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 Anna Maria
5 out of 5 average rating, 22 reviewsVeselka - Canal front w private heated pool & dock
Home in Siesta Key
4.94 out of 5 average rating, 31 reviews*NO Hurricane Damage Private Pool & 2-Car Garage
Home in Holmes Beach
5 out of 5 average rating, 23 reviewsSunkissed & Salty: Guest Favorite! Prime Island L
Home in Bradenton
5 out of 5 average rating, 118 reviewsHTDPool~2KingSuites~3BathRm~FIREpit~Airhockey~CRIB
Home in Downtown Sarasota
4.97 out of 5 average rating, 37 reviewsNomadic Abode Sarasota -heated saltwater pool!
Home in Anna Maria
5 out of 5 average rating, 9 reviewsOcean Air Oasis-New Centrally Located AMI Luxury
Home in Sarasota
5 out of 5 average rating, 54 reviewsThe Blessing House- Htd Pool/Spa, Close to Beaches
Home in Bradenton
5 out of 5 average rating, 15 reviewsCanal front, dock, heated Pool, near AMI+IMG
Weekly house rentals
Home in Sarasota
4.96 out of 5 average rating, 54 reviewsSun-filled cottage with pool, walk to beach
Home in Sarasota
4.97 out of 5 average rating, 65 reviewsMinutes to downtown renovated oasis with nostalgia
Home in Siesta Key
5 out of 5 average rating, 10 reviewsThe Shore House Private Dock Hot Tub
Home in Bradenton
4.84 out of 5 average rating, 43 reviewsThe "Love shack" Bungalow
Home in Sarasota
4.97 out of 5 average rating, 34 reviewsFenced Yard | Vry Private | 400Mb | BBQ | Netflix
Home in Anna Maria
5 out of 5 average rating, 22 reviews༄ Sunset Shore on Anna Maria Island ༄
Home in Indian Beach-Sapphire Shores
4.92 out of 5 average rating, 51 reviewsTropical Retreat w/ charming garden near downtown
Home in Sarasota
5 out of 5 average rating, 14 reviewsSwim & Soak Retreat| Master Suite| Heated Pool/Spa
Private house rentals
Home in Sarasota
4.99 out of 5 average rating, 70 reviewsSea Esta | Private Saltwater POOL + Putting Green!
Home in Anna Maria
4.9 out of 5 average rating, 50 reviewsIsland in the Sun
Home in Venice
4.94 out of 5 average rating, 36 reviewsOasis - The Jellyfish
Home in Holmes Beach
4.94 out of 5 average rating, 89 reviewsBreezy Harbor AMI pool retreat near the Beach
Home in Sarasota
5 out of 5 average rating, 6 reviewsArlington Ocean Oasis 5br 5ba Htd Saltwater Pool
Home in Indian Beach-Sapphire Shores
5 out of 5 average rating, 67 reviewsMagical Secluded Retreat
Home in Siesta Key
5 out of 5 average rating, 25 reviewsParadise In Siesta!
Home in Siesta Key
5 out of 5 average rating, 25 reviewsBeachfront 180-Degree View, Walk to Village!
Quick stats about house rentals in Longboat Key
Total rentals
230 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
3.5K reviews
Family-friendly rentals
200 properties are a good fit for families
Pet-friendly rentals
100 properties allow pets
Rentals with a pool
140 properties have a pool
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- Family travel hub Tips and inspiration
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