Oakland Hills vacation rentals

We found 167 vacation rentals — enter your dates for availability

Welcome to the enchanting Oakland Hills, where stunning beaches meet vibrant outdoor adventures. Bask in the sun at Englewood Beach's soft sands or explore the lush trails of nearby state parks, perfect for family outings and nature lovers alike. With charming accommodations ranging from cozy condos to luxurious villas, groups can unwind and reconnect in comfort. Embrace the local culture and create unforgettable memories, all while enjoying the spaciousness and amenities of a true home away from home.

Holiday rentals with weekly discounts - Oakland Hills

Showing deals for:Dec 11 - Dec 18

Dining
Private kitchen
Interior
Living area
Exceptional
(6 reviews)

Spacious waterfront 6 Bd duplex in lovely Rotonda West near oceans .

Rotonda West

8% off
$442
$3,092 for 7 nights
All fees included
Spacious waterfront 6 Bd duplex in lovely Rotonda West near oceans .
Interior
Interior
Exterior
Private kitchen
Exceptional
(28 reviews)

Modern Retreat, 3Bedroom King bed + Master Bath near ocean, 6 guests

Rotonda West

8% off
$203
$1,419 for 7 nights
All fees included
Modern Retreat, 3Bedroom King bed + Master Bath near ocean, 6 guests
Room
Private kitchen
Private kitchen
Interior
Exceptional
(14 reviews)

Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing

Rotonda West

8% off
$193
$1,352 for 7 nights
All fees included
Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing
Entry area with large open living-dining and kitchen area.
Pool
Living area with a large Sofa
Dinning table with 8 sits overlooking the kitchen island and kitchen area
Exceptional
(12 reviews)

Ultimate Privacy: 3BR/2BA Heated Pool, Screened, Green Belt, No Neighbors

Englewood

7% off
$224
$1,568 for 7 nights
All fees included
Ultimate Privacy: 3BR/2BA Heated Pool, Screened, Green Belt, No Neighbors
Dining
Living area
Pool
Exterior
Exceptional
(15 reviews)

The Blooming Sanctuary - 3br with pool and EV-Charger

Rotonda West

8% off
$155
$1,083 for 7 nights
All fees included
The Blooming Sanctuary - 3br with pool and EV-Charger
Living area
Beach
Exterior
Dining
Exceptional
(33 reviews)

NewToVRBO RELAX- Own Home Private Pool, Hot Tub, near Beaches, Golf & Pickleball

Rotonda West

16% off
$189
$1,320 for 7 nights
All fees included
NewToVRBO RELAX- Own Home Private Pool, Hot Tub, near Beaches, Golf & Pickleball
Interior
Private kitchen
Living area
Interior
Exceptional
(5 reviews)

South West Family Home , 3 Bedroom 2 Bath, King bed suite, 4 Beds , 6 Guests

Rotonda West

8% off
$216
$1,510 for 7 nights
All fees included
South West Family Home , 3 Bedroom 2 Bath, King bed suite, 4 Beds , 6 Guests

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Find out more about Oakland Hills

Why visit Oakland Hills

  • Outdoor Activities: Enjoy a variety of outdoor pursuits in nearby national and state parks, perfect for adventure seekers.
  • Family-Friendly Attractions: Discover fun activities suitable for all ages, making it an ideal destination for families.
  • Cultural Experience: Visit the Oakland Museum to immerse yourself in local art and history.
  • Tranquil Atmosphere: Relax in the serene environment, complemented by friendly locals and picturesque surroundings.
  • Diverse Accommodation Options: Choose from charming homes, modern condos, and luxurious villas to suit your vacation needs.

Popular types of accommodation around Oakland Hills

If you’re looking for the perfect getaway in Oakland Hills, you’re in the right place. Our most popular vacation rentals include charming private homes, modern condos, and luxurious villas. Whether you're searching for Oakland Hills houses for rent, features like private pools, or spacious vacation homes, we have a variety of options to suit your needs. Explore the beauty of Hayward and make your stay unforgettable.

  • Houses: The top choice for travelers in Oakland Hills, offering spacious and comfortable accommodations perfect for families and groups.
  • Condos: A popular option for those seeking a blend of convenience and amenities, ideal for couples or small families.
  • Villas: These luxurious retreats provide a serene environment with ample space and upscale features for a memorable stay.
  • Apartments: A practical choice for guests looking for a home-like experience with easy access to local attractions.
  • Cottages: Charming and quaint, these cozy spaces are perfect for a romantic getaway or a peaceful retreat.**

Top attractions near Oakland Hills

Oakland Hills in Rotonda West, Florida, offers a perfect getaway for outdoor and family vacations, with stunning beaches and urban parks nearby. Explore local attractions like national and state parks, ideal for those seeking adventure and relaxation. Don't miss the Oakland Museum for a taste of local culture. Whether you're with family or friends, Oakland Hills promises memorable experiences in a picturesque setting.

  • Englewood Beach: A serene spot with soft sands and gentle waves, perfect for relaxation and sunbathing. Enjoy the vibrant beach vibes while swimming or strolling along the shore, just 5 miles from Oakland Hills.
  • Don Pedro Island Beach: Nestled within a state park, this beach offers stunning scenery and opportunities for adventure. Explore nature trails, have a picnic, or enjoy the outdoor vibes, located only 2 miles away.
  • Gasparilla Marina: A hub for outdoor enthusiasts, this marina provides access to fishing, boating, and beach adventures. Experience the lively atmosphere and scenic views, situated 4 miles from Oakland Hills.

Things to do recommended for couples

For a romantic getaway in Oakland Hills, visit the Oyster Creek Golf Club, a luxurious private club just 3 miles away. Enjoy a round of golf amidst stunning scenery, or relax in the upscale ambiance, perfect for couples seeking a memorable experience together.

Things to do recommended for families

Your family vacation in Oakland Hills will be delightful. Visit Cedar Point Environmental Park for relaxation, enjoy a game at Charlotte Sports Park, and unwind at Englewood Recreation Center. Each spot offers a unique experience that will entertain and engage both kids and adults alike.

Things to do recommended for groups

Groups visiting Oakland Hills can enjoy shopping and entertainment at Fishermen's Village, hit the greens at the Sarasota National Golf Course, or experience culture and romance at the Lemon Bay Playhouse, all within a short drive for a memorable 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 around Oakland Hills

When traveling with a group, your family, or pets, or if you’re planning an extended stay, be sure to set your filters to match your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Oakland Hills with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Oakland Hills with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with finding 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 Oakland Hills: For many families, a trip isn’t truly complete without their furry companion. If you can relate, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Oakland Hills: If you're in search of vacation rentals that offer discounts for stays of a month or longer, 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 criteria as well.

Where to stay near Oakland Hills

Exploring Oakland Hills in Rotonda West, Florida, is a delightful experience for any traveler. This charming neighborhood offers a perfect blend of outdoor activities and family-friendly attractions. Enjoy the tranquil atmosphere while visiting nearby cities like downtown Oakland and Berkeley. Whether you're looking for relaxing beaches or secluded spots, Oakland Hills will provide a warm welcome from friendly locals, making it an ideal destination for a memorable vacation.

  • Englewood: Englewood is a charming city located 7 miles from Oakland Hills, offering a delightful mix of beach and outdoor experiences. Known for its stunning coastline, visitors flock to Englewood for its beautiful family-friendly beaches and scenic bay views. Engage in various recreational activities such as golfing, with several courses and lush green areas available. The area boasts a relaxed atmosphere, making it perfect for leisurely strolls along the shore or enjoying a picnic in one of its well-maintained parks.
  • Rotonda West: Nestled within Rotonda West is Oakland Hills itself, a vibrant community that attracts travelers seeking beach, outdoor, and scenic experiences. With its pristine beaches and recreational areas, Rotonda West is a haven for golf enthusiasts and outdoor lovers alike. Visitors can enjoy a variety of activities, from spending a day on the golf course to exploring the nearby islands. The area is characterized by its picturesque landscapes and friendly atmosphere, making it an ideal spot for relaxation and enjoyment.
  • Manasota Key: Just 5 miles from Oakland Hills, Manasota Key is a serene village celebrated for its natural beauty and island charm. This destination is perfect for those looking to bask in the sun or enjoy outdoor adventures. With its stunning beaches, including family-friendly shores and access to a national state park, Manasota Key offers endless opportunities for exploration. Visitors can indulge in shopping at local centers or unwind at beachfront resorts, making it a perfect getaway for relaxation and fun.

Best time to go to Oakland Hills

If you're planning a trip to Oakland Hills, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from January to March, while off-peak times, like August to October tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January63.7°F (17.6°C)No Rain (Dry)Mostly SunnyModerately HighAverage
February66.0°F (18.9°C)No Rain (Dry)SunnyModerately HighAverage
March68.7°F (20.4°C)No Rain (Dry)SunnyModerately HighSlightly High
April73.9°F (23.3°C)Light RainMostly SunnyAverageSlightly High
May78.1°F (25.6°C)Light RainMostly SunnyAverageAverage
June82.0°F (27.8°C)Light RainMostly SunnyAverageAverage
July83.3°F (28.5°C)Light RainMostly SunnyAverageAverage
August83.7°F (28.7°C)Light RainMostly SunnyModerately LowAverage
September81.9°F (27.7°C)Light RainMostly SunnyModerately LowSlightly Low
October77.5°F (25.3°C)Light RainMostly SunnyModerately LowSlightly Low
November71.2°F (21.8°C)No Rain (Dry)Mostly SunnyAverageSlightly Low
December67.3°F (19.6°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Are you hoping to save money on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that meets your financial needs, 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.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient platform for you to design new trips, manage your existing plans, and keep your bookings organized. Your saved or booked properties are categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Oakland Hills?
In Oakland Hills, vacation houses are the most popular type of rental accommodation, with about 69 available throughout the area. These homes typically offer spacious interiors, multiple bedrooms, and amenities such as fully equipped kitchens and private outdoor spaces for relaxation. Additionally, there are several villas, cottages, and condos that provide alternative lodging options, often featuring unique designs and proximity to local attractions. Mobile homes are also available, suiting those seeking a different style of stay.
Are there any beach house rentals in Oakland Hills?
In Oakland Hills, there are around 63 beach house rentals available, offering a variety of options for travelers. These properties typically feature spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many rentals include outdoor spaces such as decks or patios to enjoy the pleasant Florida weather. The area is known for its proximity to beautiful beaches and local attractions, providing a ideal setting for a relaxing getaway.
How much does it cost to rent a vacation home in Oakland Hills?
Prices for vacation rentals in Oakland Hills 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 Oakland Hills 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 Oakland Hills vacation house rentals?
You can find great discounts on house rentals in Oakland Hills 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.
What are popular rental amenities in Oakland Hills?
In Oakland Hills, travelers can expect a variety of popular rental amenities that enhance their stay. Most vacation rentals come equipped with a kitchen, allowing guests to prepare their meals at their convenience. Many properties also feature decks or patios, providing a great spot to relax and enjoy the surrounding views. Onsite parking is typically available, making it easy for guests to explore the area without worrying about street parking. Additional amenities often include coffee and tea makers for a refreshing beverage at any time and blenders for those who enjoy smoothies or other blended drinks.
Can I find family house rentals in Oakland Hills?
In Oakland Hills, Florida, there are numerous family-friendly house rentals available, with around 61 options to choose from. Visitors can explore charming neighborhoods that provide ample space for families, often featuring multiple bedrooms, spacious living areas, and fully equipped kitchens for preparing meals together. Many of these homes include amenities like private backyards or patios, great for outdoor activities and relaxation.The area is conveniently located near parks and recreational facilities, making it easy for families to enjoy outdoor adventures, picnics, and playgrounds. Additionally, local attractions and shopping centers are just a short drive away, providing opportunities for dining and entertainment.
Can I rent a vacation home with a pool or hot tub in Oakland Hills?
In Oakland Hills, Florida, there are plenty of vacation homes available for rent that feature pools and hot tubs, with around 52 options to choose from. This scenic area offers a mix of properties located among lush greenery, providing a tranquil escape. Travelers can expect amenities such as private swimming pools, relaxing hot tubs, spacious outdoor patios, and fully equipped kitchens, which make these homes great for both relaxation and entertaining. Many rentals also include features like barbecue grills and outdoor dining areas, enhancing the experience of enjoying the warm Florida weather.
Are there any Oakland Hills vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Oakland Hills 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.
Can I book pet-friendly vacation rentals in Oakland Hills?
Yes, you can book pet-friendly vacation rentals in Oakland Hills, Florida. The area offers a variety of vacation rentals, with around 43 options available that welcome pets. Many of these properties feature amenities such as spacious outdoor areas, which are great for pets to roam, along with fully equipped kitchens and comfortable living spaces that cater to families or groups.Oakland Hills is ideally situated near several parks where you and your furry friends can enjoy outdoor activities. For instance, the nearby Oakland Park is a great spot for walks and picnics, providing ample green space for pets to explore.
Can I find long-stay vacation rentals in Oakland Hills?
A long-stay vacation rental in Oakland Hills 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.
When is the best time to visit Oakland Hills for a vacation rental?
The peak season for vacation rentals in Oakland Hills is from February to April, a time when the region comes alive with visitors eager to bask in the warm Florida sunshine. This delightful period offers a superb blend of outdoor activities, including hiking, biking, and enjoying the scenic landscapes that characterize the area. With daytime temperatures typically ranging from the low 50s to mid-70s Fahrenheit, it's an ideal time for travelers looking to explore both the natural beauty and vibrant local culture.March stands out as the most popular month to visit Oakland Hills. During this time, you can expect a lively option filled with events and festivals that showcase the area's charm. Visitors can enjoy leisurely walks along the trails, partake in local culinary delights, and appreciate the stunning vistas that the Oakland Hills has to offer.For those seeking a more budget-friendly experience, October presents an excellent opportunity. While this month falls outside the peak tourist season, it still boasts pleasant temperatures and allows visitors to enjoy the scenic beauty without the crowds. The fall foliage adds a unique touch to the landscape, making it a wonderful time for photography and exploration.Ultimately, your choice of when to visit Oakland Hills should align with your interests—whether you're drawn to the vibrant activities of peak season or the tranquil beauty of the shoulder months.
Are there any remote work vacation rentals in Oakland Hills?
In Oakland Hills, Florida, there are ample options for remote work vacation rentals, with around 77 available throughout the area. Many of these rentals are designed with the needs of remote workers in mind, featuring amenities such as high-speed internet access, including both Wi-Fi and third-party service options, ensuring a reliable connection for video calls and online work.Travelers can expect comfortable living spaces that often include dedicated work areas, allowing for a productive environment. Additionally, many properties come equipped with fully functional kitchens, spacious common areas, and outdoor spaces, creating a pleasant atmosphere for both work and relaxation.The Oakland Hills area itself is known for its scenic beauty and proximity to natural attractions, making it a great spot to unwind after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Oakland Hills vacation rental?
Book your Oakland Hills 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 Oakland Hills, Florida, United States of America?
In Oakland Hills, Florida, visitors can enjoy a variety of attractions that showcase the natural beauty of the area. The nearby Oakland Nature Preserve offers trails for hiking and birdwatching, making it a great spot for outdoor enthusiasts. The preserve is home to diverse wildlife and scenic views of the wetlands, providing a peaceful retreat for nature lovers.For those interested in history and culture, the nearby city of Orlando features attractions such as the Orlando Science Center and the Charles Hosmer Morse Museum of American Art, which houses an extensive collection of Tiffany glass. Although not in Oakland Hills directly, these cultural gems are easily accessible for a day trip.Additionally, the area is close to Lake Apopka, where visitors can enjoy recreational activities like fishing, kayaking, and picnicking along the waterfront.
Can I change or cancel my Oakland Hills home rental booking on Vrbo?
To find Oakland Hills 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 Oakland Hills 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.

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