House vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Osprey house rentals
House rentals with a pool
Home in Sarasota
4.94 out of 5 average rating, 297 reviews☀Coastal Gem☀Heated pool & amazing location!☀
Jul 19 – 26
Home in Sarasota
4.97 out of 5 average rating, 207 reviewsYour private retreat near Siesta Key Beach.
Jul 31 – Aug 7
Home in Sarasota
4.93 out of 5 average rating, 106 reviewsLake Front House with a Pool
Sep 10 – 17
Home in Nokomis
4.88 out of 5 average rating, 147 reviews4/2.5 Oak Bahay, Heated Pool! 5min to Beach,4Acres
Dec 23 – 30
Home in Sarasota
4.81 out of 5 average rating, 107 reviews1 House 1400sq. ft. 12 min from Siesta Key!
Apr 27 – May 4
Home in Osprey
5.0 out of 5 average rating, 23 reviewsHeated Pool | 3 Beds | Near Beaches and parks
Jun 3 – 10
Home in Nokomis
4.96 out of 5 average rating, 28 reviewsTropical Pool Paradise - Minutes from the Beach!
Oct 28 – Nov 4
Home in Nokomis
4.95 out of 5 average rating, 19 reviewsBlue Sky Retreat
May 27 – Jun 3
Weekly house rentals
Home in Osprey
4.91 out of 5 average rating, 33 reviewsSand Dollar Cottage - 15m to Siesta / Casey Key
Oct 24 – 31
Home in Nokomis
4.9 out of 5 average rating, 40 reviewsCheerful, sparkling 2 bedroom cottage, 1.8 miles from beach
Oct 8 – 15
Home in Osprey
4.96 out of 5 average rating, 23 reviewsCharming Florida Cottage - Kayaks Included
Jun 25 – Jul 2
Home in Osprey
4.97 out of 5 average rating, 33 reviewsSarasota vacation Home!
Sep 6 – 13
Home in Nokomis
5.0 out of 5 average rating, 10 reviewsUpdated house close to the Beach
Oct 2 – 9
Home in Sarasota
4.96 out of 5 average rating, 26 reviewsBeach house #2
Aug 23 – 30
Home in Sarasota
5.0 out of 5 average rating, 6 reviewsCozy Heaven Studio III
Nov 17 – 24
Home in Sarasota
5.0 out of 5 average rating, 6 reviewsCute 2 bedroom home close to it all.
May 23 – 30
Private house rentals
Home in Nokomis
4.99 out of 5 average rating, 84 reviewsToes in the sand in less than 5 min.
Sep 27 – Oct 4
Home in Sarasota
4.92 out of 5 average rating, 61 reviewsSarasota Summer Beach Bliss!
Oct 17 – 24
Home in Nokomis
4.98 out of 5 average rating, 57 reviewsTiki Oasis 3bed on .6 acre paradise 5 min to Beach
Jan 3 – 10
Home in Venice
5.0 out of 5 average rating, 17 reviewsEndless Summer 3br/2ba
Jun 23 – 30
Home in Nokomis
5.0 out of 5 average rating, 17 reviewsLuxury Oasis Home 3BR 2Bath with Heated Pool
Oct 21 – 28
Home in Venice
4.93 out of 5 average rating, 59 reviewsVenice Beach House| Downtown, Shops, Restaurants
Jun 27 – Jul 4
Home in Sarasota
4.96 out of 5 average rating, 46 reviewsSandy Feet Retreat- Cozy Bungalow & Outdoor living
Oct 13 – 20
Home in Venice
4.96 out of 5 average rating, 71 reviewsFully renovated 2 bedroom coastal home
Jul 28 – Aug 4
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
G$16,682 GYD before taxes and fees
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