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 Holmes Beach
4.95 out of 5 average rating, 158 reviewsSea AMI
Oct 26 – Nov 2
Home in Tampa
4.97 out of 5 average rating, 111 reviewsDowntown Tampa Pool House! Walk to Armature Works!
Oct 24 – 31
Home in Sarasota
4.9 out of 5 average rating, 107 reviews🌴🐬Bay Haven- Resort style Backyard 🏊♀️🔥 & Game Rm⚽️
Jun 9 – 16
Home in Siesta Key
5.0 out of 5 average rating, 124 reviewsOne-of-a-kind*Beach, Village, Dock & Private Pool!
Jul 14 – 21
Home in Sarasota
5.0 out of 5 average rating, 12 reviewsWalk to Lido Beach &St. Armands -grill/HEATED POOL
Nov 12 – 19
Home in Longboat Key
5.0 out of 5 average rating, 7 reviewsZilli Villa, a 2,000 sf home right on the beach.
Dec 7 – 14
Home in Anna Maria
4.99 out of 5 average rating, 78 reviewsCHARMING HOUSE W/HEATED POOL,STEPS TO BEACH UNIT B
Aug 27 – Sep 3
Home in Anna Maria
5.0 out of 5 average rating, 3 reviewsPirates Bay by Beach Boutique Rentals
Dec 4 – 11
House rentals with a hot tub
Home in Bradenton
4.91 out of 5 average rating, 102 reviewsLuxurious 3 bedroom home with Hot Tub near AMI
Sep 26 – Oct 3
Home in Sarasota
4.89 out of 5 average rating, 103 reviewsQuiet Retreat-5mi to Beach-Hot Tub, Outdoor Shower
Jan 9 – 16
Home in Indian Rocks Beach
4.98 out of 5 average rating, 98 reviewsBeachfront Bungalow w/ Pool & Hot Tub in IRB
Jan 14 – 21
Home in Sarasota
4.98 out of 5 average rating, 160 reviewsThe Palms-Private Heated Pool Hot Tub-5mi to beach
Oct 5 – 12
Home in Bradenton
4.97 out of 5 average rating, 102 reviewsNear downtown! Saltwater Pool! HOT TUB! Games!
Jul 8 – 15
Home in Sarasota
4.98 out of 5 average rating, 144 reviewsStunning home near Siesta w/ incredible pool area!
Jul 28 – Aug 4
Home in Holmes Beach
4.97 out of 5 average rating, 31 reviewsUnit B updated 2/2 Shared pool! Walk to beach
Nov 14 – 21
Home in Sarasota
5.0 out of 5 average rating, 51 reviewsTropical Oasis Heated Pool Hot Tub Near Siesta Key
Sep 26 – Oct 3
House rentals with free parking
Home in Sarasota
4.95 out of 5 average rating, 244 reviewsLovely guest house
Aug 18 – 25
Home in Sarasota
5.0 out of 5 average rating, 22 reviewsThe Mango House Beach Cottage
Sep 19 – 26
Home in Bradenton Beach
5.0 out of 5 average rating, 10 reviewsNew! Sunset Beach View/Trolley/Bridge Street!
Jan 27 – Feb 3
Home in Sarasota
5.0 out of 5 average rating, 22 reviewsTropical tranquil abode in beautiful Sarasota
Sep 7 – 14
Home in Sarasota
4.89 out of 5 average rating, 47 reviewsCentrally Located Cozy Home
Sep 4 – 11
Home in Bradenton
4.94 out of 5 average rating, 17 reviewsLittle Love Shack by the Beach
Aug 17 – 24
Home in Sarasota
5.0 out of 5 average rating, 72 reviewsSave 15% on Tropical Getaway for 7+ Nights!
Jun 1 – 8
Home in Sarasota
5.0 out of 5 average rating, 23 reviewsLovely House in Sarasota Bay
May 27 – Jun 3
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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