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
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Popular amenities for house rentals in Longboat Key
House rentals with a pool
Home in Holmes Beach
4.95 out of 5 average rating, 158 reviewsSet AMI
26 Oct – 2 Nov
Home in Tampa
4.97 out of 5 average rating, 111 reviewsDowntown Tampa Pool House! Walk to Armature Works!
24–31 Oct
Home in Sarasota
4.9 out of 5 average rating, 107 reviews🌴🐬Bay Haven- Resort style Backyard 🏊♀️🔥 & Game Rm⚽️
9–16 Jun
Home in Siesta Key
5.0 out of 5 average rating, 124 reviewsOne-of-a-kind*Beach, Village, Dock & Private Pool!
14–21 Jul
Home in Sarasota
5.0 out of 5 average rating, 12 reviewsWalk to Lido Beach &St. Armands -grill/HEATED POOL
12–19 Nov
Home in Longboat Key
5.0 out of 5 average rating, 7 reviewsZilli Villa, a 2,000 sf home right on the beach.
7–14 Dec
Home in Anna Maria
4.99 out of 5 average rating, 78 reviewsCHARMING HOUSE W/HEATED POOL,STEPS TO BEACH UNIT B
27 Aug – 3 Sep
Home in Anna Maria
5.0 out of 5 average rating, 3 reviewsPirates Bay by Beach Boutique Rentals
4–11 Dec
Weekly house rentals
Home in Sarasota
5.0 out of 5 average rating, 22 reviewsThe Mango House Beach Cottage
19–26 Sep
Home in Bradenton Beach
5.0 out of 5 average rating, 10 reviewsNew! Sunset Beach View/Trolley/Bridge Street!
27 Jan – 3 Feb
Home in Sarasota
5.0 out of 5 average rating, 22 reviewsTropical tranquil abode in beautiful Sarasota
7–14 Sep
Home in Sarasota
4.89 out of 5 average rating, 47 reviewsCentrally Located Cozy Home
4–11 Sep
Home in Bradenton
4.94 out of 5 average rating, 17 reviewsLittle Love Shack by the Beach
17–24 Aug
Home in Sarasota
5.0 out of 5 average rating, 72 reviewsSave 15% on Tropical Getaway for 7+ Nights!
1–8 Jun
Home in Sarasota
5.0 out of 5 average rating, 23 reviewsLovely House in Sarasota Bay
27 May – 3 Jun
Home in Sarasota
5.0 out of 5 average rating, 9 reviewsUrban Serenity among Mango Trees
31 Aug – 7 Sep
Private house rentals
Home in Sarasota
4.9 out of 5 average rating, 69 reviewsChic Beach Retreat Private Upper Cottage Apartment
13–20 May
Home in Sarasota
5.0 out of 5 average rating, 59 reviewsMagical Secluded Retreat
16–23 Sep
Home in Sarasota
5.0 out of 5 average rating, 26 reviewsSarasota Banyan Retreat - Walk to Bay & Ringling!
9–16 Oct
Home in Sarasota
4.97 out of 5 average rating, 37 reviewsSunset retreat Indian Beach near downtown Sarasota
6–13 Dec
Home in Sarasota
5.0 out of 5 average rating, 29 reviewsSiesta Key Fully-Renovated Unit 5 min to the beach
24–31 Jan
Home in Treasure Island
5.0 out of 5 average rating, 3 reviewsBeachfront Private Duplex Home
15–22 Sep
Home in Sarasota
4.97 out of 5 average rating, 66 reviewsSunset Paradise by the Bay, Downtown & Beaches
25 Sep – 2 Oct
Home in Sarasota
5.0 out of 5 average rating, 14 reviewsUpdated Cozy Bungalow near Sarasota's Best Beaches
6–13 May
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
$41 SGD before taxes and fees
Destinations to explore
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