136+ Vacation Rentals in Oakland Hills |
  1. USA
  2. Florida
  3. Port Charlotte - Charlotte Harbor
  4. Oakland Hills

Oakland Hills Vacation Rentals, Hotels, & Places to Stay

About Oakland Hills Vacation Rentals

There are more than 136 places to stay that are available in Oakland Hills. These choices include hotels as well as other short-term private accommodations (including vacation rentals, cabins, condos, RVs, and more), have a wide selection of amenities at great prices, providing you with all the comforts of home or a touch of luxury. We like to help you find more room with Varoom when booking your property in Oakland Hills.

Varoom features many last-minute deals on hotels, resorts and places to stay including many that are nearby. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Varoom's places in Oakland Hills, you have the flexibility of comparing different options from multiple suppliers with a single click. Group deals, private pools, hot tubs, allows pets, or even those with huge master suite bedrooms with open-air showers? You can find vacation rentals and resorts as well as Airbnb-style properties in Oakland Hills. Places to stay near Oakland Hills are 1180.19 ft² on average, with prices averaging $228 a night.

Varoom helps you discover places to stay and suggests things to do to create great travel memories in Oakland Hills. Prices listed are often found to be at a 30-40% discount versus the rack rates. Just search for your destination and secure your perfect place to stay today.

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Top Rental Accommodation Types in Oakland Hills

Type Count
Vacation Homes 110
Villas 12
Cottages 5

Use these Quick Filters to Find a Vacation Rental in Oakland Hills

★ Pro Tip: Varoom is a meta travel and activities site, and as such we combine results from many of the leading travel websites, helping you compare the best places to stay and things to do in each market. Use the filter option to narrow down your selection and let us help you find more room to stay, play, and discover. Create new memories in Oakland Hills today.

Weather in Oakland Hills, FL

View the weather forecast for Oakland Hills before booking your Oakland Hills Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Other Places to Stay in Oakland Hills, FL


Al Lago Village 1,383 Properties

Frequently Asked Questions About Oakland Hills?

What are the top vacation rentals in Oakland Hills?

We have scoured the web to find you options in Oakland Hills. If you plan on staying near or in the Oakland Hills area, consider one of the following places to stay for a week or more. Weekly stays are a great way to unwind and unplug. These places to stay have all been rated as one of the the Top Places to Stay in Oakland Hills:

How many vacation rentals have private pools in Oakland Hills?

We have found 47 places to stay that feature a private swimming pool in or near Oakland Hills. Some of the best places to stay that feature or have access to a swimming pool are:

Which vacation homes in Oakland Hills are best for families?

If you are looking for a place to stay that is family-friendly in Oakland Hills, check out one of the following places as all are highly-rated options and have received excellent reviews for families or groups staying in Oakland Hills:

How many Varoom vacation rentals are available in Oakland Hills?

Varoom updates its properties nightly to bring you a great selection of places to stay. Currently, the total number of properties listed by Varoom in 2025 is over 136 in the Oakland Hills area, and still growing every day. When we combine listings from multiple websites and travel providers, Varoom can provide you with a diverse amount of choice of the best places to stay in Oakland Hills. 

Nearby Neighborhood (2) 
Neighborhood Property Count
White Marsh Vacation Rentals in Florida 92
Al Lago Village Vacation Rentals in Florida 1383

People Also Ask

There are 136 Oakland Hills, FL Vacation Rentals

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