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
4.97 out of 5 average rating, 32 reviewsUnit B updated 2/2 Shared pool! Walk to beach
1–8 Dec
Home in Longboat Key
5.0 out of 5 average rating, 7 reviewsZilli Villa, a 2,000 sf home right on the beach.
26 Apr – 3 May
Home in Bradenton
4.85 out of 5 average rating, 20 reviews"Paradise" by the Private (Heated) Pool light!
23–30 Aug
Home in Sarasota
4.92 out of 5 average rating, 12 reviewsFruit /Botanical Garden Estate 2 miles to downtown
22–29 Jan
Home in Holmes Beach
5.0 out of 5 average rating, 20 reviewsKey Lime Cottage by Beach Boutique Rentals
19–26 Oct
Home in Holmes Beach
4.93 out of 5 average rating, 27 reviewsBackyard Bliss Anna Maria Island
7–14 Mar
Home in Longboat Key
4.96 out of 5 average rating, 51 reviewsDirect Bay Front villa w/ private boat slip
14–21 May
Home in Anna Maria
4.96 out of 5 average rating, 52 reviewsSteps to the Beach! Pool/spa! Golf Cart Included!!
10–17 Dec
Weekly house rentals
Home in Myakka City
4.98 out of 5 average rating, 134 reviewsCharming Country Stay (Near Lakewood Ranch)
14–21 Oct
Home in Longboat Key
5.0 out of 5 average rating, 51 reviewsBeautiful Beach House
30 Dec – 6 Jan
Home in Holmes Beach
4.89 out of 5 average rating, 9 reviewsAnna Maria Island 2-bed/2 bath (side A of duplex)
30 Nov – 7 Dec
Home in Sarasota
5.0 out of 5 average rating, 22 reviewsTropical tranquil abode in beautiful Sarasota
24 Sep – 1 Oct
Home in Bradenton Beach
5.0 out of 5 average rating, 11 reviewsNew! Sunset Beach View/Trolley/Bridge Street!
15–22 Feb
Home in Bradenton
4.94 out of 5 average rating, 17 reviewsLittle Love Shack by the Beach
18–25 Jun
Home in Anna Maria
5.0 out of 5 average rating, 34 reviewsami skyview
4–11 Oct
Home in Sarasota
5.0 out of 5 average rating, 41 reviewsMinutes to downtown renovated oasis with nostalgia
21–28 Sep
Private house rentals
Home in Sarasota
4.97 out of 5 average rating, 38 reviewsSunset retreat Indian Beach near downtown Sarasota
8–15 Jul
Home in Sarasota
5.0 out of 5 average rating, 60 reviewsMagical Secluded Retreat
24–31 Oct
Home in Sarasota
4.98 out of 5 average rating, 58 reviews‘The Bella’ Cottage by Sarasota Bay!
2–9 Aug
Home in Bradenton
5.0 out of 5 average rating, 18 reviewsSun Bum ~ Close To Beaches ~ AMI ~ IMG ~ Paradise
14–21 Oct
Home in Sarasota
5.0 out of 5 average rating, 7 reviewsBrand New Luxury Home w/ Pool & Putting Green
13–20 Oct
Home in Sarasota
5.0 out of 5 average rating, 26 reviewsSarasota Banyan Retreat - Walk to Bay & Ringling!
20–27 May
Home in Bradenton
5.0 out of 5 average rating, 27 reviewsTranquility on the bay.
17–24 May
Home in Sarasota
4.92 out of 5 average rating, 64 reviewsBeautifully renovated home near the beach
17–24 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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