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Search results; Over 1,000 homes in Osprey

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Top guest favourite
Cottage in Osprey
Mattie’s Cottage by the Bay
1 bedroom, 1 bed, 1 private bathroom
24–29 Sept
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4.94 out of 5 average rating, 96 reviews
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Home in Osprey
Have your TINY house experience before you go TINY
1 queen bed, 1 bathroom
19–24 Sept
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Top guest favourite
Cottage in Nokomis
Staycation Sanctuary
1 bedroom, 2 beds, 1 bathroom
25–30 Sept
4.98 out of 5 average rating, 189 reviews
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Home in Nokomis
Nokomis Sunset Retreat w/Patio 8 mins to Beach
1 bedroom, 2 beds, 1 bathroom
15–20 Sept
New place to stay
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Home in Nokomis
Nokomis Sunset Retreat w/Pool - 8 mins to Beach
2 bedrooms, 4 beds, 2 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Nokomis
Close to Beaches~ Downtown Venice~Bike Trail~Park
3 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 47 reviews
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Top guest favourite
Guest house in Osprey
Our Paradise Place in Osprey
1 bedroom, 1 bed, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 18 reviews
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Guest favourite
Home in Osprey
Nokomis & Siesta Key Sand Dollar Retreat
2 bedrooms, 3 beds, 1 bathroom
15–20 Sept
4.94 out of 5 average rating, 33 reviews
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Guest favourite
Home in Nokomis
Blue Heron Near Nokomis Beach
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
4.93 out of 5 average rating, 15 reviews
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Top guest favourite
Apartment in Nokomis
Family Friendly Beach Condo
3 bedrooms, 6 beds, 2.5 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 89 reviews
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Top guest favourite
Camper van/Motorhome in Nokomis
"Nokomis Key" - Golf Cart Included (FREE)
1 bedroom, 4 beds, 1 bathroom
29 Sept – 4 Oct
4.91 out of 5 average rating, 81 reviews
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Top guest favourite
Home in Venice
Venice Island Home w Heated Pool
2 bedrooms, 3 beds, 2 bathrooms
15–20 Sept
4.99 out of 5 average rating, 91 reviews
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Top guest favourite
Villa in Nokomis
Oasis Getaway -Beautiful House-Infinity Pool-Beach
4 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
4.98 out of 5 average rating, 53 reviews
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Flat in Nokomis
Modern 2BR Apt | 5-Min Drive to Nokomis Beach
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
New place to stay
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Top guest favourite
Villa in Sarasota
Vacation Villa/Resort Pool 4 miles to Siesta Key
2 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
4.98 out of 5 average rating, 50 reviews
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Top guest favourite
Home in Nokomis
Peaceful Getaway just minutes from the beach
3 bedrooms, 5 beds, 2 bathrooms
15–20 Nov
4.98 out of 5 average rating, 119 reviews
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Top guest favourite
Home in Sarasota
Mid-Mod Coastal Charm - 10 mins to Siesta Key!
2 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 32 reviews
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Home in Nokomis
3BR Townhome with community pool Beaches close by
3 bedrooms, 3 beds, 2.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Flat in Osprey
Windsor Lodge Unit #18, studio
1 bedroom, 1 king bed, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 7 reviews