Osprey holiday homes

We found 7,504 holiday rentals — enter your dates for availability
Discover a selection of 14 homes 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.

Holiday rentals with weekly discounts – Osprey

Showing deals for:30 Oct - 6 Nov

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Osprey

  • Beachside bliss: Enjoy sandy shores and a relaxed coastal vibe right in Osprey.
  • Outdoor adventures: Explore urban parks, scenic jetties, and natural landscapes perfect for family outings.
  • Waterfront charm: Revel in the unique blend of historical appeal and modern coastal living.
  • Family-friendly fun: Discover local gems like Lake Suzy and enjoy sunny weather ideal for outdoor activities.
  • Cultural and natural fusion: Experience a mix of cultural touches and nature’s splendour for a memorable escape.

Top attractions near Osprey

Osprey, Florida offers a delightful blend of beachside relaxation and outdoor adventures, perfect for family holidays. Enjoy the sandy beaches, explore urban parks, and take in the scenic jetty pier. Whether you’re seeking a cultural experience or simply a spot to unwind by the sea, Osprey has plenty of attractions to ensure a memorable visit.

  • Siesta Key Beach: Famous for its powdery white sands and vibrant beach vibes, Siesta Key Beach offers stunning sunsets and crystal-clear waters perfect for swimming and sunbathing.
  • Heritage Oaks Golf and Country Club: A premier golfing destination, this club features an 18-hole championship course surrounded by beautiful landscapes, providing a relaxed yet challenging experience for golfers of all skill levels.
  • Turtle Beach: Renowned for its serene atmosphere and natural beauty, Turtle Beach is ideal for families, with soft sands and shallow waters great for swimming and beachcombing.

Things to do recommended for couples

Seeking a romantic getaway in Osprey? Enjoy a sunset picnic at the beautiful Nokomis Beach, explore the scenic trails at Oscar Scherer State Park, or indulge in a couples' massage at a local spa. Don't miss a charming dinner at a waterfront restaurant for a perfect evening.

Things to do recommended for families

Families visiting Osprey can explore the beautiful beaches at Nokomis Beach, enjoy a day at the nearby Marie Selby Botanical Gardens, and take a thrilling airboat tour in the nearby Everglades, perfect for spotting wildlife and creating lasting memories together.

Things to do recommended for groups

Experience the thrill of the TreeUmph. Adventure Course, an exciting zipline ropes course located 29km from Osprey. Perfect for groups, enjoy the great outdoors and create unforgettable memories together as you navigate through the treetops.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Osprey

If you're travelling with a group, family, or pets, or if you're seeking longer stays, be sure to select the right filters based on your priorities. Here are some helpful booking tips for Vrbo to consider.

  • Traveling to Osprey with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Osprey with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, along with ensuring access to suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Osprey: For many, a family holiday isn’t truly fulfilling without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Osprey: If you're in search of holiday rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or even a private pool to your search criteria.

Where to stay near Osprey

Osprey offers a delightful mix of waterfront living, historical charm, and family-friendly vibes. Enjoy sunny weather while exploring local gems like Lake Suzy and the scenic backdrop of Stoneybrook Golf. Whether you're on a relaxed holiday or a spirited Florida adventure, Osprey’s welcoming atmosphere and outdoor attractions make it a perfect destination for a memorable escape.

  • Siesta Key: Siesta Key is a stunning island city located 11km from Osprey, renowned for its pristine beaches and vibrant outdoor activities. Visitors flock to Siesta Key for its family-friendly atmosphere, perfect for beach outings and relaxation. The area boasts a variety of recreational spaces, shopping centres, and delightful dining options. Highlights include the famous Siesta Beach, celebrated for its soft, white sand, and the bustling local neighbourhoods that offer a blend of shops and eateries, making it a perfect getaway for those looking to soak up the sun and enjoy family time.
  • Venice: A charming city located 11km from Osprey, Venice is a delightful destination for beach lovers and outdoor enthusiasts alike. The city is known for its beautiful coastline and family-friendly beach areas. Visitors can enjoy a range of activities, including golfing at local courses and exploring scenic recreational areas. Venice's picturesque town centre features a variety of shops and cafés, inviting you to take a leisurely stroll and experience the local vibe. The welcoming atmosphere and numerous attractions make it an ideal spot for a memorable holiday.
  • Casey Key: Just 5km from Osprey, Casey Key is an idyllic island destination perfect for those seeking a relaxing beach escape. This serene location offers stunning natural beauty and is popular for outdoor family activities. Visitors can explore recreational areas and shopping centres, while the stunning beaches provide a peaceful retreat. Casey Key's inviting atmosphere and close-knit community make it a charming place to unwind, while its proximity to Osprey allows for easy access to all the area's attractions.

Best time to go to Osprey

If you're planning a trip to Osprey, it's a good idea to check both the weather and property rates. The warmest month is August.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January62.6°F (17.0°C)Light RainMostly SunnyAverage
February65.1°F (18.4°C)No Rain (Dry)Mostly SunnyAverage
March68.0°F (20.0°C)No Rain (Dry)SunnySlightly High
April73.4°F (23.0°C)Light RainMostly SunnySlightly High
May77.7°F (25.4°C)Light RainMostly SunnyAverage
June81.7°F (27.6°C)Light RainMostly SunnyAverage
July82.9°F (28.3°C)Light RainMostly SunnyAverage
August83.3°F (28.5°C)Light RainMostly SunnyAverage
September81.5°F (27.5°C)Light RainMostly SunnySlightly High
October77.2°F (25.1°C)Light RainMostly SunnySlightly Low
November70.7°F (21.5°C)No Rain (Dry)Mostly SunnySlightly Low
December66.6°F (19.2°C)No Rain (Dry)Mostly SunnySlightly Low

Booking with Vrbo is simple

Looking to save on your next adventure? Consider being flexible with your travel dates, as prices can fluctuate quite a bit. Additionally, opting for a longer stay can lead to significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to search by price, location, and type of holiday rental. We're here to help you find the perfect getaway.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a dedicated area where you can create fresh itineraries, pick up your existing plans, or review and manage your reservations. Your saved or booked properties are now neatly organised into Potential, Upcoming, or Current Trips. To discover Trip Boards, please visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

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 Lido 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:

  • Mote Marine Laboratory & Aquarium (10.9 mi / 17.5 km)
  • Sarasota Jungle Gardens (12.5 mi / 20.1 km)
  • Sarasota National Golf Course (13.7 mi / 22 km)
  • Stoneybrook Golf & Country Club (1.9 mi / 3 km)
  • Bent Tree Country Club (7.8 mi / 12.6 km)
  • Pelican Pointe Golf and Country Club (9.6 mi / 15.4 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)
  • Lido Beach (9.3 mi / 15 km)
  • Venice Beach (7.3 mi / 11.8 km)
  • Jim Neville Marine Preserve (1.6 mi / 2.5 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 home?
Among the most popular areas to get a holiday home in Osprey is Osprey Village. Find an ideal stay on Bookabach and explore this area like a local.
What is the most popular type of holiday home accommodation in Osprey?
Houses are the most popular type of holiday home in Osprey, according to our data. Even if you've got something different in mind, Bookabach 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 home 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 Bookabach holiday homes 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 Bookabach 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 homes 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 homes on Bookabach. 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 Bookabach, and then spend leisurely days splish-splashing around in a swimming pool that's for your use only.
What are popular home amenities in Osprey?
Tennis, a garden and a water view are rated the most popular home amenities in Osprey. Whether you're planning to travel alone, with a partner or as a family, Bookabach can help you find a holiday home that suits your style with all the features you're looking for.
Are there large group holiday homes 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, Bookabach will help you find the ideal space to fit the occasion.
Are there holiday homes in Osprey that welcome kids?
Osprey has 32 family-friendly holiday homes. 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 homes 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 homes in Osprey?
Take off with your loved ones and experience complete comfort and privacy in one of the 10 two-bedroom holiday homes Osprey has to offer.
Are there holiday homes with WiFi in Osprey?
There are 16 holiday homes with WiFi in Osprey. If you'd like to disconnect from daily life during your escape, but still want to be connected to the web, these getaways have just what you need. Narrow your search by applying the WiFi filter on Bookabach.
How can I find holiday homes with air conditioning in Osprey?
Pick your travel dates and then use the filter tool to view holiday homes with ac in Osprey on Bookabach. With 32 air-conditioned properties available, you can look forward to a cool and comfy stay.
How old do you have to be to rent a holiday home in Osprey?
The age limit can vary across properties on Bookabach, so be sure to check the rules of the holiday home in Osprey you want. But usually, it's 16, 18 or 21.
How long can I rent a holiday home in Osprey for?
The amount of time you can stay in an Osprey holiday home for is up to the property. Just tap in your travel dates to view available options that offer extended stays. They come with all you need to make your extended getaway more convenient and enjoyable, like air conditioning and laundries. Some properties might also offer weekly or monthly discounted prices, so you can hang around longer for less.