Osprey vacation rentals

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Handpicked vacation rentals in Osprey

Flip Flop Cottages photos Exterior
75
Flip Flop Cottages Siesta Key
8254 Midnight Pass Road, Siesta Key
from US$  184
The Inn At Turtle Beach photos Exterior
70
The Inn At Turtle Beach Siesta Key
9004 Midnight Pass Road, Siesta Key
from US$  240
Timberwoods Vacation Villas photos Exterior
9.0
PerfectBased onreviews
27
Timberwoods Vacation Villas Sarasota
8378 South Tamiami Trail, Sarasota
from US$  168
Bianco Sands By Beachside Management photos Exterior
75
Bianco Sands By Beachside Management Apartment Siesta Key
1126 Point Of Rocks Road, Siesta Key
from US$  196
Siesta Heron Suites & Villas photos Exterior
75
Siesta Heron Suites & Villas Siesta Key
8254 Midnight Pass Road, Siesta Key
from US$  165
Timberwoods Vacation Villas Sarasota photos Exterior
12
Timberwoods Vacation Villas Sarasota
8388 South Tamiami Trail #297, Sarasota
from US$  123
Casey Key Retreat photos Exterior
12
Casey Key Retreat Apartment Nokomis
217 Casey Key Road, Nokomis
from US$  199
Lj'S Cottages By Beachside Management photos Exterior
36
Lj'S Cottages By Beachside Management Siesta Key
1021 Point Of Rocks Road, Siesta Key
from US$  178
Crescent Street Villas By Beachside Management photos Exterior
29
Crescent Street Villas By Beachside Management Siesta Key
1126 Crescent Street, Siesta Key
from US$  291
Ebb Tide On Siesta Key photos Exterior
46
Ebb Tide On Siesta Key Villa Sarasota
6610 Midnight Pass Road 10, Sarasota
from US$  126

Exclusive luxury places to stay in Osprey

Beach Residences On Siesta Aka The Hyatt photos Exterior
32
Beach Residences On Siesta Aka The Hyatt Siesta Key
915 Sea Side Drive Apt 310, Siesta Key
from US$  786
Village Des Pins 3645, 2 Bedrooms, Pool Access, Wifi, Hot Tub, Sleeps 4 photos Exterior
42
Village Des Pins 3645, 2 Bedrooms, Pool Access, Wifi, Hot Tub, Sleeps 4 Sarasota
3645 White Pine Court, Sarasota
from US$  443
Sandy Cabana One Of The Cottages On The Key photos Exterior
16
Sandy Cabana One Of The Cottages On The Key Siesta Key
1104 Crescent St., Siesta Key
from US$  374
Parkdale Home, 4 Bedrooms, Private Heated Pool, Hdtv, Wifi, Sleeps 12 photos Exterior
28
Parkdale Home, 4 Bedrooms, Private Heated Pool, Hdtv, Wifi, Sleeps 12 Venice
312 Parkdale Dr., Venice
from US$  329
Buttonwood Cottage photos Exterior
13
Buttonwood Cottage Siesta Key
1105 Point Of Rocks Rd, Siesta Key
from US$  309
Parkdale Home Four Bedroom Home photos Exterior
46
Parkdale Home Four Bedroom Home Venice
312 Parkdale Dr., Venice
from US$  296
Siesta Palms By The Beach photos Exterior
13
Siesta Palms By The Beach Apartment Siesta Key
1017 Point Of Rocks Rd, Siesta Key
from US$  249
New-Casey Key Apt W/Patio & Bbq - 1 Block To Beach photos Exterior
25
New-Casey Key Apt W/Patio & Bbq - 1 Block To Beach Apartment Nokomis
Nokomis, FL, 34275, Nokomis
from US$  205
Mulberry Cottage photos Exterior
12
Mulberry Cottage Siesta Key
1105 Point Of Rocks Rd, Siesta Key
from US$  199
Wild Lime Cottage photos Exterior
9
Wild Lime Cottage Siesta Key
1105 Point Of Rocks Rd, Siesta Key
from US$  199

High graded cheap vacation homes in Osprey

Sarasota Condo W/Deck - 1/2 Mile To Turtle Beach! photos Exterior
24
Sarasota Condo W/Deck - 1/2 Mile To Turtle Beach! Siesta Key
Siesta Key, FL, 34242, Siesta Key
from US$  181
Coriander Cottage photos Exterior
10
Coriander Cottage Siesta Key
1105 Point Of Rocks Road, Siesta Key
from US$  179
Wild Coffee photos Exterior
10
Wild Coffee Villa Siesta Key
1105 Point Of Rocks Rd, Siesta Key
from US$  179
Mid-Century Modern Home 1 Mi To Nokomis Beach photos Exterior
27
Mid-Century Modern Home 1 Mi To Nokomis Beach
Nokomis, FL, 34275, Nokomis
from US$  170
Sarasota Villa W/ Pool Access ~4 Mi To Beach! photos Exterior
38
Sarasota Villa W/ Pool Access ~4 Mi To Beach!
Sarasota, Fl, 34238, Sarasota
from US$  112
Lux Waterfront Nokomis Home With Tiki Bar, Pier, Dock photos Exterior
42
Lux Waterfront Nokomis Home W/Tiki Bar, Pier, Dock
Nokomis, Fl, 34275, Nokomis
Nokomis Home W/ Yard & Lake ~3 Miles To Beach photos Exterior
28
Nokomis Home W/ Yard & Lake ~3 Miles To Beach
Nokomis, FL, 34275, Nokomis
Updated Apartment Walking Distance To Venice Beach photos Exterior
23
Updated Apartment Walking Distance To Venice Beach
Venice, FL, 34285, Venice
L' Pavia 2 Bedrooms Sleeps 8 Private 1 Car Garage Heated Pool Wifi photos Exterior
26
L' Pavia 2 Bedrooms Sleeps 8 Private 1 Car Garage Heated Pool Wifi Venice
4204 L Pavia Blvd, Venice
Bay Tree Club A407 Gulfside photos Exterior
15
Bay Tree Club A407 Gulfside Apartment Siesta Key
8630 Midnight Pass Rd Unit 407 , Siesta Key
SHOW ALL 83 VACATION RENTALS IN Osprey

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