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, 206 reviewsYour private retreat near Siesta Key Beach.
Sep 1 – 8
Home in Sarasota
4.93 out of 5 average rating, 106 reviewsLake Front House with a Pool
Apr 22 – 29
Home in Sarasota
4.81 out of 5 average rating, 107 reviews1 House 1400sq. ft. 12 min from Siesta Key!
Jan 4 – 11
Home in Siesta Key
5.0 out of 5 average rating, 125 reviewsOne-of-a-kind*Beach, Village, Dock & Private Pool!
Jul 14 – 21
Home in Osprey
5.0 out of 5 average rating, 23 reviewsHeated Pool | 3 Beds | Near Beaches and parks
Aug 20 – 27
Home in Nokomis
4.93 out of 5 average rating, 29 reviews"Starfish" at The Shore Beach Houses Resort
Sep 7 – 14
Home in Nokomis
4.95 out of 5 average rating, 19 reviewsBlue Sky Retreat
May 23 – 30
Weekly house rentals
Home in Osprey
4.96 out of 5 average rating, 23 reviewsCharming Florida Cottage - Kayaks Included
Jun 10 – 17
Home in Nokomis
5.0 out of 5 average rating, 10 reviewsUpdated house close to the Beach
Aug 18 – 25
Home in Sarasota
5.0 out of 5 average rating, 6 reviewsCute 2 bedroom home close to it all.
May 23 – 30
Home in Sarasota
5.0 out of 5 average rating, 6 reviewsCozy Heaven Studio III
Oct 4 – 11
Home in Osprey
4.97 out of 5 average rating, 33 reviewsSarasota vacation Home!
Mar 13 – 20
Home in Sarasota
4.96 out of 5 average rating, 26 reviewsBeach house #2
Jan 21 – 28
Home in Nokomis
5.0 out of 5 average rating, 46 reviewsCharming vacation home, short walk to the beach
Jul 18 – 25
Home in Venice
4.93 out of 5 average rating, 46 reviewsShell near the Sea, 2-Br Pet Friendly Home
Oct 26 – Nov 2
Private house rentals
Home in Sarasota
4.92 out of 5 average rating, 61 reviewsSarasota Summer Beach Bliss!
Mar 28 – Apr 4
Home in Nokomis
5.0 out of 5 average rating, 17 reviewsLuxury Oasis Home 3BR 2Bath with Heated Pool
Jan 14 – 21
Home in Sarasota
4.93 out of 5 average rating, 54 reviews1 Bed 1 bath 7 mins to the beach
Sep 15 – 22
Home in Nokomis
5.0 out of 5 average rating, 42 reviewsMinutes to Nokomis Beach Updated and Spacious
May 17 – 24
Home in Nokomis
4.98 out of 5 average rating, 57 reviewsTiki Oasis 3bed on .6 acre paradise 5 min to Beach
Sep 6 – 13
Home in Sarasota
5.0 out of 5 average rating, 13 reviewsSun-Kissed Cottage near Siesta Key
Jun 12 – 19
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, 22 reviewsSea Turtle Cottage
Sep 23 – 30
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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