Osprey holiday homes

We found 7,019 holiday rentals — enter your dates for availability

Select from 32 houses, 17 flats and other holiday rentals to find the perfect place for your stay in Osprey. 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:19 Dec - 26 Dec
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Why visit Osprey

  • Stunning beaches: Relax on beautiful beaches, perfect for sunbathing and swimming in the warm waters.
  • Outdoor adventures: Enjoy various outdoor activities, from kayaking to biking, amidst scenic landscapes.
  • Charming local culture: Experience the friendly vibe and historical charm of Osprey and its surrounding areas.
  • Family-friendly attractions: Discover numerous attractions that cater to families, ensuring fun for all ages.
  • Scenic walks and dining: Stroll along the picturesque Mooloolaba Esplanade, lined with shops and eateries.

Top attractions near Osprey

Osprey, Florida, offers a fantastic getaway for beach lovers and families alike, perfect for outdoor adventures. Explore local attractions such as the beautiful Mooloolaba Beach and the lively Mooloolaba Esplanade, where you can enjoy scenic walks, dining, and shopping. With its stunning beaches and vibrant urban parks, Osprey is an ideal destination for a memorable holiday experience.

  • Siesta Key Beach: Renowned for its powdery white sand and crystal-clear waters, Siesta Key Beach offers a relaxed atmosphere perfect for sunbathing, swimming, and beachcombing. With vibrant sunsets and a range of water activities, it’s a must-visit destination for beach lovers.
  • Heritage Oaks Golf and Country Club: This picturesque golf course provides a challenging yet enjoyable experience for golfers of all skill levels. Surrounded by lush landscapes, it features excellent facilities, making it a perfect spot for both a round of golf and socialising.
  • Turtle Beach: A quieter alternative to Siesta Key, Turtle Beach boasts a tranquil setting with soft sands and gentle waves. Ideal for shell collecting and picnicking, it also offers stunning views of the Gulf, making it a lovely spot to unwind.

Things to do recommended for couples

If you're after a romantic getaway in Osprey, indulge in the luxury of The Oaks Club or challenge each other at Evie's Golf Center, just 11.3km away. For a unique experience, try your hand at shooting at Sarasota Trap Skeet and Clays, only 9.7km from town.

Things to do recommended for families

Your family will love the sports atmosphere at Ed Smith Stadium, just 17.7km from Osprey, or explore the natural beauty along the Canopy Walkway and Boylston Nature Trail, located 19.3km away. Both activities offer fantastic outdoor vibes for a memorable experience.

Things to do recommended for groups

Experience the scenic Pelican Pointe Golf and Country Club for a round of golf, shop at Sarasota Square for some retail therapy, and enjoy a show at the Van Wezel Performing Arts Hall for a taste of local culture. It's a perfect mix for your group getaway.

*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 planning a trip with friends, family, pets, or extended stays, be sure to set your filters according to your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Osprey with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Osprey with young kids: Traveling with young kids can be a bit tricky. It’s important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Osprey: For many families, a holiday wouldn't be the same without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly places offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Osprey: If you’re seeking 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 include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Osprey

Osprey, Florida, is a delightful escape for Kiwis seeking sun-soaked beaches and family adventures. With its friendly atmosphere and stunning ocean views, visitors can enjoy a relaxing getaway filled with historical charm. Explore nearby regions for a taste of family-friendly fun, romantic sunsets, and vibrant local culture. Whether you’re after cozy accommodation or exciting outdoor activities, Osprey offers a perfect blend of relaxation and adventure for every traveller.

  • Siesta Key: Siesta Key is a stunning island community located a mere 11.3km from Osprey. Renowned for its pristine beaches and family-friendly atmosphere, it offers an incredible outdoor experience for visitors. You can spend your days soaking up the sun on the soft, powdery sands or exploring the local recreational areas. The shopping mall centre provides a great spot for retail therapy, while various resorts ensure a comfortable stay. Don't miss the charming local landmarks, including the beautiful family beach and vibrant town neighbourhood, perfect for leisurely strolls and quality time with loved ones.
  • Venice: Situated 11.3km from Osprey, Venice is another delightful coastal city that beckons tourists with its inviting beaches and outdoor activities. This family-friendly destination offers numerous golf courses and recreational areas for those looking to enjoy some active fun. Venice is known for its unique charm, with the local beach and family beach providing picturesque spots for relaxation and play. Explore the quaint town neighbourhood, where you can find delightful eateries and shops, making it a perfect place for a leisurely day out.
  • Casey Key: Just 4.8km away from Osprey, Casey Key is a gorgeous island that offers a tranquil escape for beach lovers and outdoor enthusiasts alike. With its scenic beaches and family-friendly environment, it’s an ideal spot for families to unwind and enjoy nature. Visitors can explore local recreational areas and indulge in some shopping at the nearby shopping mall centre. The island's beautiful beaches and family beach are the main attractions, providing a perfect backdrop for creating lasting memories with your loved ones.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 a breeze

Are you keen to save on your upcoming holiday? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, feel free to use our filters to sort by price, location, and the type of holiday rental you’re after.

Vrbo Trips: Effortless planning

Vrbo's handy Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or sort through your travel arrangements. You can easily access properties you've previously saved or booked, which are now neatly categorized under Potential, Upcoming, or Current Trips. To make the most of Trip Boards, simply 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)
  • Stoneybrook Golf & Country Club (1.9 mi / 3 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)
  • Lido Beach (9.3 mi / 15 km)
  • Turtle Beach (2.7 mi / 4.4 km)
  • Point of Rocks (4.4 mi / 7.1 km)
  • Crescent Beach (4.8 mi / 7.7 km)
  • Nokomis Beach (5.1 mi / 8.2 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.

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