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
Located in Siesta Key, Siesta Key Island Rentals is within a 15-minute drive of Siesta Key Beach and Crescent Beach.
Opens in a new windowSiesta Key Island Rentals
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.
Opens in a new windowTropical Villas of Venice 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 AU$1,404 per night from 30 Sept to 1 Oct
AU$1,404
30 Sept - 1 Oct
includes taxes & fees
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.
Opens in a new windowLuxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND
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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
With a stay at this vacation home, you'll be centrally located in Sarasota, just a 4-minute walk from Lido Beach and 11 minutes by foot from St. Armands ...
Opens in a new windowEntire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach
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.
Opens in a new windowSiesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
Charming 2-bedroom house in lovely Sarasota with yard.

Charming 2-bedroom house in lovely Sarasota with yard.

Sarasota
The price is AU$302 per night from 30 Sept to 1 Oct
AU$302
30 Sept - 1 Oct
includes taxes & fees
With a stay at this vacation home in Sarasota (Kensington Park), you'll be within a 15-minute drive of Mall at University Town Center and St. Armands ...
Opens in a new windowCharming 2-bedroom house in lovely Sarasota with yard.
Siesta Key Townhome across from Pristine Sand & Blue Waters 2b/2b king queen

Siesta Key Townhome across from Pristine Sand & Blue Waters 2b/2b king queen

Siesta Key
When you stay at this vacation home in Siesta Key, you'll be on the beach, a 2-minute drive from Siesta Key Beach and 7 minutes from Crescent Beach.
Opens in a new windowSiesta Key Townhome across from Pristine Sand & Blue Waters 2b/2b king queen
Private Home Directly on Siesta Key Beach!

Private Home Directly on Siesta Key Beach!

Siesta Key
When you stay at this vacation home in Siesta Key, you'll be on the beach, within a 15-minute drive of Siesta Key Beach and Crescent Beach.
Opens in a new windowPrivate Home Directly on Siesta Key Beach!
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

Siesta Key
When you stay at this vacation home in Siesta Key, you'll be on the beach, a 1-minute drive from Siesta Key Beach and 9 minutes from Crescent Beach.
Opens in a new windowTranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
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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
3910 Holiday Homes
Lowest Price
AU$274
Highest Price
AU$1,404
Popular accommodation
Siesta Key Island Rentals, Tropical Villas of Venice Beach, Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND, Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach, Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL", Charming 2-bedroom house in lovely Sarasota with yard., Siesta Key Townhome across from Pristine Sand & Blue Waters 2b/2b king queen , Private Home Directly on Siesta Key Beach!, Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

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
With a stay at Casey Key Resorts - Mainland in Osprey, you'll be within a 5-minute drive of Nokomis Beach and Turtle Beach.
Opens in a new windowCasey 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
When you stay at Kompose Boutique Hotel in Sarasota, you'll be near the airport, within a 15-minute drive of Lido Beach and St. Armands Circle.
Opens in a new windowKompose 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 AU$275 per night from 30 Sept to 1 Oct
AU$275
30 Sept - 1 Oct
includes taxes & fees
With a stay at Tropical Beach Resorts in Siesta Key, you'll be in the business district, within a 10-minute walk of Siesta Key Marina and Crescent Beach.
Opens in a new windowTropical Beach Resorts
Save an average of 15% on thousands of hotels when you're signed in
Carlisle Inn

Carlisle Inn

3.5 out of 5
3727 Bahia Vista, Sarasota, FL
Fully refundableReserve now, pay when you stay
The price is AU$274 per night from 16 Oct to 17 Oct
AU$274
16 Oct - 17 Oct
includes taxes & fees
With a stay at Carlisle Inn in Sarasota (Pinecraft), you'll be within a 15-minute drive of Siesta Key Beach and Mall at University Town Center.
Opens in a new windowCarlisle Inn
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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.