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
4.81 out of 5 average rating, 107 reviews1 House 1400sq. ft. 12 min from Siesta Key!
26 Sep – 3 Oct
Home in Venice
4.85 out of 5 average rating, 136 reviewsGetaway Relax Home/Beaches 5-10minutes/Heated Pool
26 Jun – 3 Jul
Home in Sarasota
4.97 out of 5 average rating, 206 reviewsYour private retreat near Siesta Key Beach.
15–22 Apr
Home in Sarasota
4.93 out of 5 average rating, 106 reviewsLake Front House with a Pool
26 Aug – 2 Sep
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
8–15 Sep
Home in Nokomis
4.96 out of 5 average rating, 27 reviewsTropical Pool Paradise - Minutes from the Beach!
29 Oct – 5 Nov
Weekly house rentals
Home in Osprey
4.92 out of 5 average rating, 38 reviewsPrivate house with loft
6–13 Oct
Home in Nokomis
4.9 out of 5 average rating, 40 reviewsCheerful, sparkling 2 bedroom cottage, 1.8 miles from beach
5–12 Sep
Home in Osprey
4.91 out of 5 average rating, 33 reviewsSand Dollar Cottage - 15m to Siesta / Casey Key
2–9 Dec
Home in Osprey
4.96 out of 5 average rating, 23 reviewsCharming Florida Cottage - Kayaks Included
24–31 Oct
Home in Sarasota
5.0 out of 5 average rating, 5 reviewsCute 2 bedroom home close to it all.
31 Aug – 7 Sep
Home in Nokomis
5.0 out of 5 average rating, 9 reviewsUpdated house close to the Beach
14–21 Aug
Home in Sarasota
4.92 out of 5 average rating, 61 reviewsSarasota Summer Beach Bliss!
24 Nov – 1 Dec
Home in Sarasota
5.0 out of 5 average rating, 5 reviewsCozy Heaven Studio III
1–8 Jun
Private house rentals
Home in Sarasota
5.0 out of 5 average rating, 12 reviewsSun-Kissed Cottage near Siesta Key
16–23 Jul
Home in Sarasota
5.0 out of 5 average rating, 9 reviewsCozy Getaway Home near Siesta Key Beach
18–25 May
Home in Nokomis
4.92 out of 5 average rating, 24 reviewsCheerful 3-bedroom
16–23 Jul
Home in Nokomis
4.99 out of 5 average rating, 84 reviewsAvailable get away 1 night, weekly or monthly
18–25 Sep
Home in Nokomis
5.0 out of 5 average rating, 42 reviewsMinutes to Nokomis Beach Updated and Spacious
14–21 May
Home in Venice
5.0 out of 5 average rating, 32 reviewsSunny Green Oasis-3 miles to beach
3–10 Oct
Home in Nokomis
5.0 out of 5 average rating, 21 reviewsSea Turtle Cottage
16–23 Sep
Home in North Port
4.96 out of 5 average rating, 51 reviewsBeautiful Modern New Home in Tropical Paradise
8–15 May
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
₹6,673 before taxes and fees
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