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 $203 per night (USD)
VRBO
Beachplace 2 BR 6th Floor Condo With Gulf Views by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Offered by FL Vacation Connection, this lovely 6th floor unit at Beachplace is ready for you to enjoy. Feel free to pla ...
From $203 per night (USD)
VRBO
From $219 per night (USD)
Expedia
Beachplace Unobstructed Beachfront Views / Direct Beach Access By FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachplace Beachfront Escape | Completely Renovated Welcome to your perfect getaway at Beachplace, a completely renov ...
From $219 per night (USD)
Expedia
From $339 per night (USD)
VRBO
2 Bedroom 5th Floor Gulf View Condo in Beachplace by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Offered by FL Vacation Connection, this lovely 5th floor unit at Beachplace is ready for you to enjoy. Feel free to pla ...
From $339 per night (USD)
VRBO
From $240 per night (USD)
Expedia
Buttonwood Cove 302C by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FL Vacation Connection welcomes you to this amazing waterfront top-floor condo on Sarasota Bay! Professionally remodeled ...
From $240 per night (USD)
Expedia
From $312 per night (USD)
VRBO
2 Bedroom 2 Bath 5th Floor Beach View Condo in Beachplace by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Professionally managed by FL Vacation Connection, this spacious unit is furnished with comfortable seating in the living ...
From $312 per night (USD)
VRBO
From $345 per night (USD)
Expedia
Updated Gulf View 2 Bedroom Corner Condo by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Professionally managed and offered by FL Vacation Connection. Guest will enjoy this corner unit that was renovated in 2 ...
From $345 per night (USD)
Expedia
From $173 per night (USD)
VRBO
2 Bedroom Bay Front Condo on Longboat Key by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FL Vacation Connection proudly presents Buttonwood Cove - Set on 5 beautifully landscaped acres, spanning from Gulf to B ...
From $173 per night (USD)
VRBO
From $422 per night (USD)
Expedia
Updated 2 Bedroom Condo With Views by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Florida Vacation Connection offers this well-maintained and comfortable two-bedroom, two-bathroom condo at the highly so ...
From $422 per night (USD)
Expedia
From $395 per night (USD)
VRBO
2 BR / 2 BA Direct Beach Access In Beachplace by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A luxurious beachfront condominium managed by Florida Vacation Connection is located on the world-renowned Longboat Key ...
From $395 per night (USD)
VRBO
From $306 per night (USD)
Expedia
2 Bedroom Condo With Lanai Exit On Longboat Key By FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Florida Vacation Connection offers this well-maintained and comfortable two-bedroom, two-bathroom condo at the highly so ...
From $306 per night (USD)
Expedia
From $537 per night (USD)
VRBO
2 Bedroom Beachfront Condo On Longboat Key By FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This beachfront condominium professionally managed by Florida Vacation Connection is located on the world-renowned Longb ...
From $537 per night (USD)
VRBO
From $558 per night (USD)
Expedia
Inn on the Beach 7304 by FVC
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Your Longboat Key Retreat with Sleepy Lagoon Views by FVC Experience the pinnacle of coastal living in this beautifully ...
From $558 per night (USD)
Expedia
From $351 per night (USD)
VRBO
2 Bedroom Corner Condo On Longboat Key By FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to this updated 2 bedroom condo at Beachplace managed by Florida Vacation Connection. FVC is pleased to offer ...
From $351 per night (USD)
VRBO
From $530 per night (USD)
Expedia
Bayview Paradise by FVC
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Bayview Paradise managed by Florida Vacation Connection. This spacious 4 bedroom/ 3 full baths private pool ...
From $530 per night (USD)
Expedia
From $764 per night (USD)
VRBO
Premium 2 Bedroom Beachfront Corner Condo by FVC
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
This beachfront condominium professionally managed by Florida Vacation Connection is located on the world-renowned Longb ...
From $764 per night (USD)
VRBO
From $157 per night (USD)
Expedia
Beachfront 2BR 2 BA at Players Club by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Players Club is a beachfront property located at the south end of Longboat Key. It is well known as an active tennis co ...
From $157 per night (USD)
Expedia
From $182 per night (USD)
VRBO
Mark III Beachfront Condo by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Wonderful location on Longboat Key. Located mid-Key, just a short distance north of Publix, right on the beach. Longboat ...
From $182 per night (USD)
VRBO
From $236 per night (USD)
Expedia
Waterfront Pool Home by FVC
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
FL Vacation Connection welcomes you to Casa Blanca. From the moment you step inside you’ll know that this is the perfect ...
From $236 per night (USD)
Expedia
From $685 per night (USD)
VRBO
Luxury Beachside 3-BR Condo at The Sanctuary by FVC
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Luxury Beachside 3-Bedroom Condo at The Sanctuary, Longboat Key, Florida professionally managed by Florida Vacation Conn ...
From $685 per night (USD)
VRBO
From $297 per night (USD)
Expedia
SeaPlace M2 512 by FVC
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Penthouse Paradise on Longboat Key – Beachfront Luxury Steps from the St. Regis Experience unparalleled coastal eleganc ...
From $297 per night (USD)
Expedia
From $239 per night (USD)
VRBO
Beachfront 2BR / 2 BA at Salty Acres on LBK by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FL Vacation Connection presents Salty Acres - a small, picturesque, beachfront community on Longboat Key. This unit h ...
From $239 per night (USD)
VRBO
From $249 per night (USD)
Expedia
Enjoy all Longboat Key has to offer from Harbor Villa Club! Beautifully updated 2/2 directly on the bay!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy all Longboat Key has to offer from Harbor Villa Club! Beautifully updated 2/2 directly on the bay! Gorgeous views ...
From $249 per night (USD)
Expedia
From $806 per night (USD)
VRBO
Pool, Dock & Close to Beach– Florida Fun Starts Here: Marbury Lane LBK by RVA
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to your perfect getaway on Longboat Key, FL! This stunning three-story vacation home is a dream come true for fa ...
From $806 per night (USD)
VRBO
From $492 per night (USD)
Expedia
Luxury Waterfront Longboat Key Home Steps to Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Located in Longboat Key, enjoy what this 3-bedroom house has to offer. View With 1 full bed and 2 king beds, guests can ...
From $492 per night (USD)
Expedia
From $310 per night (USD)
VRBO
Updated 2-bedroom pet friendly condo with stunning Bay views in Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to this beautifully updated penthouse 4th floor condo (with elevator access) overlooking the Sarasota Bay in Lon ...
From $310 per night (USD)
VRBO
From $164 per night (USD)
Expedia
Longboat Harbour Bay Front 2 BR / 2 BA by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This 2-bedroom, 2-bath condo offers stunning bayfront views and is located in the desirable Longboat Harbour community. ...
From $164 per night (USD)
Expedia
From $654 per night (USD)
VRBO
Charming 3-bedroom house with AC and WiFi in fantastic Longboat Key
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Make yourself at home in this brilliant 3-bedroom Longboat Key retreat. With a king bed, queen bed, full bed, and twin b ...
From $654 per night (USD)
VRBO
From $881 per night (USD)
Expedia
Luxury on the Sand – Large Oceanfront Condo La Playa #202D by RVA
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Experience the coastal charm of Longboat Key at our newest addition: La Playa, Unit 202D. This oceanfront getaway offers ...
From $881 per night (USD)
Expedia
From $233 per night (USD)
VRBO
Bayside Beauty-250 feet to beach-available October through January
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Updated and comfortably furnished, this spacious split plan condo gives you PLENTY of room to spread out. The main bedro ...
From $233 per night (USD)
VRBO
Click For Pricing
Expedia
Beautiful 3 bedroom with views of the Beach of Longboat Key.
Bedrooms:
3
Bathrooms:
3
Sleeps:
4
This exquisite 3 bed, 3 bath condo, nestled in the heart of the amazing Pierre community, is an exceptional opportunity ...
Click For Pricing
Expedia
From $491 per night (USD)
VRBO
Direct Beachfront Condo Birds eye view
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Imagine waking up to breathtaking views of the Gulf and the Sarasota skyline - every single room boasts this incredible ...
From $491 per night (USD)
VRBO
From $3284 per night (USD)
Expedia
Best of both worlds! Luxury 6000+ sq ft Bay front home also next to Beach
Bedrooms:
7
Bathrooms:
7
Sleeps:
18
One of the finest luxury vacation homes on AMI! Mandalay Bay has recently completed a major freshen up renovation with n ...
From $3284 per night (USD)
Expedia
From $300 per night (USD)
VRBO
Gulf Views & Cozy Comfort w Large Lanai Tern's Nest #22 Condo by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to paradise in this stunning Longboat Key condo, where every day starts with incredible water views and ends with ...
From $300 per night (USD)
VRBO
From $428 per night (USD)
Expedia
Gorgeous Beachside Condo in superior Longboat Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Amazing Direct Beach views from your balcony, living room, kitchen, dining room and bedroom in this Islands West Condo. ...
From $428 per night (USD)
Expedia
$A Lush + Tropical Beachside Sanctuary\n2BR/2BA Condo w/ Fully Equipped Kitchen$
From $456 per night (USD)
VRBO
A Lush + Tropical Beachside Sanctuary\n2BR/2BA Condo w/ Fully Equipped Kitchen
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to your peaceful beachside + tropical retreat, nestled in desirable South Longboat Key on 31 acres of private bea ...
From $456 per night (USD)
VRBO
From $434 per night (USD)
Expedia
Beach front newly renovated 2.5 bedroom condo with private beach access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Luxury Longboat Key Condo – Fully Renovated (Dec 2024) & Steps from the beach (private access). Welcome to Sea Pines Co ...
From $434 per night (USD)
Expedia
From $198 per night (USD)
VRBO
Bay Harbour A306 by FVC
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to this exquisite top-floor, 3 bedroom, 2 bath, end-unit condo at Bay Harbour by FVC. Newly furnished in 2022 an ...
From $198 per night (USD)
VRBO
From $1149 per night (USD)
Expedia
Coastal Elegance by FVC
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Welcome to Coastal Elegance managed by Florida Vacation Connection! Experience unparalleled luxury in this magnificent ...
From $1149 per night (USD)
Expedia
From $578 per night (USD)
VRBO
4-bedroom house on Longboat Key with beach only 150 yards away.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Make yourself at home in this large recently remodeled 4-bedroom 3 bathroom Longboat Key retreat with 1 king bed and 3 q ...
From $578 per night (USD)
VRBO
From $615 per night (USD)
Expedia
Gulf-Access Waterfront Home Near the Beach in LBK: Penfield Paradise by RVA
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Discover a private slice of paradise on Longboat Key, where waterfront tranquility meets tropical luxury. This stunning ...
From $615 per night (USD)
Expedia
From $216 per night (USD)
VRBO
Welcome to Blue Crane by Florida Vacation Connections
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Blue Crane by Florida Vacation Connections: Your Eclectic Florida Getaway on one of Millar Bays Canals! Disc ...
From $216 per night (USD)
VRBO
From $657 per night (USD)
Expedia
Beachplace 8-601 by FGC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience Coastal Elegance at Beachplace Penthouse Welcome to your dream beachfront retreat, where coastal living meet ...
From $657 per night (USD)
Expedia
From $417 per night (USD)
VRBO
Completely Renovated, Brand New Furnishings, Beach Castle 21
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to Beach Castle Resort Unit 21 – Your Dream Getaway! This fully renovated, ground-floor beach condo blends moder ...
From $417 per night (USD)
VRBO
From $513 per night (USD)
Expedia
Islander Club #16N Premier Beachfront Condo-1st Floor & Ocean Views by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your perfect vacation getaway at the Islander Club of Longboat Key! Islander Club #16N is a 2-bedroom, 2-bat ...
From $513 per night (USD)
Expedia
From $208 per night (USD)
VRBO
Charming Longboat Key 3-bedroom house with 3 min walk to beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover the best of Longboat Key and Sarasota from our cozy 3 bedroom rental. Just down the road is beautiful St. Arman ...
From $208 per night (USD)
VRBO
From $373 per night (USD)
Expedia
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 $373 per night (USD)
Expedia
From $265 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 $265 per night (USD)
VRBO
From $463 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 $463 per night (USD)
VRBO
$Cottage A of Historic Waterfront Fish Camp. \nPrivate Dock. Minute walk to Beach$
From $299 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 $299 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 $169 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 $169 per night (USD)
VRBO
From $210 per night (USD)
Expedia
Beach place in Longboat Key.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your dream getaway! Our beautifully appointed 2-bedroom, 2- bath condo offers the perfect balance of comfort, ...
From $210 per night (USD)
Expedia
From $325 per night (USD)
VRBO
Ground floor 2/2! Glass Lanai! Sleeps 5!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Enjoy all Longboat Key has to offer from Harbor Villa Club! Beautiful 2/2 directly on the bay! Gorgeous views off the pa ...
From $325 per night (USD)
VRBO
From $399 per night (USD)
Expedia
Beachplace 9-302 by FGC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beachfront renting at its finest: relax, unwind, and enjoy the magnificent views of the pristine white sandy beach and t ...
From $399 per night (USD)
Expedia
From $534 per night (USD)
VRBO
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 $534 per night (USD)
VRBO
From $155 per night (USD)
Expedia
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 $155 per night (USD)
Expedia
From $186 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 $186 per night (USD)
VRBO
From $322 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 $322 per night (USD)
Expedia
From $352 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 $352 per night (USD)
VRBO
From $275 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 $275 per night (USD)
Expedia
From $255 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 $255 per night (USD)
VRBO
From $484 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 $484 per night (USD)
Expedia
From $186 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 $186 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 $629 per night (USD)
VRBO
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 $629 per night (USD)
VRBO
From $275 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 $275 per night (USD)
Expedia
From $365 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 $365 per night (USD)
VRBO
From $308 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 $308 per night (USD)
VRBO
From $355 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 $355 per night (USD)
VRBO
From $424 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 $424 per night (USD)
Expedia
From $424 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 $424 per night (USD)
VRBO
From $390 per night (USD)
Expedia
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 $390 per night (USD)
Expedia
From $145 per night (USD)
VRBO
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)
VRBO
From $201 per night (USD)
Expedia
Waterfront 2-Bedroom Retreat in Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Welcome to this stunning 2-bedroom, 2-bath residence on Longboat Key. - Expansive water views from the living ...
From $201 per night (USD)
Expedia
From $342 per night (USD)
VRBO
Charming 2-bedroom condo with WiFi and AC in beautiful Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience Longboat Key like a local in this 2-bedroom condo. This lovely property features 2 queen beds, AC, WiFi, heat ...
From $342 per night (USD)
VRBO
From $248 per night (USD)
Expedia
Longboat Key tennis resort minutes to beach - Ospreys Nest
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Welcome to your perfect coastal escape in the heart of Cedars East on Longboat Key, Florida! Professionally managed by G ...
From $248 per night (USD)
Expedia
From $343 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 $343 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 $225 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 $225 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $750 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 $750 per night (USD)
VRBO
From $306 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 $306 per night (USD)
Expedia
From $743 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 $743 per night (USD)
VRBO
From $412 per night (USD)
Expedia
⚓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 $412 per night (USD)
Expedia
From $334 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 $334 per night (USD)
VRBO
From $332 per night (USD)
Expedia
Top Floor, Oceanview: Open Thursday Night, $99 + Fees!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This sublime oceanfront condo is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Lo ...
From $332 per night (USD)
Expedia
From $240 per night (USD)
VRBO
Luxury Beachfront Retreat in 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 $240 per night (USD)
VRBO
From $664 per night (USD)
VRBO
Precise Realty presents The Limetree Oasis
Bedrooms:
2
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 $664 per night (USD)
VRBO
From $340 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 $340 per night (USD)
VRBO
From $243 per night (USD)
Expedia
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 $243 per night (USD)
Expedia
From $253 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 $253 per night (USD)
VRBO
From $208 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 $208 per night (USD)
Expedia
From $948 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 $948 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $289 per night (USD)
VRBO
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)
VRBO
From $312 per night (USD)
Expedia
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 $312 per night (USD)
Expedia
From $329 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 $329 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 $710 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 $710 per night (USD)
VRBO
From $328 per night (USD)
Expedia
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 $328 per night (USD)
Expedia

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Results: 740 Rentals