Book Holiday Homes in Osprey

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Featured Holiday Homes in Osprey

3-bedroom 2-bathroom Siesta Key townhome close to beaches, city and airport.

3-bedroom 2-bathroom Siesta Key townhome close to beaches, city and airport.

Siesta Key FL
The price is NZ$555 per night from 30 Dec to 31 Dec
NZ$555
30 Dec - 31 Dec
includes taxes & fees
Stay at this holiday home in Siesta Key. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Siesta Key Beach and Lido Beach are located ...
Opens in a new window3-bedroom 2-bathroom Siesta Key townhome close to beaches, city and airport.
Tropical Villas of Venice Beach

Tropical Villas of Venice Beach

3.5 out of 5
505 Menendez St Venice FL
Stay at this holiday home in Venice. Enjoy free Wi-Fi, free parking and free bicycles on-site. Popular attractions Venice Beach and Nokomis Beach are located ...
Opens in a new windowTropical Villas of Venice Beach
Siesta Key Island Rentals

Siesta Key Island Rentals

3 out of 5
515 Beach Rd Siesta Key FL
The price is NZ$511 per night from 18 Dec to 19 Dec
NZ$511
18 Dec - 19 Dec
includes taxes & fees
Stay at this holiday home in Siesta Key. Enjoy free Wi-Fi, free parking and laundry facilities. Popular attractions Siesta Key Beach and Lido Beach are located ...
Opens in a new windowSiesta Key Island Rentals
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3-bedroom house in sarasota fl

3-bedroom house in sarasota fl

Sarasota FL
Stay at this holiday home in Sarasota. Enjoy a water park, a garden and laundry facilities. Popular attractions Sarasota Ballet and Asolo Theatre for the Performing ...
Opens in a new window3-bedroom house in sarasota fl
Coastal Retreat – Pool, Private Yard, Near Beach, RV & Boat Friendly

Coastal Retreat – Pool, Private Yard, Near Beach, RV & Boat Friendly

Venice FL
Stay at this holiday home in Venice. Enjoy private pools, laundry facilities and patios. Popular attractions Caspersen Beach and Venice Beach are located ...
Opens in a new windowCoastal Retreat – Pool, Private Yard, Near Beach, RV & Boat Friendly
Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village

Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village

Siesta Key FL
Stay at this family-friendly holiday home in Siesta Key. Enjoy free Wi-Fi, private pools and laundry facilities. Popular attractions Siesta Key Beach and Lido ...
Opens in a new windowSiesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village
Sarasota-Indian Beach Zen Home (private-pet friendly)

Sarasota-Indian Beach Zen Home (private-pet friendly)

Sarasota FL
Stay at this family-friendly holiday home in Sarasota. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Lido Beach and St. Armands Circle ...
Opens in a new windowSarasota-Indian Beach Zen Home (private-pet friendly)
Siesta Heron Suites & Villas

Siesta Heron Suites & Villas

3.5 out of 5
8254 Midnight Pass Rd Siesta Key FL
The price is NZ$784 per night from 25 Dec to 26 Dec
NZ$784
25 Dec - 26 Dec
includes taxes & fees
Stay at this holiday home in Siesta Key. Enjoy free Wi-Fi, free parking and a garden. Popular attractions Siesta Key Beach and Turtle Beach are located ...
Opens in a new windowSiesta Heron Suites & Villas
Luxury House Walking Distance to Ocean - Sleeps 12

Luxury House Walking Distance to Ocean - Sleeps 12

Sarasota FL
Stay at this holiday home in Sarasota. Enjoy laundry facilities, an in-room coffee maker and in-room fireplaces. Popular attractions Lido Beach and Siesta Key ...
Opens in a new windowLuxury House Walking Distance to Ocean - Sleeps 12
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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
3899 Holiday Homes
Lowest Price
NZ$253
Highest Price
NZ$784
Popular accommodation
3-bedroom 2-bathroom Siesta Key townhome close to beaches, city and airport., Tropical Villas of Venice Beach, Siesta Key Island Rentals, 3-bedroom house in sarasota fl, Coastal Retreat – Pool, Private Yard, Near Beach, RV & Boat Friendly, Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village, Sarasota-Indian Beach Zen Home (private-pet friendly) , Siesta Heron Suites & Villas, Luxury House Walking Distance to Ocean - Sleeps 12

Top trending hotels in Osprey

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

2.5 out of 5
1650 South Tamiami Trail Osprey FL
Fully refundableReserve now, pay when you stay
The price is NZ$253 per night from 18 Dec to 19 Dec
NZ$253
18 Dec - 19 Dec
includes taxes & fees
Stay at this hotel in Osprey. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the pool and the restaurant in their reviews. Popular ...
Opens in a new windowCasey 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
Stay at this business-friendly hotel in Sarasota. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the breakfast and the ...
Opens in a new windowKompose Boutique Hotel
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
6717 Sara Sea Circle Siesta Key FL
The price is NZ$286 per night from 18 Dec to 19 Dec
NZ$286
18 Dec - 19 Dec
includes taxes & fees
Stay at this beach aparthotel in Siesta Key. Enjoy free Wi-Fi, free parking and daily housekeeping. Our guests praise the pool and the helpful staff in their ...
Opens in a new windowTropical Beach Resorts
Save an average of 15% on thousands of hotels when you're signed in
Carlisle Inn

Carlisle Inn

3.5 out of 5
3727 Bahia Vista Sarasota FL
Fully refundableReserve now, pay when you stay
The price is NZ$350 per night from 22 Dec to 23 Dec
NZ$350
22 Dec - 23 Dec
includes taxes & fees
Stay at this hotel in Sarasota. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. Popular attractions ...
Opens in a new windowCarlisle Inn
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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.