Hotels Near
Oakland

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Featured Oakland Hotels

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! (6,294 reviews)
"Everything was great totally different than the embarrassment at the SeaWorld location which i vow never to return."

Reviewed on May 30, 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
Marriott's Grande Vista
Marriott's Grande Vista
4 out of 5
5925 Avenida Vista, Orlando, FL
Fully refundableReserve now, pay when you stay
Stay at this 4-star spa hotel in Orlando. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. ...
8.8/10 Excellent! (2,447 reviews)
"Beautiful"

Reviewed on May 29, 2025

Marriott's Grande Vista
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! (2,961 reviews)
"We booked online and were extremely happy with the entire resort. Everyone working there was wonderful from check in to check out. Our room was immaculate and the pool and marketplace were gorgeous. We will be back!!"

Reviewed on May 28, 2025

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Kompose Boutique Resort at Theme Parks
Kompose Boutique Resort at Theme Parks
4 out of 5
7491 W Irlo Bronson Memorial Hwy, Kissimmee, FL
Fully refundableReserve now, pay when you stay
Stay at this 4-star business-friendly resort in Kissimmee. Enjoy free WiFi, free parking, and 2 hot tubs. Popular attractions Disney's Animal Kingdom® Theme ...
9.4/10 Exceptional! (193 reviews)
"Kids loved the pool area"

Reviewed on May 31, 2025

Kompose Boutique Resort at Theme Parks
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 6 outdoor pools, 3 restaurants, and 2 hot tubs. Our guests praise the pool and the helpful ...
7.8/10 Good! (7,724 reviews)
"Was quiet and perfect for kids"

Reviewed on May 29, 2025

The Grove Resort & Water Park Orlando
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
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! (4,449 reviews)
"This is my fifth or sixth time staying at this hotel. Staff are always so kind and helpful! The rooms are clean and consistent. Alexis and Ivonne at the front desk helped me when our door lock malfunctioned and they were so kind and patient. Will definitely be back again (:"

Reviewed on May 31, 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! (5,175 reviews)
"We really enjoyed the atmosphere. The whole 50s/60s theme was done very nicely and I felt.transported in time to an era that predates my birth, but always found to be cool. The staff was helpful and courteous at all times. Walking distance to Volcano Bay and early entry to the other Universal Parks ..."

Reviewed on May 30, 2025

Universal's Cabana Bay Beach Resort
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! (3,075 reviews)
"The rooms great the pool and waterslide area was great was renovation going on so some areas was not that great and of course everything was expensive but it is a hotel resort so what do you expect but the most ridiculous thing was they charge you for the pool floaties to make sure your kids don't ..."

Reviewed on May 28, 2025

Holiday Inn Resort Orlando Suites - Waterpark by IHG
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! (4,955 reviews)
"I enjoyed my stay at the property but couldn’t help to notice that some cooks handled food with their hands. This seemed unsanitary and I was not able to eat from that station. But overall, I had a great time with my partner. The place was great and relaxing. Drinks were not bad. Food was ok."

Reviewed on May 29, 2025

Westgate Lakes Resort & Spa Universal Studios Area
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
Stay at this 4-star eco-certified hotel in Orlando. Enjoy free WiFi, 5 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
9.2/10 Wonderful! (1,671 reviews)
"Great pool, good room. Quiet. Overall 9.5 Only negatives were toilet rocked a little and alarm clock did not work."

Reviewed on May 28, 2025

Sheraton Vistana Villages Resort Villas, I-Drive/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! (3,107 reviews)
"Room and pool as well as staff very nice"

Reviewed on May 29, 2025

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Drury Plaza Hotel Orlando - Disney Springs Area
Drury Plaza Hotel Orlando - Disney Springs Area
3 out of 5
2000 Hotel Plaza Boulevard, Lake Buena Vista, FL
Fully refundableReserve now, pay when you stay
Stay at this 3-star business-friendly hotel in Lake Buena Vista. Enjoy free breakfast, free WiFi, and 3 restaurants. Our guests praise the breakfast and the ...
9.6/10 Exceptional! (4,069 reviews)
"Perfect location for Disney"

Reviewed on May 31, 2025

Drury Plaza Hotel Orlando - Disney Springs Area
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 $94
  • 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.