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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Lakeland - Winter Haven holiday rentals

A swimming pool with a waterfall feature, lounge chairs, and a gazebo.

1. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
4.0 star property
Orlando
9.2 out of 10, 6750, (6,750 reviews)
"Great resort"
United States
christina
The price is ฿4,521
฿5,086 total
includes taxes & fees
5 Oct - 6 Oct
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
A golf course with a large rock formation, palm trees, and a well-maintained green.

2. Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Holiday Inn Club Vacations Orlando Breeze Resort by IHG
3.5 star property
Davenport
9.2 out of 10, 578, (578 reviews)
"First time experience. The stay was pretty good."
United States
Anquanice
The price is ฿3,819
฿4,966 total
includes taxes & fees
15 Oct - 16 Oct
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
An aerial view of a resort with multiple swimming pools, a large central pool, and surrounding greenery.

3. Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
4.0 star property
Kissimmee
9.0 out of 10, 2258, (2,258 reviews)
"nice place to stay!"
United States
Victor
The price is ฿6,742
฿16,518 total
includes taxes & fees
16 Sept - 17 Sept
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
An aerial view of a resort with multiple swimming pools, lounge areas, and palm trees.

4. Reunion Resort & Golf Club

Reunion Resort & Golf Club
5.0 star property
Reunion
8.8 out of 10, 1621, (1,621 reviews)
"Great stay! Will visit again."
United States
RYAN
The price is ฿7,611
฿10,206 total
includes taxes & fees
16 Sept - 17 Sept
Reunion Resort & Golf Club
A large hotel complex with multiple high-rise buildings, a central swimming pool, and surrounding greenery.

5. Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, 5033, (5,033 reviews)
"Nice hotel and great location close to the Parks."
United States
Monica
The price is ฿2,518
฿3,688 total
includes taxes & fees
17 Sept - 18 Sept
Vacation Village Orlando, Celebration
A modern lobby with a wooden ceiling, a TV mounted on a wooden panel, and a seating area with blue chairs and a white sofa.

6. Marriott's Royal Palms

Marriott's Royal Palms
4.0 star property
Orlando
9.4 out of 10, 322, (322 reviews)
"Place is minutes from away from Disney Springs and major attractions, clean and modern, with a wonderful golf course."
United States
Ernie
The price is ฿6,610
฿7,436 total
includes taxes & fees
5 Oct - 6 Oct
Marriott's Royal Palms

7. WorldQuest Orlando Resort

WorldQuest Orlando Resort
4.0 star property
Orlando
8.4 out of 10, 4093, (4,093 reviews)
"One of my favorite places to stay in Orlando"
United States
Jodi
The price is ฿5,676
฿12,057 total
includes taxes & fees
16 Sept - 17 Sept
WorldQuest Orlando Resort
A living room with a large mural of marine life, a ceiling fan, a flat-screen TV, and a dining area in the background.

8. BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
10.0 out of 10, 6, (6 reviews)
"We loved this place! It was perfect for all of us! It was nice and clean as well!"
United States
Ericka
The price is ฿2,227
฿8,527 total
includes taxes & fees
20 Sept - 21 Sept
BlockHaven near Legoland & Disney
A spacious lobby with modern furniture, large windows, and a grand piano.

9. Marriott's Sabal Palms

Marriott's Sabal Palms
4.0 star property
Orlando
9.6 out of 10, 238, (238 reviews)
"The Hotel was fantastic and made travel to Disney World super easy"
United States
Marco
The price is ฿5,387
฿6,061 total
includes taxes & fees
9 Oct - 10 Oct
Marriott's Sabal Palms
An aerial view of a resort with two large swimming pools, a tennis court, and a small playground.

10. Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, 1920, (1,920 reviews)
"Was very handy having the laundry and was next door to old town so plenty of options for food"
United Kingdom
juliette
The price is ฿3,155
฿4,234 total
includes taxes & fees
16 Sept - 17 Sept
Barefoot Suites
A building with a sign reading "High Point World Resort Welcome Center."

11. High Point World Resort

High Point World Resort
3.5 star property
Kissimmee
8.8 out of 10, 175, (175 reviews)
"great place to stay!"
United States
Dylan
The price is ฿4,610
฿5,233 total
includes taxes & fees
16 Sept - 17 Sept
High Point World Resort
A riverside cabin with a dock, surrounded by lush greenery and a cloudy sky.

12. Camp Mack Lodge, Marina & RV Resort

Camp Mack Lodge, Marina & RV Resort
3.0 star property
Lake Wales
9.0 out of 10, 223, (223 reviews)
"Camp Mack is an awesome place for getting away for a few days or longer. The surroundings are beautiful, and the people are so friendly."
United States
Terri
The price is ฿3,534
฿3,958 total
includes taxes & fees
11 Oct - 12 Oct
Camp Mack Lodge, Marina & RV Resort

13. Bahama Bay Resort

Bahama Bay Resort
3.5 star property
Bahama Bay
8.6 out of 10, 2100, (2,100 reviews)
"Had a wonderful stay at Bahama Bay Resort. The property was clean, comfortable, and had everything we needed for a relaxing stay. The resort itself was beautiful and peaceful, and the location was convenient. Everything went smoothly from check-in to check-out. Would definitely stay here again!"
United States
Kavya
The price is ฿6,321
฿15,136 total
includes taxes & fees
21 Sept - 22 Sept
Bahama Bay 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.
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Top Lakeland - Winter Haven Hotel Reviews

Westgate Town Center Resort

Westgate Town Center Resort

10/10 Excellent
"Everything was great will return thanks"
Corey 4-night trip
Posted 3 hours ago
Westgate Town Center Resort

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