The spacious three bedroom, t ...
From $234 per night (USD)
VRBO
From $602 per night (USD)
VRBO
Sea Club Iii Beachside Condo ON Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sea Club Iii - Weekly Vacation Rental - Beachside Condo ON Longboat Key. Perfect Location on the beaches of Longboat K ...
From $602 per night (USD)
VRBO
From $75 per night (USD)
VRBO
Bermuda-esque Island Cottage! Steps to Sand! Beach to Bay
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to this cozy, light-filled cottage, completely rebuilt in 2025 with a brand-new kitchen featuring stainless steel ...
From $75 per night (USD)
VRBO
From $144 per night (USD)
VRBO
Classic Cottage w/Boat Parking! Steps to Sand!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover this quaint one-bedroom guest house tucked away in a peaceful corner. Perfect blend of classic charm and modern ...
From $144 per night (USD)
VRBO
From $193 per night (USD)
VRBO
Beachplace 11-305 (3BR) by FGC
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
3 Bedroom and 2 Bath condo located in the resort community of Beachplace Association. Faces the golf course and has ac ...
From $193 per night (USD)
VRBO
From $338 per night (USD)
VRBO
Breathtaking view of Gulf of Mexico in every room. Located right on beach.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Great Gulf front condo perfect for your beach vacation. Amazing beach views and stylish beach decor Unit A303 is a great ...
From $338 per night (USD)
VRBO
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VRBO
Full Beachfront 2 BR Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful beachfront unit on the 5th floor with amazing beach and sunset views. 2 bedroom, 2 bath unit with many modern ...
Click For Pricing
VRBO
From $534 per night (USD)
VRBO
Longboat Key Townhouse in Cedars East, Longboat Key Florida
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Enjoy the beach life on Longboat Key! This property is ready for you to enjoy Longboat Key beaches. Kick back and relax ...
From $534 per night (USD)
VRBO
From $515 per night (USD)
VRBO
Beach Penthouse sleeps 10 - luxurious Longboat Key Beach Florida!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Up to Two weeks winter retreat- Penthouse on beach of Longboat sleeps up to 10! Jan 9th to the 23rd availibility! Verand ...
From $515 per night (USD)
VRBO
From $337 per night (USD)
VRBO
Fantastic Beach Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A one minute walk to the spectacular beach on the Gulf of Mexico, with sunshiny days and gorgeous sunsets! The complex o ...
From $337 per night (USD)
VRBO
From $182 per night (USD)
VRBO
Longboat Key 1st Floor 2 bed/2 bath, Bayside Recreation-Beach Across the Street
Bedrooms:
2
Bathrooms:
2
Sleeps:
2
Available March 1 for monthly or long-term rental. Updated Listing-Just Renovated Ground Floor 2 bed/2 bath Villa with a ...
From $182 per night (USD)
VRBO
From $360 per night (USD)
Expedia
Beachfront Condo in Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
TWO WEEK MINIMUM REQUIRED. Welcome to your ideal beachfront retreat in Longboat Key! This fully renovated condominium o ...
From $360 per night (USD)
Expedia
From $362 per night (USD)
VRBO
Luxury Longboat Key Condo - Walk to Beach Access!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to the sun-kissed shores of Longboat Key at this sunny 2-bedroom, 2-bathroom vacation rental. Just steps away fro ...
From $362 per night (USD)
VRBO
From $250 per night (USD)
Expedia
2 Bedroom Longboat Key Beachside Paradise. Steps from the Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your dream escape on Longboat Key, where breathtaking Gulf and Bay views greet you from every room. This full ...
From $250 per night (USD)
Expedia
From $425 per night (USD)
VRBO
Longboat Key Condo with a View
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Looking for a condo on the beach? This three bedroom condo is perfect. Located in the middle of the island it is walki ...
From $425 per night (USD)
VRBO
From $246 per night (USD)
Expedia
Adorable Villa at Cedars East, Tennis Resort, Longboat Key Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Your Dream Getaway on Longboat Key! This spacious 3-story townhome is located in the popular Cedars East Reso ...
From $246 per night (USD)
Expedia
From $345 per night (USD)
VRBO
Piece of Paradise
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Located on a most welcoming friendly street. This house with 3 bedrooms & 3 full bathrooms sits on a canal with dock and ...
From $345 per night (USD)
VRBO
From $487 per night (USD)
Expedia
Beautiful Oceanfront Beach Haven
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hurricane Update: Condo will be ready as of July 1, 2025. However the pool wont be ready till Aug 2025. During the month ...
From $487 per night (USD)
Expedia
From $346 per night (USD)
VRBO
Tiffany Plaza in Longboat Key, FL
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Longboat Key Gulf Front Vacation Rental! Enjoy fabulous views from almost every window in this 2 bed, 2 bath condo on th ...
From $346 per night (USD)
VRBO
From $309 per night (USD)
Expedia
Adorable Beachfront Studio, Private Beach, Originally Part of Starfish Motel
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Las Hermanas Unit 1, an adorable cozy beachfront studio nestled directly on the pristine shores of Longboat K ...
From $309 per night (USD)
Expedia
From $373 per night (USD)
VRBO
Beach Front Hidden Gem Steps to the Gulf and Sand
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Adorable hidden gem directly on the beach and Gulf of Mexico. Your own private beach with sun loungers and all the beach ...
From $373 per night (USD)
VRBO
From $397 per night (USD)
Expedia
Beachfront Cozy Condo: Sand n Gulf Steps Away
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape to the enchanting coastal haven of Las Hermanas #3, a hidden gem nestled within the idyllic landscape of Longboat ...
From $397 per night (USD)
Expedia
From $310 per night (USD)
VRBO
Charming Beach Front Studio Steps to the Sand and Gulf
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to paradise at Las Hermanas #4, a charming beachfront studio on Longboat Key. Nestled among three other units, th ...
From $310 per night (USD)
VRBO
From $541 per night (USD)
Expedia
Full Beach View 2 Bedroom Penthouse
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Penthouse level fully renovated 2 bedroom condo offers modern luxury. It is paradise within paradise. This is a very ra ...
From $541 per night (USD)
Expedia
From $588 per night (USD)
VRBO
Unit #202 Sand Cay Beach Resort Gulf Front
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Gulf Front Unit with panoramic gulf views in 3 directions. Fully remodeled in 2024, new to the rental program at Sand C ...
From $588 per night (USD)
VRBO
From $556 per night (USD)
Expedia
Newly renovated 2 bedroom beachfront condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Two full bedroom with bath- completely renovated beachfront condo on Longboat Key. Located on The Longboat Key resort a ...
From $556 per night (USD)
Expedia
From $524 per night (USD)
VRBO
Aqua Bay 3BR by RVA-Poolside Luxury, Pets Too
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Aqua Bay in Longboat Key Modern Key West Luxury | Walk to Beach | Monthly Longboat Key Vacation Rental Welcome to Aqua ...
From $524 per night (USD)
VRBO
From $1415 per night (USD)
VRBO
February 2027 NOW available! 3 minute walk to the beautiful white quartz sand.
Bedrooms:
5
Bathrooms:
6
Sleeps:
10
Embrace yourself with pure luxury and privacy, surrounded by lush landscaping and steps from the gorgeous Gulf of Mexico ...
From $1415 per night (USD)
VRBO
From $527 per night (USD)
VRBO
RENOVATED 4/3 Canal Front, Pool and Dock
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Soaring Spirits – A Newly Renovated Coastal Escape Proudly offered by FL Vacation Connection Step inside this beaut ...
From $527 per night (USD)
VRBO
From $1445 per night (USD)
Expedia
2/2 Beachfront, VIEWS, Pool, Private Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Luxurious 2-Bedroom Condo at Inn on the Beach - Longboat Key by Florida Vacation Connection. Immerse yourself in the ep ...
From $1445 per night (USD)
Expedia
From $255 per night (USD)
VRBO
Longboat Key Bay view and Walk to Beach on Gulf of Mexico
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Quiet Peaceful with great view of the pool while looking at the docks on the bay or walk to your own private beach. T ...
From $255 per night (USD)
VRBO
From $205 per night (USD)
VRBO
Longboat Key North Shore, BEAUTIFUL PRIVATE BEACH 1.5 blocks away.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Best beaches on the gulf coast are right here. This is a private 2 bed/2 bath beach cottage with a tropical backyard and ...
From $205 per night (USD)
VRBO
From $368 per night (USD)
VRBO
Sutton Place #102A Condo by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sutton Place is perfectly situated on the tropical grounds of the Longboat Harbour Community. The two-bedroom, two-bathr ...
From $368 per night (USD)
VRBO
From $283 per night (USD)
Expedia
Tropical Canal Home–Pool, Sun & Water Access: Paradise Cottage in LBK by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Prime Location! Discover this newly decorated seasonal rental on Longboat Key's picturesque canal. Nestled in South Long ...
From $283 per night (USD)
Expedia
From $239 per night (USD)
VRBO
Tranquil Waterfront home- Water, peace, sunshine, & sand, this is your place.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
If you like water, peace, sunshine, and sand, this is your place. Country Club Shores is one of the few single-family ...
From $239 per night (USD)
VRBO
From $520 per night (USD)
Expedia
Beach and Pool View 2 Bedroom Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to Your Beachfront Oasis Awaits! Imagine waking up to the sparkling turquoise waters of the Gulf just steps away ...
From $520 per night (USD)
Expedia
From $255 per night (USD)
VRBO
Updated, Adorable, Close to Beach and Shops
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your coastal oasis on Longboat Key, where relaxation meets sophistication in this beautifully updated 2 bedro ...
From $255 per night (USD)
VRBO
From $1086 per night (USD)
VRBO
Stunning 3 bedroom Gulf View Condo! Paradise awaits you!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to your luxurious Gulf-front retreat at En Provence! This stunning 3-bedroom, 3.5-bathroom condo offers 3400 squ ...
From $1086 per night (USD)
VRBO
From $533 per night (USD)
VRBO
Longboat Key Vacation Rental - Steps From Beach & Restaurants
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your island retreat! Now priced even more attractively and boasting coastal charm, this lushly landscaped res ...
From $533 per night (USD)
VRBO
From $901 per night (USD)
Expedia
Perfect Beach View Large 2 bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Short Term Stays available Imagine waking up to a breathtaking panorama of the Gulf of Mexico,. This completely remodele ...
From $901 per night (USD)
Expedia
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VRBO
Longboat Key Beach House
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
This quaint beach house with a private backyard and outdoor shower is everything you need to enjoy your relaxing Florida ...
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VRBO
From $306 per night (USD)
VRBO
Arbomar #701 - 4485 GMD - ON the Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
7th floor corner unit with balcony offering wide, sweeping view of the beach and Gulf. Both bedrooms offer clear view of ...
From $306 per night (USD)
VRBO
From $222 per night (USD)
VRBO
Turquoise Gem 1st Floor [no stairs] BEACH - TOP EATS - Longboat KeyFL
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Private BEACH Access! *Designer Renovation* Single level/Ground Level, 8 minute Walk to Bright White Quartz Sand, Welcom ...
From $222 per night (USD)
VRBO
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Expedia
3/2 Golf Course View, Pool, Private Beach Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Harbour Oaks, a stunning condo nestled within the Bay Isle community, offering a luxurious and spacious livin ...
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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. Seaplace is a wonderful community with two swimming pools ...
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VRBO
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Expedia
Longboat Key Towers 1004S by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Florida Vacation Connection proudly presents this exceptional corner-unit condo at the exclusive Longboat Key Towers—off ...
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Expedia
From $312 per night (USD)
VRBO
Family-friendly beachfront condo with pool and private lanai
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Relax with the whole family at this peaceful beachfront condo on private beach in beautiful Longboat Key. 2 Bedrooms, 2 ...
From $312 per night (USD)
VRBO
From $374 per night (USD)
Expedia
Weekly / Monthly Rental - Spacious Condo IN Longboat Key Resort Close TO Pool, Tennis And Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Vacation Rental - Spacious Townhouse IN Longboat Key Tennis Resort Close TO Pool And Beach! Located in the beautiful Ce ...
From $374 per night (USD)
Expedia
From $914 per night (USD)
VRBO
Sleepy Lagoon 4+bd/3.5ba canal home, 5 min walk to beach on LBK
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
Sleeps 10+ in 3 King ensuite bedrooms, 1 Queen sized in office, and 2 double beds bonus room. BRAND NEW turf backyard wi ...
From $914 per night (USD)
VRBO
From $233 per night (USD)
Expedia
Chic Longboat Key Retreat, Close to Beach and Dining!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Seven Palms Beach House by AMI Locals Welcome to Seven Palms Beach House, a stunning three-bedroom, three-bath coastal ...
From $233 per night (USD)
Expedia
From $681 per night (USD)
VRBO
Welcome to your seaside sanctuary! Nestled along the shores of Longboat Key.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Nestled along the tranquil shores , this modern 2-bedroom beach condo invites you to experience the ultimate coastal ret ...
From $681 per night (USD)
VRBO
From $270 per night (USD)
Expedia
Beautifully Updated, Cedars East, Beach, Pool and Tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover a slice of paradise at our beautifully updated vacation rental in the prestigious Cedars East Tennis Resort and ...
From $270 per night (USD)
Expedia
From $448 per night (USD)
VRBO
Tranquil 2BR at Whitney Beach–Sunroom, Pool View & Deeded Beach Access by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your dream getaway at Longboat Key! This charming, condo offers a delightful beach-to-bay lifestyle, making i ...
From $448 per night (USD)
VRBO
From $595 per night (USD)
Expedia
Luxurious 4BR pool home on Longboat Key steps to the beach - Longboat Dream
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Welcome to Longboat Dream! Professionally managed by Gulf Coast Vacation Rentals, experience this brand new 3-story resi ...
From $595 per night (USD)
Expedia

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Results: 761 Rentals