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 Venice
4.89 out of 5 average rating, 161 reviewsVenice Pool Villa with Bikes Kayaks Great Beaches!
Oct 15 – 22
Home in Sarasota
4.97 out of 5 average rating, 206 reviewsYour private retreat near Siesta Key Beach.
Jun 20 – 27
Home in Sarasota
4.97 out of 5 average rating, 159 reviewsThe Palms-Private Heated Pool Hot Tub-5mi to beach
Aug 21 – 28
Home in Venice
4.93 out of 5 average rating, 99 reviewsGorgeous Private Pool! Fountains! Near Beach- os
Dec 6 – 13
Home in Sarasota
4.93 out of 5 average rating, 106 reviewsLake Front House with a Pool
Sep 1 – 8
Home in Nokomis
4.88 out of 5 average rating, 147 reviews4/2.5 Oak Bahay, Heated Pool! 5min to Beach,4Acres
Aug 29 – Sep 5
Home in Sarasota
4.82 out of 5 average rating, 125 reviewsVacation Paradise Close to Beach!
Oct 19 – 26
Home in Sarasota
4.97 out of 5 average rating, 109 reviewsGorgeous Home / Heated Pool and Spa
Sep 21 – 28
Weekly house rentals
Home in Osprey
4.92 out of 5 average rating, 38 reviewsPrivate house with loft
Oct 4 – 11
Home in Osprey
4.96 out of 5 average rating, 23 reviewsCharming Florida Cottage - Kayaks Included
May 9 – 16
Home in Nokomis
4.9 out of 5 average rating, 40 reviewsCheerful, sparkling 2 bedroom cottage, 1.8 miles from beach
Sep 11 – 18
Home in Nokomis
5.0 out of 5 average rating, 9 reviewsUpdated house close to the Beach
Jul 6 – 13
Home in Sarasota
5.0 out of 5 average rating, 4 reviewsCute 2 bedroom home close to it all.
Aug 31 – Sep 7
Home in Osprey
4.91 out of 5 average rating, 33 reviewsSand Dollar Cottage - 15m to Siesta / Casey Key
Jan 11 – 18
Home in Osprey
4.97 out of 5 average rating, 33 reviewsSarasota vacation Home!
Sep 19 – 26
Home in Sarasota
4.92 out of 5 average rating, 61 reviewsSarasota Summer Beach Bliss!
Nov 21 – 28
Private house rentals
Home in Nokomis
5.0 out of 5 average rating, 46 reviewsCharming vacation home, short walk to the beach
Jul 24 – 31
Home in Sarasota
5.0 out of 5 average rating, 12 reviewsSun-Kissed Cottage near Siesta Key
Jul 23 – 30
Home in Nokomis
4.99 out of 5 average rating, 83 reviewsAvailable get away 1 night, weekly or monthly
Sep 1 – 8
Home in Nokomis
5.0 out of 5 average rating, 41 reviewsMinutes to Nokomis Beach Updated and Spacious
May 14 – 21
Home in Sarasota
4.92 out of 5 average rating, 53 reviews1 Bed 1 bath 7 mins to the beach
Sep 6 – 13
Home in Venice
5.0 out of 5 average rating, 12 reviewsPerfect for you and your pets
May 19 – 26
Home in Sarasota
4.97 out of 5 average rating, 79 reviewsWalk to Benderson/UTC. Big Lot, Private Home
Jun 14 – 21
Home in Nokomis
4.98 out of 5 average rating, 55 reviewsTiki Oasis 3bed on .6 acre paradise 5 min to Beach
Sep 17 – 24
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
$80 before taxes and fees
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