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 $606 per night (USD)
VRBO
The Beach on Longboat Key #225 Resort by RVA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
RVA features The Beach on Longboat Key. Savor warm Gulf breezes while resting lavishly in this Gulf-front condominium co ...
From $606 per night (USD)
VRBO
$Beachfront Bliss: 2\/2 with Stunning Gulf Views!$
From $249 per night (USD)
Expedia
Beachfront Bliss: 2\/2 with Stunning Gulf Views!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Dolphin's Retreat, where you can experience the ultimate beachfront vacation! 🏡 Property Highlights: ✨ Bea ...
From $249 per night (USD)
Expedia
From $294 per night (USD)
VRBO
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 $294 per night (USD)
VRBO
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Expedia
Contemporary Beach Condo available for SEASON and 6+ month stay options.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Designer owned 2BR/2BA beach condo featuring open concept floorplan surrounded by water views of both the Gulf of Mexico ...
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Expedia
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VRBO
Longboat Key Beach House
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
We have a completely designer renovated one story beach house with private beach access (15 feet from the back of the ho ...
Click For Pricing
VRBO
$Sutton Place with Private Beach, Pavilion with Grills\/Showers, 2 Pools$
From $275 per night (USD)
Expedia
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 $275 per night (USD)
Expedia
From $121 per night (USD)
VRBO
Studios near AMI Beach, Fully Furnished, Kitchenette, Enclosed Lanai”
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to our fully furnished newly renovated Seashell I & II studio located just one mile away from the beautiful Anna ...
From $121 per night (USD)
VRBO
From $296 per night (USD)
Expedia
Villas of Avignon #105 Condo by RVA
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Welcome to Villas of Avignon by Resort Vacation Accommodations! Experience the perfect beachfront escape on Longboat Key ...
From $296 per night (USD)
Expedia
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VRBO
Remodeled Gulf & beachfront condo with pool, tennis, beach access, balcony, AC
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Gulf Front Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
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VRBO
From $632 per night (USD)
Expedia
Home near the beach with a grill, jetted tub, bikes, & AC - snowbird-friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Gone Coastal Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $632 per night (USD)
Expedia
From $290 per night (USD)
VRBO
Gulf Front 2BDR 2BA Fully Furnished Club Longboat Condo Beach Tennis Association
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 $290 per night (USD)
VRBO
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Expedia
Vida Oceana - Steps from the Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Vida Oceana by AMI Locals Home in Bradenton Beach, FL 34217 Welcome to Vida Oceana, a beachcomber’s paradise perfectl ...
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Expedia
From $717 per night (USD)
VRBO
Fairway Bay - Luxury Beachfront Condo with Pool by Gulfcoast Holiday Homes
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
FULLY OPERATIONAL POST HURRICANE - Luxury Vacation Rental condo, recently remodeled, with 3 bedrooms, 2 bathrooms, and s ...
From $717 per night (USD)
VRBO
From $360 per night (USD)
Expedia
Starfish Paradise #23 Condo by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcoming Starfish Paradise to RVA's collection of vacation rentals, where a well-deserved beach vacation is guaranteed. ...
From $360 per night (USD)
Expedia
From $270 per night (USD)
VRBO
Beachplace 8-505 Gulf Front by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A luxurious beachfront 2 bedroom condominium managed by Florida Vacation Connection located on Longboat Key and only min ...
From $270 per night (USD)
VRBO
From $1436 per night (USD)
Expedia
Rooftop deck with Gulf views - Villa Rayo Del Sol
Bedrooms:
6
Bathrooms:
5
Sleeps:
13
Villa Rayo Del Sol by AMI Locals Home in Bradenton Beach, FL 34217 Welcome to Villa Rayo Del Sol, a stunning new thre ...
From $1436 per night (USD)
Expedia
From $269 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 $269 per night (USD)
VRBO
From $1109 per night (USD)
Expedia
Luxury 5 bedroom on canal
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Welcome to Villa Sereno, managed by Florida Vacation Connection. BRING YOUR BOAT! This stunning five-bedroom private p ...
From $1109 per night (USD)
Expedia
From $442 per night (USD)
VRBO
Stunning 2 Bedroom Condo is located on Longboat Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Casual yet elegant living area directly on the gulf and just steps from the beach. Enjoy breathtaking sunsets on the Gul ...
From $442 per night (USD)
VRBO
From $297 per night (USD)
VRBO
Stunning one bedroom Cape Cod style Cottage on Long Boat Key, Florida
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy breathtaking sunrises on Sarasota Bay. This one bedroom, well appointed cottage sleeps four. Unit 11 features one ...
From $297 per night (USD)
VRBO
$Bay-view condo with boat access, 2 outdoor pools, balcony, BBQ area, W\/Ds$
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VRBO
Bay-view condo with boat access, 2 outdoor pools, balcony, BBQ area, W\/Ds
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Another Day In Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
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VRBO
From $220 per night (USD)
Expedia
Gorgeous Newly 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 $220 per night (USD)
Expedia
Click For Pricing
VRBO
Longboat Key Vacation Rental: Direct Beach Access!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Experience the coastal charm of Longboat Key when you book this fantastic 1-bedroom, 1-bathroom condo! Perfect for coupl ...
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VRBO
From $286 per night (USD)
Expedia
SUNSET VISTA ON LONGBOAT KEY
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Gorgeous 1,110 sq.ft., renovated condo on the 3rd floor in Beach Harbor Club. This 2 bedroom/ 2 bath condo has been comp ...
From $286 per night (USD)
Expedia
From $721 per night (USD)
VRBO
Absolute Tranquility by FVC
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Professionally managed by Florida Vacation Connection, we welcome you to our exquisite rental property nestled in a sere ...
From $721 per night (USD)
VRBO
From $303 per night (USD)
Expedia
Bradenton Vacation Rental: Gas Grill & Water Views
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Escape to paradise when you book a stay at this stunning 3-bedroom, 2-bathroom home in Bradenton! Perfectly situated nea ...
From $303 per night (USD)
Expedia
$3bed\/2bath Beachfront Condo on Longboat Key!$
From $294 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 $294 per night (USD)
VRBO
From $444 per night (USD)
Expedia
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 spacious ...
From $444 per night (USD)
Expedia
From $495 per night (USD)
VRBO
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. Ent ...
From $495 per night (USD)
VRBO
From $193 per night (USD)
Expedia
Whitney Beach 320 1brm beachfront condo
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: A completely renovated ground-floor 1 brm/1bath beachfront condo awaits you in Longboat Key's lifestyle of luxu ...
From $193 per night (USD)
Expedia
$LBK’s LOCATION LOCATION LOCATION! \nAvailable for SEASON or longer term rental.$
From $178 per night (USD)
VRBO
LBK’s LOCATION LOCATION LOCATION! \nAvailable for SEASON or longer term rental.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Closest building to the beach with views of both the Gulf of Mexico and Sarasota Bay over the marina. Located mid-key ma ...
From $178 per night (USD)
VRBO
From $1614 per night (USD)
Expedia
Pirate House: Gulf Front, Pool, #1 Location Lido Key, St. Armands One Block.
Bedrooms:
5
Bathrooms:
5
Sleeps:
16
AJ Vacations - Elevating Your Vacation Experience! At AJ Vacations, we redefine luxury vacation homes for the discernin ...
From $1614 per night (USD)
Expedia
From $356 per night (USD)
VRBO
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 $356 per night (USD)
VRBO
From $318 per night (USD)
Expedia
Hy Tee: House 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 $318 per night (USD)
Expedia
From $810 per night (USD)
VRBO
Recently updated 5 bedroom home, private pool and steps to the beach.
Bedrooms:
6
Bathrooms:
5
Sleeps:
16
Newly updated home!!!!! Updates include: pool re-finished and new components, interior and exterior of home painted comp ...
From $810 per night (USD)
VRBO
From $365 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 $365 per night (USD)
Expedia
$650 Norton - Longboat Key - Canal Home with private Pool - 3 Bedroom\/ 2 Bath,...$
From $522 per night (USD)
VRBO
650 Norton - Longboat Key - Canal Home with private Pool - 3 Bedroom\/ 2 Bath,...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
650 Norton - Longboat Key - 3 Bedroom/ 2 Bath, maximum occupancy of 6 people. Canal Home - Private Pool - Distance ...
From $522 per night (USD)
VRBO
From $182 per night (USD)
Expedia
Updated, Ground Floor, Bay Views, Pool, Walk to the Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Adorable, ground floor, nicely appointed furnishings with bay views from private patio. Amazing amenities include a comm ...
From $182 per night (USD)
Expedia
$Longboat Key home rental w\/ PRIVATE Pool & 1 minute to private beach access!$
From $466 per night (USD)
VRBO
Longboat Key home rental w\/ PRIVATE Pool & 1 minute to private beach access!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to your dream rental home, perfectly positioned amid the Harbourside Course of the prestigious Longboat Key Club ...
From $466 per night (USD)
VRBO
From $171 per night (USD)
Expedia
Steps to private beach and Gulf Coast Florida sunsets!!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cozy Condo by the Sea!! Come and make yourself at home in this bright and beautiful 5th floor condo and enjoy sunrises o ...
From $171 per night (USD)
Expedia
From $343 per night (USD)
VRBO
Sandy Daze on the Gulf. Beachfront condo on quiet luxurious Longboat Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This prime location situates you directly on the sugar-white sands and emerald waters of the Gulf of Mexico. You can fin ...
From $343 per night (USD)
VRBO
From $406 per night (USD)
Expedia
Bayfront home with dock, amazing views, outdoor areas, & kayak
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Beach to Bay View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $406 per night (USD)
Expedia
$Beach Castle Resort, 1st Floor, Pool, Tennis, Walk to Beach\/Bay$
From $426 per night (USD)
VRBO
Beach Castle Resort, 1st Floor, Pool, Tennis, Walk to Beach\/Bay
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Beach Castle Resort is a charming and cozy beach complex on Longboat Key with a variety of great amenities and one of th ...
From $426 per night (USD)
VRBO
From $499 per night (USD)
Expedia
Coquina Moorings 205 ~ Beach, Bay, Pool, Docking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Coquina Moorings 205 - Beautiful, second floor bay front/gulf front condo near Coquina Beach. Wonderful bay v ...
From $499 per night (USD)
Expedia
$🏖Home W\/ AMAZING Heated Pool only 2 miles to the Beach!🏖B$
From $298 per night (USD)
VRBO
🏖Home W\/ AMAZING Heated Pool only 2 miles to the Beach!🏖B
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This vacation home is a newly remodeled, stylish 2 bedroom and 2 bath that will sleep 6 with an additional Queen sofa be ...
From $298 per night (USD)
VRBO
$🏖Home W\/ AMAZING Heated Pool only 2 miles to the Beach!🏖A$
From $314 per night (USD)
Expedia
🏖Home W\/ AMAZING Heated Pool only 2 miles to the Beach!🏖A
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This vacation home is a newly remodeled, stylish 2 bedroom and 2 bath that will sleep 6 with an additional Queen sofa be ...
From $314 per night (USD)
Expedia
From $217 per night (USD)
VRBO
Whitney Beach Hidden Gem
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to the north shore of pristine Longboat Key. Whitney beach is a beach lovers paradise, with 800 feet of deeded ...
From $217 per night (USD)
VRBO
From $476 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 $476 per night (USD)
Expedia
From $232 per night (USD)
VRBO
Anna Maria near the sea- 30 seconds to the Gulf Of Mexico!
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
The Sailor Park provides an overnight vacation rental offering nightly, weekly, and monthly overnight rentals in one of ...
From $232 per night (USD)
VRBO
$Entire guesthouse w\/ Heated Pool$
From $225 per night (USD)
Expedia
Entire guesthouse w\/ Heated Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover your ideal retreat at this recently remodeled Anna Maria Island vacation rental, where comfort meets convenienc ...
From $225 per night (USD)
Expedia
From $118 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 $118 per night (USD)
VRBO
From $344 per night (USD)
Expedia
Beach Castle Resort, Pool, Tennis, Private Beach n Bayfront
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Beach Castle Resort is a family-friendly, fun community on Longboat Key with numerous on-site amenities and one of the r ...
From $344 per night (USD)
Expedia
From $300 per night (USD)
VRBO
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 ...
From $300 per night (USD)
VRBO
From $489 per night (USD)
Expedia
Turtle Shores BEACHFRONT Retreat! Waterfront oasis to completely unwind!
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 $489 per night (USD)
Expedia
$2 bedroom\/2bath private home in Longbeach Village on Longboat Key$
From $217 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 $217 per night (USD)
VRBO
From $89 per night (USD)
Expedia
Beach Harbor Club, Sea Ya
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Furnished, 2 bedrooms, 2 bath condo located in Beach Harbor Club on Longboat Key. This ground floor unit is centrally l ...
From $89 per night (USD)
Expedia
From $158 per night (USD)
VRBO
Gulf View, 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 $158 per night (USD)
VRBO
From $223 per night (USD)
Expedia
Community Pool & Spa, Club Longboat, Longboat Key, Just Beachy
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Just Beachy! In need of a view? We have you covered. This 2-bedroom, 2-bath third floor end unit condo located in the hi ...
From $223 per night (USD)
Expedia
From $362 per night (USD)
VRBO
Snow On The Beach | 2 Bed, 2 Bath
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This unit is located in the Islander Club, one of the best communities on the Gulf of Mexico. With this privileged loca ...
From $362 per night (USD)
VRBO
From $310 per night (USD)
Expedia
Beachfront, Longboat Key, Flirty Flamingo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in the highly sought-after Beachplace on Longboat Key, this beautiful 2 bedroom, 2 bath condo is located on the ...
From $310 per night (USD)
Expedia
From $818 per night (USD)
VRBO
Waterfront, Private Pool, Longboat Key, Walk to Beach, Just Coastin
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to the popular Country Club Shores community on South Longboat Key, one of the quietest areas to enjoy your stay ...
From $818 per night (USD)
VRBO
From $515 per night (USD)
Expedia
Private Pool, Longboat Key, walk to Beach, Clear Skies
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful and spacious 3 bedroom, 2.5 bath ranch home, nestled in the quaint Buttonwood Harbour neighborhood of Longboat ...
From $515 per night (USD)
Expedia
From $378 per night (USD)
VRBO
Private Pool, Longboat Key, Near Beach, Haven on Hughes
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Welcome to Haven on Hughes! This one-of-a-kind 3-bedroom, 2-bath, two-story spacious private pool home is located on the ...
From $378 per night (USD)
VRBO
From $476 per night (USD)
Expedia
Pool & Spa, The Captain's Quarters
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to The Captain's Quarters! This newly built Luxury Rental Home on Longboat Key has everything for you and your f ...
From $476 per night (USD)
Expedia
$Waterfront, Spa\/Pool, Private Paradise On Longboat Key!$
From $444 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 $444 per night (USD)
VRBO
From $233 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 $233 per night (USD)
Expedia
From $434 per night (USD)
VRBO
Club Longboat #312 Condo by RVA
Bedrooms:
2
Bathrooms:
2
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 $434 per night (USD)
VRBO
From $115 per night (USD)
VRBO
Bikini Bottom Cottage in the historic village of Longboat Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Bikini bottom Cottage is on an alley way that lead directly to the kayak and boat launch. Walk down to view the sun ...
From $115 per night (USD)
VRBO
From $144 per night (USD)
VRBO
Longboat Key, Once Upon A Tide
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This magnificent Gulf front vacation retreat sits on the 6th floor of the prestigious Westchester of Longboat Key, while ...
From $144 per night (USD)
VRBO
$Beachfront 4th floor 4\/4 Longboat Key Condo With Stunning Gulf Views$
From $765 per night (USD)
Expedia
Beachfront 4th floor 4\/4 Longboat Key Condo With Stunning Gulf Views
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Paradis Sur Mer! In need of an ocean view? We have you covered. This fourth floor 4-bedroom, 4-bath condo has ...
From $765 per night (USD)
Expedia
From $296 per night (USD)
VRBO
Luxurious bungalow in Longboat Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Welcome to the newest Double Rainbow International property, Suncoast Shangrila! Suncoast Shangrila offers a private, l ...
From $296 per night (USD)
VRBO
From $244 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 $244 per night (USD)
VRBO
From $1000 per night (USD)
VRBO
Tranquil Oasis with Pool and Beach Access
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Special Offer: Enjoy special monthly rates for extended stays—perfect for a relaxing getaway or remote work retreat! Our ...
From $1000 per night (USD)
VRBO
$Magnificent sunlit beach retreat with pool, grill, balcony, W\/D - close to water$
From $284 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 $284 per night (USD)
Expedia
From $413 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 $413 per night (USD)
VRBO
From $512 per night (USD)
Expedia
Beachplace 3 - 502 by FGC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
30 day rental required. Beautiful beachfront unit on the 5th floor with Gulf view. Beautifully appointed 2 bedroom, 2 ...
From $512 per night (USD)
Expedia
From $641 per night (USD)
VRBO
Full Beach View 2 Bedroom Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
New Listing! Perfect beach view elevated walkdown level fully renovated 2 bedroom condo offers modern luxury. It is par ...
From $641 per night (USD)
VRBO
From $389 per night (USD)
VRBO
Club Longboat - 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 $389 per night (USD)
VRBO
From $219 per night (USD)
VRBO
Ocean Front, LBK, The Lookout
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to The Lookout! This charming fourth-floor 2-bedroom, 2-bathroom waterfront condo is on the beach and boasts ful ...
From $219 per night (USD)
VRBO
From $151 per night (USD)
Expedia
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 $151 per night (USD)
Expedia
From $320 per night (USD)
VRBO
Sunset Beach on Longboat Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Welcome to your amazing beachfront vacation. The apartment has a fully appointed updated kitchen with plenty of storage ...
From $320 per night (USD)
VRBO
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Expedia
One-of-a-Kind Villa in Beach Castle Direct Views of the Bay, Walk to Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Hidden gem in Beach Castle Resort on Longboat Key. The only 3 bedroom, 3 bathroom with a two private parking spaces. Dir ...
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Expedia
$1st Floor Updated, Beach Castle Resort, Walk to Beach\/Bay$
From $465 per night (USD)
VRBO
1st Floor Updated, Beach Castle Resort, Walk to Beach\/Bay
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Beach Castle Resort is a charming and cozy beach complex on Longboat Key with a variety of great amenities and one of th ...
From $465 per night (USD)
VRBO
From $393 per night (USD)
Expedia
Pristine, emerald waters of Gulf of Mexico - 5 minute walk to Gulf of Mexico
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Paradise - postcard perfect. High-quality furnishings (2023). Walk to beach and bay. Fish from the dock in your backyar ...
From $393 per night (USD)
Expedia
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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 ...
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VRBO
$Castle on-the-Bay - St. Armand’s\/Lido Beach 6 BD, Pool\/Spa, Boat & Jet Ski Dock$
From $4440 per night (USD)
VRBO
Castle on-the-Bay - St. Armand’s\/Lido Beach 6 BD, Pool\/Spa, Boat & Jet Ski Dock
Bedrooms:
6
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 $4440 per night (USD)
VRBO
From $312 per night (USD)
VRBO
Beach lovers dream
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Be one of the first to stay at this newly renovated, 1st floor beachside condominium, just steps from the beach on Longb ...
From $312 per night (USD)
VRBO
From $268 per night (USD)
Expedia
Modern LBK condo with partial ocean view! 15 steps from private beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Newly renovated, 2 bedroom and 2 bath (~1100 sq ft) condo steps with partial view of the beach (looking SW). Condo renov ...
From $268 per night (USD)
Expedia
$Incredible 2bed\/2bath DIRECT gulf front view on the 4th floor!$
From $391 per night (USD)
VRBO
Incredible 2bed\/2bath DIRECT gulf front view on the 4th floor!
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 $391 per night (USD)
VRBO
From $535 per night (USD)
VRBO
Sea Club Iii Beachside Condo On Longboat Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
SEA CLUB III - WEEKLY VACATION RENTAL - BEACHSIDE CONDO ON LONGBOAT KEY. Perfect Location on the beaches o ...
From $535 per night (USD)
VRBO
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Expedia
Super Rate drop on 3 BR condo on Longboat Key, FL for Jan & Feb
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Near Sarasota, Florida….. Our condo is located within SEAPLACE, a gated residential condominium community on Longboat Ke ...
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Expedia
Click For Pricing
Expedia
Bermuda-esque Island Cottage! Steps to Sand!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover this charming cottage tucked away on a serene corner lot. Inside this delightful space, you'll find a nice remo ...
Click For Pricing
Expedia
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VRBO
LITTLE GULL COTTAGES UNIT 9 BAYSIDE
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Little Gull Cottages, located on Longboat Key, is the perfect base for Gulf Coast fun in Florida. Enjoy the attractions ...
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VRBO
$Classic Cottage w\/Boat Parking! Steps to Sand!$
From $144 per night (USD)
Expedia
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)
Expedia
From $284 per night (USD)
VRBO
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 ...
From $284 per night (USD)
VRBO
Click For Pricing
Expedia
LITTLE GULL COTTAGES UNIT 3 GULFSIDE
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Little Gull Cottages, located on Longboat Key, is the perfect base for Gulf Coast fun in Florida. Enjoy the attractions ...
Click For Pricing
Expedia
Click For Pricing
Expedia
Stunning Bayfront Home with Unrivaled Views
Bedrooms:
5
Bathrooms:
4
Sleeps:
2
Private, open concept, treetop pool, panoramic water views. Beach access across street, walking distance to restaurants ...
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Expedia
$Island vacay spot for relaxation w\/ private beach access and bay access.$
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Expedia
Island vacay spot for relaxation w\/ private beach access and bay access.
Bedrooms:
2
Bathrooms:
2
Sleeps:
2
Private beach, bay access, fishing pier, kayaking access, Olympic size swimming pool, fitness center, lush grounds with ...
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Expedia
From $315 per night (USD)
VRBO
Beach Harbor Club B305 Condo 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 $315 per night (USD)
VRBO
From $336 per night (USD)
Expedia
Updated 2 Bedroom with Pool, Beach, and Tennis Access 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 $336 per night (USD)
Expedia

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