Hotels Near
Oakland

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Featured Oakland Hotels

Holiday Inn Resort Orlando Suites - Waterpark by IHG
Holiday Inn Resort Orlando Suites - Waterpark by IHG
3.5 out of 5
14500 Continental Gateway, Orlando, FL
Fully refundable
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy 2 outdoor pools, 5 restaurants, and 2 hot tubs. Our guests praise the clean rooms and the family ...
7.2/10 Good! (2,634 reviews)
"This resort has everything the kids didn’t even want to leave the resort because of the arcade area. The lobby is made up like a mini mall"

Reviewed on Apr 12, 2025

Holiday Inn Resort Orlando Suites - Waterpark by IHG
Rosen Inn at Pointe Orlando
Rosen Inn at Pointe Orlando
3 out of 5
9000 International Drive, Orlando, FL
Stay at this 3-star family-friendly hotel in Orlando. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the helpful staff in ...
8.4/10 Very Good! (4,145 reviews)
"Good location, walkable, clean"

Reviewed on Apr 13, 2025

Rosen Inn at Pointe Orlando
Universal's Cabana Bay Beach Resort
Universal's Cabana Bay Beach Resort
3.5 out of 5
6550 Adventure Way, Orlando, FL
Fully refundableReserve now, pay when you stay
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
8.8/10 Excellent! (5,190 reviews)
"Best stay ever !!"

Reviewed on Apr 12, 2025

Universal's Cabana Bay Beach Resort
The Grove Resort & Water Park Orlando
The Grove Resort & Water Park Orlando
4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
Fully refundableReserve now, pay when you stay
Stay at this 4-star family-friendly resort in Winter Garden. Enjoy free WiFi, 5 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful ...
8/10 Very Good! (7,427 reviews)
"Quite and clean"

Reviewed on Apr 14, 2025

The Grove Resort & Water Park Orlando
DoubleTree by Hilton Hotel Orlando at SeaWorld
DoubleTree by Hilton Hotel Orlando at SeaWorld
4 out of 5
10100 International Drive, Orlando, FL
Fully refundableReserve now, pay when you stay
Stay at this 4-star family-friendly resort in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the breakfast and the pool in our ...
7.2/10 Good! (5,848 reviews)
"The room was great. They do need more parking spaces. Pool area was clean and fun."

Reviewed on Apr 14, 2025

DoubleTree by Hilton Hotel Orlando at SeaWorld
DoubleTree by Hilton at the Entrance to Universal Orlando
DoubleTree by Hilton at the Entrance to Universal Orlando
4 out of 5
5780 Major Blvd, Orlando, FL
Fully refundableReserve now, pay when you stay
Stay at this 4-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
8.2/10 Very Good! (6,280 reviews)
"I liked that it had a bar at the pool. Not enough umbrellas at the pool"

Reviewed on Apr 12, 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
Caribe Royale Orlando
Caribe Royale Orlando
4.5 out of 5
8101 World Center Dr, Orlando, FL
Fully refundableReserve now, pay when you stay
Book a stay at this luxury hotel in Orlando. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the pool and the restaurant in our ...
9/10 Wonderful! (3,975 reviews)
"loved the staff at every stop. teh bar staff at both Calyposos and the rum bar were super good at their jobs. friendly and efficient! We were not fans of the breakfast buffet at the Tropical (?) in lower level. Staff there were great but food was not. I'd replace the gravy and biscuits ..."

Reviewed on Apr 12, 2025

Caribe Royale Orlando
Westgate Lakes Resort & Spa Universal Studios Area
Westgate Lakes Resort & Spa Universal Studios Area
4 out of 5
9500 Turkey Lake Rd, Orlando, FL
Stay at this 4-star spa hotel in Orlando. Enjoy free parking, 7 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8/10 Very Good! (4,712 reviews)
"We had a great time at Westgate!! The room was very clean and neat. The rooms were very spacious as well as the patio. The pool area is nice with a jacuzzi and the water park is fun with lots of things for kids to do. I enjoyed the lazy river lol we will be back again."

Reviewed on Apr 13, 2025

Westgate Lakes Resort & Spa Universal Studios Area
Hyatt Regency Orlando
Hyatt Regency Orlando
4.5 out of 5
9801 International Dr, Orlando, FL
Fully refundableReserve now, pay when you stay
Stay at this 4.5-star luxury hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (1,634 reviews)
"The property is located directly across from the convention center and there are plenty of dining options in the surrounding area."

Reviewed on Apr 10, 2025

Hyatt Regency Orlando
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
2.5 out of 5
631 FLAGLER AVE, Winter Garden, FL
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Winter Garden. Enjoy free breakfast, free WiFi, and a free theme park shuttle. Our guests praise the breakfast ...
9.4/10 Exceptional! (2,832 reviews)
"Feel safe n goo good service"

Reviewed on Apr 14, 2025

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Hilton Vacation Club Grande Villas Orlando
Hilton Vacation Club Grande Villas Orlando
3.5 out of 5
12118 Turtle Cay Circle, Orlando, FL
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the bar in our reviews. ...
9.2/10 Wonderful! (2,937 reviews)
"Just noisy at night with kids running around and screaming at midnight when people are trying to sleep"

Reviewed on Apr 12, 2025

Hilton Vacation Club Grande Villas Orlando
Vacation Village at Parkway
Vacation Village at Parkway
3 out of 5
2975 Arabian Nights Blvd, Kissimmee, FL
Fully refundableReserve now, pay when you stay
Stay at this 3-star family-friendly condo in Kissimmee. Enjoy free WiFi, 7 outdoor pools, and 7 hot tubs. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (1,941 reviews)
"I loved the space. Nice and clean."

Reviewed on Apr 14, 2025

Vacation Village at Parkway
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.

Hotels in Oakland

Winter Garden is a city that has a lot going on, but you have your sights set on Oakland. This part of town is perfect for what you want to be doing, and that is everything that is not on everyone’s radar. For all that Oakland has going on, you’ll still need a place to crash, eventually. But you don’t want any old shack, you need something that fits the trip. We have a slew of Oakland hotels that will do the trick.

A beautiful day in the neighborhood

As much as you like getting out there, it’s also good to know a part of Winter Garden so well you’ll be telling the tourists where to go. Make friends with the concierge or be bold and chat up a local. It’s your trip, so choose your own adventure. And when you get in at night, you’ll have a comfy room and plenty of amenities to help you settle in. Call a friend and spin tales from the Oakland underground. What’s a journey without a good story to go with it?

Beyond the block

We’re not talking about the Oakland city block. We’re talking about looking beyond that block of hotels you always focus on. We give you tons of ways to sort our stash of Oakland cheap hotels. And if you feel like living a little, but not killing your vacation vibes, choose the Hotwire Hot Rate deal. Filter by:

  • Hotwire Hot Rate: Snag some of the best hotels in Oakland at an almost too good to be true rate. After you book, we’ll reveal the name of the hotel. You can get a luxury hotel at a budget price.
  • Price: You have a price in mind, and we have solutions. Hotels start as low as $95
  • Amenities: Rooftop lounge, designer furniture, 24-7 room service, and everything else you look for to live it up large.

Find the Oakland hotel you want, book it, and never look back. Because your great escape is ahead of you.

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