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 $338 per night (USD)
VRBO
Charming 2 BR Longboat Key condo with ocean view - Flirty Flamingo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in the highly sought-after Beachplace on Longboat Key and professionally managed by Gulf Coast Vacation Rentals, ...
From $338 per night (USD)
VRBO
From $567 per night (USD)
Expedia
Exquisite 3 BR / 3.5 BA home with pool and spa on Longboat Key - The Captain's Quarters
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to The Captain's Quarters! Professionally managed by Gulf Coast Vacation Rentals. This newly built Luxury Rental ...
From $567 per night (USD)
Expedia
From $433 per night (USD)
VRBO
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 $433 per night (USD)
VRBO
From $234 per night (USD)
Expedia
Condo- steps to the sand
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your beachfront paradise! Escape to the ultimate seaside getaway and create lasting memories at our stunning ...
From $234 per night (USD)
Expedia
From $315 per night (USD)
VRBO
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 $315 per night (USD)
VRBO
From $700 per night (USD)
Expedia
Beachfront 4th floor 4/4 Longboat Key Condo With Stunning Gulf Views - Paradise Sur Mer
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Paradis Sur Mer! Professionally managed by Gulf Coast Vacation Rentals, in need of an ocean view? We have you ...
From $700 per night (USD)
Expedia
From $404 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 $404 per night (USD)
VRBO
From $216 per night (USD)
Expedia
Magnificent sunlit beach retreat with pool, grill, balcony, W/D - close to water
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Freesia at Seaside Gardens Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $216 per night (USD)
Expedia
From $284 per night (USD)
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 ...
From $284 per night (USD)
VRBO
From $352 per night (USD)
VRBO
Longboat Key Beachfront Resort with Tennis by Gulfcoast Holiday Homes
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy a newly remodeled beachside vacation rental condo featuring 3 bedrooms and 2 bathrooms, just steps from the sandy ...
From $352 per night (USD)
VRBO
From $233 per night (USD)
VRBO
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 $233 per night (USD)
VRBO
From $153 per night (USD)
VRBO
Gorgeous canal front condo, fully equipped and just minutes from the beach.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
You'll love the carefree living at this condo. It's fully equipped for your daily needs with updates throughout. Spend y ...
From $153 per night (USD)
VRBO
From $423 per night (USD)
VRBO
Precise Realty presents Sunset Serenity
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your amazing beachfront vacation. The apartment has a fully appointed updated kitchen with plenty of storage ...
From $423 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
From $3312 per night (USD)
VRBO
Castle on-the-Bay - St. Armand’s/Lido Beach 6 BD, Pool/Spa, Boat & Jet Ski Dock
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
This St. Armand's bayfront estate home has spectacular panoramic views of Sarasota Bay and the downtown city lights. Th ...
From $3312 per night (USD)
VRBO
From $285 per night (USD)
Expedia
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 $285 per night (USD)
Expedia
From $322 per night (USD)
VRBO
DIRECT Gulf Front view from the 4th floor condo at Tiffany Plaza
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Looking to work remotely during the summer and fall? Why not consider working right on the beach? Direct Gulf Front Ren ...
From $322 per night (USD)
VRBO
From $524 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 o ...
From $524 per night (USD)
VRBO
From $135 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 $135 per night (USD)
VRBO
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Expedia
Spectacular penthouse on white sandy Longboat Key beach with incredible views.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located on the barrier island complete with wetlands, biking paths, and plenty of wild birds, Gulf Tides is a fantastic ...
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Expedia
From $328 per night (USD)
VRBO
Modern Beach Condo–Walk to Gulf, Pool + More Beach Harbor Club B305 by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to our exquisite beachfront getaway on Longboat Key – a newly updated 2-bedroom, 2-bath condo that promises an i ...
From $328 per night (USD)
VRBO
From $1102 per night (USD)
Expedia
Waterfront w/Putting Green, Heated Pool, Dock -Manatee Cove
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Manatee Cove by Lido Key Vacations Home in Sarasota, FL 34236 VR24-00003 Minimum stay duration of 7 days/nights Welcom ...
From $1102 per night (USD)
Expedia
From $1757 per night (USD)
VRBO
Waterfront home with private beach, a private pool, and water activities! Moku
Bedrooms:
5
Bathrooms:
5
Sleeps:
15
Moku by AMI Locals 7147 La Lenaire Dr Longboat Key, Florida BTR#12879.2025 and RRR-00784.2023 Welcome to Moku, a water ...
From $1757 per night (USD)
VRBO
From $221 per night (USD)
Expedia
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 $221 per night (USD)
Expedia
From $550 per night (USD)
VRBO
Full Beach View 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 ...
From $550 per night (USD)
VRBO
From $494 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 $494 per night (USD)
VRBO
From $520 per night (USD)
VRBO
Your warm, winter, paradise in luxurious Longboat Key Florida!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
One week Penthouse on beach of Longboat sleeps up to 10! Jan 18th to the 25th availibility! Veranda Longboat Key Beach R ...
From $520 per night (USD)
VRBO
From $300 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 $300 per night (USD)
VRBO
From $348 per night (USD)
VRBO
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 $348 per night (USD)
VRBO
From $305 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 $305 per night (USD)
VRBO
From $321 per night (USD)
VRBO
2BR East Unit of Beach to Bay Cottage...just 100 feet from Gulf Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
WE ARE BACK IN BUSINESS following the hurricanes! Come enjoy the 2 BR half of our 2- Unit Beach to Bay Cottage. New f ...
From $321 per night (USD)
VRBO
From $215 per night (USD)
Expedia
Longboat Key Beachside Paradise
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 $215 per night (USD)
Expedia
From $405 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 $405 per night (USD)
VRBO
From $242 per night (USD)
Expedia
Adorable Villa at Cedars East, Tennis Resort, Beach, Clubhouse
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Your Dream Getaway on Longboat Key Spacious 3-Story Townhome Located in Cedars East Resort and Club, this vib ...
From $242 per night (USD)
Expedia
From $412 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 $412 per night (USD)
VRBO
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Expedia
North Shore Six at Longboat Pass
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to your coastal haven on Longboat Key, where charm meets comfort in this beautiful 1-bedroom waterfront condo. T ...
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Expedia
From $376 per night (USD)
VRBO
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 $376 per night (USD)
VRBO
From $186 per night (USD)
Expedia
Beach Villa in Spanish Main
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
2bed/2bath stand-alone villa in Spanish Main Yacht Club. Two queen beds, plus an additional sleeper couch allow room for ...
From $186 per night (USD)
Expedia
From $405 per night (USD)
VRBO
Tiffany Plaza in Longboat Key
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 $405 per night (USD)
VRBO
From $364 per night (USD)
Expedia
Adorable Gulf Front Studio, Private Beach, Originally Part of Starfish Motel
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Adorable hidden oasis in the heart of Longboat Key. Beachfront studio with spectacular views of the beach and Gulf of Me ...
From $364 per night (USD)
Expedia
From $470 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 $470 per night (USD)
VRBO
From $412 per night (USD)
Expedia
Beachfront Cozy Condo: Sand n Gulf Steps Away
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Private oasis directly on Longboat Key beach and steps to the Gulf of Mexico. Fully equipped with all the essentials, co ...
From $412 per night (USD)
Expedia
From $308 per night (USD)
VRBO
Charming Beach Front Studio Steps to the Sand and Gulf
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Charming hidden gem directly on Longboat Key Beach for a secluded getaway. Amazing views of the Gulf of Mexico, and just ...
From $308 per night (USD)
VRBO
From $347 per night (USD)
Expedia
Coquina Moorings 203 | Pool & Boat Dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bayfront Elegance | Unmatched Waterfront Living Perched at the southernmost point of Anna Maria Island, this one-of-a-ki ...
From $347 per night (USD)
Expedia
From $602 per night (USD)
VRBO
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 $602 per night (USD)
VRBO
From $565 per night (USD)
Expedia
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 $565 per night (USD)
Expedia
From $515 per night (USD)
VRBO
N Longboat Charm-Stylish Beach House w Pool Access & Pets OK: Aqua Bay by RVA
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Experience the serene charm of North Longboat Key with an unforgettable stay at this meticulously maintained beach house ...
From $515 per night (USD)
VRBO
From $1111 per night (USD)
VRBO
Great Summer Rate! 3 minute walk to the sand. Luxurious 6 bedroom.
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 $1111 per night (USD)
VRBO
From $666 per night (USD)
VRBO
Beautiful Bayfront home with Pool and Dock!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Best of Boat Worlds by AMI Locals Home in Bradenton Beach, FL 34217 Welcome to Best of Boat Worlds, a meticulously craf ...
From $666 per night (USD)
VRBO
From $321 per night (USD)
Expedia
Country Club Shores 4brm pool home by FVC
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Soaring Spirits – A Newly Renovated Coastal Escape Proudly offered by FL Vacation Connection Step inside this beaut ...
From $321 per night (USD)
Expedia
From $963 per night (USD)
VRBO
Renovated Beachfront 2 Bedroom Condo by FVC
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 $963 per night (USD)
VRBO
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Expedia
Wunderschöne 185 qm Wohnung auf Longboat Key Florida Direkt am Meer Sarasota Bay
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
<p>Located in Longboat Key, this welcoming condo brings it all within your reach. With the property's convenient onsite ...
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Expedia
From $250 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 $250 per night (USD)
VRBO
From $447 per night (USD)
Expedia
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 $447 per night (USD)
Expedia
From $198 per night (USD)
VRBO
Beautiful Longboat Key, Perfect Location, Sarasota ~FL~
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
****BACK ON THE MARKET**** Beautiful Longboat Key, Sarasota, FL! * Newly remodeled, 2 bedroom, 2 bath condo, overlook ...
From $198 per night (USD)
VRBO
From $423 per night (USD)
Expedia
Tropical Canal Home–Pool, Sun & Water Access: Paradise Cottage in LBK by RVA
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Prime Location! Discover this newly decorated seasonal rental on Longboat Key's picturesque canal. Nestled in South Long ...
From $423 per night (USD)
Expedia
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VRBO
Premier Beach View 2 Bedroom Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
New Listing! Ultra-Luxury level expertly renovated 2 bedroom condo offers modern elegance. Thoughtful updating inclu ...
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VRBO
From $330 per night (USD)
Expedia
Updated, Adorable, Close to Beach and Shops
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Cozy coastal beach retreat a short walk to the beach and shops. Comfy furnishings, fully equipped kitchen, beach essenti ...
From $330 per night (USD)
Expedia
From $989 per night (USD)
VRBO
Luxury Gulf Views 3 bedroom 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 $989 per night (USD)
VRBO
From $395 per night (USD)
Expedia
Beachfront Elegance-Gulf Views & Sunsets at Castillian #111N Condo by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
RVA offers Gulf front living in this two-bedroom, two-bath condominium on Longboat Key. Enjoy your private lanai, or tak ...
From $395 per night (USD)
Expedia
From $351 per night (USD)
VRBO
Castillian Coastal Comfort Condo– Right on the Beach! Castillian #202 by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
RVA offers direct Gulf front vacations with expansive views of the white sand beach on Longboat Key at Castillian. Stay ...
From $351 per night (USD)
VRBO
From $935 per night (USD)
Expedia
3 bedroom pool home by FVC
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Coastal Luxury Meets Island Charm – Your St. Armands Bayfront Escape Welcome to your serene escape on beautiful St. Arm ...
From $935 per night (USD)
Expedia
From $400 per night (USD)
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 ...
From $400 per night (USD)
VRBO
From $400 per night (USD)
Expedia
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 $400 per night (USD)
Expedia
From $236 per night (USD)
VRBO
Turquoise Gem 1st Floor no stairs Longboat Key FL
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Private BEACH Access! *Designer Renovation* Single level/Ground Level, 4 minute Walk to Bright White Quartz Sand, Welcom ...
From $236 per night (USD)
VRBO
From $190 per night (USD)
Expedia
Harbour Oaks 2121 by FVC
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 ...
From $190 per night (USD)
Expedia
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Expedia
Blue Heron Home by FVC
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Welcome to your coastal sanctuary! Nestled at 445 Northshore Road on Longboat Key, this completely renovated 3-bedroom g ...
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Expedia
From $583 per night (USD)
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 ...
From $583 per night (USD)
Expedia
From $345 per night (USD)
VRBO
Weekly / Monthly Rental - Spacious Condo In Longboat Key Resort Close To...
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 $345 per night (USD)
VRBO
From $658 per night (USD)
Expedia
Luxe Oasis | Private Pool, In St Armands Circle, Near Lido Key Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
🌴 Luxe Oasis | Private Pool, Walk to Lido Beach & St. Armands 💖 Why You'll Love This Home Tucked into a lush, walkabl ...
From $658 per night (USD)
Expedia
From $917 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 $917 per night (USD)
VRBO
From $289 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 Longboat Key Oceanview Retreat Welcome to Seven Palms Beach House, a stunning t ...
From $289 per night (USD)
Expedia
From $934 per night (USD)
VRBO
Quiet peaceful home on the canal with a dock; 2 minute walk to St Armands Circle
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Relax at Edgewater Escape, the ultimate waterfront home on Lido Key. This magnificent 3-bedroom, 3-bathroom home offers ...
From $934 per night (USD)
VRBO
From $624 per night (USD)
Expedia
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 $624 per night (USD)
Expedia
From $227 per night (USD)
VRBO
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 $227 per night (USD)
VRBO
From $354 per night (USD)
Expedia
Bayfront Beauty–Spacious Condo w Stunning Views: The Atrium #613 Condo by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your dream vacation retreat! Discover unparalleled luxury and comfort in this stunning 2-bedroom plus den con ...
From $354 per night (USD)
Expedia
From $534 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 $534 per night (USD)
VRBO
From $309 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 $309 per night (USD)
Expedia
From $315 per night (USD)
VRBO
Historic Gulf Breeze Getaway Near Dining & Beaches
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Gulf Breeze Getaway by AMI Locals 350 N Shore Rd Longboat Key Welcome to Gulf Breeze Getaway, a historic three bedr ...
From $315 per night (USD)
VRBO
From $384 per night (USD)
Expedia
Beach Castle Resort, 2nd Floor, Updated, Walk to Beach/Bay, Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your ideal getaway at Beach Castle Resort on Longboat Key! This charming second-floor condo offers a cozy coa ...
From $384 per night (USD)
Expedia
From $309 per night (USD)
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 ...
From $309 per night (USD)
VRBO
From $343 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 $343 per night (USD)
Expedia
From $208 per night (USD)
VRBO
Seaplace G6 306 by FVC
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 $208 per night (USD)
VRBO
From $512 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 $512 per night (USD)
Expedia
From $794 per night (USD)
VRBO
Mansion on Canal, Pool, Dock, Arcade, Gym, Theater, Outdoor Kitchen
Bedrooms:
3
Bathrooms:
5
Sleeps:
16
Welcome to your exclusive retreat on Longboat Key, a luxurious 5-bedroom mansion that promises an unparalleled vacation ...
From $794 per night (USD)
VRBO
From $283 per night (USD)
Expedia
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 $283 per night (USD)
Expedia
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VRBO
Charming Waterfront 3-bedroom house with Boatlift in marvelous Longboat Key
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Make yourself at home in this brilliant 3-bedroom midcentury modern canal front retreat. Nestled in the heart of Longboa ...
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VRBO
From $348 per night (USD)
VRBO
Kayaks, Bikes & Bay Access: Bradenton Escape!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Pet Friendly w/ Fee | Beach Chairs & Towels Provided | Close to Fine Dining Nestled within a picturesque waterfront com ...
From $348 per night (USD)
VRBO
From $423 per night (USD)
VRBO
Steps to the Gulf of Mexico, luxurious space with pool, AC, and WIFI
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Longboat Key Oasis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $423 per night (USD)
VRBO
From $192 per night (USD)
Expedia
Enjoy The Perfect Condo, 3 minutes to Beach with Pool Access on Longboat Key!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Perfect Condo by AMI Locals Longboat Key Beachfront Vacation Retreat Welcome to The Perfect Condo, your ideal get ...
From $192 per night (USD)
Expedia
From $416 per night (USD)
VRBO
Ground Floor, Oceanview: October Availability!
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 $416 per night (USD)
VRBO
From $476 per night (USD)
Expedia
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 ...
From $476 per night (USD)
Expedia
From $396 per night (USD)
VRBO
Charming Longboat Key Bungalow with beach access minutes away…
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Looking for an “island style getaway” this is it! Walk to private beach minutes away or head next-door to the beautiful ...
From $396 per night (USD)
VRBO
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Expedia
2 Bedroom Beachfront Condo by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A luxurious beachfront condominium professionally managed by Florida Vacation Connection is located on the world-renowne ...
Click For Pricing
Expedia
From $517 per night (USD)
VRBO
Beachfront 2 BR Corner Unit at Beachplace 1-401 by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A luxurious beachfront condominium professionally managed by Florida Vacation Connection is located on the world-renowne ...
From $517 per night (USD)
VRBO
From $300 per night (USD)
Expedia
Seaplace M1 105 by FVC
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 ...
From $300 per night (USD)
Expedia
From $225 per night (USD)
VRBO
Grand Bay 2 BR / 2 BA Condo on LBK by FVC
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 $225 per night (USD)
VRBO
From $147 per night (USD)
Expedia
Seaplace G4 309 by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Professionally managed and offered by FL Vacation Connection. Seaplace is a wonderful community with two swimming pools ...
From $147 per night (USD)
Expedia
From $604 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 $604 per night (USD)
VRBO
From $599 per night (USD)
Expedia
Beautiful 2BR Beachfront Walkout at Beachplace 9-102 by FVC
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 $599 per night (USD)
Expedia

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Results: 740 Rentals