House vacation rentals in Longboat Key
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Top-rated house rentals in Longboat Key
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Longboat Key house rentals
House rentals with a pool
Home in Siesta Key
5.0 out of 5 average rating, 127 reviewsOne-of-a-kind*Beach, Village, Dock & Private Pool!
Home in Sarasota
4.94 out of 5 average rating, 302 reviews☀Coastal Gem☀Heated pool & amazing location!☀
Home in Anna Maria
4.94 out of 5 average rating, 154 reviewsPrivate 30' Pool and Boat Dock - Rated best on AMI
Home in Holmes Beach
4.97 out of 5 average rating, 125 reviewsTwin Palms: Big House Steps to Beach w/Lush Pool
Home in Longboat Key
5.0 out of 5 average rating, 7 reviewsZilli Villa, a 2,000 sf home right on the beach.
Home in Anna Maria
5.0 out of 5 average rating, 4 reviewsPirates Bay by Beach Boutique Rentals
Home in Holmes Beach
4.93 out of 5 average rating, 29 reviewsBackyard Bliss Anna Maria Island
Home in Holmes Beach
4.95 out of 5 average rating, 79 reviewsBreezy Harbor AMI pool retreat near the Beach
Weekly house rentals
Home in Longboat Key
5.0 out of 5 average rating, 53 reviewsBeautiful Beach House
Home in Holmes Beach
4.89 out of 5 average rating, 9 reviewsAnna Maria Island 2-bed/2 bath (side A of duplex)
Home in Bradenton Beach
5.0 out of 5 average rating, 19 reviewsDirect Beachfront/Sunset Views!Next to AMI Trolley
Home in Sarasota
4.91 out of 5 average rating, 55 reviewsCentrally Located Cozy Home
Home in Sarasota
4.98 out of 5 average rating, 55 reviewsCentral to beaches, Nathan Benderson Park, & UTC.
Home in Anna Maria
5.0 out of 5 average rating, 38 reviewsami skyview
Home in Bradenton Beach
4.88 out of 5 average rating, 40 reviewsLivin' the dream at The Beach Dreams Resort unit E
Home in Bradenton
4.95 out of 5 average rating, 19 reviewsThe "Love shack" Bungalow
Private house rentals
Home in Anna Maria
4.96 out of 5 average rating, 57 reviewsMy Private Beach
Home in Bradenton
5.0 out of 5 average rating, 26 reviewsSun Bum ~ Close To Beaches ~ AMI ~ IMG ~ Paradise
Home in Anna Maria
5.0 out of 5 average rating, 42 reviewsBean Pt. Bungalow - Half duplex w/private pool
Home in Anna Maria
5.0 out of 5 average rating, 14 reviewsVeselka - Canal front w private heated pool & dock
Home in Holmes Beach
4.93 out of 5 average rating, 28 reviewsAnna Maria - 3 Bd 2 Bth Home -Pool -Walk to Beach
Home in Bradenton
4.97 out of 5 average rating, 33 reviewsWaterfront Home! Heated Pool, Spa & Boat Dock
Home in Anna Maria
5.0 out of 5 average rating, 63 reviewsNew Prof Decorated-Pool/Spa 5 minute walk 2 Ocean
Home in Sarasota
4.83 out of 5 average rating, 40 reviewsLIDO KEY Perfect Florida Coastal Cottage Getaway
Quick stats about house rentals in Longboat Key
Total rentals
190 properties
Rentals with a pool
120 properties have a pool
Pet-friendly rentals
80 properties allow pets
Family-friendly rentals
170 properties are a good fit for families
Total number of reviews
3K reviews
Nightly prices starting at
$30 before taxes and fees
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- Family travel hub Tips and inspiration
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