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Search results; Over 1,000 places in Osprey

Guest favorite
Cottage in Osprey
Mattie’s Cottage by the Bay
1 queen bed
May 29 – Jun 3
4.95 out of 5 average rating, 19 reviews
Guest favorite
Home in Sarasota
Renovated Cozy Cottage "The Nest" Close to SIESTA
3 beds
Apr 29 – May 4
4.92 out of 5 average rating, 116 reviews
Guest favorite
Guesthouse in Osprey
Cozy Cottage by the Bay
1 queen bed
Apr 7 – 12
4.99 out of 5 average rating, 281 reviews
Guest favorite
Home in Osprey
Private house with loft
3 beds
Apr 21 – 26
4.94 out of 5 average rating, 34 reviews
Guest favorite
Home in Osprey
Casey Key Paradise
3 beds
Apr 15 – 20
5.0 out of 5 average rating, 24 reviews
Guest favorite
Home in Osprey
Bayview House - Osprey - 1 block to Bay!
4 beds
Apr 14 – 19
4.98 out of 5 average rating, 41 reviews
Guest favorite
Home in Osprey
Charming Florida Cottage - Kayaks Included
2 king beds
Apr 8 – 13
4.95 out of 5 average rating, 21 reviews
Guest favorite
Home in Osprey
Private Oasis | Heated Pool | 3 Bed | Near Beaches
3 beds
Apr 15 – 20
5.0 out of 5 average rating, 20 reviews
Home in Nokomis
Casey Key Island House!
7 beds
May 7 – 12
4.67 out of 5 average rating, 6 reviews
Guest favorite
Home in Osprey
Sand Dollar Cottage - 15m to Siesta / Casey Key
3 beds
Apr 6 – 11
4.9 out of 5 average rating, 30 reviews
Guest favorite
Home in Osprey
LIME ON GREEN Osprey, Florida 34229
3 beds
Apr 22 – 27
4.8 out of 5 average rating, 45 reviews
Home in Osprey
Smart Home Sarasota Family Getaway
4 beds
Apr 10 – 15
5.0 out of 5 average rating, 10 reviews
Guest favorite
Apartment in Nokomis
Charming 1 bedroom apartment for 2 with pool.
1 queen bed
Apr 27 – May 2
4.98 out of 5 average rating, 64 reviews
Superhost
Condo in Osprey
Lovely 2 bedroom condo with pool & tennis courts
2 beds
Apr 1 – 6
5.0 out of 5 average rating, 8 reviews
Guest favorite
Island in Sarasota
*MAY SALE! Sarasota #1 Luxury Villa Pool/Beach!*
3 beds
Apr 27 – May 2
4.97 out of 5 average rating, 298 reviews
Guest favorite
Home in Nokomis
Peaceful Getaway just minutes from the beach
5 beds
Jun 17 – 22
4.99 out of 5 average rating, 70 reviews
Guest favorite
Home in Nokomis
Tiki Oasis 3bed on .6 acre paradise 5 min to Beach
5 beds
Apr 27 – May 2
4.98 out of 5 average rating, 52 reviews
Guest favorite
Vacation home in Nokomis
Modern Beach Home. 2 Blocks to Beach. 3BD/2BA
3 beds
May 15 – 20
4.98 out of 5 average rating, 55 reviews