Osprey Vacation Rentals, Florida: house rentals & more

Discover a selection of 27 homes, 10 apartments, and other vacation rentals in Osprey that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation rentals have the best amenities for hanging out with the people that matter most, which might include hot tub and a washer and dryer. You'll be sure to find a rental to meet everyone's needs, including places that are non-smoking or accessible.

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Condo/Apartment

Find properties near top attractions in Osprey

Great national park to take your RV and lots of hiking and biking trails.

Oscar Scherer State Park

Find the best place to stay - Osprey

Huge Pool, Close to Beaches, Restaurants, Shopping & More!

Sleeps 8 · 3 bedrooms · 2 bathrooms

Top rated rentals - Osprey

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Find out more about Osprey

Why visit Osprey

Beautiful Beaches: Enjoy the pristine shores perfect for sunbathing and relaxation.
Outdoor Activities: Engage in fishing, hiking, and exploring local parks and marinas.
Charming Communities: Discover nearby towns with friendly atmospheres and rich histories.
Vacation Rentals: Choose from a variety of accommodations, including cozy condos and beach apartments.
Natural Wonders: Explore the breathtaking Florida Keys and unique wildlife in the area.

Popular types of accommodation in Osprey

Planning a getaway to Osprey? You're in for a treat! Discover the best vacation rentals, from cozy condos and houses to stylish beach apartments. Whether you're searching for a friendly private pool rental or an oceanfront escape, Osprey has it all. Enjoy transparency, savings, and reassurance as you find the perfect place to unwind and create lasting memories with your loved ones.

Condos: These are the top choice for vacation rentals in Osprey, offering modern amenities and easy access to local attractions.
Houses: Ideal for families or groups, these homes provide comfort and privacy for a more personalized experience.
Apartments: A convenient option for solo travelers or couples, apartments combine affordability with essential conveniences.
Cottages: Quaint and charming, cottages offer a cozy atmosphere perfect for a peaceful getaway.
Villas: Luxurious and spacious, villas are ideal for those seeking an upscale vacation experience in Osprey.**

Top attractions in Osprey

Osprey, Florida, is a fantastic destination for beach lovers and outdoor enthusiasts alike. With its beautiful beaches, urban parks, and marinas, there's something for everyone in the family. Visitors can enjoy a variety of activities, including fishing at the local pier, making it a perfect spot for memorable vacations. Whether you're traveling solo, with friends, or as a family, Osprey offers a delightful blend of relaxation and adventure.

Siesta Key Beach: Renowned for its powdery white sand and crystal-clear waters, Siesta Key Beach offers a perfect blend of relaxation and recreation. Enjoy sunbathing, swimming, and beach activities while soaking up the vibrant beach vibes just 6 miles from Osprey.
St. Armands Circle: A sophisticated shopping and dining district, St. Armands Circle boasts charming boutiques and restaurants. Experience the lively city atmosphere 10 miles away, where you can indulge in unique shopping and gourmet dining.
Point of Rocks: A natural wonder located 4 miles from Osprey, Point of Rocks features stunning coastal scenery and excellent snorkeling opportunities. Connect with nature and enjoy outdoor adventures in this picturesque setting.

Things to do recommended for couples

Osprey offers a perfect romantic getaway for couples. Enjoy luxury vibes at The Oaks Club, immerse yourselves in captivating performances at Beatrice Friedman Symphony Center, or have fun together at Fish Hole Miniature Golf in Lakewood Ranch. Create unforgettable memories in this charming locale!

Things to do recommended for families

Your family can enjoy a day at Ed Smith Stadium for an exciting sports experience, unwind at Nathan Benderson Park with its serene atmosphere, or explore the Robert L. Taylor Community Complex, perfect for relaxation and recreation, all conveniently located within a short drive from Osprey.

Things to do recommended for groups

Experience a round of golf at Stoneybrook Golf & Country Club, just 2 miles from Osprey. For shopping and family fun, visit the Mall at University Town Center, 13 miles away. Enjoy a night of culture and entertainment at the Van Wezel Performing Arts Hall, located 11 miles from Osprey.

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

If you're planning a trip with a group, traveling with family, bringing along your pets, or seeking an extended stay, it's important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

Traveling to Osprey with a group: Think about how many bedrooms you'll require, along with any amenities 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: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities like a private 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, a family vacation isn't truly fulfilling without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds to ensure that all family members feel comfortable and at home.
Planning for a long term stay visiting Osprey: If you’re in search of vacation rentals that offer discounts for month-long stays, 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 amenities such as a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay in Osprey

Osprey, Florida, offers a delightful blend of beachside relaxation and outdoor adventures perfect for family vacations. Explore the charming nearby communities and soak in the friendly atmosphere while enjoying historical sites and vibrant art scenes. Discover the natural beauty of the nearby Florida Keys and Sanibel's wildlife, or venture into South Carolina for a taste of its rich heritage. Whether you're seeking relaxation or excitement, Osprey has something for everyone.

Sarasota: Located approximately 10 miles from Osprey, Sarasota is a vibrant city known for its stunning beaches and rich cultural experiences. Visitors flock to Sarasota for a family-friendly atmosphere, with plenty of outdoor activities to enjoy. The city boasts a variety of shopping options, including a bustling mall center and unique boutiques. Notable attractions include the beautiful beaches, family-friendly parks, and the renowned Ringling Museum of Art, making it a perfect spot for art lovers and beachgoers alike.
Siesta Key: Just 7 miles away from Osprey, Siesta Key is a picturesque barrier island celebrated for its soft white sand beaches and crystal-clear waters. This destination is ideal for families looking for outdoor fun and relaxation. Visitors can enjoy a wide range of recreational activities, from swimming and sunbathing to shopping at local mall centers and indulging in resort amenities. The island's public beaches, particularly Siesta Beach, are often ranked among the best in the nation, offering stunning sunsets and vibrant beach activities.
Venice: Also located 7 miles from Osprey, Venice is a charming city known for its beautiful beaches and outdoor recreation. This family-oriented destination offers a variety of activities, including golf at scenic courses and leisurely walks through picturesque parks. Venice's quaint downtown area features unique shops and restaurants, making it a great place to explore. The city's beautiful beaches, combined with its relaxed atmosphere, make it a perfect spot for families and outdoor enthusiasts alike.

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 Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	62.6°F (17.0°C)	Light Rain	Mostly Sunny	Average	Average
February	65.1°F (18.4°C)	No Rain (Dry)	Mostly Sunny	Average	Slightly High
March	68.0°F (20.0°C)	No Rain (Dry)	Sunny	Slightly High	Slightly High
April	73.4°F (23.0°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
May	77.7°F (25.4°C)	Light Rain	Mostly Sunny	Average	Average
June	81.7°F (27.6°C)	Light Rain	Mostly Sunny	Average	Average
July	82.9°F (28.3°C)	Light Rain	Mostly Sunny	Average	Average
August	83.3°F (28.5°C)	Light Rain	Mostly Sunny	Average	Average
September	81.5°F (27.5°C)	Light Rain	Mostly Sunny	Slightly High	Slightly Low
October	77.2°F (25.1°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
November	70.7°F (21.5°C)	No Rain (Dry)	Mostly Sunny	Slightly Low	Slightly Low
December	66.6°F (19.2°C)	No Rain (Dry)	Mostly Sunny	Slightly Low	Average

Booking with Vrbo is simple

Are you eager to save on your upcoming journey? Being flexible with your travel dates can make a difference since prices often fluctuate. Additionally, booking a longer stay can lead to considerable savings. To discover a Vrbo property that suits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your booking. Being the planner has its rewards! When you join our travel rewards program, One Key, you gain immediate access to member discounts and the ability to earn and redeem OneKeyCash™ on eligible reservations. Sign up now and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your trips, pick up right where you left off, and manage your travel arrangements. You can easily access properties you’ve saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

The historic city of Osprey awaits you

The area's history and live music are just a few of the reasons to vacation in 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-sees in the area. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Osprey

Are you searching for attractions to visit while you're in the area? Venture out of your cozy vacation rental and check out everything that makes Osprey a one-of-a-kind vacation spot. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

Mote Marine Laboratory & Aquarium (10.9 mi / 17.5 km)
Sarasota National Golf Course (13.7 mi / 22 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 exciting outdoor activities or just want to spend some time taking in the scenery, Osprey is a great spot to appreciate mother nature. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

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 vacation, August, July, September and June are the hottest months to visit, when temperatures average 82°F.

Transportation options to and around Osprey

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

Frequently asked questions

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

Osprey Village is one of the more desired locations to book a vacation property in Osprey. Spend your break here to delight in the relaxation and comfort that comes with having the entire place to yourself.

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

The most sought-after types of vacation rentals in Osprey are condos. Searching for something different? Vrbo has numerous options to match the unique needs of our guests, so you’ll see vacation homes in all shapes and sizes. The ideal fit is waiting for you — find yours today.

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

Property type, season and length of stay are some of the things that can affect the price of a vacation home. Simply click on your travel dates to find your perfect escape. From cozy country cottages to sprawling luxury villas, all Vrbo vacation rentals offer incredible value.

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

When you travel and the style and size of the property will determine the cost of your beachside stay. Enter your Osprey travel dates to view your options on Vrbo. Did someone just say “hot tub”? Use our filters to choose the features and amenities you need.

Are there pet-friendly vacation rentals in Osprey?

Yes. You’ll have your pick of 40 vacation rentals that cater to pets in Osprey. Many of our pet-friendly vacation rentals come with a backyard for your four-legged friend to play in, special dog beds, complimentary treats and proximity to parks. Apply the “Pets allowed” filter to find your pawfect place on Vrbo.

Can I rent a house with a pool in Osprey?

Grab your swimwear and inflatable lounger, because there are 26 houses with a private pool in Osprey. Book one of these popular vacation rentals and enjoy a pool day every day. Simply enter your dates into Vrbo, then check the “pool” filter to find the perfect place for a splashing good time!

What are popular rental amenities in Osprey?

The most popular rental amenities people search for in Osprey are a nearby river, a sauna and a lake view. Whether you’re traveling with your besties, family or even pets, Vrbo vacation rentals have the best amenities for making new memories with the people you cherish the most.

Are there large group vacation rentals in Osprey?

Yes, you can pick from one of 24 vacation homes in Osprey that can accommodate five or more people. From family getaways to special occasions like birthday parties, these stays have ample space to chill out with the people that matter the most.

Are there vacation rentals in Osprey that welcome kids?

Osprey has 40 family-friendly vacation rentals to choose from. And discovering a stay that welcomes youngsters is super easy with Vrbo’s “Properties good for families” filter. On top of having the entire place to yourselves, you can also look forward to perks and conveniences such as bunk beds, pools and kitchens.

What are the top attractions for families in Osprey?

You’ll find lots of exciting things to see and do with the family in Osprey, such as:

Oscar Scherer State Park
The Oaks Club
Historic Spanish Point

Are there one-bedroom vacation rentals in Osprey?

Yes, Osprey has seven one-bedroom rentals available. Often positioned in popular areas due to their compact size, a one-bedroom vacation property is ideal if you’re traveling with a buddy or your partner. And with comforts like wireless internet and more privacy than a standard hotel, you’ll be able to kick back while discovering this top destination.

Can I find two-bedroom vacation rentals in Osprey?

Take off with your besties and relax in total privacy and comfort in one of the 15 two-bedroom vacation properties Osprey has to offer.

Are there vacation rentals with WiFi in Osprey?

Whether you’d like to keep up with world events, look over emails or update your social media, there are 22 vacation homes with WiFi in Osprey. Check the “WiFi” box when searching on Vrbo and stay connected on your getaway.

How can I find vacation rentals with air conditioning in Osprey?

You can pick from 40 Vrbo vacation rentals with air conditioning in Osprey providing that gentle, cool breeze and extra touch of comfort. Simply enter your travel dates and then take advantage of our filters to find stays with air conditioning.

How old do you have to be to rent a vacation rental in Osprey?

We recommend you check with the Osprey vacation rental you want on Vrbo as age restrictions differ. However, normally it’s 16, 18 or 21.

How long can I rent a vacation rental in Osprey for?

The length of time you can book a vacation rental in Osprey is up to the property. Just enter your selected travel dates to display a list of options offering extended stays. With loads of features such as washing machines and kitchens, as well as some offering discounted weekly or monthly prices, you’re sure to get somewhere just right to call your home away from home in Osprey.

Does Vrbo offer discounts for vacation homes in Osprey?

On Vrbo, you’ll find incredible deals and discounts for Osprey. Take a look at our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you’re after a short getaway or a much longer stay, Vrbo offers options for every budget and style.