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 Holmes Beach
4.95 out of 5 average rating, 158 reviewsSet AMI
22–29 Nov
Home in Siesta Key
5.0 out of 5 average rating, 124 reviewsOne-of-a-kind*Beach, Village, Dock & Private Pool!
10–17 Oct
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 Holmes Beach
4.92 out of 5 average rating, 24 reviewsBackyard Bliss Anna Maria Island
17–24 Nov
Home in Sarasota
5.0 out of 5 average rating, 10 reviewsFruit /Botanical Garden Estate 2 miles to downtown
5–12 Apr
Home in Anna Maria
4.96 out of 5 average rating, 50 reviewsSteps to the Beach! Pool/spa! Golf Cart Included!!
14–21 Sep
Home in Sarasota
5.0 out of 5 average rating, 12 reviewsWalk to Lido Beach &St. Armands -grill/HEATED POOL
21–28 Sep
Home in Bradenton
4.83 out of 5 average rating, 18 reviews"Paradise" by the Private (Heated) Pool light!
6–13 Sep
Weekly house rentals
Home in Sarasota
5.0 out of 5 average rating, 20 reviewsThe Mango House Beach Cottage
14–21 Aug
Home in Sarasota
5.0 out of 5 average rating, 22 reviewsTropical tranquil abode in beautiful Sarasota
3–10 Sep
Home in Sarasota
4.89 out of 5 average rating, 47 reviewsCentrally Located Cozy Home
8–15 Sep
Home in Sarasota
4.97 out of 5 average rating, 36 reviewsSunset retreat Indian Beach near downtown Sarasota
16–23 Aug
Home in Anna Maria
5.0 out of 5 average rating, 32 reviewsami skyview
1–8 Dec
Home in Sarasota
5.0 out of 5 average rating, 29 reviewsSiesta Key Fully-Renovated Unit 5 min to the beach
26 Sep – 3 Oct
Home in Sarasota
5.0 out of 5 average rating, 6 reviewsBrand New Luxury Home w/ Pool & Putting Green
27 Sep – 4 Oct
Home in Sarasota
4.95 out of 5 average rating, 22 reviewsLovely Home by Sarasota Bay
7–14 Sep
Private house rentals
Home in Sarasota
5.0 out of 5 average rating, 58 reviewsMagical Secluded Retreat
5–12 Oct
Home in Longboat Key
4.96 out of 5 average rating, 50 reviewsDirect Bay Front villa w/ private boat slip
5–12 Jul
Home in Sarasota
4.9 out of 5 average rating, 69 reviewsChic Beach Retreat Private Upper Cottage Apartment
12–19 May
Home in Sarasota
4.98 out of 5 average rating, 57 reviews‘The Bella’ Cottage by Sarasota Bay!
10–17 Oct
Home in Sarasota
4.78 out of 5 average rating, 63 reviewsPool house by the bay
1–8 Aug
Home in Holmes Beach
4.91 out of 5 average rating, 46 reviewsGorgeous Bay house in AMI! 5 min walk to beach!
17–24 Sep
Home in Siesta Key
5.0 out of 5 average rating, 22 reviewsBeachfront 180-Degree View, Walk to Village!
21–28 Sep
Home in Sarasota
5.0 out of 5 average rating, 9 reviewsUrban Serenity among Mango Trees
31 Aug – 7 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
€ 28 before taxes and fees
Destinations to explore
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