House vacation rentals in Osprey
Find and book unique houses on Airbnb
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
4.93 out of 5 average rating, 106 reviewsLake Front House with a Pool
Sep 6 – 13
Home in Sarasota
4.97 out of 5 average rating, 206 reviewsYour private retreat near Siesta Key Beach.
Jun 15 – 22
Home in Venice
4.89 out of 5 average rating, 144 reviewsVENICE Near Beaches/Heated Pool 5 Star LUXE
Jun 11 – 18
Home in Sarasota
4.81 out of 5 average rating, 107 reviews1 House 1400sq. ft. 12 min from Siesta Key!
Apr 16 – 23
Home in Osprey
5.0 out of 5 average rating, 23 reviewsHeated Pool | 3 Beds | Near Beaches and parks
Jul 24 – 31
Home in Nokomis
4.95 out of 5 average rating, 19 reviewsBlue Sky Retreat
May 20 – 27
Home in Nokomis
4.93 out of 5 average rating, 29 reviews"Starfish" at The Shore Beach Houses Resort
Oct 1 – 8
Home in Nokomis
4.94 out of 5 average rating, 16 reviewsThe Pineapple Escape
Oct 28 – Nov 4
Weekly house rentals
Home in Osprey
4.96 out of 5 average rating, 23 reviewsCharming Florida Cottage - Kayaks Included
Sep 29 – Oct 6
Home in Sarasota
5.0 out of 5 average rating, 6 reviewsCute 2 bedroom home close to it all.
May 29 – Jun 5
Home in Nokomis
5.0 out of 5 average rating, 10 reviewsUpdated house close to the Beach
Oct 27 – Nov 3
Home in Osprey
4.91 out of 5 average rating, 33 reviewsSand Dollar Cottage - 15m to Siesta / Casey Key
Dec 26 – Jan 2
Home in Osprey
4.97 out of 5 average rating, 33 reviewsSarasota vacation Home!
Nov 8 – 15
Home in Sarasota
5.0 out of 5 average rating, 6 reviewsCozy Heaven Studio III
Jan 9 – 16
Home in Sarasota
4.92 out of 5 average rating, 61 reviewsSarasota Summer Beach Bliss!
Mar 24 – 31
Home in Sarasota
4.96 out of 5 average rating, 26 reviewsBeach house #2
Jul 15 – 22
Private house rentals
Home in Nokomis
4.99 out of 5 average rating, 84 reviewsToes in the sand in less than 5 min.
Sep 25 – Oct 2
Home in Sarasota
5.0 out of 5 average rating, 29 reviewsSiesta Key Fully-Renovated Unit 5 min to the beach
Apr 4 – 11
Home in Nokomis
5.0 out of 5 average rating, 51 reviewsWelcome to Paradise Palms! Canal home/Pet friendly
Nov 22 – 29
Home in Nokomis
4.9 out of 5 average rating, 40 reviewsCheerful, sparkling 2 bedroom cottage, 1.8 miles from beach
Feb 12 – 19
Home in Nokomis
5.0 out of 5 average rating, 42 reviewsMinutes to Nokomis Beach Updated and Spacious
May 15 – 22
Home in Venice
4.97 out of 5 average rating, 65 reviewsVenice Getaway 3 bedrooms, private heated pool
Sep 24 – Oct 1
Home in Sarasota
4.93 out of 5 average rating, 54 reviews1 Bed 1 bath 7 mins to the beach
Sep 29 – Oct 6
Home in Nokomis
5.0 out of 5 average rating, 34 reviewsMinutes to Floridas most beautiful beaches!
Aug 29 – Sep 5
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
€ 74 before taxes and fees
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