Find hotels with pools in Oakland, Winter Garden from $55

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Check availability on Oakland Hotels with a Pool

Our top choices for Oakland hotels with a pool

Outdoor pool
The Oak View Place..

The Oak View Place..

The Oak View Place..
Oakland
9.2 out of 10, Wonderful, (10)
"The VRBO looked brand new and I only knew it was not because of the reviews from previous years. The live oak trees on the property added to the beauty of the surroundings."
United States
Libba F.
$260 nightly
The price is $289
Dec 14 - Dec 15
Total with taxes and fees
The Oak View Place..
Outdoor pool, pool umbrellas, sun loungers
Hyatt House Orlando International Drive

Hyatt House Orlando International Drive

Hyatt House Orlando International Drive
4.0 star property
International Drive District
9.4 out of 10, Exceptional, (1353)
"Room, Breakfast, location AAAA+ "
United States
Ahmed Gabriel
$98 nightly
The price is $110
Dec 14 - Dec 15
Total with taxes and fees
Hyatt House Orlando International Drive
Reception
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (1966)
"Beautiful resort with very friendly staff. "
United States
kristie
$103 nightly
The price is $117
Dec 14 - Dec 15
Total with taxes and fees
Kompose Boutique Resort at Theme Parks
Terrace/patio
Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South
4.0 star property
Kissimmee
9.4 out of 10, Exceptional, (1234)
"Nice place very good"
United States
Hugo
$104 nightly
The price is $118
Dec 14 - Dec 15
Total with taxes and fees
Embassy Suites by Hilton Orlando Lake Buena Vista South
Outdoor pool, pool umbrellas, sun loungers
Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center
3.5 star property
International Drive District
7.4 out of 10, Good, (3884)
"Room was good hotel was nice and clean"
United States
Amy
$80 nightly
The price is $90
Dec 14 - Dec 15
Total with taxes and fees
Wyndham I-Drive Avanti Resort & Conference Center
Outdoor pool, pool umbrellas, sun loungers
Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista
3.0 star property
Orlando
8.8 out of 10, Excellent, (1902)
"Great rooms, staff, and property!"
United States
Cindy
$74 nightly
The price is $83
Dec 14 - Dec 15
Total with taxes and fees
Aloft Orlando Lake Buena Vista
Outdoor banquet area
Rosen Shingle Creek

Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
Orlando
9.4 out of 10, Exceptional, (4351)
"Great resort "
United States
Camille
$99 nightly
The price is $112
Dec 14 - Dec 15
Total with taxes and fees
Rosen Shingle Creek
Front of property
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
Kissimmee
8.2 out of 10, Very Good, (5146)
"Overall good experience would stay again"
United States
Jacquelyn
$66 nightly
The price is $75
Dec 17 - Dec 18
Total with taxes and fees
Palazzo Lakeside 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.
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Top Oakland Hotel Reviews

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Staff was very helpful "
Sarah 1-night trip
Posted 1 day ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Frequently asked questions

What are some accommodations with pools in Oakland?
Universal's Cabana Bay Beach Resort: Hotel, 5-minute walk from Universal Orlando Resort. Features a lazy river, 2 outdoor pools, and 2 restaurants. Rosen Inn at Pointe Orlando: Hotel, 2-minute walk from Pointe Orlando. Offers 2 coffee shops/cafes, 3 outdoor pools, and complimentary wireless internet access. DoubleTree by Hilton at the Entrance to Universal Orlando: Hotel, 2-minute walk from Universal Orlando Resort. Provides a children's pool, an outdoor pool, and 2 restaurants. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Hotel located near Disney Springs™. Features 6 outdoor pools, a children's pool, and 3 restaurants. Hyatt Regency Orlando: Hotel, 2-minute walk from Orange County Convention Center. Offers a children's pool, an outdoor pool, and 3 restaurants.
What is there to see and do in Oakland?
While you're in the area, consider exploring places like Magic Kingdom® Park, Walt Disney World® Resort, and Universal Studios Florida. Make a point to visit attractions like Beachcomber Beach and Lake Louisa State Park.

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