Osprey holiday lettings

We found 6,682 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 30 homes, 10 apartments and other holiday rentals in Osprey that are perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the amenities that you expect for your stay, which might include a garden and hot tub. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

  • Peace of mind
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  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

The historical city of Osprey awaits you

The area's history and live music are just some of the reasons to come on holiday to Osprey. This welcoming city is known for its beaches, bars and gardens. Siesta Key Beach and Venice Beach are just a couple of the must-see attractions in the area. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Osprey

Do you want to find things to do during your stay? Venture out of your holiday home and check out everything that makes Osprey a fun place to get away to. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Stoneybrook Golf & Country Club (1.9 mi / 3 km)
  • Mote Marine Laboratory & Aquarium (10.9 mi / 17.5 km)
  • Sarasota National Golf Course (13.7 mi / 22 km)
  • Pelican Pointe Golf and Country Club (9.6 mi / 15.4 km)
  • Islandside Golf Course at Longboat Key Club (11.3 mi / 18.1 km)
  • Harborside Golf Course at Longboat Key Club (11.3 mi / 18.1 km)

Exploring the beaches and other natural features in Osprey

Whether you're looking for fun outdoor activities or just want to take in the scenery, Osprey is a great place to get outside. Here are some of the area’s most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Siesta Key Beach (6.2 mi / 10 km)
  • Venice Beach (7.3 mi / 11.8 km)
  • Lido Beach (9.3 mi / 15 km)
  • St. Armands Circle (10 mi / 16.1 km)
  • Turtle Beach (2.7 mi / 4.4 km)
  • Point of Rocks (4.4 mi / 7.1 km)

Seasonal weather averages in Osprey

If you're hoping to enjoy some warm-weather activities on your holiday, August, July, September and June are the hottest months to visit, when temperatures average 28°C.

Transport options to and around Osprey

Fly into Sarasota, FL (SRQ-Sarasota-Bradenton Intl.), the closest airport, located 13.8 mi (22.2 km) from the city centre.

Frequently asked questions

What is the best area to stay in Osprey when booking a holiday rental?

Among the most popular areas to get a holiday rental in Osprey is Osprey Village. Find an ideal stay on Vrbo and explore this area like a local.

What is the most popular type of holiday rental accommodation in Osprey?

Houses are the most popular type of holiday rental in Osprey, according to our data. Even if you've got something different in mind, Vrbo has properties in loads of sizes and shapes. Compare our options to find your ideal match.

How much does it cost to rent a holiday rental in Osprey?

Property type, length of stay and season are some of the conditions that can determine the price of a holiday home. Simply enter your travel dates to find your ideal escape. From cosy country cottages to sprawling villas, all Vrbo holiday rentals offer incredible value.

How much does it cost to rent a beach house in Osprey?

The average price for a holiday home by the beach in Osprey depends on when you're going and the type and size of property you're searching for. Find prices quickly and easily on Vrbo by entering your destination and preferred travel dates. Then use our handy filter tool to select the number of bedrooms and amenities essential to you, like a pool, air conditioning and WiFi.

Are there pet-friendly holiday rentals in Osprey?

Pack a squeezy toy and a bone for your beloved pooch because Osprey has 32 holiday homes that put out the welcome mat to pets. Let your happy hound join in with the family fun at one of our pet-friendly holiday rentals on Vrbo. Simply enter your destination and travel dates, then check our "Pets allowed" filter box.

Can I rent a house with a pool in Osprey?

Add a whole new level of fun to your getaway by booking one of the 22 houses with a private pool in Osprey. Use our search filter to find the kind of property you want on Vrbo, and then spend leisurely days splish-splashing around in a swimming pool that's for your use only.

What are popular rental amenities in Osprey?

Tennis, a garden and a water view are rated the most popular rental amenities in Osprey. Whether you're planning to travel alone, with a partner or as a family, Vrbo can help you find a holiday rental that suits your style with all the features you're looking for.

Are there large group holiday rentals in Osprey?

With 16 Osprey properties that can sleep five or more people, you can invite a few extra family members or buddies along. Whether you're planning an informal gathering or a special celebration, Vrbo will help you find the ideal space to fit the occasion.

Are there holiday rentals in Osprey that welcome kids?

Osprey has 32 family-friendly holiday rentals. And booking a stay that welcomes children is a cinch with our "Properties good for families" filter. As well as having the entire place to yourselves, you'll have access to amenities and perks like living rooms, yards and private pools.

What are the top attractions for families in Osprey?

Keeping the kids entertained during your Osprey holiday is a cinch with these awesome family-friendly attractions:

  • Siesta Key Beach
  • Venice Beach
  • Turtle Beach

Are there one-bedroom holiday rentals in Osprey?

Yes, there are six one-bedroom properties in Osprey to pick from. A one-bedroom holiday property is a superb choice if it's just the two of you or if you're travelling solo. Toss in more convenience, space and privacy than a regular hotel, and you're sure to have a trip to remember.

Can I find two-bedroom holiday rentals in Osprey?

Take off with your loved ones and experience complete comfort and privacy in one of the 10 two-bedroom holiday rentals Osprey has to offer.

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