House holiday 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.
Holiday 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 Sarasota
4.82 out of 5 average rating, 198 reviewsPrivate Siesta Beach House Oasis with Heated Pool.
Home in Siesta Key
5.0 out of 5 average rating, 127 reviewsOne-of-a-kind*Beach, Village, Dock & Private Pool!
Home in Holmes Beach
4.97 out of 5 average rating, 124 reviewsTwin Palms: Big House Steps to Beach w/Lush Pool
Home in Bradenton
4.95 out of 5 average rating, 100 reviewsEndless Outdoor FUN! Pool/Spa/Golf/Games/Near IMG
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 Holmes Beach
4.93 out of 5 average rating, 28 reviewsBackyard Bliss Anna Maria Island
Home in Anna Maria
5.0 out of 5 average rating, 3 reviewsPirates Bay by Beach Boutique Rentals
Home in Sarasota
5.0 out of 5 average rating, 12 reviewsWalk to Lido Beach &St. Armands -grill/HEATED POOL
Weekly house rentals
Home in Bradenton
5.0 out of 5 average rating, 23 reviewsSun Bum ~ Close To Beaches ~ AMI ~ IMG ~ Paradise
Home in Bradenton
5.0 out of 5 average rating, 16 reviewsThe "Love shack" Bungalow
Home in Anna Maria
5.0 out of 5 average rating, 15 reviewsLamantin- 2 bed/2bath North End, beach 2 min walk
Home in Bradenton
4.97 out of 5 average rating, 29 reviewsAnna Maria Island Beach Gulf Shore Cottage
Home in Anna Maria
5.0 out of 5 average rating, 36 reviewsami skyview
Home in Sarasota
4.91 out of 5 average rating, 53 reviewsCentrally Located Cozy Home
Home in Sarasota
4.98 out of 5 average rating, 58 reviews‘The Bella’ Cottage by Sarasota Bay!
Home in Anna Maria
5.0 out of 5 average rating, 20 reviewsStunning new 4 bed/4.5 bath home with heated pool
Private house rentals
Home in Holmes Beach
4.95 out of 5 average rating, 38 reviewsTrue beach front home - 3 beds/2 bath, heated pool
Home in Bradenton Beach
4.87 out of 5 average rating, 38 reviewsLivin' the dream at The Beach Dreams Resort unit E
Home in Holmes Beach
4.95 out of 5 average rating, 78 reviewsBreezy Harbor AMI pool retreat near the Beach
Home in Anna Maria
5.0 out of 5 average rating, 61 reviewsNew Prof Decorated-Pool/Spa 5 minute walk 2 Ocean
Home in Bradenton Beach
4.98 out of 5 average rating, 84 reviewsWaterfront home with heated pool walk to Beach!
Home in Holmes Beach
5.0 out of 5 average rating, 31 reviewsTip’Sea Turtle Anna Maria island
Home in Sarasota
4.9 out of 5 average rating, 41 reviewsTropical Retreat w/ charming garden near downtown
Home in Bradenton
5.0 out of 5 average rating, 20 reviewsSrq Heated Pool w/Golf Course + Bocce Ball Court!
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
$49 NZD before taxes and fees
Destinations to explore
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