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 Siesta Key
5.0 out of 5 average rating, 124 reviewsOne-of-a-kind*Beach, Village, Dock & Private Pool!
10–17 Aug
Home in Sarasota
4.9 out of 5 average rating, 107 reviews🌴🐬Bay Haven- Resort style Backyard 🏊♀️🔥 & Game Rm⚽️
9–16 Jun
Home in Sarasota
4.93 out of 5 average rating, 150 reviewsModern, Bright Downtown SRQ A-Frame West of Trail
9–16 Oct
Home in Tampa
4.97 out of 5 average rating, 111 reviewsDowntown Tampa Pool House! Walk to Armature Works!
21–28 Dec
Home in Sarasota
4.78 out of 5 average rating, 63 reviewsPool house by the bay
11–18 Jun
Home in Sarasota
5.0 out of 5 average rating, 12 reviewsWalk to Lido Beach &St. Armands -grill/HEATED POOL
6–13 Sep
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
4.96 out of 5 average rating, 51 reviewsSteps to the Beach! Pool/spa! Golf Cart Included!!
10–17 Dec
Weekly house rentals
Home in Sarasota
5.0 out of 5 average rating, 22 reviewsTropical tranquil abode in beautiful Sarasota
9–16 Sep
Home in Sarasota
4.89 out of 5 average rating, 47 reviewsCentrally Located Cozy Home
23–30 Oct
Home in Sarasota
5.0 out of 5 average rating, 9 reviewsUrban Serenity among Mango Trees
31 Aug – 7 Sep
Home in Sarasota
4.97 out of 5 average rating, 38 reviewsSunset retreat Indian Beach near downtown Sarasota
11–18 Oct
Home in Sarasota
5.0 out of 5 average rating, 72 reviewsSave 15% on Tropical Getaway for 7+ Nights!
1–8 Jun
Home in Anna Maria
5.0 out of 5 average rating, 33 reviewsami skyview
17–24 Jan
Home in Longboat Key
4.96 out of 5 average rating, 50 reviewsDirect Bay Front villa w/ private boat slip
11–18 May
Home in Bradenton Beach
5.0 out of 5 average rating, 33 reviewsAMI*Steps to the beach-Modern luxury POOL SPA
30 Oct – 6 Nov
Private house rentals
Home in Bradenton
4.97 out of 5 average rating, 31 reviewsWaterfront Home! Heated Pool, Spa & Boat Dock
25 Aug – 1 Sep
Home in Bradenton Beach
4.87 out of 5 average rating, 38 reviewsLivin' the dream at The Beach Dreams Resort unit E
12–19 Jan
Home in Sarasota
4.98 out of 5 average rating, 57 reviews‘The Bella’ Cottage by Sarasota Bay!
28 Jun – 5 Jul
Home in Sarasota
5.0 out of 5 average rating, 39 reviewsMinutes to downtown renovated oasis with nostalgia
19–26 Nov
Home in Holmes Beach
4.92 out of 5 average rating, 25 reviewsBackyard Bliss Anna Maria Island
5–12 Mar
Home in Bradenton
5.0 out of 5 average rating, 17 reviewsSun Bum ~ Close To Beaches ~ AMI ~ IMG ~ Paradise
6–13 Oct
Home in Holmes Beach
4.95 out of 5 average rating, 37 reviewsTrue beach front home - 3 beds/2 bath, heated pool
8–15 Dec
Home in Siesta Key
5.0 out of 5 average rating, 7 reviewsVintage Coastal
21–28 Sep
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
$50 NZD before taxes and fees
Destinations to explore
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