Oakland Hills vacation rentals

We found 156 vacation rentals — enter your dates for availability

Discover a selection of 70 homes and other vacation rentals in Oakland Hills that are perfect for your trip. Vacation homes provide the amenities you need and want for you and your friends, family, or even pets, such as a fireplace and garden. At the end of the day, you'll be able to choose a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Oakland Hills

Showing deals for:Nov 14 - Nov 21
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Find out more about Oakland Hills

Find out more about Oakland Hills

Why visit Oakland Hills

  1. Beautiful Beaches: Relax on stunning beaches nearby, perfect for sunbathing and swimming.
  2. Outdoor Activities: Engage in various outdoor adventures like hiking and biking in scenic parks.
  3. Family-Friendly Atmosphere: Enjoy a welcoming environment with activities suitable for all ages.
  4. Charming Local Communities: Explore the quaint charm of Rotonda West and its friendly locals.
  5. Variety of Accommodations: Choose from a range of vacation rentals to suit your comfort and needs.

Popular types of accommodation around Oakland Hills

Planning a getaway to Oakland Hills? You're in for a treat! Explore a variety of popular vacation rentals, including private homes, condos, and villas. Whether you're searching for spacious bedroom rentals or charming houses for rent, Oakland has something for everyone. Enjoy the perfect blend of comfort and convenience as you discover the best Oakland Hills apartments and vacation homes that suit your needs. Start your adventure today!

  • Houses: A top choice for visitors to Oakland Hills, these spacious residences offer comfort and privacy, perfect for families or groups.
  • Condos: A popular second option, condos provide a blend of modern amenities and communal facilities, ideal for a relaxed stay.
  • Villas: These luxurious retreats are the third most sought-after accommodation, featuring upscale living spaces and beautiful surroundings.
  • Apartments: Fourth on the list, apartments deliver convenience and a home-like atmosphere for solo travellers or couples.
  • Cottages: Rounding out the list, cottages offer a quaint and charming getaway, perfect for a peaceful escape.**

Top attractions around Oakland Hills

Oakland Hills in Rotonda West, Florida, is a fantastic destination for outdoor and family vacations, offering a variety of attractions such as beautiful beaches, urban parks, and national/state parks. Whether you're seeking relaxation by the shore or engaging activities in nature, there's something for everyone. This charming area provides ample opportunities for exploration and enjoyment, making it an ideal spot for travellers looking to create lasting memories with loved ones.

  1. Englewood Beach: A serene beach with soft sands and inviting waves, perfect for relaxation and beach vibes. Enjoy sunbathing, swimming, and stunning sunsets just 8.0km from Oakland Hills.
  2. Don Pedro Island Beach: This state park offers a blend of adventure and breathtaking scenery, ideal for nature lovers. Explore hiking trails and pristine beaches just 3.2km away.
  3. Gasparilla Marina: A vibrant marina offering outdoor adventures, from fishing to boating, with a laid-back beach atmosphere located 6.4km from Oakland Hills.

Things to do recommended for couples

For a romantic getaway in Oakland Hills, consider a round of golf at the luxurious Oyster Creek Golf Club, located 4.8km away. Enjoy the serene surroundings and unwind together in this beautiful setting, perfect for couples seeking a memorable experience.

Things to do recommended for families

Your family will love exploring CoolToday Park's sports atmosphere, unwinding at Cedar Point Environmental Park's serene trails, and enjoying activities at Englewood Recreation Center. Each destination, within a short drive from Oakland Hills, offers unique experiences that cater to both fun and relaxation.

Things to do recommended for groups

Explore the vibrant Fishermen's Village for shopping and entertainment, tee off at the scenic Riverwood Golf and Country Club, or enjoy a captivating performance at the Lemon Bay Playhouse. Each experience is perfect for creating lasting memories with your group in sunny Rotonda West.

What do I need to keep in mind when booking a vacation around Oakland Hills

If you're planning a trip with a group, family, or pets, or if you're seeking extended stays, it’s important to prioritise your preferences while filtering options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Oakland Hills with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and many others on Vrbo.
  • Traveling to Oakland Hills with young kids: Travelling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with 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 fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds to ensure that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Oakland Hills: If you’re in search of vacation rentals with special offers 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 as well.

Where to stay around Oakland Hills

Oakland Hills in Rotonda West, Florida, offers a delightful blend of outdoor adventures and family-friendly activities. Visitors can enjoy the serene atmosphere, explore nearby beautiful beaches, and experience the charm of local communities. This oasis is perfect for relaxing getaways, with opportunities for excursions in the surrounding areas. Whether it's a stroll through the scenic landscapes or soaking up the sun, Oakland Hills promises a memorable vacation experience for all.

  • Englewood: Located 11.3km from Oakland Hills, Englewood is a charming city known for its beautiful beaches and outdoor scenery. Visitors flock to Englewood for its relaxing atmosphere, where you can enjoy a variety of recreational activities, including golfing at nearby courses or lounging on the pristine family-friendly beaches. The picturesque bay offers stunning views and opportunities for water sports, making it an ideal destination for nature lovers and families alike. Englewood's welcoming vibe and scenic landscapes are sure to enhance your Florida vacation experience.
  • Placida: Just 6.4km from Oakland Hills, Placida is a quaint city that captures the essence of coastal living. Renowned for its stunning beaches and outdoor recreational opportunities, Placida offers visitors access to various activities, including shopping at local centres and enjoying the amenities of nearby resorts. Families can explore the beautiful beaches and islands that dot the coast, perfect for a day of sun, sand, and adventure. The laid-back atmosphere of Placida ensures that you can unwind while soaking in the natural beauty of Florida’s Gulf Coast.
  • Al Lago Village: A mere 805m from Oakland Hills, Al Lago Village is a delightful neighbourhood perfect for families and sports enthusiasts. This vibrant community offers a range of activities, including golf at local courses and fun-filled adventures at the arcade adventure zone. The nearby urban park and family beaches provide ample opportunities for outdoor enjoyment and relaxation. Al Lago Village's close-knit environment and convenient location make it a fantastic stop for those looking to experience the best of outdoor fun and family-friendly activities.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 simple

Are you hoping to save on your upcoming journey? It might be beneficial to remain flexible with your travel dates, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to narrow down your options by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan new adventures, pick up right where you left off, or easily view and manage your travel arrangements. You can now conveniently find previously saved and booked properties under Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/en-ca/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, with around 68 available across the area. These properties typically feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many also include outdoor amenities such as private gardens or patios, great for enjoying the warm Florida climate. Additionally, several cottages, villas, and condos can be found, each offering a unique charm and comfortable living spaces.
Are there any beach house rentals in Oakland Hills?
In Oakland Hills, Florida, there are about 64 beach house rentals available, making it a popular destination for those seeking a coastal getaway. These properties are often found in picturesque neighbourhoods that provide easy access to the beautiful beaches. Most beach houses come equipped with amenities such as fully furnished kitchens, spacious living areas, and outdoor decks or patios ideal for enjoying the warm Florida weather. Many rentals also feature private pools, BBQ facilities, and multiple bedrooms, making them great for families or groups looking to relax and unwind by the sea.
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 travelling 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.
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.
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 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.
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. 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.
When is the best time to visit Oakland Hills for a vacation rental?
The best time to visit Oakland Hills for a vacation rental is during the peak season from February to April. This period is particularly popular among travellers seeking sunny weather and vibrant outdoor activities. With temperatures typically ranging from the low 20s Celsius, it's an ideal time for those who enjoy hiking, biking, and exploring the natural beauty of the area.

During these months, you can immerse yourself in the stunning landscapes and take advantage of the numerous trails and parks that Oakland Hills has to offer. The comfortable climate invites visitors to partake in leisurely strolls or picnics, making it a great setting for families and adventure enthusiasts alike.

If you're looking for a more budget-friendly option, consider visiting in October. This month offers a quieter experience, allowing you to enjoy the beautiful autumn scenery without the crowds. The changing foliage provides a picturesque backdrop for outdoor activities such as walking and photography, while still enjoying the pleasant temperatures.
Are there any remote work vacation rentals in Oakland Hills?
In Oakland Hills, Florida, there are numerous remote work vacation rentals available, with around 71 options to choose from. This area is well-suited for those seeking a productive environment while enjoying a relaxing getaway. Many properties come equipped with essential remote work amenities, including Wi-Fi, dedicated desk spaces, desk chairs, and sometimes even computer monitors or laptop workspaces, ensuring that you can work efficiently from the comfort of your rental. 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.
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 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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