Osprey Vacation Rentals

Renovated Waterfront Home
Renovated Waterfront Home
Renovated Waterfront Home
Renovated Waterfront Home
Renovated Waterfront Home
Renovated Waterfront Home
Renovated Waterfront Home
Renovated Waterfront Home
Renovated Waterfront Home
Renovated Waterfront Home
Renovated Waterfront Home
Renovated Waterfront Home
Renovated Waterfront Home
Renovated Waterfront Home
Renovated Waterfront Home
3 Bedrooms
2 Bathrooms
4.4IconIconIconIconIcon
5 reviews
$150 / night (excl. fees & taxes)
Siesta Key Beachfront Condo
Siesta Key Beachfront Condo
Siesta Key Beachfront Condo
Siesta Key Beachfront Condo
Siesta Key Beachfront Condo
Siesta Key Beachfront Condo
Siesta Key Beachfront Condo
Siesta Key Beachfront Condo
Siesta Key Beachfront Condo
Siesta Key Beachfront Condo
Siesta Key Beachfront Condo
Siesta Key Beachfront Condo
Siesta Key Beachfront Condo
Siesta Key Beachfront Condo
Siesta Key Beachfront Condo
2 Bedrooms
2 Bathrooms
$292 / night (excl. fees & taxes)
Sarasota Home w/ Swimming Pool near Siesta Key
Sarasota Home w/ Swimming Pool near Siesta Key
Sarasota Home w/ Swimming Pool near Siesta Key
Sarasota Home w/ Swimming Pool near Siesta Key
Sarasota Home w/ Swimming Pool near Siesta Key
Sarasota Home w/ Swimming Pool near Siesta Key
Sarasota Home w/ Swimming Pool near Siesta Key
Sarasota Home w/ Swimming Pool near Siesta Key
Sarasota Home w/ Swimming Pool near Siesta Key
Sarasota Home w/ Swimming Pool near Siesta Key
Sarasota Home w/ Swimming Pool near Siesta Key
Sarasota Home w/ Swimming Pool near Siesta Key
Sarasota Home w/ Swimming Pool near Siesta Key
Sarasota Home w/ Swimming Pool near Siesta Key
Sarasota Home w/ Swimming Pool near Siesta Key
3 Bedrooms
2 Bathrooms
$230 / night (excl. fees & taxes)
Beach, Bay, Food, Fun - 2BD/2BA
Beach, Bay, Food, Fun - 2BD/2BA
Beach, Bay, Food, Fun - 2BD/2BA
Beach, Bay, Food, Fun - 2BD/2BA
Beach, Bay, Food, Fun - 2BD/2BA
Beach, Bay, Food, Fun - 2BD/2BA
Beach, Bay, Food, Fun - 2BD/2BA
Beach, Bay, Food, Fun - 2BD/2BA
Beach, Bay, Food, Fun - 2BD/2BA
Beach, Bay, Food, Fun - 2BD/2BA
Beach, Bay, Food, Fun - 2BD/2BA
Beach, Bay, Food, Fun - 2BD/2BA
Beach, Bay, Food, Fun - 2BD/2BA
Beach, Bay, Food, Fun - 2BD/2BA
Beach, Bay, Food, Fun - 2BD/2BA
2 Bedrooms
2 Bathrooms
4.67IconIconIconIconIcon
9 reviews
$189 / night (excl. fees & taxes)
Prime Location: 1 Mile  to Siesta Key South Bridge
Prime Location: 1 Mile  to Siesta Key South Bridge
Prime Location: 1 Mile  to Siesta Key South Bridge
Prime Location: 1 Mile  to Siesta Key South Bridge
Prime Location: 1 Mile  to Siesta Key South Bridge
Prime Location: 1 Mile  to Siesta Key South Bridge
Prime Location: 1 Mile  to Siesta Key South Bridge
Prime Location: 1 Mile  to Siesta Key South Bridge
Prime Location: 1 Mile  to Siesta Key South Bridge
Prime Location: 1 Mile  to Siesta Key South Bridge
Prime Location: 1 Mile  to Siesta Key South Bridge
Prime Location: 1 Mile  to Siesta Key South Bridge
Prime Location: 1 Mile  to Siesta Key South Bridge
Prime Location: 1 Mile  to Siesta Key South Bridge
Prime Location: 1 Mile  to Siesta Key South Bridge
2 Bedrooms
1 Bathroom
$125 / night (excl. fees & taxes)
Palm View at Siesta Dunes
Palm View at Siesta Dunes
Palm View at Siesta Dunes
Palm View at Siesta Dunes
Palm View at Siesta Dunes
Palm View at Siesta Dunes
Palm View at Siesta Dunes
Palm View at Siesta Dunes
Palm View at Siesta Dunes
Palm View at Siesta Dunes
Palm View at Siesta Dunes
Palm View at Siesta Dunes
Palm View at Siesta Dunes
Palm View at Siesta Dunes
Palm View at Siesta Dunes
2 Bedrooms
2 Bathrooms
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8 reviews
$263 - $500 / night (excl. fees & taxes)
Casa Blanca Ranch Home near Siesta Key Beach
Casa Blanca Ranch Home near Siesta Key Beach
Casa Blanca Ranch Home near Siesta Key Beach
Casa Blanca Ranch Home near Siesta Key Beach
Casa Blanca Ranch Home near Siesta Key Beach
Casa Blanca Ranch Home near Siesta Key Beach
Casa Blanca Ranch Home near Siesta Key Beach
Casa Blanca Ranch Home near Siesta Key Beach
Casa Blanca Ranch Home near Siesta Key Beach
Casa Blanca Ranch Home near Siesta Key Beach
Casa Blanca Ranch Home near Siesta Key Beach
Casa Blanca Ranch Home near Siesta Key Beach
Casa Blanca Ranch Home near Siesta Key Beach
Casa Blanca Ranch Home near Siesta Key Beach
Casa Blanca Ranch Home near Siesta Key Beach
3 Bedrooms
2 Bathrooms
5IconIconIconIconIcon
18 reviews
$339 / night (excl. fees & taxes)
Gulf Gate Paradise near Siesta Key beaches
Gulf Gate Paradise near Siesta Key beaches
Gulf Gate Paradise near Siesta Key beaches
Gulf Gate Paradise near Siesta Key beaches
Gulf Gate Paradise near Siesta Key beaches
Gulf Gate Paradise near Siesta Key beaches
Gulf Gate Paradise near Siesta Key beaches
Gulf Gate Paradise near Siesta Key beaches
Gulf Gate Paradise near Siesta Key beaches
Gulf Gate Paradise near Siesta Key beaches
Gulf Gate Paradise near Siesta Key beaches
Gulf Gate Paradise near Siesta Key beaches
Gulf Gate Paradise near Siesta Key beaches
Gulf Gate Paradise near Siesta Key beaches
Gulf Gate Paradise near Siesta Key beaches
1 Bedroom
1 Bathroom
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71 reviews
$189 - $254 / night (excl. fees & taxes)
2 Bedroom/2 Bath, One Floor condominium
2 Bedroom/2 Bath, One Floor condominium
2 Bedroom/2 Bath, One Floor condominium
2 Bedroom/2 Bath, One Floor condominium
2 Bedroom/2 Bath, One Floor condominium
2 Bedroom/2 Bath, One Floor condominium
2 Bedroom/2 Bath, One Floor condominium
2 Bedroom/2 Bath, One Floor condominium
2 Bedroom/2 Bath, One Floor condominium
2 Bedroom/2 Bath, One Floor condominium
2 Bedroom/2 Bath, One Floor condominium
2 Bedroom/2 Bath, One Floor condominium
2 Bedroom/2 Bath, One Floor condominium
2 Bedroom/2 Bath, One Floor condominium
2 Bedroom/2 Bath, One Floor condominium
2 Bedrooms
2 Bathrooms
$100 / night (excl. fees & taxes)
Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool
3 Bedrooms
2 Bathrooms
5IconIconIconIconIcon
26 reviews
$347 - $525 / night (excl. fees & taxes)
The Funky Fish House
The Funky Fish House
The Funky Fish House
The Funky Fish House
The Funky Fish House
The Funky Fish House
The Funky Fish House
The Funky Fish House
The Funky Fish House
The Funky Fish House
The Funky Fish House
The Funky Fish House
The Funky Fish House
The Funky Fish House
The Funky Fish House
2 Bedrooms
2 Bathrooms
4.99IconIconIconIconIcon
96 reviews
$255 - $588 / night (excl. fees & taxes)
Art Deco Masterpiece High Season Multi-Month
Art Deco Masterpiece High Season Multi-Month
Art Deco Masterpiece High Season Multi-Month
Art Deco Masterpiece High Season Multi-Month
Art Deco Masterpiece High Season Multi-Month
Art Deco Masterpiece High Season Multi-Month
Art Deco Masterpiece High Season Multi-Month
Art Deco Masterpiece High Season Multi-Month
Art Deco Masterpiece High Season Multi-Month
Art Deco Masterpiece High Season Multi-Month
Art Deco Masterpiece High Season Multi-Month
Art Deco Masterpiece High Season Multi-Month
Art Deco Masterpiece High Season Multi-Month
Art Deco Masterpiece High Season Multi-Month
Art Deco Masterpiece High Season Multi-Month
2 Bedrooms
2 Bathrooms
$259 / night (excl. fees & taxes)
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Downtown Compound |Pet Friendly | Families |Groups
Downtown Compound |Pet Friendly | Families |Groups
Downtown Compound |Pet Friendly | Families |Groups
Downtown Compound |Pet Friendly | Families |Groups
Downtown Compound |Pet Friendly | Families |Groups
Downtown Compound |Pet Friendly | Families |Groups
Downtown Compound |Pet Friendly | Families |Groups
Downtown Compound |Pet Friendly | Families |Groups
Downtown Compound |Pet Friendly | Families |Groups
Downtown Compound |Pet Friendly | Families |Groups
Downtown Compound |Pet Friendly | Families |Groups
Downtown Compound |Pet Friendly | Families |Groups
Downtown Compound |Pet Friendly | Families |Groups
Downtown Compound |Pet Friendly | Families |Groups
Downtown Compound |Pet Friendly | Families |Groups
8 Bedrooms
9 Bathrooms
$1078 - $2820 / night (excl. fees & taxes)
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Downtown Sarasota | 1 Bd 1 Ba | Beach | + Pets | Symphony |Opera | The Arts
Downtown Sarasota | 1 Bd 1 Ba | Beach | + Pets | Symphony |Opera | The Arts
Downtown Sarasota | 1 Bd 1 Ba | Beach | + Pets | Symphony |Opera | The Arts
Downtown Sarasota | 1 Bd 1 Ba | Beach | + Pets | Symphony |Opera | The Arts
Downtown Sarasota | 1 Bd 1 Ba | Beach | + Pets | Symphony |Opera | The Arts
Downtown Sarasota | 1 Bd 1 Ba | Beach | + Pets | Symphony |Opera | The Arts
Downtown Sarasota | 1 Bd 1 Ba | Beach | + Pets | Symphony |Opera | The Arts
Downtown Sarasota | 1 Bd 1 Ba | Beach | + Pets | Symphony |Opera | The Arts
Downtown Sarasota | 1 Bd 1 Ba | Beach | + Pets | Symphony |Opera | The Arts
Downtown Sarasota | 1 Bd 1 Ba | Beach | + Pets | Symphony |Opera | The Arts
Downtown Sarasota | 1 Bd 1 Ba | Beach | + Pets | Symphony |Opera | The Arts
Downtown Sarasota | 1 Bd 1 Ba | Beach | + Pets | Symphony |Opera | The Arts
Downtown Sarasota | 1 Bd 1 Ba | Beach | + Pets | Symphony |Opera | The Arts
Downtown Sarasota | 1 Bd 1 Ba | Beach | + Pets | Symphony |Opera | The Arts
Downtown Sarasota | 1 Bd 1 Ba | Beach | + Pets | Symphony |Opera | The Arts
1 Bedroom
1 Bathroom
5IconIconIconIconIcon
7 reviews
$118 - $464 / night (excl. fees & taxes)
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Sarasota Downtown Pet-Friendly 1BD/1BA-Lido Beach | Opera | The Arts
Sarasota Downtown Pet-Friendly 1BD/1BA-Lido Beach | Opera | The Arts
Sarasota Downtown Pet-Friendly 1BD/1BA-Lido Beach | Opera | The Arts
Sarasota Downtown Pet-Friendly 1BD/1BA-Lido Beach | Opera | The Arts
Sarasota Downtown Pet-Friendly 1BD/1BA-Lido Beach | Opera | The Arts
Sarasota Downtown Pet-Friendly 1BD/1BA-Lido Beach | Opera | The Arts
Sarasota Downtown Pet-Friendly 1BD/1BA-Lido Beach | Opera | The Arts
Sarasota Downtown Pet-Friendly 1BD/1BA-Lido Beach | Opera | The Arts
Sarasota Downtown Pet-Friendly 1BD/1BA-Lido Beach | Opera | The Arts
Sarasota Downtown Pet-Friendly 1BD/1BA-Lido Beach | Opera | The Arts
Sarasota Downtown Pet-Friendly 1BD/1BA-Lido Beach | Opera | The Arts
Sarasota Downtown Pet-Friendly 1BD/1BA-Lido Beach | Opera | The Arts
Sarasota Downtown Pet-Friendly 1BD/1BA-Lido Beach | Opera | The Arts
Sarasota Downtown Pet-Friendly 1BD/1BA-Lido Beach | Opera | The Arts
Sarasota Downtown Pet-Friendly 1BD/1BA-Lido Beach | Opera | The Arts
1 Bedroom
1 Bathroom
4.9IconIconIconIconIcon
20 reviews
$128 - $254 / night (excl. fees & taxes)
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Downtown Sarasota Compound |Pet Friendly | Extended Stays |Large Groups
Downtown Sarasota Compound |Pet Friendly | Extended Stays |Large Groups
Downtown Sarasota Compound |Pet Friendly | Extended Stays |Large Groups
Downtown Sarasota Compound |Pet Friendly | Extended Stays |Large Groups
Downtown Sarasota Compound |Pet Friendly | Extended Stays |Large Groups
Downtown Sarasota Compound |Pet Friendly | Extended Stays |Large Groups
Downtown Sarasota Compound |Pet Friendly | Extended Stays |Large Groups
Downtown Sarasota Compound |Pet Friendly | Extended Stays |Large Groups
Downtown Sarasota Compound |Pet Friendly | Extended Stays |Large Groups
Downtown Sarasota Compound |Pet Friendly | Extended Stays |Large Groups
Downtown Sarasota Compound |Pet Friendly | Extended Stays |Large Groups
Downtown Sarasota Compound |Pet Friendly | Extended Stays |Large Groups
Downtown Sarasota Compound |Pet Friendly | Extended Stays |Large Groups
Downtown Sarasota Compound |Pet Friendly | Extended Stays |Large Groups
Downtown Sarasota Compound |Pet Friendly | Extended Stays |Large Groups
8 Bedrooms
8 Bathrooms
$2000 / night (excl. fees & taxes)
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Spacious Downtown |Pet Friendly | 2-Car Garage| Lido Beach | St. Armands Circle | Opera House
Spacious Downtown |Pet Friendly | 2-Car Garage| Lido Beach | St. Armands Circle | Opera House
Spacious Downtown |Pet Friendly | 2-Car Garage| Lido Beach | St. Armands Circle | Opera House
Spacious Downtown |Pet Friendly | 2-Car Garage| Lido Beach | St. Armands Circle | Opera House
Spacious Downtown |Pet Friendly | 2-Car Garage| Lido Beach | St. Armands Circle | Opera House
Spacious Downtown |Pet Friendly | 2-Car Garage| Lido Beach | St. Armands Circle | Opera House
Spacious Downtown |Pet Friendly | 2-Car Garage| Lido Beach | St. Armands Circle | Opera House
Spacious Downtown |Pet Friendly | 2-Car Garage| Lido Beach | St. Armands Circle | Opera House
Spacious Downtown |Pet Friendly | 2-Car Garage| Lido Beach | St. Armands Circle | Opera House
Spacious Downtown |Pet Friendly | 2-Car Garage| Lido Beach | St. Armands Circle | Opera House
Spacious Downtown |Pet Friendly | 2-Car Garage| Lido Beach | St. Armands Circle | Opera House
Spacious Downtown |Pet Friendly | 2-Car Garage| Lido Beach | St. Armands Circle | Opera House
Spacious Downtown |Pet Friendly | 2-Car Garage| Lido Beach | St. Armands Circle | Opera House
Spacious Downtown |Pet Friendly | 2-Car Garage| Lido Beach | St. Armands Circle | Opera House
Spacious Downtown |Pet Friendly | 2-Car Garage| Lido Beach | St. Armands Circle | Opera House
3 Bedrooms
3 Bathrooms
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43 reviews
$198 - $552 / night (excl. fees & taxes)
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Sarasota Pet Friendly Vaca Home | Balcony + Garage | The Arts & Opera |Beach | St. Armands Circle
Sarasota Pet Friendly Vaca Home | Balcony + Garage | The Arts & Opera |Beach | St. Armands Circle
Sarasota Pet Friendly Vaca Home | Balcony + Garage | The Arts & Opera |Beach | St. Armands Circle
Sarasota Pet Friendly Vaca Home | Balcony + Garage | The Arts & Opera |Beach | St. Armands Circle
Sarasota Pet Friendly Vaca Home | Balcony + Garage | The Arts & Opera |Beach | St. Armands Circle
Sarasota Pet Friendly Vaca Home | Balcony + Garage | The Arts & Opera |Beach | St. Armands Circle
Sarasota Pet Friendly Vaca Home | Balcony + Garage | The Arts & Opera |Beach | St. Armands Circle
Sarasota Pet Friendly Vaca Home | Balcony + Garage | The Arts & Opera |Beach | St. Armands Circle
Sarasota Pet Friendly Vaca Home | Balcony + Garage | The Arts & Opera |Beach | St. Armands Circle
Sarasota Pet Friendly Vaca Home | Balcony + Garage | The Arts & Opera |Beach | St. Armands Circle
Sarasota Pet Friendly Vaca Home | Balcony + Garage | The Arts & Opera |Beach | St. Armands Circle
Sarasota Pet Friendly Vaca Home | Balcony + Garage | The Arts & Opera |Beach | St. Armands Circle
Sarasota Pet Friendly Vaca Home | Balcony + Garage | The Arts & Opera |Beach | St. Armands Circle
Sarasota Pet Friendly Vaca Home | Balcony + Garage | The Arts & Opera |Beach | St. Armands Circle
Sarasota Pet Friendly Vaca Home | Balcony + Garage | The Arts & Opera |Beach | St. Armands Circle
3 Bedrooms
3 Bathrooms
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28 reviews
$198 - $552 / night (excl. fees & taxes)
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Florida Pool Villa Happy Gator
Florida Pool Villa Happy Gator
Florida Pool Villa Happy Gator
Florida Pool Villa Happy Gator
Florida Pool Villa Happy Gator
Florida Pool Villa Happy Gator
Florida Pool Villa Happy Gator
Florida Pool Villa Happy Gator
Florida Pool Villa Happy Gator
Florida Pool Villa Happy Gator
Florida Pool Villa Happy Gator
Florida Pool Villa Happy Gator
Florida Pool Villa Happy Gator
Florida Pool Villa Happy Gator
Florida Pool Villa Happy Gator
3 Bedrooms
2 Bathrooms
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102 reviews
$185 - $270 / night (excl. fees & taxes)
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