Osprey Village vacation rentals

We found 5,989 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Osprey Village that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, vacation homes have the amenities you expect for your stay, which might include air conditioning and a pool. You'll be sure to find a rental that has what everyone needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Osprey Village

Showing deals for:Jul 3 - Jul 10

Image gallery for Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key

Pool
10 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)

Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key

Siesta Key

9% off
Price is $1,847
$12,927 for 7 nights
All fees included
Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Osprey Village

Why visit Osprey Village

  • Beautiful Beaches: Osprey Village boasts stunning beaches perfect for sunbathing and water activities.
  • Outdoor Activities: Enjoy a range of adventures, from hiking in urban parks to exploring scenic jetties.
  • Family-Friendly Environment: The village offers a lively atmosphere ideal for creating memorable family experiences.
  • Charming Accommodations: Choose from cozy vacation homes, condos, and apartments tailored to every traveler's needs.
  • Proximity to Culture: A short drive to vibrant cities like New Orleans enhances your travel experience.

Popular types of accommodation in Osprey Village

Osprey Village offers a variety of vacation rentals to suit every traveler's needs, including spacious houses, cozy condos, and comfortable apartments. Whether you're seeking a relaxing retreat in a charming driftwood cottage or a senior-friendly apartment, you'll find affordable options with inviting lounge areas. Discover the perfect home base for your adventure in Osprey Village, where comfort and convenience meet.

  • Houses: The top choice for visitors in Osprey Village, these homes offer a spacious and comfortable setting for families and groups seeking a home-away-from-home experience.
  • Condos: A popular option for travelers, condos provide modern amenities and a community feel, perfect for those looking for convenience.
  • Apartments: Ideal for solo travelers or couples, apartments offer a cozy and practical space to relax after a day of exploring.
  • Villas: Offering luxury and elegance, villas are perfect for those seeking a more upscale vacation experience.
  • Cottages: Charming and quaint, cottages provide a rustic retreat for those wanting a peaceful getaway.**

Top attractions near Osprey Village

Osprey Village, Florida, is perfect for beach and outdoor family vacations. Visitors can explore popular attractions such as beautiful beaches, urban parks, and scenic jetties. The area's points of interest cater to those seeking outdoor adventures and memorable family experiences, making it an ideal destination for travelers looking to enjoy the sun and nature.

  • Siesta Key Beach: Renowned for its powdery white sand and vibrant beach vibes, Siesta Key Beach offers a perfect spot for sunbathing, swimming, and enjoying stunning sunsets. With ample amenities and a lively atmosphere, it’s ideal for families and beach lovers alike.
  • Oscar Scherer State Park: A haven for adventure seekers, this state park features scenic trails for hiking and biking, diverse wildlife, and opportunities for kayaking. The lush landscapes and outdoor vibes make it a fantastic place to explore nature.
  • Point of Rocks: Known for its picturesque scenery, Point of Rocks offers a unique coastal experience with stunning views, excellent snorkeling, and a tranquil atmosphere. It’s a great spot for nature lovers and photographers.

Things to do recommended for couples

Osprey Village offers delightful experiences for couples. Indulge in the luxury of The Oaks Club just 0.4 miles away, or enjoy a fun mini-golf outing at Evie's Golf Center, located 7 miles away. For a unique twist, try your hand at shooting at Sarasota Trap Skeet and Clays, 6 miles away.

Things to do recommended for families

Families visiting Osprey Village can catch a game at Ed Smith Stadium, just 11 miles away, soaking in the lively sports atmosphere. For outdoor adventures, the Canopy Walkway and Boylston Nature Trail, located 12 miles away, offer a delightful tree-top experience amidst nature.

Things to do recommended for groups

Experience a round of golf at Stoneybrook Golf & Country Club, explore shopping and entertainment at Sarasota Square, or enjoy a show at Van Wezel Performing Arts Hall for a taste of culture and family fun, all within a short drive from Osprey Village.

*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 Village

If you're planning a trip with a group, traveling with family, bringing along your pets, or seeking extended stays, be sure to filter your options based on your top priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Osprey Village with a group: Take into account how many bedrooms you'll require, as well as features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Osprey Village with young kids: Traveling with little ones can be a bit tough. It’s important to prioritize their comfort and safety, along with amenities suited for their age, like a private swimming pool. Additionally, keeping in mind how close you are to family-friendly attractions can make a big difference in your trip.
  • Taking your pets with you to Osprey Village: For many, a family vacation isn’t truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Osprey Village: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the right filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a great kitchen, or a private pool in your search as well.

Where to stay in Osprey Village

Osprey Village is a charming destination perfect for family vacations, offering beautiful beaches and a lively atmosphere. Just a short drive away, you'll find the vibrant culture of nearby cities like New Orleans, where friendly locals and romantic settings await. Enjoy sunny weather while exploring outdoor activities that make this area ideal for relaxation and adventure. Whether lounging on the beach or discovering hidden gems, Osprey Village promises an unforgettable getaway.

  • Siesta Key: Siesta Key is a charming island city located 7 miles from Osprey Village, renowned for its stunning beaches and family-friendly atmosphere. Travelers flock to Siesta Key for a perfect outdoor experience, with soft white sands and crystal-clear waters inviting sunbathers and water sports enthusiasts alike. Popular activities include visiting the scenic Siesta Beach, exploring the local shopping mall, and enjoying luxurious resorts. Don't miss the chance to stroll through the vibrant town neighborhood, where you can find delightful dining and entertainment options.
  • Venice: Also situated 7 miles from Osprey Village, Venice is a delightful city known for its picturesque beaches and outdoor recreational activities. Families can enjoy a day at the beach or engage in various outdoor sports, including golf at one of the area’s many golf courses. Venice boasts a charming town neighborhood filled with quaint shops and restaurants, making it perfect for leisurely strolls. Local landmarks, including the beautiful beaches, provide excellent photo opportunities and a chance to unwind in a serene setting.
  • Osprey: Osprey is a welcoming city that encompasses Osprey Village, offering visitors a blend of beach fun and outdoor activities. Located close to the shoreline, Osprey is ideal for families seeking an engaging vacation experience. Explore the local recreational areas or challenge yourself at one of the many golf courses in the vicinity. With its family beach and inviting town neighborhood, Osprey provides a relaxed atmosphere while being conveniently close to the attractions of neighboring cities.

Best time to go to Osprey Village

If you're planning a trip to Osprey Village, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in February to March and July, while off-peak times, like September to November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January62.6°F (17.0°C)Light RainMostly SunnyAverageSlightly Low
February65.1°F (18.4°C)No Rain (Dry)Mostly SunnyModerately HighAverage
March68.0°F (20.0°C)No Rain (Dry)SunnyModerately HighSlightly High
April73.4°F (23.0°C)Light RainMostly SunnyAverageSlightly 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 SunnyModerately HighSlightly High
August83.3°F (28.5°C)Light RainMostly SunnyAverageAverage
September81.5°F (27.5°C)Light RainMostly SunnyModerately LowSlightly Low
October77.2°F (25.1°C)Light RainMostly SunnyModerately LowSlightly Low
November70.7°F (21.5°C)No Rain (Dry)Mostly SunnyModerately LowAverage
December66.6°F (19.2°C)No Rain (Dry)Mostly SunnyAverageAverage

Booking with Vrbo is simple

Are you aiming to save on your upcoming vacation? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits 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 best options for your trip.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform for planning your next adventures. You can easily start new trips, continue from where you last stopped, or review and organize your travel plans. Your saved or booked properties will be neatly sorted into categories like Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply head over to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Choose a vacation rental for your Osprey Village getaway

Learn about the unique charm of Osprey Village with a stay in a private vacation home. You'll find plenty to explore during your stay in the area. Siesta Key Beach and Lido Beach are just a couple of the must-sees in the area. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Osprey Village

Are you looking for attractions to see in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Osprey Village a one-of-a-kind vacation spot. These 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 / 17.6 km)
  • Sarasota Jungle Gardens (12.5 mi / 20.2 km)
  • Stoneybrook Golf & Country Club (1.8 mi / 3 km)
  • Gulf Gate Golf Club (4.3 mi / 6.9 km)
  • Pelican Pointe Golf and Country Club (9.4 mi / 15.2 km)
  • Jacaranda West Country Club (10.8 mi / 17.3 km)

Exploring the natural features in Osprey Village

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Osprey Village is a great place to spend some time outside. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Siesta Key Beach (6.3 mi / 10.2 km)
  • Lido Beach (9.5 mi / 15.2 km)
  • Jim Neville Marine Preserve (1.7 mi / 2.7 km)
  • Turtle Beach (2.8 mi / 4.6 km)
  • Point of Rocks (4.6 mi / 7.3 km)
  • Crescent Beach (4.9 mi / 7.8 km)

Transportation to and around Osprey Village

Fly into Sarasota-Bradenton Intl. Airport (SRQ), the closest airport, located 13.8 mi (22.3 km) from the city center.

Frequently asked questions

What is the best area to stay in Osprey Village, Florida, United States of America when booking a vacation rental?
When considering a vacation rental in Osprey Village, Florida, a popular area to stay is near the charming waterfront along the Intracoastal Waterway. This location not only offers stunning views but also provides easy access to outdoor activities like kayaking and fishing. The nearby Oscar Scherer State Park is a fantastic attraction, featuring beautiful trails and diverse wildlife, great for nature enthusiasts and families alike. Additionally, the vibrant shopping and dining options at the local plaza make it a delightful spot to explore.

In terms of vacation rental options, the area boasts a variety of properties, from cozy cottages to spacious family homes, accommodating different group sizes and preferences.
How much does it cost to rent a vacation home in Osprey Village?
Prices for vacation rentals in Osprey Village 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 Village 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 Village vacation house rentals?
You can find great discounts on house rentals in Osprey Village 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.
Can I find long-stay vacation rentals in Osprey Village?
A long-stay vacation rental in Osprey Village is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any Osprey Village vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Osprey Village with parking available—perfect for families or travelers 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.
How early should I book a Osprey Village vacation rental?
Book your Osprey Village vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Osprey Village, Florida, United States of America?
In Osprey Village, visitors can enjoy a range of attractions that highlight the area's natural beauty and cultural offerings. The nearby Oscar Scherer State Park is a popular destination, featuring hiking trails, picnicking areas, and opportunities for birdwatching, particularly for the endangered Florida Scrub-Jay. Vacation rentals in this area often provide easy access to the park's amenities.

Another highlight is the historic Spanish Point, a cultural site that showcases the region's history through various exhibits and beautiful gardens. The scenic views along the Intracoastal Waterway also attract visitors, offering opportunities for kayaking and fishing.

For beach lovers, Siesta Key is just a short drive away, renowned for its powdery white sand beaches and vibrant setting. Staying in Osprey Village provides a peaceful retreat while still being close to these attractions and the lively activities available on Siesta Key.
Can I change or cancel my Osprey Village home rental booking on Vrbo?
To find Osprey Village vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 Village vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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.

More Vacation Ideas