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Check prices for these dates

This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

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Our top choices for Oakland Hills hotels

A modern kitchen with white cabinets, a dining area with a wooden table and chairs, and a view of a pool through a glass door.

1. Dreams Away - Sleeps 10 Pool Golf Fun

Dreams Away - Sleeps 10 Pool Golf Fun
2.0 star property
Oakland Hills
The price is £327
includes taxes & fees
12 Oct - 13 Oct
Dreams Away - Sleeps 10 Pool Golf Fun
A hotel room with a large bed, two bedside lamps, a nightstand, a mirror, and a curtain.

2. Sun Coast Inn

Sun Coast Inn
2.5 star property
4.2 mi from Oakland Hills
8.0 out of 10, Very good, (1,000 reviews)
"VERY NICE PLACE."
United States
John
The price is £61
includes taxes & fees
24 Oct - 25 Oct
Sun Coast Inn
A reception area with a counter, seating, and a view of the outside.

3. Lemon Bay Motel

Lemon Bay Motel
2.0 star property
4.8 mi from Oakland Hills
8.4 out of 10, Very good, (149 reviews)
"Staff was nice, Rooms were clean Great stay"
United States
Alexander
The price is £48
includes taxes & fees
11 Oct - 12 Oct
Lemon Bay Motel
A modern kitchen with grey cabinets, a black refrigerator, and a white countertop.

4. Englewood Inn & Suites

Englewood Inn & Suites
2.5 star property
3.8 mi from Oakland Hills
8.0 out of 10, Very good, (112 reviews)
"The property is exceptionally clean and well maintained for the price. The staff that I made contact with were very friendly. I'll stay their again without a doubt."
United States
DANIEL
The price is £57
includes taxes & fees
11 Oct - 12 Oct
Englewood Inn & Suites
A compact kitchen with white cabinets, a microwave, stove, and a glass dining table with chairs.

5. Grove City Motel

Grove City Motel
3.5 star property
3.3 mi from Oakland Hills
7.2 out of 10, Good, (315 reviews)
"Great trip by the way"
United States
Christian
The price is £59
includes taxes & fees
9 Oct - 10 Oct
Grove City Motel
A spacious indoor area with a central table and chairs, surrounded by potted plants and a tiled floor.

6. Boca Grande Hotel

Boca Grande Hotel
2.5 star property
5.9 mi from Oakland Hills
8.8 out of 10, Excellent, (670 reviews)
"Loved our stay!"
United States
Ayse
The price is £106
includes taxes & fees
11 Oct - 12 Oct
Boca Grande Hotel
A hotel lobby with a reception desk, two patterned armchairs, a sofa, a coffee table, and a TV screen.

7. Best Western Plus Ambassador Suites Venice

Best Western Plus Ambassador Suites Venice
2.5 star property
16.5 mi from Oakland Hills
9.0 out of 10, Wonderful, (1,004 reviews)
"Great breakfast and very nice staff"
United States
Nicholas
The price is £67
includes taxes & fees
28 Oct - 29 Oct
Best Western Plus Ambassador Suites Venice
An aerial view of a coastal town with beachfront properties, a marina, and clear blue waters.

8. Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
5 mi from Oakland Hills
8.8 out of 10, Excellent, (30 reviews)
"Without a doubt, the best place—very spacious and in an excellent location. You have the beach right out front, and Gasparilla Beach—which is very beautiful—is just 25 minutes away. Communication with the owner was excellent, the sunsets were fantastic, and the terrace overlooking the bay—with the breeze blowing—was a delight. We will definitely be back!"
United States
Niovys
The price is £464
includes taxes & fees
19 Oct - 20 Oct
Chadwick Cove Resort & Marina
An outdoor patio with grey sofas, a glass-top table, and a fire feature.

9. Hampton Inn & Suites North Port

Hampton Inn & Suites North Port
2.5 star property
11.4 mi from Oakland Hills
9.4 out of 10, Exceptional, (775 reviews)
"Great experience very nice hotel"
United States
Diana
The price is £112
includes taxes & fees
15 Oct - 16 Oct
Hampton Inn & Suites North Port
A hotel room with two beds, a desk, a chair, and a large beach-themed painting on the wall.

10. Days Inn by Wyndham Port Charlotte/Punta Gorda

Days Inn by Wyndham Port Charlotte/Punta Gorda
3.0 star property
12.7 mi from Oakland Hills
7.8 out of 10, Good, (1,000 reviews)
"Pleasant 5 day stay, close to beaches and commerce."
United States
Christina
The price is £62
includes taxes & fees
16 Oct - 17 Oct
Days Inn by Wyndham Port Charlotte/Punta Gorda
A hotel room with a large bed, a desk, a chair, a TV, and a window with a view.

11. Holiday Inn Express & Suites Punta Gorda by IHG

Holiday Inn Express & Suites Punta Gorda by IHG
2.5 star property
17.4 mi from Oakland Hills
9.4 out of 10, Exceptional, (1,001 reviews)
"Nice place to stay and easy to find when traveling."
United States
Virginia
The price is £89
includes taxes & fees
12 Oct - 13 Oct
Holiday Inn Express & Suites Punta Gorda by IHG
A beachfront walkway with palm trees wrapped in lights, a thatched-roof structure, and a wooden fence.

12. Four Points by Sheraton Punta Gorda Harborside

Four Points by Sheraton Punta Gorda Harborside
3.5 star property
14.9 mi from Oakland Hills
8.8 out of 10, Excellent, (1,000 reviews)
"We loved our short stay! Friendly staff, the pool was great, and we loved TTs tiki bar. Great location in Punta Gorda"
United States
Tricia
The price is £123
includes taxes & fees
16 Oct - 17 Oct
Four Points by Sheraton Punta Gorda Harborside
A bar area with seating and a counter.

13. Wyvern Hotel, an Ascend Collection Hotel

Wyvern Hotel, an Ascend Collection Hotel
4.0 star property
15 mi from Oakland Hills
9.0 out of 10, Wonderful, (1,001 reviews)
"Very clean, centrally located, great staff! A must stay."
United States
April
The price is £102
includes taxes & fees
15 Oct - 16 Oct
Wyvern Hotel, an Ascend Collection Hotel
A spacious living area with a curved sofa, a glass coffee table, and a flat-screen TV.

14. Baymont by Wyndham Punta Gorda/Port Charlotte

Baymont by Wyndham Punta Gorda/Port Charlotte
2.5 star property
17.4 mi from Oakland Hills
8.6 out of 10, Excellent, (1,239 reviews)
"Great place to stay."
United States
Troy
The price is £54
includes taxes & fees
28 Oct - 29 Oct
Baymont by Wyndham Punta Gorda/Port Charlotte
A rocky beach with large boulders in the foreground and a clear blue sky.

15. Fairfield Inn & Suites by Marriott Venice

Fairfield Inn & Suites by Marriott Venice
3.0 star property
16.4 mi from Oakland Hills
9.2 out of 10, Wonderful, (1,000 reviews)
"Super clean rooms and soft towels great breakfast plenty food and selection Very happy to stop here coming back again next week"
United States
Maritza
The price is £83
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Venice
A modern hotel lobby with wooden furniture, a central bar area, and large windows offering a view of palm trees.

16. SpringHill Suites by Marriott Punta Gorda Harborside

SpringHill Suites by Marriott Punta Gorda Harborside
3.0 star property
15 mi from Oakland Hills
9.6 out of 10, Exceptional, (904 reviews)
"Pool was very nice and clean"
United States
Minh
The price is £118
includes taxes & fees
11 Oct - 12 Oct
SpringHill Suites by Marriott Punta Gorda Harborside
A hotel room with two beds, a desk, a chair, a window with curtains, and a wall-mounted heater.

17. Red Roof Inn Port Charlotte - Punta Gorda

Red Roof Inn Port Charlotte - Punta Gorda
2.5 star property
13.9 mi from Oakland Hills
7.2 out of 10, Good, (1,000 reviews)
"We stay here because it is really close to where my son lives. It is clean, the staff is friendly and bed is comfortable."
United States
Robert
The price is £54
includes taxes & fees
16 Oct - 17 Oct
Red Roof Inn Port Charlotte - Punta Gorda
A bedroom with a bed, bedside tables, a ceiling fan, and artwork on the wall.

18. The Palmetto Inn

The Palmetto Inn
3.0 star property
9.6 mi from Oakland Hills
8.2 out of 10, Very good, (127 reviews)
"Great service and great place. Live the hot plate to cook on!!"
United States
Lindsay
The price is £122
includes taxes & fees
12 Oct - 13 Oct
The Palmetto Inn
A beach with a thatched-roof structure, palm trees, and a view of the sea.

19. The Suites at Fishermen’s Village

The Suites at Fishermen’s Village
3.0 star property
14.1 mi from Oakland Hills
9.8 out of 10, Exceptional, (1,339 reviews)
"Stay here every time I visit Florida. Highly recommend"
United States
Dawn
The price is £148
includes taxes & fees
30 Oct - 31 Oct
The Suites at Fishermen’s Village
A hotel room with a bed, a ceiling fan, a TV, and a refrigerator.

20. Island Sun Inn & Suites - Historic Venice & Beach Getaway

Island Sun Inn & Suites - Historic Venice & Beach Getaway
2.0 star property
16.9 mi from Oakland Hills
7.6 out of 10, Good, (1,000 reviews)
"This place was decent for the price."
United States
Jacqueline
The price is £49
includes taxes & fees
15 Oct - 16 Oct
Island Sun Inn & Suites - Historic Venice & Beach Getaway
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Where to stay in Oakland Hills

Find the best Oakland Hills areas for the activities you enjoy most.
A wooden bridge over a calm river, surrounded by lush greenery and trees.

Rotonda Sands

While there might not be top attractions in Rotonda Sands, you can explore the larger area and discover places like Don Pedro Island State Park and Little Gasparilla Island Beach.

A boat on calm waters during sunset with a clear sky.

Pebble Beach

While Pebble Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Don Pedro Island State Park and Stump Pass Beach State Park.

A golf course with water hazards, sand bunkers, and palm trees.

White Marsh

Though White Marsh may not have many top sights, you can venture to the surrounding area to see attractions like Don Pedro Island State Park and Little Gasparilla Island Beach.

A golf course with water hazards, sand bunkers, and palm trees.

Pinehurst

When in Pinehurst, you can plan a visit to Don Pedro Island State Park and Stump Pass Beach State Park, some noteworthy sights in the nearby area.

A bridge over a calm river, surrounded by greenery and houses.

Rotonda Lakes

While Rotonda Lakes isn't home to many top sights, Cape Haze Pioneer Trail Park and Oyster Creek Golf Club are some notable places to visit nearby.

Top Oakland Hills Hotel Reviews

Comfort Inn & Suites

Comfort Inn & Suites

10/10 Excellent
"Excellent!"
Timothy 2-night trip
Posted 3 hours ago
Comfort Inn & Suites

Frequently asked questions

When is the best time to go to Oakland Hills?
The best time to visit Oakland Hills, Florida, is typically from late autumn through spring, specifically October to May, when the weather is most agreeable.

During these months, you'll experience comfortable temperatures, generally ranging from 20°C to 28°C, with lower humidity. This makes it ideal for outdoor activities like exploring the area's golf courses, visiting the nearby state parks, or simply enjoying a stroll through the more residential parts of the Hills. You'll find it's a pleasant time for couples looking for a relaxing escape without the intense heat and humidity of the summer.

Solo travellers who enjoy outdoor pursuits will also appreciate this period. The drier conditions are great for hiking and cycling, and many local events and markets are held when the weather is cooler. You can comfortably explore the various golf courses or take a short drive to nearby natural attractions.

While the summer months (June to September) offer higher temperatures and humidity, along with a higher chance of afternoon thunderstorms, they can still be a good option for those looking for value, as it's considered the off-peak season.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Oakland Hills.
How much is the nightly rate at a Oakland Hills hotel?
Hotel prices in Oakland Hills often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.