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 house rentals in Longboat Key
House rentals with a pool
Home in Siesta Key
5.0 out of 5 average rating, 126 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 Holmes Beach
4.93 out of 5 average rating, 28 reviewsBackyard Bliss Anna Maria Island
Home in Sarasota
4.92 out of 5 average rating, 12 reviewsFruit /Botanical Garden Estate 2 miles to downtown
Home in Anna Maria
4.96 out of 5 average rating, 52 reviewsSteps to the Beach! Pool/spa! Golf Cart Included!!
Home in Anna Maria
5.0 out of 5 average rating, 3 reviewsPirates Bay by Beach Boutique Rentals
Home in Holmes Beach
4.95 out of 5 average rating, 66 reviewsModern Island Home/Walk 2 Beaches-Rest./Gulf Views
Home in Sarasota
5.0 out of 5 average rating, 38 reviewsThe Blessing House- Htd Pool/Spa, Close to Beaches
Weekly house rentals
Home in Bradenton
5.0 out of 5 average rating, 14 reviewsThe "Love shack" Bungalow
Home in Anna Maria
5.0 out of 5 average rating, 35 reviewsami skyview
Home in Sarasota
4.98 out of 5 average rating, 58 reviews‘The Bella’ Cottage by Sarasota Bay!
Home in Bradenton Beach
5.0 out of 5 average rating, 33 reviewsAMI*Steps to the beach-Modern luxury POOL SPA
Home in Sarasota
4.97 out of 5 average rating, 38 reviewsSunset retreat Indian Beach near downtown Sarasota
Home in Sarasota
5.0 out of 5 average rating, 24 reviewsLovely House in Sarasota Bay
Home in Bradenton
5.0 out of 5 average rating, 18 reviewsSrq Heated Pool w/Golf Course + Bocce Ball Court!
Home in Holmes Beach
4.95 out of 5 average rating, 78 reviewsBreezy Harbor AMI pool retreat near the Beach
Private house rentals
Home in Sarasota
4.9 out of 5 average rating, 71 reviewsChic Beach Retreat Private Upper Cottage Apartment
Home in Siesta Key
5.0 out of 5 average rating, 22 reviewsBeachfront 180-Degree View, Walk to Village!
Home in Anna Maria
4.91 out of 5 average rating, 34 reviewsBeach House w/ pool on the north end of AMI 3b/2ba
Home in Anna Maria
5.0 out of 5 average rating, 60 reviewsNew Prof Decorated-Pool/Spa 5 minute walk 2 Ocean
Home in Bradenton
5.0 out of 5 average rating, 20 reviewsSun Bum ~ Close To Beaches ~ AMI ~ IMG ~ Paradise
Home in Anna Maria
5.0 out of 5 average rating, 78 reviewsManatee Harbour - heated pool, on the canal
Home in Holmes Beach
4.78 out of 5 average rating, 27 reviewsWalk to beach | Anna Maria home w/ pool | Pets ok!
Home in Bradenton
5.0 out of 5 average rating, 28 reviewsTranquility on the bay.
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
€ 28 before taxes and fees
Destinations to explore
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