Hotels Near
Oakland

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Featured Oakland Hotels

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
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
8.8/10 Excellent! (5,801 reviews)
Good price for family. We went for epic universe and I enjoyed the vintage feel of this hotel. Also way cheaper than the disney older hotels. Food was cold. Luckily they had microwaves next to the dining tables

Reviewed on Dec 20, 2025

Universal's Cabana Bay Beach Resort
Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

3.5 out of 5
6515 International Drive Orlando FL
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, free parking, and private pools. Our guests praise the pool and the clean rooms in our ...
7.2/10 Good! (3,924 reviews)
😍

Reviewed on Dec 20, 2025

Wyndham I-Drive Avanti Resort & Conference Center
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

3 out of 5
9000 International Drive Orlando FL
Fully refundableReserve now, pay when you stay
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 3 outdoor pools, and 2 coffee shops/cafes. Our guests praise the pool and the helpful ...
8.4/10 Very Good! (5,402 reviews)
Clean room but sink is gurgling and dirty like water has come up. And drains slow

Reviewed on Dec 21, 2025

Rosen Inn at Pointe Orlando
Avanti International Resort

Avanti International Resort

4 out of 5
8738 International Dr Orlando FL
Fully refundableReserve now, pay when you stay
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the pool and the helpful ...
7.8/10 Good! (4,326 reviews)
Staff

Reviewed on Dec 18, 2025

Avanti International Resort
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 refundable
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
8.4/10 Very Good! (6,896 reviews)
Friendly staff, easy checkin, great breakfast (thanks to our server Brenda)

Reviewed on Dec 21, 2025

DoubleTree by Hilton at the Entrance to Universal 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
Book a stay at this family-friendly resort in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the breakfast and the pool in our ...
7.4/10 Good! (6,282 reviews)
Friendly people

Reviewed on Dec 21, 2025

DoubleTree by Hilton Hotel Orlando at SeaWorld
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
Book a stay at this family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
7.8/10 Good! (8,806 reviews)
Room was very spacious and clean. The only two downside’s was the food mart was extremely expensive and the master bathroom had a leak.

Reviewed on Dec 20, 2025

The Grove Resort & Water Park Orlando
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4 out of 5
8800 Vistana Centre Dr Orlando FL
Fully refundableReserve now, pay when you stay
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff in ...
9.2/10 Wonderful! (4,130 reviews)
Best for family, very clean spacious rooms and well lite parking

Reviewed on Dec 19, 2025

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

4 out of 5
12401 International Dr Orlando FL
Fully refundableReserve now, pay when you stay
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 5 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (2,773 reviews)
Good value

Reviewed on Dec 20, 2025

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
Hyatt Regency Orlando

Hyatt Regency Orlando

4.5 out of 5
9801 International Dr Orlando FL
Fully refundableReserve now, pay when you stay
Book a stay at this luxury hotel in Orlando. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the pool and the helpful staff in our ...
9.2/10 Wonderful! (1,877 reviews)
This property is one of our new favorites in the Orlando area. Location is great, close to restaurants, airport and disney. (We did have a rental car). Rooms are spacious and clean, lobby is grand and beautiful, on site food was delicious. (Although one bar we wanted to try for a bite to eat was ...

Reviewed on Dec 21, 2025

Hyatt Regency Orlando
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

5 out of 5
14200 Bonnet Creek Resort Lane Orlando FL
Fully refundableReserve now, pay when you stay
Book a stay at this luxury resort in Orlando. Enjoy 2 outdoor pools, a full-service spa, and 12 restaurants. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (423 reviews)
Great stay

Reviewed on Dec 20, 2025

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
CoCo Key Hotel and Water Resort 

CoCo Key Hotel and Water Resort 

3.5 out of 5
7400 International Dr Orlando FL
Fully refundableReserve now, pay when you stay
Book a stay at this family-friendly hotel in Orlando. Enjoy 3 outdoor pools, 4 restaurants, and 2 poolside bars. Our guests praise the pool and the helpful staff ...
7.8/10 Good! (3,734 reviews)
Very enjoyable establishment with friendly staff

Reviewed on Dec 17, 2025

CoCo Key Hotel and Water Resort 
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 $92
  • 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.