Hotels Near
Oakland

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Featured Oakland Hotels

Rosen Inn Lake Buena Vista
Rosen Inn Lake Buena Vista
3.5 out of 5
8442 Palm Parkway, 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 breakfast and the pool in our ...
8.4/10 Very Good! (4,638 reviews)
"Super clean and friendly staff! The front desk is so nice!"

Reviewed on Feb 4, 2025

Rosen Inn Lake Buena Vista
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 spa resort in Four Corners. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in ...
8/10 Very Good! (6,836 reviews)
"We enjoyed our stay and had a great time. We would probably return again. The only thing that we did not enjoy was the strong scent of cat litter box in our room, the kids commented on how bad it was non stop in room 3735 . But we did think everythingg else was great!"

Reviewed on Feb 2, 2025

The Grove Resort & Water Park 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 ...
7.8/10 Good! (4,192 reviews)
"I really recommend this place to anyone. only I don't like is the blinds isn't closed very much."

Reviewed on Feb 2, 2025

Westgate Lakes Resort & Spa Universal Studios Area
Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
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 spa tubs. Our guests praise the clean rooms and the family ...
7/10 Good! (1,954 reviews)
"Love it"

Reviewed on Feb 2, 2025

Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
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
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! (6,458 reviews)
"I recently stayed at DoubleTree by Hilton at the Entrance to Universal Orlando, and it was an amazing experience! The staff were friendly and welcoming from the moment I arrived. The room was spacious, clean, and beautifully designed with all the amenities I could ask for. The bed was incredibly ..."

Reviewed on Feb 1, 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
Hilton Vacation Club Mystic Dunes Orlando
Hilton Vacation Club Mystic Dunes Orlando
7600 Mystic Dunes Lane, Kissimmee, FL
Book a stay at this golf property in Kissimmee. Enjoy free WiFi, free parking, and 4 outdoor pools. Our guests praise the pool and the restaurant in our reviews. ...
8.8/10 Excellent! (3,592 reviews)
"Very comfortable instalations"

Reviewed on Feb 2, 2025

Hilton Vacation Club Mystic Dunes Orlando
Rosen Inn International
Rosen Inn International
3 out of 5
7600 International Drive, Orlando, FL
Stay at this 3-star family-friendly hotel in Orlando. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the breakfast and the pool in our ...
8.2/10 Very Good! (5,106 reviews)
"Great"

Reviewed on Feb 2, 2025

Rosen Inn International
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 ...
8.2/10 Very Good! (3,833 reviews)
"I had a great stay. The resort is enormous but surprisingly quiet. Great breakfast buffet (additional cost) pn property. The beds were comfortable and the shower had very hot water which was amazing. Would certainly stay here again! The staff was amazing."

Reviewed on Feb 2, 2025

Rosen Inn at Pointe Orlando
Margaritaville Resort Orlando
Margaritaville Resort Orlando
4 out of 5
8000 Fins Up Circle, Kissimmee, FL
Stay at this 4-star spa resort in Kissimmee. Enjoy 3 outdoor pools, a full-service spa, and 3 restaurants. Our guests praise the pool and the restaurant in our ...
8.8/10 Excellent! (3,210 reviews)
"Nice resort but they couldn’t provide the king bed that I had booked. Also, $50 resort fee is excessive."

Reviewed on Feb 2, 2025

Margaritaville Resort Orlando
DoubleTree by Hilton Hotel Orlando at SeaWorld
DoubleTree by Hilton Hotel Orlando at SeaWorld
4 out of 5
10100 International Drive, Orlando, FL
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! (5,807 reviews)
"After being in the car for 30 hours driving from Iowa to Key West, this was a much-needed stop. The hotel and property were BEAUTIFUL, and the room was so comfortable. We will definitely be back, hopefully for a longer stay next time! We loved the cabana bar by one of the pools called the Barefoot! ..."

Reviewed on Feb 3, 2025

DoubleTree by Hilton Hotel Orlando at SeaWorld
Sheraton Orlando Lake Buena Vista Resort
Sheraton Orlando Lake Buena Vista Resort
4 out of 5
12205 S Apopka Vineland Rd, Orlando, FL
Book a stay at this spa hotel in Orlando. Enjoy 2 outdoor pools, a full-service spa, and 2 spa tubs. Our guests praise the pool and the bar in our reviews. Popular ...
7.4/10 Good! (1,014 reviews)
"Will come back and stay here agin"

Reviewed on Jan 31, 2025

Sheraton Orlando Lake Buena Vista Resort
Holiday Inn Resort Orlando - Lake Buena Vista, an IHG Hotel
Holiday Inn Resort Orlando - Lake Buena Vista, an IHG Hotel
3.5 out of 5
13351 State Road 535, Orlando, FL
Stay at this 3.5-star family-friendly resort in Orlando. Enjoy free WiFi, 2 spa tubs, and breakfast (surcharge). Our guests praise the pool and the bar in our ...
8.4/10 Very Good! (2,924 reviews)
"Have stayed here for years now and have loved it closeness to the theme parks"

Reviewed on Feb 2, 2025

Holiday Inn Resort Orlando - Lake Buena Vista, an IHG Hotel
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 $86
  • 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.