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 $434 per night (USD)
VRBO
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 $434 per night (USD)
VRBO
From $360 per night (USD)
Expedia
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 $360 per night (USD)
Expedia
From $305 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 $305 per night (USD)
VRBO
From $345 per night (USD)
Expedia
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)
Expedia
From $168 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 $168 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 $372 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, 2-bath condo at the Islander Club located ...
From $372 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 $229 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 $229 per night (USD)
VRBO
From $245 per night (USD)
VRBO
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 $245 per night (USD)
VRBO
From $291 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 $291 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 Bathroom • Balcony overlooking tranquil Bishop ...
From $1271 per night (USD)
Expedia
From $414 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 $414 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 Bathroom • 1 King, 1 Queen, 1 Twin Trundle Bed • Two heat ...
From $482 per night (USD)
Expedia
From $299 per night (USD)
VRBO
LBK Whitney Beach Retreat 1
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Highlights • Three-minute Walk to Whitney Beach • 1 Bedroom, 2 Bathroom • 1 King, 1 Queen sleeper sofa • Two heated comm ...
From $299 per night (USD)
VRBO
From $205 per night (USD)
Expedia
Coastal Bay Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Tucked away in the charming fishing village of Cortez, Florida, Coastal Bay Retreat is a br ...
From $205 per night (USD)
Expedia
From $332 per night (USD)
VRBO
2-bedroom condo in beautiful Longboat Key with fitness room, AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This charming condo in Longboat Key is a fabulous choice for guests looking for a cozy retreat. With 2 bedrooms includin ...
From $332 per night (USD)
VRBO
From $265 per night (USD)
Expedia
Spacious 2-BR/2 Bath Condo in desirable Seaplace Community in Longboat Key, FL
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Available January - March 2026! 3 month minimum stay Spacious (1257 sqft), 2nd floor, non-smoking, 2 bedroom/2 bathroom ...
From $265 per night (USD)
Expedia
From $217 per night (USD)
VRBO
Azure By The Sea: Sea Twig #202
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Gorgeous Beachfront ~ Spacious & Updated 2/2 ~ Heated Saltwater Pool This luxury beach getaway is waiting for you to en ...
From $217 per night (USD)
VRBO
From $246 per night (USD)
VRBO
Longboat Key Private Beach Access Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautiful Longboat Key oversized 2/2 condo with plenty of space to enjoy the peace and quiet of island life. Enjoy the ...
From $246 per night (USD)
VRBO
From $258 per night (USD)
VRBO
2-bedroom, 1.5-bath townhome-style condo by FVC
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Sutton Place 577 – Old Florida Charm on Longboat Key Offered by Florida Vacation Connection, Sutton Place 577 invites y ...
From $258 per night (USD)
VRBO
From $278 per night (USD)
Expedia
Longboat Harbour D303 by FVC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Longboat Harbour D303 – Waterfront Getaway Welcome to Longboat Harbour D303, a bright and inviting 2-bedroom, 2-bath co ...
From $278 per night (USD)
Expedia
From $193 per night (USD)
VRBO
Bayfront Escape- Beach Harbor Club F202 by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
2
Bayfront Escape at Beach Harbor Club Wake up to sparkling Sarasota Bay views in this beautifully appointed 2-bedroom, 2 ...
From $193 per night (USD)
VRBO
From $520 per night (USD)
Expedia
Peacock Place LBK - Gorgeous 3-bedroom house in Longboat Key
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Welcome to paradise! This tropical island retreat is located in a quiet residential area on the north end of Longboat ...
From $520 per night (USD)
Expedia
From $476 per night (USD)
VRBO
Canal-Front Charmer with Private Beach Access!
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
Escape to this beautiful 4-bedroom, 2-bath canal-front retreat on Longboat Key—perfect for families or groups seeking t ...
From $476 per night (USD)
VRBO
From $2224 per night (USD)
VRBO
Luxury Villa • 9BR/9BA • Steps to Lido Key Beach
Bedrooms:
9
Bathrooms:
9
Sleeps:
10
Welcome to Lido Dreams! This 4600 sqft brand new, 9 bedroom/9-bathroom luxury home sits in the heart of St. Armand’s Cir ...
From $2224 per night (USD)
VRBO
From $189 per night (USD)
VRBO
Longboat Arms #302C by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Island Living Rental – 2BR/2BA Condo in Longboat Arms, Steps from the Beach! Live the beachside lifestyle in this brigh ...
From $189 per night (USD)
VRBO
From $746 per night (USD)
Expedia
Beautiful 4-bedroom house walking distance to beach and restaurants Longboat Key
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Consider this house your home away from home while you visit Longboat Key. This wonderful property boasts 4 luxurious be ...
From $746 per night (USD)
Expedia
From $182 per night (USD)
VRBO
Beach to Bay Beauty- available for season 2026-Pet friendly!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Bayport Beach and Tennis Club! This charming corner condo is light, spacious and has everything for carefree, ...
From $182 per night (USD)
VRBO
From $189 per night (USD)
Expedia
Longboat Snowbird Getaway • Beach & Bay
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Escape winter in style at this beautifully updated 2-bedroom, 2-bath condo located in the intimate, bayfront Lo ...
From $189 per night (USD)
Expedia
From $208 per night (USD)
VRBO
Wonderful Gulf and Sunset Views Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Privateer North 305, an exceptional beachfront condo located on the prestigious south end of Longboat Key, be ...
From $208 per night (USD)
VRBO
From $256 per night (USD)
Expedia
Charming 2-bedroom house in gorgeous Longboat Key
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This 2-bedroom house is perfect for your escape to Longboat Key. With 2 queen beds, nicely renovated bathroom, full kitc ...
From $256 per night (USD)
Expedia
From $286 per night (USD)
VRBO
Tranquility at the Water’s Edge- Egret's Landing #22
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 $286 per night (USD)
VRBO
From $203 per night (USD)
Expedia
Beach Villa on Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Your home away from home in Longboat Key with 2 bedrooms. This adorable villa features 1 king bed and 1 queen bed, perfe ...
From $203 per night (USD)
Expedia
From $1739 per night (USD)
VRBO
Aria #203 A Gorgeous 3-Bedroom + Theater Room Luxury Retreat
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Gorgeous 3-Bedroom Luxury Retreat with Theater Room | The Aria, Longboat Key Welcome to paradise at The Aria on Longboa ...
From $1739 per night (USD)
VRBO
From $424 per night (USD)
Expedia
HVC #203 - Spa/Pool - Private Paradise on LBK!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Looking for the ULTIMATE Beach getaway? This is it! Welcome to paradise at the Harbour Villa Club. 2 Bedrooms, 2 Bath ...
From $424 per night (USD)
Expedia
From $280 per night (USD)
VRBO
Tiffany Plaza #207 Condo by RVA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to upscale island living at Tiffany Place exclusively with RVA Vacation Rentals. This nicely appointed 2-Bedroom ...
From $280 per night (USD)
VRBO
From $513 per night (USD)
Expedia
Whitney Breeze Longboat Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Highlights • 3-minute walk to Whitney Beach • 2 Bedroom / 2 Bath • 1 King, 1 Queen, 1 Twin Trundle Bed • Two heated comm ...
From $513 per night (USD)
Expedia
From $244 per night (USD)
VRBO
The Players Club C101 by RVA
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Luxury 3-Bedroom Beachfront Retreat at The Players Club Welcome to your slice of paradise at The Players Club on Longbo ...
From $244 per night (USD)
VRBO
From $328 per night (USD)
Expedia
Stunning gulf front 6th floor Longboat Key Condo with endless views - 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 $328 per night (USD)
Expedia

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Longboat Key Rentals

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Results: 740 Rentals