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 $433 per night (USD)
VRBO
Charming 1-bedroom, beachfront condo in marvelous Longboat Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Consider this condo your home away from home while you visit Longboat Key. This fantastic rental offers 1 cozy bedroom, ...
From $433 per night (USD)
VRBO
From $420 per night (USD)
Expedia
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 $420 per night (USD)
Expedia
From $241 per night (USD)
VRBO
Fairway Bay #155 by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Fairway Bay Fifth-Floor Retreat: Unparalleled Sarasota Bay Views Offered by Florida Vacation Connections Experience ...
From $241 per night (USD)
VRBO
From $431 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 $431 per night (USD)
VRBO
$Cottage A of Historic Waterfront Fish Camp. \nPrivate Dock. Minute walk to Beach$
From $295 per night (USD)
VRBO
Cottage A of Historic Waterfront Fish Camp. \nPrivate Dock. Minute walk to Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cottage A is part of the 1936 Historic Fish Camp located directly on the bay. 115 7th St S. This cottage is perfect f ...
From $295 per night (USD)
VRBO
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Expedia
Chic studio with WiFi and AC in tranquil Longboat Key #2
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located in Longboat Key, this brilliant studio is a dream. Complete with a cozy living room featuring 1 sofa bed and 2 m ...
Click For Pricing
Expedia
From $1153 per night (USD)
VRBO
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 $1153 per night (USD)
VRBO
From $174 per night (USD)
Expedia
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 $174 per night (USD)
Expedia
From $154 per night (USD)
VRBO
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 $154 per night (USD)
VRBO
From $156 per night (USD)
Expedia
Coastal Living at Its Finest
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to Beach Harbor Club on Longboat Key, where unforgettable experiences await! Start your day with a sunrise over ...
From $156 per night (USD)
Expedia
From $891 per night (USD)
VRBO
St Armands Mid Century Rad Pad with Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This unique retreat in the heart of St Armand's Circle was just freshly renovated and ready for fun! Stroll to pristine ...
From $891 per night (USD)
VRBO
From $420 per night (USD)
Expedia
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 $420 per night (USD)
Expedia
From $201 per night (USD)
VRBO
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 $201 per night (USD)
VRBO
From $304 per night (USD)
Expedia
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 $304 per night (USD)
Expedia
From $397 per night (USD)
VRBO
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 $397 per night (USD)
VRBO
From $460 per night (USD)
Expedia
Beachplace 8-603 by FGC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
COMING SOON Experience Coastal Elegance at Beachplace Penthouse Welcome to Your Dream Beachfront Retreat! Discover th ...
From $460 per night (USD)
Expedia
From $165 per night (USD)
VRBO
2 Bedroom Beach View Condo by FVC
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 $165 per night (USD)
VRBO
From $429 per night (USD)
Expedia
Beach View Condo-Quiet & Secluded Private Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Relax with your loved ones at this quiet, beachfront condo at the Beach Castle Resort with views of the Gulf of Mexico f ...
From $429 per night (USD)
Expedia
From $185 per night (USD)
VRBO
2 Bedroom townhome Seaplace by FGC
Bedrooms:
2
Bathrooms:
2
Sleeps:
2
NEW LISTING. This home located in the sought after Seaplace community has a very personal feel to it and the beach is st ...
From $185 per night (USD)
VRBO
From $310 per night (USD)
Expedia
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 $310 per night (USD)
Expedia
From $358 per night (USD)
VRBO
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 $358 per night (USD)
VRBO
From $305 per night (USD)
Expedia
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 $305 per night (USD)
Expedia
From $220 per night (USD)
VRBO
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 $220 per night (USD)
VRBO
From $376 per night (USD)
Expedia
581 Yardarm Lane by FGC
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Rental located directly on a Canal with a boat lift available for use. This is a single family home that contains 2,192 ...
From $376 per night (USD)
Expedia
From $170 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 $170 per night (USD)
VRBO
From $427 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 $427 per night (USD)
Expedia
From $226 per night (USD)
VRBO
Charming 2-bedroom condo with WiFi and AC in beautiful Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
2
Make yourself at home in this 2-bedroom Longboat Key retreat. This condo offers AC, WiFi, a washing machine, heating, an ...
From $226 per night (USD)
VRBO
From $553 per night (USD)
Expedia
Grand Waterfront Home–Private Pool & Dock Access Emerald Bay in LBK by RVA
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Escape to paradise in this stunning waterfront vacation home located in the coveted Emerald Harbor neighborhood. Perfect ...
From $553 per night (USD)
Expedia
From $281 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 $281 per night (USD)
VRBO
From $247 per night (USD)
Expedia
Bright condo with private balcony, washer/dryer, & WiFi- close to the beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Paradise Found Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $247 per night (USD)
Expedia
From $337 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 $337 per night (USD)
VRBO
From $303 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 $303 per night (USD)
VRBO
From $298 per night (USD)
VRBO
Beach and Tennis Paradise in Beautiful Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Consider this condo directly on the beach your home away from home while you visit beautiful Longboat Key. This property ...
From $298 per night (USD)
VRBO
From $314 per night (USD)
Expedia
Grand Bay 626 by FVC
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 $314 per night (USD)
Expedia
From $270 per night (USD)
VRBO
Beachplace 6-205 by FVC
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 $270 per night (USD)
VRBO
From $788 per night (USD)
Expedia
Tropical Haven - 4503/05
Bedrooms:
5
Bathrooms:
5
Sleeps:
16
Premier local manager, Destination Paradise welcomes you to “Tropical Haven”… a poolside resort experience, without the ...
From $788 per night (USD)
Expedia
From $394 per night (USD)
VRBO
Waterfront home with private pool, boat dock, & serene views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Serenity Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired d ...
From $394 per night (USD)
VRBO
From $145 per night (USD)
Expedia
Coastal Living at Its Finest at Longboat Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to Beach Harbor Club on Longboat Key, where unforgettable experiences await! Start your day with a sunrise over S ...
From $145 per night (USD)
Expedia
From $195 per night (USD)
VRBO
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, perfect for up to 4 guests. - Expansive ...
From $195 per night (USD)
VRBO
From $415 per night (USD)
VRBO
Longboat Key, FL Spectacular Full OceanView Beachfront First Floor 1 Bed 1 Bath
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Longboat Key is waiting for you at this 1-bedroom condo. This peaceful retreat offers all the essentials for a terrific ...
From $415 per night (USD)
VRBO
From $730 per night (USD)
VRBO
Beachfront Luxury with Spectacular Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Islands West 12F, a luxurious beachfront condo located in the prestigious and secure Islands West building on ...
From $730 per night (USD)
VRBO
From $342 per night (USD)
Expedia
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 $342 per night (USD)
Expedia
From $318 per night (USD)
VRBO
2-bedroom condo in welcoming Longboat Key with AC, WiFi
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This 2-bedroom condo is perfect for your escape to Longboat Key. The enchanting space features 1 king bed, 1 queen bed, ...
From $318 per night (USD)
VRBO
From $764 per night (USD)
Expedia
Villa Sereno Summary:
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Summary: Welcome to the picture-perfect, social media dream that is Villa Sereno by LUXVP. This 5-bedroom, 4.5 bathroo ...
From $764 per night (USD)
Expedia
From $487 per night (USD)
Expedia
Beachfront with Beautiful Views on Longboat Key
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: This inviting beachfront condo on Longboat Key offers comfortable living with stunning bay, golf course, and ci ...
From $487 per night (USD)
Expedia
From $239 per night (USD)
Expedia
Stylish Longboat Key townhome 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 $239 per night (USD)
Expedia
From $303 per night (USD)
VRBO
Coquina Moorings 205: Condo with Gulf-to-Bay views!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Coquina Moorings 205, a beautiful second-floor bayfront and gulf-front condo near Coquina Beach. Enjoy stunni ...
From $303 per night (USD)
VRBO
From $482 per night (USD)
Expedia
Lido Beach Renovated House by Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
NEW PROPERTY Dreaming of sunshine, beautiful sandy beaches, and warm turquoise Gulf waters? Your airy and bright 3-bedr ...
From $482 per night (USD)
Expedia
From $194 per night (USD)
VRBO
Charming 2-bedroom fully renovated condo on Longboat Key with bay/ocean views.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Make yourself at home in this terrific 2-bedroom Longboat Key retreat. Fully renovated in 2025 with a king bed, queen be ...
From $194 per night (USD)
VRBO
From $457 per night (USD)
Expedia
Beachfront with Gulf Views in Longboat Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Enjoy peaceful Gulf views from nearly every room in this bright corner condo. Relax on the wraparound terrace, ...
From $457 per night (USD)
Expedia
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VRBO
LBK Dreamin' Beach Bungalow
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Highlights/Resort-Style Amenities: - 5-minute walk to beautiful white sand beach and numerous restaurants - On-site Te ...
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VRBO
From $349 per night (USD)
Expedia
Gorgeous 2 bedroom, 3 level townhouse on bay, next to beach, mid Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Kick back in this calm stylish place. In Cedars East across from the beach and on the bay, on Longboat Key, simply in pa ...
From $349 per night (USD)
Expedia
From $610 per night (USD)
VRBO
Luxurious Oceanfront Sanctuary - St. Regis Resort, Longboat Key - Serenity Oasis
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Welcome Serenity Oasis! Professionally managed by Gulf Coast Vacation Rentals. Your paradise at The Residences at the St ...
From $610 per night (USD)
VRBO
From $293 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 $293 per night (USD)
Expedia
From $708 per night (USD)
VRBO
St Armands Key Walk to Beach - 3 Bedrooms 4+ Bathrooms Private Heated Pool
Bedrooms:
4
Bathrooms:
3
Sleeps:
7
Roomy contemporary single family home in the heart of St. Armand's Key available for monthly rental with discounts for l ...
From $708 per night (USD)
VRBO
Click For Pricing
Expedia
Longboat Bay Club
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
<p>While you're here, you can enjoy all the comforts of home and more, including a refrigerator and an oven, as well as ...
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Expedia
From $471 per night (USD)
VRBO
⚓Whispering Palms! Private canal side dock + pool w/spa!⚓
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to Whispering Palms! ⚓Short drive to the World Class Beaches of Anna Maria Island ⚓Canal Front with Quick Ac ...
From $471 per night (USD)
VRBO
From $423 per night (USD)
Expedia
Bay Views from a Condo in Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Enjoy panoramic views of the Gulf and Sarasota Bay from this beautifully furnished condo in the heart of Longbo ...
From $423 per night (USD)
Expedia
From $458 per night (USD)
VRBO
Charming 2-bedroom condo in fabulous Longboat Key with AC, WiFi
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Nestled in Longboat Key, this delightful condo offers 2 bedrooms with 1 queen bed and 1 king bed. The 2 bathrooms are eq ...
From $458 per night (USD)
VRBO
From $335 per night (USD)
VRBO
Available now through the end of the year, off season only
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Available now through the end of the year, off season only. Welcome to coastal elegance at Tangerine Bay Club, where swe ...
From $335 per night (USD)
VRBO
From $401 per night (USD)
VRBO
Condo with a View 4: Open Sunday Nite, $199/nt!
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 $401 per night (USD)
VRBO
From $231 per night (USD)
Expedia
Luxury Beachfront Retreat on Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Escape to paradise at this spacious 2-story beachfront retreat on Longboat Key! - 2 bedrooms and 2 bathrooms, ...
From $231 per night (USD)
Expedia
From $721 per night (USD)
VRBO
Breathtaking New 4 Bed/3 Bath Pool Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Looking for a 3 month renter for January, February, and March or atleast January 2026. Limetree House. This fabulous new ...
From $721 per night (USD)
VRBO
From $463 per night (USD)
Expedia
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 $463 per night (USD)
Expedia
From $416 per night (USD)
VRBO
Beachfront Bliss on Longboat Key- Steps to the sand
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Step out your door and onto the sand—this beachfront gem on Longboat Key is the perfect escape for couples or solo trave ...
From $416 per night (USD)
VRBO
From $288 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 $288 per night (USD)
VRBO
From $267 per night (USD)
VRBO
The Pink Pelican- 3 bedroom with pool and dock.
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 $267 per night (USD)
VRBO
From $423 per night (USD)
Expedia
Beachfront Condo with Panoramic Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Enjoy stunning Gulf, Bay, and skyline views from this beautifully updated 2-bed, 2-bath condo. Features include ...
From $423 per night (USD)
Expedia
From $246 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 $246 per night (USD)
VRBO
From $151 per night (USD)
Expedia
Buttonwood Cove 204B by FVC
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 $151 per night (USD)
Expedia
From $952 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 $952 per night (USD)
VRBO
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Expedia
Sutton Place #205A Condo by RVA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Wake up to stunning sunrise views over Sarasota Bay in this beautifully appointed 1-bedroom, 1-bathroom condo. Perfectly ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Beachfront condo in Longboat Key with pool, fitness room, WiFi, & more!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beachfront Bliss at Veranda Beach Club – Longboat Key, FL Escape to the tranquil shores of Longboat Key with this beaut ...
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VRBO
From $289 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 $289 per night (USD)
Expedia
From $296 per night (USD)
VRBO
Sutton Place #101A Condo by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sutton Place is perfectly situated on the tropical grounds of the Longboat Harbour Community. This spacious 2-bedroom, 2 ...
From $296 per night (USD)
VRBO
From $308 per night (USD)
Expedia
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 $308 per night (USD)
Expedia
From $3209 per night (USD)
VRBO
Longboat Key, FL 2bd, 2ba condo available, Dec’25 & Jan’26. Steps to the beach!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautifully and tastefully updated 2 bedroom, 2 bathroom 1076 sq. ft. condo, on Longboat Key Florida, is now available D ...
From $3209 per night (USD)
VRBO
From $308 per night (USD)
Expedia
Pelican Harbour, Beach Club T2 Condo by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Looking for a laid-back getaway with water views and island vibes? Welcome to your home away from home on the beautiful ...
From $308 per night (USD)
Expedia
From $271 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 $271 per night (USD)
VRBO
From $698 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 $698 per night (USD)
VRBO
From $414 per night (USD)
VRBO
Courtside Coastal Retreat- Cedars East 2BR Tennis Getaway Unit #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 $414 per night (USD)
VRBO
From $335 per night (USD)
Expedia
Inn on the Beach #6203
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Kick back and unwind in this bright and breezy waterfront studio at the beautiful Inn on the Beach, tucked away on the s ...
From $335 per night (USD)
Expedia
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VRBO
Huge Discount for any stay over 2 weeks Longboat Key with Private Boat Docking
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Historic Village - Walk to Beach Welcome to Longboat Key and our home in Historic Longbeach Village situated on the nort ...
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VRBO
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Expedia
Stylish Oceanfront Villa With Pool + Lanai, Steps From Beach | 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 ...
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Expedia
From $528 per night (USD)
VRBO
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 $528 per night (USD)
VRBO
From $192 per night (USD)
Expedia
Cozy 1-bedroom condo with private Gulf and Bay access in charming Longboat Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy a peaceful stay at this 1-bedroom condo in Longboat Key. The bedroom features a comfortable king bed, perfect for ...
From $192 per night (USD)
Expedia
From $271 per night (USD)
VRBO
Seaplace #605 Condo by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to a serene coastal retreat at this stunning 2-bedroom, 2-bath, condo nestled in the sought-after Seaplace commun ...
From $271 per night (USD)
VRBO
From $220 per night (USD)
Expedia
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 $220 per night (USD)
Expedia
From $345 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 $345 per night (USD)
VRBO
From $333 per night (USD)
Expedia
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 $333 per night (USD)
Expedia
From $249 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 $249 per night (USD)
VRBO
From $399 per night (USD)
Expedia
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 $399 per night (USD)
Expedia
From $417 per night (USD)
VRBO
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 condo with ~350 feet of private beach on t ...
From $417 per night (USD)
VRBO
From $571 per night (USD)
Expedia
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 $571 per night (USD)
Expedia
From $236 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 $236 per night (USD)
VRBO
From $242 per night (USD)
Expedia
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 $242 per night (USD)
Expedia
From $254 per night (USD)
VRBO
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 $254 per night (USD)
VRBO
From $1271 per night (USD)
Expedia
LBK Whitney Bayside Retreat
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Highlights • Half-mile walk or bike ride to Whitney Beach • 3 Bedroom / 2 Bath • Balcony overlooking tranquil Bishop Bay ...
From $1271 per night (USD)
Expedia
From $1140 per night (USD)
VRBO
Longboat Key Waterfront 3BR house w/Pool in most desirable Country Club Shores
Bedrooms:
3
Bathrooms:
3
Sleeps:
5
Private home located in the prime desirable quiet neighborhood of Country Club Shores. (sought after southern end of L ...
From $1140 per night (USD)
VRBO
From $482 per night (USD)
Expedia
Whitney Beach Retreat 2
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Highlights • Three-minute Walk to Whitney Beach • 2 Bedroom / 2 Bath • 1 King, 1 Queen, 1 Twin Trundle Bed • Two heated ...
From $482 per night (USD)
Expedia

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