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 ...
Tropical Villas of Venice Beach
New Waterfront Unit, Sleeps 4, Heated Pool, Gym, Tiki Bar & Grill, Kitchenette

New Waterfront Unit, Sleeps 4, Heated Pool, Gym, Tiki Bar & Grill, Kitchenette

Sarasota
The price is NZ$317 per night from 15 May to 16 May
NZ$317
includes taxes & fees
15 May - 16 May
Stay at this vacation home in Sarasota. Enjoy free WiFi, a fitness center, and patios. Popular attractions John and Mable Ringling Museum of Art and Mote Marine ...
New Waterfront Unit, Sleeps 4, Heated Pool, Gym, Tiki Bar & Grill, Kitchenette
Siesta Key Island Rentals

Siesta Key Island Rentals

3 out of 5
515 Beach Rd, Siesta Key, FL
Stay at this 3-star vacation home in Siesta Key. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Siesta Key Beach and Lido Beach are ...
Siesta Key Island Rentals
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SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND

SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND

Siesta Key
The price is NZ$2,402 per night from 4 May to 5 May
NZ$2,402
includes taxes & fees
4 May - 5 May
Book a stay at this beach vacation home in Siesta Key. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Siesta Key Beach and Lido Beach are ...
SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND
Close to Beach Access #7, Short Walk to the Village

Close to Beach Access #7, Short Walk to the Village

Siesta Key
The price is NZ$915 per night from 2 May to 3 May
NZ$915
includes taxes & fees
2 May - 3 May
Stay at this vacation home in Siesta Key. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Siesta Key Beach and Lido Beach are ...
Close to Beach Access #7, Short Walk to the Village
Private Oasis in Sarasota Florida

Private Oasis in Sarasota Florida

Sarasota
Stay at this vacation home in Sarasota. Enjoy free WiFi, private pools, and patios. Popular attractions Lido Beach and Siesta Key Beach are located nearby.
Private Oasis in Sarasota Florida
Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach

Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach

Sarasota
The price is NZ$371 per night from 11 May to 12 May
NZ$371
includes taxes & fees
11 May - 12 May
Stay at this vacation home in Sarasota. Enjoy free WiFi, a garden, and furnished lanais. Popular attractions Siesta Key Beach and Turtle Beach are located ...
Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach
Private pool House with Fountains & Beach Walkable

Private pool House with Fountains & Beach Walkable

Venice
Stay at this vacation home in Venice. Enjoy free WiFi, private pools, and a garden. Popular attractions Venice Beach and Caspersen Beach are located nearby.
Private pool House with Fountains & Beach Walkable
Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches

Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches

Venice
The price is NZ$837 per night from 12 May to 13 May
NZ$837
includes taxes & fees
12 May - 13 May
Book a stay at this family-friendly vacation home in Venice. Enjoy free WiFi, private pools, and tennis courts. Popular attractions Venice Beach and Caspersen ...
Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches
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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
3696 Holiday Homes
Lowest Price
NZ$165
Highest Price
NZ$2,402
Popular accommodation
Tropical Villas of Venice Beach, New Waterfront Unit, Sleeps 4, Heated Pool, Gym, Tiki Bar & Grill, Kitchenette, Siesta Key Island Rentals, SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND, Close to Beach Access #7, Short Walk to the Village, Private Oasis in Sarasota Florida, Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach, Private pool House with Fountains & Beach Walkable, Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches

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$324 per night from 5 May to 6 May
NZ$324
includes taxes & fees
5 May - 6 May
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
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$165 per night from 4 May to 5 May
NZ$165
includes taxes & fees
4 May - 5 May
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
Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

3 out of 5
4675 N Tamiami Trl, Sarasota, FL
Fully refundable
The price is NZ$170 per night from 4 May to 5 May
NZ$170
includes taxes & fees
4 May - 5 May
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
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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$191 per night from 20 May to 21 May
NZ$191
includes taxes & fees
20 May - 21 May
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 ...
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.

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