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 AU$588 per night from 19 May to 20 May
AU$588
19 May - 20 May
includes taxes & fees
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.
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
With a stay at Tropical Villas of Venice Beach in Venice (Venice Island), you'll be a 2-minute drive from Venice Beach and 7 minutes from Caspersen Beach.
Opens in a new windowTropical Villas of Venice Beach
3-bed 2-bathroom Siesta Key townhome close to village,beaches, city and airport

3-bed 2-bathroom Siesta Key townhome close to village,beaches, city and airport

Siesta Key FL
The price is AU$363 per night from 20 May to 21 May
AU$363
20 May - 21 May
includes taxes & fees
With a stay at this vacation home, you'll be centrally located in Siesta Key, a 2-minute drive from Siesta Key Beach and 7 minutes from Sarasota Memorial ...
Opens in a new window3-bed 2-bathroom Siesta Key townhome close to village,beaches, city and airport
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Last Minute Luxury Beachside Home 100 ft Walk to Siesta Key Beach Pool

Last Minute Luxury Beachside Home 100 ft Walk to Siesta Key Beach Pool

Siesta Key FL
With a stay at this vacation home in Siesta Key, you'll be a 1-minute drive from Siesta Key Beach and 9 minutes from Crescent Beach.
Opens in a new windowLast Minute Luxury Beachside Home 100 ft Walk to Siesta Key Beach Pool
Steps to Siesta Key Beach & Village - 2BR w Balcony,   1945 Triplex 2nd Floor

Steps to Siesta Key Beach & Village - 2BR w Balcony, 1945 Triplex 2nd Floor

Siesta Key FL
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 windowSteps to Siesta Key Beach & Village - 2BR w Balcony, 1945 Triplex 2nd Floor
Coastal Cottage - Direct Beach Access

Coastal Cottage - Direct Beach Access

Siesta Key FL
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 windowCoastal Cottage - Direct Beach Access
Seashell Esta – Luxe Siesta Key Escape

Seashell Esta – Luxe Siesta Key Escape

Siesta Key FL
The price is AU$5,627 per night from 15 June to 16 June
AU$5,627
15 June - 16 June
includes taxes & fees
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 10 minutes from Sarasota Memorial ...
Opens in a new windowSeashell Esta – Luxe Siesta Key Escape
WOW! THE ULTIMATE LUXURY BEACH FRONT HOME with FULL PRIVATE GULF FRONT BEACH!

WOW! THE ULTIMATE LUXURY BEACH FRONT HOME with FULL PRIVATE GULF FRONT BEACH!

Englewood FL
When you stay at this vacation home in Englewood, you'll be on the beach, within a 5-minute walk of Englewood Beach and Lemon Bay.
Opens in a new windowWOW! THE ULTIMATE LUXURY BEACH FRONT HOME with FULL PRIVATE GULF FRONT BEACH!
COCO BUNGALOW - All new w/ heated pool, bikes, beach equipment & more

COCO BUNGALOW - All new w/ heated pool, bikes, beach equipment & more

Englewood FL
When you stay at this vacation home in Englewood, you'll be near the beach, within a 5-minute walk of Englewood Beach and Lemon Bay.
Opens in a new windowCOCO BUNGALOW - All new w/ heated pool, bikes, beach equipment & more
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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
4005 Holiday Homes
Lowest Price
AU$116
Highest Price
AU$5,627
Popular accommodation
Siesta Key Island Rentals, Tropical Villas of Venice Beach, 3-bed 2-bathroom Siesta Key townhome close to village,beaches, city and airport, Last Minute Luxury Beachside Home 100 ft Walk to Siesta Key Beach Pool, Steps to Siesta Key Beach & Village - 2BR w Balcony, 1945 Triplex 2nd Floor, Coastal Cottage - Direct Beach Access, Seashell Esta – Luxe Siesta Key Escape, WOW! THE ULTIMATE LUXURY BEACH FRONT HOME with FULL PRIVATE GULF FRONT BEACH!, COCO BUNGALOW - All new w/ heated pool, bikes, beach equipment & more

Top trending hotels in Osprey

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

4 out of 5
1650 South Tamiami Trail Osprey FL
Fully refundableReserve now, pay when you stay
The price is AU$178 per night from 31 May to 1 June
AU$178
31 May - 1 June
includes taxes & fees
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
The price is AU$128 per night from 17 May to 18 May
AU$128
17 May - 18 May
includes taxes & fees
When you stay at Kompose Boutique Hotel in Sarasota, you'll be near the airport, within a 15-minute drive of Sarasota Memorial Hospital and St. Armands ...
Opens in a new windowKompose 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 AU$116 per night from 17 May to 18 May
AU$116
17 May - 18 May
includes taxes & fees
With a stay at Golden Host Resort - Sarasota in Sarasota (North Trail), you'll be within a 10-minute drive of Lido Beach and Sarasota Memorial Hospital.
Opens in a new windowGolden Host Resort - Sarasota
Save an average of 15% on thousands of hotels when you're signed in
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$287 per night from 20 May to 21 May
AU$287
20 May - 21 May
includes taxes & fees
Located in Siesta Key (South Village), Tropical Beach Resorts is within a 10-minute walk of Siesta Key Marina and Crescent Beach.
Opens in a new windowTropical Beach Resorts
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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.

Top Picks

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