Book Holiday Homes in Osprey

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Featured Holiday Homes in Osprey

Tropical Villas of Venice Beach

Tropical Villas of Venice Beach

3.5 out of 5
505 Menendez St, Venice, FL
When you stay at Tropical Villas of Venice Beach in Venice, you'll be near the beach, a 2-minute drive from Venice Beach and 7 minutes from Caspersen Beach.
Tropical Villas of Venice Beach
Siesta Key Island Rentals

Siesta Key Island Rentals

3 out of 5
515 Beach Rd, Siesta Key, FL
With a stay at Siesta Key Island Rentals in Siesta Key, you'll be a 1-minute drive from Siesta Key Beach and 9 minutes from Sarasota Memorial Hospital.
Siesta Key Island Rentals
Siesta Heron Suites & Villas

Siesta Heron Suites & Villas

3.5 out of 5
8254 Midnight Pass Rd, Siesta Key, FL
The price is AU$627 per night from 12 Jun to 13 Jun
AU$627
per night
12 Jun - 13 Jun
When you stay at Siesta Heron Suites & Villas in Siesta Key, you'll be on the waterfront, within a 5-minute drive of Turtle Beach and Crescent Beach.
Siesta Heron Suites & Villas
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LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.

LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.

Siesta Key
The price is AU$999 per night from 2 Jul to 3 Jul
AU$999
per night
2 Jul - 3 Jul
When you stay at this vacation home in Siesta Key, you'll be on the waterfront, a 3-minute drive from Siesta Key Beach and 8 minutes from Crescent Beach.
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.
Steps From Beach. Private entrance.

Steps From Beach. Private entrance.

Englewood
When you stay at this vacation home in Englewood, you'll be by the ocean, within a 5-minute walk of Englewood Beach and Lemon Bay.
Steps From Beach. Private entrance.
Chic Downtown Gem - The Cocoanut Hut, newly constructed

Chic Downtown Gem - The Cocoanut Hut, newly constructed

SARASOTA
With a stay at this vacation home, you'll be centrally located in Sarasota, within a 10-minute drive of St. Armands Circle and Lido Beach.
Chic Downtown Gem - The Cocoanut Hut, newly constructed
Retreat Half-Mile to Beach/Siesta Key Village

Retreat Half-Mile to Beach/Siesta Key Village

Siesta Key
When you stay at this vacation home in Siesta Key, you'll be by the sea, a 2-minute drive from Siesta Key Beach and 7 minutes from Crescent Beach.
Retreat Half-Mile to Beach/Siesta Key Village
Private Beach and Incredible Sunsets-Exquisite Home

Private Beach and Incredible Sunsets-Exquisite Home

Englewood
With a stay at this vacation home in Englewood, you'll be on the beach, within a 10-minute drive of Englewood Beach and Lemon Bay.
Private Beach and Incredible Sunsets-Exquisite Home
4bedroom/3bath HOUSE ACROSS FROM BEACH/Private Pool -

4bedroom/3bath HOUSE ACROSS FROM BEACH/Private Pool -

Sarasota
When you stay at this vacation home in Siesta Key, you'll be near the beach, a 1-minute drive from Siesta Key Beach and 5 minutes from Crescent Beach.
4bedroom/3bath HOUSE ACROSS FROM BEACH/Private Pool -
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Osprey Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Osprey vacation homes are the perfect way for you to wing it.

Holiday houses in Osprey let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Osprey in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Osprey adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Osprey with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Osprey vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Osprey Holiday Homes essential information

Accommodation
2817 Holiday Homes
Lowest Price
AU$169
Highest Price
AU$999
Popular accommodation
Tropical Villas of Venice Beach, Siesta Key Island Rentals, Siesta Heron Suites & Villas, LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕., Steps From Beach. Private entrance. , Chic Downtown Gem - The Cocoanut Hut, newly constructed, Retreat Half-Mile to Beach/Siesta Key Village, Private Beach and Incredible Sunsets-Exquisite Home, 4bedroom/3bath HOUSE ACROSS FROM BEACH/Private Pool -

Top trending hotels in Osprey

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

3 out of 5
1650 South Tamiami Trail, Osprey, FL
Fully refundableReserve now, pay when you stay
The price is AU$326 per night from 2 Jun to 3 Jun
AU$326
per night
2 Jun - 3 Jun
With a stay at Casey Key Resorts - Mainland in Osprey, you'll be within a 5-minute drive of Nokomis Beach and Turtle Beach.
Casey Key Resorts - Mainland
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
The price is AU$169 per night from 11 Jun to 12 Jun
AU$169
per night
11 Jun - 12 Jun
When you stay at Kompose Boutique Hotel in Sarasota, you'll be near the airport, within a 15-minute drive of St. Armands Circle and Lido Beach.
Kompose Boutique Hotel
Hyatt Regency Sarasota

Hyatt Regency Sarasota

4 out of 5
1000 Blvd Of The Arts, Sarasota, FL
Fully refundable
The price is AU$270 per night from 9 Jun to 10 Jun
AU$270
per night
9 Jun - 10 Jun
With a stay at Hyatt Regency Sarasota, you'll be centrally located in Sarasota, a 4-minute drive from Sarasota Memorial Hospital and 6 minutes from St. Armands ...
Hyatt Regency Sarasota
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Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

3 out of 5
6600 S Tamiami Trl, Sarasota, FL
Fully refundableReserve now, pay when you stay
The price is AU$215 per night from 16 Jun to 17 Jun
AU$215
per night
16 Jun - 17 Jun
Located in Sarasota, Spark by Hilton Sarasota Siesta Key Gateway is a 3-minute drive from Siesta Key Beach and 6 minutes from Turtle Beach.
Spark by Hilton Sarasota Siesta Key Gateway
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.