Vacation rentals near The Oaks Club

We found 6,042 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals within easy reach of The Oaks Club that provide the perfect home base for your trip. Whether you're traveling with your kids or with friends, vacation homes have the best amenities for hanging out with the people that matter most, which might include a garden and pool. You'll be sure to find a rental for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - The Oaks Club

Showing deals for:Aug 21 - Aug 28

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

Pool
10 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)

Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key

Siesta Key

9% off
Price is $1,858
$13,009 for 7 nights
All fees included
Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key

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Find out more about The Oaks Club

Why visit The Oaks Club

  1. Beautiful Beaches: Enjoy stunning sandy shores perfect for sunbathing and water activities.
  2. Lush Urban Parks: Explore scenic parks ideal for picnics, hiking, and family outings.
  3. Charming Neighborhoods: Discover friendly communities with a relaxed vibe and family-friendly atmospheres.
  4. Diverse Accommodations: Choose from private homes, cozy condos, or stylish apartments to suit your stay.
  5. Engaging Local Culture: Connect with friendly locals and immerse yourself in the regional lifestyle.

Popular types of accommodation around The Oaks Club

Planning your getaway to The Oaks Club? Exciting times await as you choose your perfect accommodation! Discover the charm of houses, cozy condos, and stylish apartments within the Osprey Oaks Apartment Community. With a variety of available apartments for rent, you’re sure to find the ideal spot for your stay. Enjoy transparency, savings, and reassurance while making unforgettable memories in this beautiful destination!

  • Houses: These spacious homes are the top choice for visitors to The Oaks Club, perfect for families or groups seeking comfort and privacy.
  • Condos: A popular option, condos offer a blend of convenience and amenities, ideal for couples or small families.
  • Apartments: Affordable and versatile, apartments provide a home-like atmosphere for those looking to explore the area.
  • Villas: Luxurious villas offer upscale accommodations, perfect for a lavish getaway.
  • Cottages: Charming and quaint, cottages provide a cozy retreat for a peaceful vacation experience.**

Top attractions near The Oaks Club

At The Oaks Club in Osprey, Florida, you'll find a variety of attractions perfect for outdoor enthusiasts and families. Explore beautiful beaches, enjoy the lush urban parks, or take a stroll along the jetty and pier. Whether you're looking for relaxation or adventure, there's something for everyone to enjoy in this picturesque area.

  1. Siesta Key Beach: Renowned for its powdery white sand and vibrant beach vibes, Siesta Key Beach is the perfect spot for sunbathing, swimming, and beach sports, located 6 miles from The Oaks Club.
  2. Oscar Scherer State Park: Just 2 miles away, this state park offers adventure and stunning scenery, with trails for hiking, biking, and opportunities for wildlife spotting in a lush natural setting.
  3. Point of Rocks: A hidden gem located 4 miles from The Oaks Club, Point of Rocks features beautiful coastal scenery, ideal for snorkeling and exploring unique rock formations amidst the ocean waves.

Things to do recommended for couples

Looking for a romantic getaway near The Oaks Club? Experience luxury at Sarasota Trap Skeet and Clays, enjoy family fun at Evie's Golf Center, or indulge in an enchanting evening at the Beatrice Friedman Symphony Center. Each offers a unique vibe perfect for couples!

Things to do recommended for families

While staying at The Oaks Club in Osprey, Florida, families can catch a game at Ed Smith Stadium, just 10 miles away, or explore the Canopy Walkway and Boylston Nature Trail, located 12 miles away, for a delightful outdoor adventure amidst nature.

What do I need to keep in mind when booking a vacation around The Oaks Club

When planning your trip—be it with a group, family, pets, or for an extended stay—be sure to prioritize your preferences using the right filters. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to The Oaks Club with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to The Oaks Club with young kids: Traveling with little ones can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, thinking about how close you are to family-friendly attractions can be beneficial.
  • Taking your pets with you to The Oaks Club: For many families, a vacation isn’t truly fulfilling without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations offer amenities like feeding bowls and beds, ensuring that all members of your family feel comfortable and at home.
  • Planning for a long term stay visiting The Oaks Club: If you're in search of vacation rentals offering discounts 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 options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near The Oaks Club

Your vacation at The Oaks Club in Osprey, Florida, promises an enriching experience. Explore charming neighborhoods with family-friendly atmospheres and a relaxed vibe. Discover beautiful family homes and exclusive lifestyle communities, offering easy access to local attractions. Enjoy the sunny weather while indulging in romantic strolls or engaging with friendly locals. Whether you're seeking relaxation or adventure, the area surrounding The Oaks Club has something special for every traveler.

  • Siesta Key: Siesta Key is a picturesque island located approximately 7 miles from The Oaks Club, renowned for its stunning white sandy beaches and vibrant atmosphere. Travelers flock to Siesta Key for a quintessential beach experience, ideal for families and outdoor enthusiasts. The area offers a variety of recreational activities such as swimming, paddleboarding, and beach volleyball. In addition to its natural beauty, Siesta Key features charming shops, delightful restaurants, and resorts that cater to diverse tastes. Local landmarks include the famous Siesta Key Beach and the quaint village, making it a perfect spot for relaxation and exploration.
  • Venice: Venice, located about 7 miles from The Oaks Club, is a delightful city known for its beautiful beaches and outdoor recreational opportunities. This vibrant destination attracts families and nature lovers alike, offering activities such as golf, biking, and walking along scenic paths. Visitors can enjoy the remarkable Venice Beach and the family-friendly atmosphere of the local neighborhoods. The city is also home to several golf courses and recreational areas, providing ample opportunities for leisure and sport. With its charming downtown area filled with shops and eateries, Venice is a lovely place to spend a day.
  • Osprey Village: Just 0.4 miles from The Oaks Club, Osprey Village is a quaint community that offers a friendly atmosphere and easy access to nearby attractions. Known for its beautiful beaches and outdoor spaces, Osprey Village is perfect for families seeking relaxation and fun. The village features golf courses and private country clubs, making it ideal for golf enthusiasts. Visitors can enjoy the local urban parks and family-friendly beaches, providing a great mix of leisure and adventure. Osprey Village’s close proximity to The Oaks Club ensures convenience while exploring the area's highlights.

Best time to go to The Oaks Club

If you're planning a trip to The Oaks Club, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from February to April, while off-peak times, like September to November 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 SunnyModerately HighAverage
March68.0°F (20.0°C)No Rain (Dry)SunnyModerately HighSlightly High
April73.4°F (23.0°C)Light RainMostly SunnyModerately 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 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 a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash™ on the total booking amount. Being the planner truly has its rewards! When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash™ on qualifying reservations. Sign up today and begin enjoying your savings!

Vrbo Trips: Planning as easy as it gets

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

**Based on Vrbo properties bookings.

Frequently asked questions

What are the best vacation rentals near The Oaks Club?
The best vacation rentals near The Oaks Club are usually found in Osprey, Florida. You will find a great selection here, ranging from private vacation homes to condos. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties.

Many top-rated rentals feature amenities so you can have a comfortable stay, such as a pool, a deck or patio, and laundry facilities. These homes are ideal for family trips or group retreats where everyone needs a little extra room.
Are there any cheap vacation rentals near The Oaks Club?
There are several affordable vacation rentals near The Oaks Club, especially if you are flexible with location and travel dates. Budget-friendly stays are typically around $150 per night. Some stays even have good deals in September and August during the off-season, making it a great option for guests looking to experience the area without overspending. These rentals often include free amenities such as WiFi, toiletries, and self-parking, and can range from cozy private homes to modest condos, providing a clean, comfortable base for your stay.

To get the best value, consider staying slightly outside major hubs. If you're willing to drive a bit further, renting around nearby areas can be an affordable option. With a little planning, it is absolutely possible to find a comfortable stay near The Oaks Club while keeping costs down.
What are the top vacation rentals with pools near The Oaks Club?
There are over 360 vacation rentals near The Oaks Club that feature swimming pools. Guests can choose from a variety of options, including properties with private backyard pools, shared community pools, and even some with indoor pool facilities. These rentals are concentrated in the surrounding areas of Osprey and range from spacious private vacation homes to comfortable condos. Most properties come fully equipped with amenities like full kitchens, multiple bedrooms, Wi-Fi, and outdoor decks, making them superb for families or groups seeking a well-appointed home base.

When selecting your ideal rental, consider whether a private pool for exclusive use or a shared pool with potential access to additional facilities like hot tubs or fitness centers best suits your preferences. For cooler months, many properties offer heated pools, ensuring year-round enjoyment. Always confirm pool availability and heating options when making your reservation, especially for peak season dates.
What are the best family vacation rentals near The Oaks Club?
There are over 277 family-friendly vacation rentals near The Oaks Club, primarily private homes and condos. These properties often boast multiple bedrooms and bathrooms, full kitchens for meal preparation, and outdoor play areas like yards or gardens. Many also include amenities such as washers/dryers, and entertainment options like WiFi and video games, ensuring a comfortable stay for all guests.

When selecting a vacation rental, consider properties that offer separate spaces for adults and children, allowing everyone to relax. Look for practical amenities like a well-equipped kitchen to make family meals easier and a washer/dryer for convenience.
Are there any luxury vacation rentals near The Oaks Club?
Near The Oaks Club, guests can find several luxury vacation rentals that combine natural surroundings with modern comfort. These properties often feature amenities such as private heated pools, private secured pools, onsite golf, private beach access, and lake views. Many homes also boast gourmet kitchens, premium bedding, and air conditioning for a comfortable stay.

These homes are ideal for families or larger groups, offering spaces for relaxation and entertainment. Many of these top-tier stays are managed by highly rated Vrbo hosts, ensuring a professional and premium experience.
How much is a vacation rental near The Oaks Club?
Vacation rentals near The Oaks Club offer a wide range of options to suit different budgets, making it easy for guests to enjoy a memorable stay. Budget-friendly properties typically start around $150 per night, providing an affordable option. Mid-range rentals, including private homes, are generally around $280 per night, offering more comfort and privacy. Upscale options can cost $355 or more per night, especially for properties with premium amenities like a pool or deck/patio.

Enter your destination, travel dates, and number of guests on search to see the best options. You can use filters to set a minimum and maximum nightly price range along with other preferences. Rates may vary based on the season and specific amenities, but with a little planning, guests can find a rental that perfectly balances convenience and value.
Where should I stay when visiting The Oaks Club?
When visiting The Oaks Club, several excellent areas offer convenient vacation rental properties.

The immediate Osprey area provides properties that are just a short drive from The Oaks Club, offering easy access to the club's amenities and local attractions. This area is known for its peaceful residential feel and proximity to the coast.

Another wonderful option is staying in the nearby city of Venice. Properties here offer access to beautiful beaches, a charming downtown area with shops and dining, and are a short drive from The Oaks Club. Venice provides a relaxed, coastal experience.

For those desiring a slightly more active environment with a wider array of dining and entertainment options, Sarasota is an excellent choice. Vacation rentals in Sarasota are a convenient drive from The Oaks Club and offer access to cultural attractions, shopping, and stunning beaches.
What is the cheapest month to stay near The Oaks Club?
The cheapest time to find vacation rentals near The Oaks Club is typically during the late Summer to early Autumn (August to September). August and September are frequently the cheapest months, often providing the best deals on properties with rates often 15-25% lower compared to the peak season. Guests can often find various savings during these months, along with greater availability.
Are there any lakefront vacation rentals near The Oaks Club
Lakefront vacation rentals near The Oaks Club are available, primarily located on lakes such as the Intracoastal Waterway or various nearby freshwater lakes. These properties are a short drive from The Oaks Club, offering convenient access to water activities such as kayaking, fishing, swimming, or simply relaxing by the shore.

These homes often feature spacious decks, fire pits, hot tubs, and full kitchens, making them ideal for families and larger groups. Guests can enjoy the water views and the peaceful surroundings.
Are there any top beachfront vacation rentals near The Oaks Club
Beachfront vacation rentals near The Oaks Club offer direct access to the sand, with many properties boasting ocean-view balconies or being just steps from the water. Guests can find properties along the coast in Osprey, providing easy access to lively dining, nightlife, and shopping areas, while other nearby locations offer quieter spots for relaxation.

Accommodation options range from private vacation homes to condos, with many properties offering amenities such as beach chairs, umbrellas, and oceanfront pools. Guests can choose from ocean-facing rooms, suites, or multi-bedroom units with private terraces or extra living space, suitable for various group sizes.
Are there any monthly vacation rentals near The Oaks Club?
Vrbo offers excellent options for monthly vacation rentals near The Oaks Club, making it a great choice for those who want to combine work and adventure. Monthly rentals often feel like a true home away from home, with fully furnished properties equipped with essential amenities like high-speed Wi-Fi, full kitchens, and comfortable workspaces, perfect for remote work or a summer vacation with the family. With flexible monthly rental options, Vrbo is a convenient and comfortable choice for extended stays near The Oaks Club.
Are there any last-minute vacation rentals near The Oaks Club?
Vrbo makes it simple to find last-minute vacation rentals near The Oaks Club that blend comfort, style, and great value. Vrbo offers plenty of options for guests ready to pack up and go. Families and groups will find these deals especially appealing. Many spacious homes, complete with full kitchens, private pools, and multiple bedrooms, often become available when hosts want to fill open dates on their calendars.

Finding these stays is easy. Just enter your destination and travel dates, then use Vrbo's "Last Minute" or "Discounts" filter to uncover the best offers. You'll see reduced rates in the listings. Vrbo's last-minute rentals are a smart way to save while you explore. Whether you're planning a quick trip or a weekend getaway with friends, your last-minute escape is waiting, you just have to decide where to go next.
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.

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