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
When you stay at Tropical Villas of Venice Beach in Venice, you'll be near the beach, a 2-minute drive from Venice Beach and 7 minutes from Caspersen Beach.
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
With a stay at this vacation home in Sarasota (Whitfield Estates), you'll be within a 15-minute drive of St. Armands Circle and IMG Academy.
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
With a stay at Siesta Key Island Rentals in Siesta Key, you'll be a 1-minute drive from Siesta Key Beach and 9 minutes from Sarasota Memorial Hospital.
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 AU$2,084 per night from 6 Apr to 7 Apr
AU$2,084
includes taxes & fees
6 Apr - 7 Apr
With a stay at this vacation home, you'll be centrally located in Siesta Key, steps from Siesta Key Beach and within a 5-minute drive of Crescent Beach.
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
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 5 minutes from Crescent Beach.
Close to Beach Access #7, Short Walk to the Village
Private Oasis in Sarasota Florida

Private Oasis in Sarasota Florida

Sarasota
With a stay at this vacation home in Sarasota, you'll be a 2-minute drive from Sarasota Memorial Hospital and 8 minutes from Siesta Key Beach.
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 AU$373 per night from 2 May to 3 May
AU$373
includes taxes & fees
2 May - 3 May
When you stay at this vacation home in Sarasota, you'll be near the beach, within a 10-minute drive of Siesta Key Beach and Nokomis Beach.
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
When you stay at this vacation home in Venice, you'll be by the sea, within a 5-minute drive of Venice Beach and Caspersen Beach.
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
With a stay at this vacation home in Venice (South Venice), you'll be within a 15-minute drive of Venice Beach and Lemon Bay.
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
3678 Holiday Homes
Lowest Price
AU$160
Highest Price
AU$2,084
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 AU$281 per night from 5 May to 6 May
AU$281
includes taxes & fees
5 May - 6 May
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$160 per night from 5 May to 6 May
AU$160
includes taxes & fees
5 May - 6 May
With a stay at Golden Host Resort - Sarasota in Sarasota (North Trail), you'll be within a 10-minute drive of St. Armands Circle and Lido Beach.
Golden Host Resort - Sarasota
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 AU$184 per night from 10 Apr to 11 Apr
AU$184
includes taxes & fees
10 Apr - 11 Apr
When you stay at Kompose Boutique Hotel in Sarasota, you'll be near the airport, within a 15-minute drive of St. Armands Circle and Lido Beach.
Kompose Boutique Hotel
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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$228 per night from 5 May to 6 May
AU$228
includes taxes & fees
5 May - 6 May
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
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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.