Oakland Hills holiday lettings

We found 171 holiday rentals — enter your dates for availability

Discover a selection of 69 homes and other holiday rentals in Oakland Hills that are perfect for your trip. Holiday homes provide the amenities that you need and want for you and your friends, family or even pets, such as Wi-Fi and parking. At the end of the day, you'll be able to choose a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

Why visit Oakland Hills

  • Outdoor Activities: Enjoy a range of outdoor pursuits, from hiking in nearby parks to relaxing on stunning beaches.
  • Family-Friendly Atmosphere: The neighbourhood offers a welcoming environment, ideal for family excursions and adventures.
  • Diverse Accommodation Options: Choose from a variety of holiday rentals, including charming homes, condos, and villas.
  • Natural Beauty: Experience Florida's picturesque landscapes, perfect for both relaxation and exploration.
  • Community Engagement: Discover vibrant local interactions and hidden gems within the friendly community.

Popular types of accommodation around Oakland Hills

Discover a variety of vacation rentals in Oakland Hills, including private homes, condos, and villas. Whether you're seeking a charming house for rent or a spacious holiday home, you'll find the perfect accommodation to suit your needs. With our transparent information and commitment to customer satisfaction, planning your stay in Oakland has never been easier. Explore your options and make unforgettable memories in this beautiful region.

  • Houses: The top choice for many holidaymakers in Oakland Hills, these homes offer a homely atmosphere, perfect for families or groups of friends.
  • Condos: A popular option for those seeking modern amenities and a communal setting, condos provide comfort and convenience.
  • Villas: Ideal for a luxurious getaway, villas in Oakland Hills offer spacious living and beautiful surroundings.
  • Apartments: A practical choice for solo travellers or couples, apartments offer self-catering facilities and easy access to local attractions.
  • Cottages: Quaint and charming, cottages provide a cosy retreat, perfect for a peaceful escape in nature.**

Top attractions near Oakland Hills

Oakland Hills in Rotonda West is perfect for outdoor and family holidays, offering a delightful mix of beach and urban park experiences. Visitors can explore various points of interest, including beautiful beaches and nearby national and state parks, ensuring a memorable getaway for all ages. Whether you seek relaxation or adventure, Oakland Hills has something to suit every traveller's taste.

  • Englewood Beach: A stunning stretch of sand, Englewood Beach offers a relaxing seaside atmosphere with warm waters perfect for swimming and sunbathing. It’s an ideal spot to unwind and soak in the sun, surrounded by beautiful coastal scenery.
  • Don Pedro Island Beach: Nestled within a state park, Don Pedro Island Beach is a haven for outdoor enthusiasts. With its pristine landscapes, it invites adventure seekers to explore its trails and enjoy the breathtaking scenery.
  • Gasparilla Marina: A vibrant hub for nautical adventures, Gasparilla Marina features a variety of water activities. Enjoy fishing, boating, and exploring the beautiful coastal waters, all while soaking up the beach vibes.

Things to do recommended for couples

For a delightful couple's retreat in Oakland Hills, consider a visit to the Oyster Creek Golf Club, merely 1.9km away. With its luxurious ambiance, it offers a perfect setting for a romantic day of golf or a leisurely stroll amidst stunning surroundings.

Things to do recommended for families

Families will delight in the sporting atmosphere at CoolToday Park, located 6.2km from Oakland Hills. For a touch of nature, Cedar Point Environmental Park, just 2.5km away, offers wellness and relaxation, while the Englewood Recreation Center, 4.3km from Oakland Hills, provides further recreational opportunities.

Things to do recommended for groups

Groups visiting Oakland Hills can enjoy a vibrant day at Fishermen's Village for shopping and dining, challenge themselves at Riverwood Golf and Country Club, or catch a captivating performance at Lemon Bay Playhouse, immersing themselves in the local culture and entertainment.

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

When you're planning a trip, whether it's with a group, family, pets, or for an extended stay, it's important to refine your search according to your specific needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to Oakland Hills with a group: Think about how many bedrooms you’ll require, along with features like a fully-equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Oakland Hills with young kids: Travelling with young children can present its challenges. It's essential to prioritise 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 getaway isn't quite the same without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Oakland Hills: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right place. 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 Oakland Hills

Exploring Oakland Hills in Rotonda West, Florida, promises a delightful family vacation filled with outdoor activities and serene beach experiences. This friendly neighbourhood offers a relaxing atmosphere, perfect for excursions and family-friendly adventures. Nearby cities provide opportunities for hunting and discovering charming family homes for rent, ensuring a memorable stay. Whether you seek secluded spots or vibrant community interactions, Oakland Hills is an ideal base to enjoy the best of Florida's natural beauty.

  • Englewood: Englewood is a charming coastal city situated 4.3km from Oakland Hills. Renowned for its stunning beaches and outdoor recreational opportunities, visitors are drawn to its picturesque scenery and relaxed atmosphere. Popular activities include golf at local courses and exploring the nearby recreational areas. The local landmarks, such as the beautiful family beach and the serene bay, offer perfect spots for sunbathing and picnicking, making it an idyllic destination for families and nature lovers alike.
  • Rotonda West: Located a mere 124m from Oakland Hills, Rotonda West is a delightful community that embodies the essence of Florida living. It is celebrated for its stunning beaches and numerous outdoor activities. Golf enthusiasts will appreciate the area's well-maintained courses, while the recreational areas provide ample opportunity for outdoor fun. With nearby attractions including family-friendly beaches and tranquil islands, Rotonda West is an ideal getaway for those seeking a blend of relaxation and adventure in a scenic setting.
  • Manasota Key: Just 3.1km from Oakland Hills, Manasota Key is a picturesque village that boasts the charm of an island paradise. This tranquil destination is perfect for beach lovers and outdoor enthusiasts alike, offering breathtaking natural beauty and a laid-back vibe. Visitors can enjoy recreational areas, visit local shopping centres, or unwind at luxurious resorts. Notable attractions include pristine family beaches and the nearby national state park, which provides ample opportunities for hiking and wildlife spotting, ensuring a memorable experience for all.

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

Looking to cut costs on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate significantly. Moreover, extending your stay can often result in substantial savings. To discover the ideal Vrbo property that suits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, continue with your existing arrangements, or review and organise your bookings. The properties you’ve saved or booked are neatly categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

How much does it cost to rent a holiday home in Oakland Hills?
Prices for holiday 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 holiday 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 holiday rentals with parking?
Vrbo offers a wide selection of holiday 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 holiday rentals in Oakland Hills?
A long-stay holiday 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 holiday rental?
March is the most popular month to visit Oakland Hills, as it falls within the vibrant peak season from February to April. During this time, visitors flock to the area to enjoy the beautiful weather and partake in a variety of outdoor activities. With temperatures ranging from a pleasant 10 to 25 degrees Celsius, it's ideal for hiking, golfing, and exploring the local parks and nature trails.

The peak season attracts a lively crowd, making it superb for those who thrive on socializings and community events. Whether you're attending local festivals or simply soaking up the sun, there's an abundance of activities to keep you engaged.

For those seeking a more budget-friendly option, consider planning your visit in October. This month offers a quieter atmosphere with comfortable temperatures, making it a great time for leisurely strolls and enjoying the natural beauty of the area without the hustle and bustle of peak season tourists.

Ultimately, your ideal time to visit Oakland Hills will depend on whether you prefer the vibrant energy of spring or the tranquil charm of autumn.
How early should I book a Oakland Hills holiday rental?
Book your Oakland Hills holiday 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 holiday 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 highlight the area's natural beauty and recreational opportunities. The stunning parks and nature reserves, such as the nearby Oakland Park, offer lovely walking trails, picnic areas, and the chance to appreciate local wildlife.

The neighbourhood is also close to the scenic coastline, where visitors can partake in activities such as swimming, fishing, and sunbathing. Additionally, the community boasts golf courses that are popular among residents and tourists alike, providing a relaxing way to spend a day outdoors.

For those interested in local culture, nearby towns may host events or festivals that showcase the area's heritage, enhancing the overall experience for visitors.
Can I change or cancel my Oakland Hills home rental booking on Vrbo?
To find Oakland Hills holiday 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 cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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 holiday ideas