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
Stay at this vacation home in Siesta Key. Enjoy free WiFi, private pools, and a garden. Popular attractions Lido Beach and Siesta Key Beach are located ...
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
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 Centennial Park ...
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
Stay at this vacation home in Sarasota. Enjoy air conditioning. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
New home 3/2 renovation 3 miles to Siesta Key
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Casa Azul 2bed/1bath

Casa Azul 2bed/1bath

Sarasota
Stay at this vacation home in Sarasota. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Lido Beach and St. Armands Circle are located ...
Casa Azul 2bed/1bath
Bohemian Sunrise

Bohemian Sunrise

Englewood
Stay at this vacation home in Englewood. Enjoy free WiFi, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Lemon Bay and Indian Mound ...
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
Stay at this vacation home in North Port. Enjoy an in-room coffeemaker, housekeeping, and air conditioning. Popular attractions Heron Creek Golf Course and North ...
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
Stay at this vacation home in Bradenton. Enjoy free WiFi, private pools, and a garden. Our guests praise the pool in our reviews. Popular attractions 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 NZ$301 per night from 25 Mar to 26 Mar
NZ$301
includes taxes & fees
25 Mar - 26 Mar
Stay at this vacation home in Sarasota. Enjoy free WiFi, a fitness center, and a garden. Popular attractions John and Mable Ringling Museum of Art and 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
Stay at this vacation home in Siesta Key. Enjoy free WiFi, concierge services, and patios. Our guests praise the helpful staff in our reviews. Popular attractions ...
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
2975 Holiday Homes
Lowest Price
NZ$268
Highest Price
NZ$529
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 NZ$388 per night from 25 Feb to 26 Feb
NZ$388
includes taxes & fees
25 Feb - 26 Feb
Stay at this 3-star business-friendly hotel in Osprey. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the restaurant ...
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 NZ$268 per night from 3 Mar to 4 Mar
NZ$268
includes taxes & fees
3 Mar - 4 Mar
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the pool and the bar in our ...
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 NZ$529 per night from 9 Mar to 10 Mar
NZ$529
includes taxes & fees
9 Mar - 10 Mar
Book a stay at this eco-certified hotel in Sarasota. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
Hyatt Regency Sarasota
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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 NZ$398 per night from 3 Mar to 4 Mar
NZ$398
includes taxes & fees
3 Mar - 4 Mar
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool ...
Kompose Boutique Hotel
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.