Book Holiday Homes in Osprey

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Featured Holiday Homes in Osprey

LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.

LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.

Siesta Key
The price is AU$887 per night from 10 Feb to 11 Feb
AU$887
includes taxes & fees
10 Feb - 11 Feb
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 😀🐕.
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, within a 15-minute walk of Venice Beach and Manasota Beach.
Tropical Villas of Venice Beach
New home 3/2 renovation 3 miles to Siesta Key

New home 3/2 renovation 3 miles to Siesta Key

Sarasota
The price is AU$535 per night from 2 Feb to 3 Feb
AU$535
includes taxes & fees
2 Feb - 3 Feb
With a stay at this vacation home in Sarasota, you'll be a 4-minute drive from Siesta Key Beach and 7 minutes from Turtle Beach.
New home 3/2 renovation 3 miles to Siesta Key
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Casa Azul 2bed/1bath

Casa Azul 2bed/1bath

Sarasota
The price is AU$271 per night from 3 Feb to 4 Feb
AU$271
includes taxes & fees
3 Feb - 4 Feb
With a stay at this vacation home, you'll be centrally located in Sarasota, a 4-minute drive from John and Mable Ringling Museum of Art and 9 minutes from St. ...
Casa Azul 2bed/1bath
Bohemian Sunrise

Bohemian Sunrise

Englewood
When you stay at this vacation home in Englewood, you'll be on the waterfront, within a 15-minute drive of Englewood Beach and Manasota Beach.
Bohemian Sunrise
Heated Pool - Backyard Privacy- Camping in the Suburbs- 25 min. to the beach

Heated Pool - Backyard Privacy- Camping in the Suburbs- 25 min. to the beach

North Port
With a stay at this vacation home in North Port, you'll be within a 10-minute drive of North Charlotte Regional Park and North Port Performing Arts Center.
Heated Pool - Backyard Privacy- Camping in the Suburbs- 25 min. to the beach
Private Pool House 6 miles from the Beach

Private Pool House 6 miles from the Beach

Bradenton
With a stay at this vacation home, you'll be centrally located in Bradenton, within a 10-minute drive of IMG Academy and LECOM Park.
Private Pool House 6 miles from the Beach
Ramada Sarasota Waterfront and Marina Community with Tikki Bar and Grill

Ramada Sarasota Waterfront and Marina Community with Tikki Bar and Grill

Sarasota
The price is AU$269 per night from 4 Feb to 5 Feb
AU$269
includes taxes & fees
4 Feb - 5 Feb
With a stay at this vacation home in Sarasota (Whitfield Estates), you'll be a 5-minute drive from John and Mable Ringling Museum of Art and 8 minutes from LECOM ...
Ramada Sarasota Waterfront and Marina Community with Tikki Bar and Grill
Siesta Key- 2 Bed/1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

Siesta Key- 2 Bed/1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

Siesta Key
With a stay at this vacation home in Siesta Key (Siesta Key Village), you'll be a 1-minute drive from Siesta Key Beach and 8 minutes from Crescent Beach.
Siesta Key- 2 Bed/1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
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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
2978 Holiday Homes
Lowest Price
AU$181
Highest Price
AU$887
Popular accommodation
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕., Tropical Villas of Venice Beach, New home 3/2 renovation 3 miles to Siesta Key, Casa Azul 2bed/1bath, Bohemian Sunrise , Heated Pool - Backyard Privacy- Camping in the Suburbs- 25 min. to the beach, Private Pool House 6 miles from the Beach, Ramada Sarasota Waterfront and Marina Community with Tikki Bar and Grill, Siesta Key- 2 Bed/1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

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$333 per night from 11 Feb to 12 Feb
AU$333
includes taxes & fees
11 Feb - 12 Feb
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
Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

3 out of 5
4675 N Tamiami Trl, Sarasota, FL
Fully refundable
The price is AU$181 per night from 3 Feb to 4 Feb
AU$181
includes taxes & fees
3 Feb - 4 Feb
With a stay at Golden Host Resort - Sarasota in Sarasota (North Trail), you'll be a 2-minute drive from John and Mable Ringling Museum of Art and 9 minutes from ...
Golden Host Resort - Sarasota
Hyatt Regency Sarasota

Hyatt Regency Sarasota

4 out of 5
1000 Blvd Of The Arts, Sarasota, FL
Fully refundableReserve now, pay when you stay
The price is AU$449 per night from 3 Mar to 4 Mar
AU$449
includes taxes & fees
3 Mar - 4 Mar
With a stay at Hyatt Regency Sarasota, you'll be centrally located in Sarasota, within a 5-minute drive of Sarasota Memorial Hospital and Ed Smith Stadium.
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$306 per night from 2 Feb to 3 Feb
AU$306
includes taxes & fees
2 Feb - 3 Feb
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
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.