House holiday rentals in Osprey
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Top-rated house rentals in Osprey
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 Osprey
House rentals with a pool
Home in Sarasota
4.97 out of 5 average rating, 206 reviewsYour private retreat near Siesta Key Beach.
11–18 Oct
Home in Sarasota
4.81 out of 5 average rating, 107 reviews1 House 1400sq. ft. 12 min from Siesta Key!
26 Sep – 3 Oct
Home in Sarasota
4.93 out of 5 average rating, 106 reviewsLake Front House with a Pool
27 Oct – 3 Nov
Home in Nokomis
4.88 out of 5 average rating, 147 reviews4/2.5 Oak Bahay, Heated Pool! 5min to Beach,4Acres
23–30 Dec
Home in Sarasota
4.95 out of 5 average rating, 181 reviews2bed/2bath with POOL house, close by SIESTA KEY!!!
19–26 Sep
Home in Osprey
5.0 out of 5 average rating, 23 reviewsHeated Pool | 3 Beds | Near Beaches and parks
12–19 Jun
Home in Nokomis
5.0 out of 5 average rating, 17 reviews"Jellyfish" at The Shore Beach Houses Resort
16–23 Aug
Home in Venice
4.91 out of 5 average rating, 22 reviewsHeated Salt Water Pool/Dog Friendly
7–14 May
Weekly house rentals
Home in Osprey
4.92 out of 5 average rating, 38 reviewsPrivate house with loft
2–9 Oct
Home in Nokomis
4.9 out of 5 average rating, 40 reviewsCheerful, sparkling 2 bedroom cottage, 1.8 miles from beach
11–18 Aug
Home in Nokomis
5.0 out of 5 average rating, 9 reviewsUpdated house close to the Beach
7–14 Apr
Home in Osprey
4.96 out of 5 average rating, 23 reviewsCharming Florida Cottage - Kayaks Included
19–26 May
Home in Sarasota
5.0 out of 5 average rating, 6 reviewsCute 2 bedroom home close to it all.
16–23 Sep
Home in Sarasota
4.92 out of 5 average rating, 61 reviewsSarasota Summer Beach Bliss!
3–10 Jun
Home in Sarasota
5.0 out of 5 average rating, 5 reviewsCozy Heaven Studio III
28 May – 4 Jun
Home in Sarasota
4.96 out of 5 average rating, 25 reviewsBeach house #2
27 Oct – 3 Nov
Private house rentals
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 Nokomis
5.0 out of 5 average rating, 21 reviewsSea Turtle Cottage
20–27 Sep
Home in Venice
5.0 out of 5 average rating, 33 reviewsSunny Green Oasis-3 miles to beach
5–12 Sep
Home in Osprey
4.97 out of 5 average rating, 33 reviewsSarasota vacation Home!
17–24 Jul
Home in Sarasota
5.0 out of 5 average rating, 9 reviewsCozy Getaway Home near Siesta Key Beach
1–8 Aug
Home in Nokomis
4.96 out of 5 average rating, 27 reviewsTropical Pool Paradise - Minutes from the Beach!
7–14 Feb
Home in Nokomis
5.0 out of 5 average rating, 34 reviewsMinutes to Floridas most beautiful beaches!
18–25 Jul
Home in Nokomis
5.0 out of 5 average rating, 17 reviewsLuxury Oasis Home 3BR 2Bath with Heated Pool
3–10 Dec
Quick stats about house rentals in Osprey
Total rentals
40 properties
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
540 reviews
Nightly prices starting at
$109 SGD before taxes and fees
Destinations to explore
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