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
Stay at this 3.5-star vacation home in Venice. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions Venice Beach and Nokomis Beach are ...
Opens in a new windowTropical Villas of Venice Beach
2 Bedrooms, Bay WaterViews, Beaches, shops, Marina, fishing, all near by

2 Bedrooms, Bay WaterViews, Beaches, shops, Marina, fishing, all near by

Sarasota
Stay at this vacation home in Sarasota. Enjoy free WiFi, laundry facilities, and patios. Popular attractions St. Armands Circle and Ca’ d’Zan are located ...
Opens in a new window2 Bedrooms, Bay WaterViews, Beaches, shops, Marina, fishing, all near by
Heated pool private yard S Venice 3.8 mi. to beach OVER-SIZED DRIVEWAY RV/BOAT

Heated pool private yard S Venice 3.8 mi. to beach OVER-SIZED DRIVEWAY RV/BOAT

Venice, FL
Stay at this vacation home in Venice. Enjoy private pools, laundry facilities, and patios. Popular attractions Caspersen Beach and Venice Beach are located ...
Opens in a new windowHeated pool private yard S Venice 3.8 mi. to beach OVER-SIZED DRIVEWAY RV/BOAT
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IMG, Bradenton Beach, Anna Maria, Siesta Key Beach Beautiful & Centrally Located

IMG, Bradenton Beach, Anna Maria, Siesta Key Beach Beautiful & Centrally Located

Sarasota
The price is NZ$503 per night from 6 Nov to 7 Nov
NZ$503
6 Nov - 7 Nov
includes taxes & fees
Stay at this vacation home in Sarasota. Enjoy a garden, laundry facilities, and in-room jetted tubs. Popular attractions Sarasota Ballet and Asolo Theatre for ...
Opens in a new windowIMG, Bradenton Beach, Anna Maria, Siesta Key Beach Beautiful & Centrally Located
120 steps to beach!  Safely on the beach side of the road!

120 steps to beach! Safely on the beach side of the road!

Englewood
Book a stay at this beach vacation home in Englewood. Enjoy free WiFi, a beach locale, and a water park. Popular attractions Englewood Beach and Stump Pass Beach ...
Opens in a new window120 steps to beach! Safely on the beach side of the road!
New home 3/2 renovation 3 miles to Siesta Key

New home 3/2 renovation 3 miles to Siesta Key

Sarasota
The price is NZ$591 per night from 6 Nov to 7 Nov
NZ$591
6 Nov - 7 Nov
includes taxes & fees
Stay at this vacation home in Sarasota. Enjoy air conditioning. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Opens in a new windowNew home 3/2 renovation 3 miles to Siesta Key
Coastal Cottage - Direct Beach Access

Coastal Cottage - Direct Beach Access

Siesta Key, FL
Book a stay at this beach vacation home in Siesta Key. Enjoy a beach locale, a water park, and balconies. Popular attractions Siesta Key Beach and Lido Beach ...
Opens in a new windowCoastal Cottage - Direct Beach Access
Paradise Retreat  with  HEATED POOL-- Need We Say More

Paradise Retreat with HEATED POOL-- Need We Say More

Bradenton
The price is NZ$668 per night from 10 Nov to 11 Nov
NZ$668
10 Nov - 11 Nov
includes taxes & fees
Book a stay at this family-friendly vacation home in Bradenton. Enjoy private pools, a fitness center, and laundry facilities. Our guests praise the helpful ...
Opens in a new windowParadise Retreat with HEATED POOL-- Need We Say More
The Turtle House-Miles and Miles of Private Beach-Sunset Views

The Turtle House-Miles and Miles of Private Beach-Sunset Views

Englewood
Book a stay at this beach vacation home in Englewood. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Englewood Beach and Blind Pass Beach ...
Opens in a new windowThe Turtle House-Miles and Miles of Private Beach-Sunset Views
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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$226
Highest Price
NZ$668
Popular accommodation
Tropical Villas of Venice Beach, 2 Bedrooms, Bay WaterViews, Beaches, shops, Marina, fishing, all near by, Heated pool private yard S Venice 3.8 mi. to beach OVER-SIZED DRIVEWAY RV/BOAT, IMG, Bradenton Beach, Anna Maria, Siesta Key Beach Beautiful & Centrally Located, 120 steps to beach! Safely on the beach side of the road!, New home 3/2 renovation 3 miles to Siesta Key, Coastal Cottage - Direct Beach Access, Paradise Retreat with HEATED POOL-- Need We Say More, The Turtle House-Miles and Miles of Private Beach-Sunset Views

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$339 per night from 30 Nov to 1 Dec
NZ$339
30 Nov - 1 Dec
includes taxes & fees
Stay at this hotel in Osprey. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the restaurant in our 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 3-star business-friendly hotel in Sarasota. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast ...
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
Fully refundableReserve now, pay when you stay
The price is NZ$358 per night from 9 Nov to 10 Nov
NZ$358
9 Nov - 10 Nov
includes taxes & fees
Stay at this 3.5-star beach aparthotel in Siesta Key. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the pool and the helpful staff ...
Opens in a new windowTropical Beach Resorts
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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 NZ$226 per night from 11 Nov to 12 Nov
NZ$226
11 Nov - 12 Nov
includes taxes & fees
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Opens in a new windowSpark by Hilton Sarasota Siesta Key Gateway
Don't see what you're looking for?
See all available properties in Osprey
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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.