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
Stay at this holiday home in Siesta Key. Enjoy free Wi-Fi, free parking and laundry facilities. Popular attractions Siesta Key Beach and Lido Beach are located ...
Opens in a new windowSiesta Key Island Rentals
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

Siesta Key FL
Stay at this holiday home in Siesta Key. Enjoy free Wi-Fi, a beach locale and laundry facilities. Popular attractions Siesta Key Beach and Lido Beach are located ...
Opens in a new windowTranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
Gull Villa – Spacious 2BR, Walk to Siesta Key & Village

Gull Villa – Spacious 2BR, Walk to Siesta Key & Village

Siesta Key FL
Stay at this holiday home in Siesta Key. Enjoy free Wi-Fi, a fitness centre and laundry facilities. Our guests praise the helpful staff in their reviews. Popular ...
Opens in a new windowGull Villa – Spacious 2BR, Walk to Siesta Key & Village
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Family Vacation Home with Pool

Family Vacation Home with Pool

Sarasota FL
The price is NZ$1,207 per night from 5 Apr to 6 Apr
NZ$1,207
5 Apr - 6 Apr
includes taxes & fees
Stay at this holiday home in Sarasota. Enjoy private pools, laundry facilities and an in-room coffee maker. Popular attractions Mall at University Town Center ...
Opens in a new windowFamily Vacation Home with Pool
Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village

Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village

Siesta Key FL
Stay at this family-friendly holiday home in Siesta Key. Enjoy free Wi-Fi, private pools and laundry facilities. Popular attractions Siesta Key Beach and Lido ...
Opens in a new windowSiesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village
Heated Pool & Waterfront Haven with Kayaks, Steps to Lido Beach & St. Armands Circle

Heated Pool & Waterfront Haven with Kayaks, Steps to Lido Beach & St. Armands Circle

Lido Key FL
Stay at this holiday home in Sarasota. Enjoy free Wi-Fi, private pools and patios. Popular attractions St. Armands Circle and Lido Beach are located nearby.
Opens in a new windowHeated Pool & Waterfront Haven with Kayaks, Steps to Lido Beach & St. Armands Circle
Luxury Home w/ Heated Pool and Private Beach Access

Luxury Home w/ Heated Pool and Private Beach Access

Siesta Key FL
Stay at this holiday home in Siesta Key. Enjoy free Wi-Fi, private pools and laundry facilities. Popular attractions Siesta Key Beach and Lido Beach are located ...
Opens in a new windowLuxury Home w/ Heated Pool and Private Beach Access
Pineapple House - near beaches - private SOUTH facing POOL & HOT TUB - walkable

Pineapple House - near beaches - private SOUTH facing POOL & HOT TUB - walkable

Sarasota FL
Stay at this family-friendly holiday home in Sarasota. Enjoy free Wi-Fi, private pools and a fitness centre. Popular attractions Lido Beach and St. Armands Circle ...
Opens in a new windowPineapple House - near beaches - private SOUTH facing POOL & HOT TUB - walkable
Charming 2-bedroom beach themed Englewood house with heated pool and large yard.

Charming 2-bedroom beach themed Englewood house with heated pool and large yard.

Englewood FL
Enjoy private pools, laundry facilities and an in-room coffee maker. Popular attractions Englewood Recreation Center and Englewood Village Park are located ...
Opens in a new windowCharming 2-bedroom beach themed Englewood house with heated pool and large yard.
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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
3925 Holiday Homes
Lowest Price
NZ$146
Highest Price
NZ$1,207
Popular accommodation
Siesta Key Island Rentals, Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool, Gull Villa – Spacious 2BR, Walk to Siesta Key & Village, Family Vacation Home with Pool , Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village, Heated Pool & Waterfront Haven with Kayaks, Steps to Lido Beach & St. Armands Circle, Luxury Home w/ Heated Pool and Private Beach Access, Pineapple House - near beaches - private SOUTH facing POOL & HOT TUB - walkable, Charming 2-bedroom beach themed Englewood house with heated pool and large yard.

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 NZ$302 per night from 3 May to 4 May
NZ$302
3 May - 4 May
includes taxes & fees
Stay at this hotel in Osprey. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the pool and the restaurant in their reviews. Popular ...
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 NZ$195 per night from 4 Apr to 5 Apr
NZ$195
4 Apr - 5 Apr
includes taxes & fees
Stay at this business-friendly hotel in Sarasota. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the breakfast and the ...
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 NZ$146 per night from 3 May to 4 May
NZ$146
3 May - 4 May
includes taxes & fees
Stay at this business-friendly hotel in Sarasota. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the pool and the helpful staff in ...
Opens in a new windowGolden Host Resort - Sarasota
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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$444 per night from 29 Apr to 30 Apr
NZ$444
29 Apr - 30 Apr
includes taxes & fees
Stay at this beach aparthotel in Siesta Key. Enjoy free Wi-Fi, free parking and daily housekeeping. Our guests praise the pool and the helpful staff in their ...
Opens in a new windowTropical Beach Resorts
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.