Osprey holiday lettings

We found 7,821 holiday rentals — enter your dates for availability
Discover a selection of 13 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:29 Jan - 5 Feb

Image gallery for Rare private beachfront estate on the Gulf.

Pool
10 out of 10, Exceptional, (28 reviews)
Exceptional
(28 reviews)

Rare private beachfront estate on the Gulf.

Nokomis

8% off
Price is £21,643
for 7 nights, 1 home
£3,092 per night
includes taxes & fees
Rare private beachfront estate on the Gulf.

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Why visit Osprey

  • Scenic Waterfront: Osprey boasts beautiful waterfront views, perfect for leisurely strolls and relaxation.
  • Outdoor Adventures: The town is ideal for outdoor activities, including beach outings and exploring local parks.
  • Stoneybrook Golf Club: Enjoy a round of golf at this renowned course, set amidst picturesque landscapes.
  • Family-Friendly Atmosphere: Osprey offers a welcoming environment, making it perfect for family vacations and memorable experiences.
  • Charming Accommodations: Choose from a variety of vacation rentals to ensure a comfortable stay during your visit.

Popular types of accommodation in Osprey

Discover the charm of Osprey, Florida, a delightful town brimming with natural beauty and local attractions. From scenic parks to vibrant waterways, this picturesque destination offers a range of experiences for every traveller. When it comes to accommodation, you’ll find a variety of options including houses, condos, and apartments, perfect for a relaxing getaway. Enjoy the comfort of home with Osprey rentals that cater to your needs and ensure a memorable stay.

  • Houses: The top choice for holidaymakers in Osprey, offering spacious accommodations with the comforts of home.
  • Condos: A popular option, these stylish units provide modern amenities and often stunning views.
  • Apartments: Ideal for couples or solo travellers, these self-contained spaces are conveniently located.
  • Villas: Luxurious and often set in picturesque surroundings, villas cater to those seeking an upscale experience.
  • Cottages: Quaint and charming, these delightful retreats offer a cosy atmosphere for a relaxing getaway.**

Top attractions in and around Osprey

Osprey, Florida, is a charming destination perfect for beach and outdoor family vacations. Visitors can enjoy picturesque beaches, explore urban parks, and stroll along the jetty pier. This vibrant area offers a variety of attractions tailored for those seeking outdoor adventures and family-friendly experiences, ensuring that every traveller can create lasting memories in this delightful coastal town.

  • Siesta Key Beach: Located a mere 10km from Osprey, this pristine beach is renowned for its powdery white sands and vibrant beach vibes, perfect for sunbathing and water sports.
  • Historic Spanish Point: Situated within Osprey, this archaeological site offers a fascinating glimpse into the region's rich history and culture, featuring beautiful gardens and ancient artifacts.
  • Point of Rocks: Just 6km away, this unique rock formation provides stunning outdoor scenery, ideal for photography and exploring marine life during low tide.

Things to do recommended for couples

Osprey offers a charming escape for couples. Enjoy a romantic sunset at Nokomis Beach or take a leisurely kayak tour through serene waters. Don't miss a delightful dinner at a waterfront restaurant, where you can savour fresh seafood while watching the sun dip below the horizon.

Things to do recommended for families

Families visiting Osprey can explore the beautiful Oscar Scherer State Park, perfect for hiking and spotting wildlife, or enjoy a fun-filled day at Sharky's on the Pier, where kids can play on the beach and savour delicious seafood.

Things to do recommended for groups

Experience the thrill of the TreeUmph. Adventure Course, an exciting zipline and ropes course located 29km from Osprey. Perfect for groups seeking adventure and outdoor fun, it offers a unique way to bond while enjoying Florida's beautiful scenery.

*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, pets, or planning an extended stay, it’s important to refine your search according to your specific needs. Here are some helpful booking tips for Vrbo.

  • Traveling to Osprey with a group: Think about how many bedrooms you'll require, as well as amenities like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Osprey with young kids: Travelling with young children can be demanding. It's important to prioritise their comfort and safety, along with suitable amenities, such as 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 isn’t truly finished without their furry companions. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels completely at home.
  • Planning for a long term stay visiting Osprey: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay near Osprey

Osprey, Florida, is a delightful destination perfect for beach and outdoor family vacations. Visitors can immerse themselves in its historical charm while enjoying the friendly atmosphere. Explore the scenic waterfront, relax in the sunny weather, or indulge in a round of golf at the renowned Stoneybrook Golf Club. With its inviting vibe and opportunities for romantic strolls, Osprey offers a unique blend of relaxation and adventure for every traveller.

  • Siesta Key: Siesta Key is a stunning island city located 11km from Osprey, renowned for its powdery white sandy beaches and vibrant outdoor activities. This tropical paradise is perfect for families seeking a fun-filled experience, with numerous recreational areas and resorts to choose from. Visitors can enjoy beach volleyball, water sports, and sunbathing on the picturesque shoreline. Siesta Key is also home to charming shops and eateries, making it a delightful spot to explore. The local landmark, the Siesta Key Beach, is consistently ranked among the best beaches in the USA, offering a perfect blend of relaxation and adventure.
  • Venice: Located 11km from Osprey, Venice is a quaint city known for its lovely beaches and family-friendly atmosphere. This charming coastal town offers visitors a variety of outdoor activities, including golf at its scenic courses and relaxing afternoons at the beach. Venice's downtown area is filled with delightful shops and restaurants, creating a vibrant community spirit. The local landmarks, such as the Venice Beach and the picturesque town neighbourhood, provide a perfect backdrop for family outings and leisurely strolls. Venice is an ideal destination for those seeking a blend of excitement and tranquillity.
  • Vamo: Just 3km from Osprey, Vamo is a serene neighbourhood that offers a peaceful retreat for families and outdoor enthusiasts. With easy access to beautiful beaches and recreational areas, visitors can indulge in activities such as golf and leisurely walks along the shore. The local atmosphere is relaxed, making it a great place to unwind and connect with nature. Vamo is an excellent choice for those looking to enjoy the charm of Florida's coast while still being close to the vibrant attractions of nearby cities.

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. Peak season runs in March to April and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

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

Booking with Vrbo is simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay often results in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers an easy-to-use platform for planning your journeys. You can start new trips, resume from where you last left off, or manage your existing plans all in one place. You'll find your saved or booked properties neatly organised under Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-gb/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:

  • Pelican Pointe Golf and Country Club (9.6 mi / 15.4 km)
  • Mote Marine Laboratory & Aquarium (10.9 mi / 17.5 km)
  • Sarasota Jungle Gardens (12.5 mi / 20.1 km)
  • University Park Country Club (14.5 mi / 23.3 km)
  • Stoneybrook Golf & Country Club (1.9 mi / 3 km)
  • Jacaranda West Country Club (10.9 mi / 17.5 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 rental?
When considering a holiday rental in Osprey, Florida, a popular area to stay is near the charming coastal community of Casey Key. This picturesque neighbourhood offers a serene atmosphere and stunning waterfront views, making it an ideal spot for those looking to unwind. Visitors can enjoy the natural beauty of the nearby beaches, such as Nokomis Beach, which is superb for sunbathing or taking a leisurely stroll along the shore.

In addition to the beaches, the area is close to the Oscar Scherer State Park, where you can explore scenic trails and observe local wildlife, adding a touch of adventure to your stay. Osprey has a variety of properties available, from quaint cottages to luxurious waterfront homes, ensuring that you can find accommodation that suits your needs and preferences.
How much does it cost to rent a holiday home in Osprey?
Prices for holiday rentals in Osprey vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Osprey to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Osprey holiday house rentals?
You can find great discounts on house rentals in Osprey on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Osprey?
For renting a beach house in Osprey, Florida, the area around Casey Key is particularly desirable. This charming barrier island is known for its stunning sandy beaches and a laid-back atmosphere. Properties here often feature direct beach access, spacious decks for outdoor dining, and amenities such as private pools and hot tubs, great for relaxing after a day in the sun. Many of these beach houses also come equipped with modern kitchens and laundry facilities, suiting families or groups looking for a comfortable stay.

The nearby Siesta Key, renowned for its powdery white sand beaches, is also a fantastic option. Here, visitors can find a variety of rentals, from beachfront condos to larger family homes, often boasting amenities like beach gear, outdoor showers, and community pools. The vibrant local area offers plenty of dining and shopping choices, making it easy for travellers to enjoy the local culture.

Additionally, the proximity to the scenic Myakka River State Park provides opportunities for outdoor activities such as kayaking and hiking, enhancing the appeal of the Osprey area for nature lovers.
What is the most popular type of holiday rental accomodation in Osprey?
In Osprey, holiday houses are the most popular type of holiday rental, with around 116 available in the area. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and private outdoor areas, making them ideal for families or groups looking to enjoy the sunny Florida weather. Many of these houses are located near attractions such as the historic Spanish Point and the beautiful beaches along the Gulf Coast.

In addition to holiday houses, there are approximately 52 condos and 36 apartments available, offering a more compact living option with amenities like community pools, fitness centres, and easy access to local dining and shopping. For those seeking a quaint escape, several cottages and villas provide a charming and intimate atmosphere, often set in picturesque surroundings.
Are there any family house rentals in Osprey?
In Osprey, Florida, there are numerous family-friendly house rentals available, with around 25 options to choose from. This charming area is known for its proximity to beautiful beaches and vibrant outdoor activities, making it an ideal spot for families. Many of these properties feature spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces great for children to play.

Visitors can enjoy amenities such as private pools, game rooms, and access to nearby parks. The locale is conveniently situated near attractions like the Oscar Scherer State Park, which offers hiking trails and wildlife viewing, as well as the stunning Gulf Coast beaches, great for a day of sun and sand.
Can I rent a holiday home with a pool or hot tub in Osprey?
In Osprey, there are plenty of holiday homes available for rent that come equipped with pools and hot tubs, with around 32 options to choose from. This charming area, located near the beautiful Gulf Coast of Florida, offers a range of neighbourhoods where travellers can find these properties, including the serene Bay Preserve and the picturesque Osprey Harbour.

Guests can expect a variety of amenities in these rentals, such as private pools, relaxing hot tubs, spacious outdoor areas for lounging, and fully equipped kitchens great for preparing meals after a day of exploring. Many properties also feature additional comforts like barbecue grills and outdoor dining spaces, allowing for enjoyable evenings under the stars.
Can I find long-stay holiday rentals in Osprey?
A long-stay holiday rental in Osprey is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Osprey?
In Osprey, Florida, there are several pet-friendly house rentals available, with a good selection to choose from. Many of these properties are equipped with amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups travelling with pets.

The area offers easy access to beautiful parks and beaches, including nearby Oscar Scherer State Park, which is known for its scenic trails and opportunities for outdoor activities, great for walks with your furry companions. Additionally, the charming waterfront neighbourhood provides a relaxing atmosphere, and many rentals are conveniently located near local shops and dining options, adding to the convenience for travellers.
Are there any remote work holiday rentals in Osprey?
In Osprey, Florida, there are numerous holiday rentals suitable for remote work, with around 168 options available. This charming area, located near the stunning Gulf Coast, offers properties that cater to the needs of remote workers. Many rentals come equipped with high-speed internet and Wi-Fi, ensuring that guests can stay connected while enjoying the serenity of their surroundings.

Travellers can expect amenities such as spacious workspaces, comfortable seating areas, and fully equipped kitchens, allowing for both productivity and relaxation. The proximity to beautiful beaches and parks, like the nearby Oscar Scherer State Park, provides excellent opportunities for outdoor activities during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Osprey holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Osprey with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Osprey?
In Osprey, popular holiday rental amenities include fully-equipped kitchens, allowing guests to prepare their own meals with ease. Onsite parking is also a common feature, providing convenience for those travelling by car. Many properties offer decks or patios, great for enjoying the warm Florida weather and outdoor relaxation. Additionally, coffee and tea makers are typically provided for guests who enjoy their morning brew. Notably, some rentals permit pets, making it easier for travellers to bring their furry friends along for the stay.
When is the best time to visit Osprey for a holiday rental?
The best time to visit Osprey for a holiday rental is during the peak season from February to April, with March being particularly popular. This period attracts sun seekers and outdoor enthusiasts, keen to enjoy the stunning beaches and nature parks that Osprey has to offer. With pleasant temperatures averaging between 15 to 25 degrees Celsius, visitors can comfortably engage in a variety of activities like kayaking, fishing, and exploring the scenic Myakka River State Park.

During these months, the area bustles with activity, providing ample opportunities for sightseeing and relaxation. The pleasant climate encourages leisurely strolls along the picturesque Gulf Coast beaches, where you can soak up the sun or enjoy a refreshing swim in the ocean.

If you're looking for a more budget-friendly option, consider visiting in October. This month offers a quieter atmosphere and is superb for enjoying the beauty of Osprey without the crowds. The weather is still warm, making it an excellent time for outdoor adventures and peaceful beach days.

Ultimately, your choice of when to visit Osprey will depend on whether you prefer the vibrant energy of peak season or the tranquil charm of the shoulder months.
How early should I book a Osprey holiday rental?
Book your Osprey holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Osprey?
In Osprey, visitors can enjoy a range of attractions that highlight both natural beauty and cultural experiences. The serene Oscar Scherer State Park is a prominent feature, offering hiking trails, wildlife viewing, and access to the lovely South Creek, ideal for canoeing and kayaking. This park is a great spot for nature enthusiasts and those looking to explore Florida's natural habitats.

Another top attraction is the historic Spanish Point, an archaeological site that provides insight into the area's history and early Native American cultures. Visitors can wander through beautiful gardens, see historical buildings, and learn about the region's past.

For beach lovers, Siesta Key is just a short drive away, famed for its powdery white sands and vibrant beach atmosphere, making it great for sunbathing and water activities. The nearby Legacy Trail is great for cycling and walking, connecting Osprey to Sarasota and providing scenic views along the way.
Can I change or cancel my Osprey home rental booking on Vrbo?
To find Osprey holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Osprey holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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