Book Holiday Homes in Osprey

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Featured Holiday Homes in Osprey

Siesta Key Island Rentals

Siesta Key Island Rentals

3 out of 5
515 Beach Rd, Siesta Key, FL
The price is NZ$464 per night from 7 Sept to 8 Sept
NZ$464
7 Sept - 8 Sept
includes taxes & fees
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
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
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach

Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach

Sarasota
Book a stay at this family-friendly vacation home in Sarasota. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Lido Beach and Siesta Key ...
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach
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Private Home Directly on Siesta Key Beach!

Private Home Directly on Siesta Key Beach!

Siesta Key
Book a stay at this beach vacation home in Siesta Key. Enjoy free WiFi, a beach locale, and laundry facilities. Popular attractions Siesta Key Beach and Lido ...
Private Home Directly on Siesta Key Beach!
Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND

Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND

Siesta Key
The price is NZ$1,331 per night from 8 Sept to 9 Sept
NZ$1,331
8 Sept - 9 Sept
includes taxes & fees
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 ...
Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND
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, laundry facilities, and concierge services. Our guests praise the helpful staff in our reviews. Popular ...
Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
Siesta Key 2BR 1Bath unit COZY Barefoot Bungalows 1500 ft from beach access#3

Siesta Key 2BR 1Bath unit COZY Barefoot Bungalows 1500 ft from beach access#3

Sarasota
Stay at this villa in Siesta Key. Enjoy free WiFi, laundry facilities, and concierge services. Our guests praise the helpful staff in our reviews. Popular attractions ...
Siesta Key 2BR 1Bath unit COZY Barefoot Bungalows 1500 ft from beach access#3
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

Siesta Key
Stay at this vacation home in Siesta Key. Enjoy free WiFi, a beach locale, and laundry facilities. Popular attractions Siesta Key Beach and Lido Beach are located ...
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
Siesta Heron Suites & Villas

Siesta Heron Suites & Villas

3.5 out of 5
8254 Midnight Pass Rd, Siesta Key, FL
Stay at this 3.5-star vacation home in Siesta Key. Enjoy free WiFi, free parking, and a garden. Popular attractions Siesta Key Beach and Turtle Beach are located ...
Siesta Heron Suites & Villas
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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
3947 Holiday Homes
Lowest Price
NZ$306
Highest Price
NZ$1,331
Popular accommodation
Siesta Key Island Rentals, Tropical Villas of Venice Beach, Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach, Private Home Directly on Siesta Key Beach!, Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND, Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL", Siesta Key 2BR 1Bath unit COZY Barefoot Bungalows 1500 ft from beach access#3, Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool, Siesta Heron Suites & Villas

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
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 ...
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
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
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$306 per night from 8 Sept to 9 Sept
NZ$306
8 Sept - 9 Sept
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 ...
Tropical Beach Resorts
Save an average of 15% on thousands of hotels when you're signed in
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
140 Columbus Blvd., Siesta Key, FL
Fully refundableReserve now, pay when you stay
Stay at this 3-star beach hotel in Siesta Key. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in ...
Tropical Breeze Resort
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.