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Lakeland - Winter Haven Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Lakeland - Winter Haven vacation 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, Wonderful, (7,067 reviews)
"Great place to stay!"
United States
Melissa
$137 nightly
The price is $154
Nov 5 - Nov 6
Total with taxes and fees
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
A large hotel complex with multiple high-rise buildings, a central swimming pool, and surrounding greenery.

2. Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (5,171 reviews)
"Great friendly staff close to the parks and great food and transportation to local fun spots it was my second visit and ill deffinetly be back again"
United States
Zachary
$101 nightly
The price is $115
Nov 11 - Nov 12
Total with taxes and fees
Vacation Village Orlando, Celebration
A two-story house with a porch, surrounded by palm trees and greenery.

3. Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (376 reviews)
"Nice rooms pool was great definitely will be back"
United States
Gilbert
$100 nightly
The price is $114
Oct 18 - Oct 19
Total with taxes and fees
Barefoot'n Resort Kissimmee Orlando
A riverside cabin with a dock, surrounded by lush greenery and a cloudy sky.

4. Camp Mack Lodge, Marina & RV Resort

Camp Mack Lodge, Marina & RV Resort
3.0 star property
Lake Wales
9.0 out of 10, Wonderful, (225 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
$99 nightly
The price is $110
Oct 21 - Oct 22
Total with taxes and fees
Camp Mack Lodge, Marina & RV 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.

5. BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
10.0 out of 10, Exceptional, (8 reviews)
"Very nice house for a small family! Close to everything!"
United States
Yuliett
$214 nightly
The price is $240
Nov 12 - Nov 13
Total with taxes and fees
BlockHaven near Legoland & Disney
A cozy cabin-style bedroom with a large bed, a sitting area with a couch, and a kitchenette.

6. The Lake Alfred Citrus Wood Guest Cabin

The Lake Alfred Citrus Wood Guest Cabin
Lake Alfred
9.6 out of 10, Exceptional, (62 reviews)
"While staying at Lake Alfred Citrus Wood Cabin we were very comfortable felt like home and it is a very friendly atmosphere. Pets WELCOME. We plan to stay again in the near future."
United States
stephen s.
$119 nightly
The price is $131
Oct 16 - Oct 17
Total with taxes and fees
The Lake Alfred Citrus Wood Guest Cabin
A swimming pool with lounge chairs, surrounded by palm trees and a dock extending into a body of water, during sunset.

7. The Russell Lake House

The Russell Lake House
Winter Haven
9.8 out of 10, Exceptional, (24 reviews)
"Host was attentive and excellent!!!"
United States
jason s.
$190 nightly
The price is $210
Oct 18 - Oct 19
Total with taxes and fees
The Russell Lake House
A swimming pool with a fence, lounge chairs, and a palm tree.

8. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (198 reviews)
"Clean room and private area loved it"
United States
Heather
$66 nightly
The price is $73
Nov 15 - Nov 16
Total with taxes and fees
Lake Ida Beach Resort
An aerial view of a resort with multiple swimming pools, a large central pool, and surrounding greenery.

9. 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, Wonderful, (2,315 reviews)
"Our stay was amazing. The cottage was fantastic and the property offers so many amenities. Will definitely stay here again."
United States
Michael
$393 nightly
The price is $447
Oct 26 - Oct 27
Total with taxes and fees
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
A spacious indoor area with a seating area, a counter, and a kitchen visible in the background.

10. Dundee | 2 Queen Bed Nmsk

Dundee | 2 Queen Bed Nmsk
Dundee FL
10.0 out of 10, Exceptional, (90 reviews)
"Location is close to Legoland, so perfect for families visiting with kids."
United States
Anonymous traveler
$94 nightly
The price is $104
Oct 16 - Oct 17
Total with taxes and fees
Dundee | 2 Queen Bed Nmsk
Interior

11. Upstay: Stylish 3BR Condo w Pationear Disney

Upstay: Stylish 3BR Condo w Pationear Disney
4.0 star property
Winter Garden
$243 nightly
The price is $273
Oct 16 - Oct 17
Total with taxes and fees
Upstay: Stylish 3BR Condo w Pationear Disney
An aerial view of a resort with two large swimming pools, a tennis court, and a small playground.

12. Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1,937 reviews)
"Great place to stay!"
United States
David
$107 nightly
The price is $121
Oct 18 - Oct 19
Total with taxes and fees
Barefoot Suites
A thatched-roof gazebo with a wooden fence, surrounded by white lounge chairs on a sandy area.

13. Lifetime of Vacations Resort

Lifetime of Vacations Resort
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (183 reviews)
"We absolutely love coming to lifetime and grand lake resort. This is our favorite place to stay!!"
United States
Alena
$100 nightly
The price is $111
Oct 18 - Oct 19
Total with taxes and fees
Lifetime of Vacations Resort
A hotel room with a bed, a framed picture on the wall, and a view of the outside.

14. King Bed|Non smoking

King Bed|Non smoking
Bartow FL
10.0 out of 10, Exceptional, (120 reviews)
"Location is key when you're busy exploring, it was easy getting back after sightseeing all day!"
United States
Anonymous traveler
$118 nightly
The price is $131
Oct 16 - Oct 17
Total with taxes and fees
King Bed|Non smoking
A golf course with a large rock formation, palm trees, and a well-maintained green.

15. 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, Wonderful, (582 reviews)
"Very nice and clean"
United States
Rob
$118 nightly
The price is $132
Oct 18 - Oct 19
Total with taxes and fees
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
A building with a red door, numbered 132C, and a small porch area with a metal stool and a green bucket with a wooden stick.

16. Tiny Paradise

Tiny Paradise
Winter Haven
9.4 out of 10, Exceptional, (16 reviews)
"Check in was easy, this little house had everything we needed! Owner very responsive to needs very quickly through app. We would stay again!"
United States
Cheryl K.
$118 nightly
The price is $130
Oct 25 - Oct 26
Total with taxes and fees
Tiny Paradise
A modern living room with a glass dining table, leather sofas, and a flat-screen TV.

17. Grand Lake Resort

Grand Lake Resort
3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (267 reviews)
"Place was very clean and staff was a great help very friendly and helpful."
United States
Raymond
$93 nightly
The price is $105
Oct 18 - Oct 19
Total with taxes and fees
Grand Lake Resort
A reception area with a check-in counter, two red chairs, and a tiled floor.

18. 2 Full Beds|Non-Smoking

2 Full Beds|Non-Smoking
Bartow FL
10.0 out of 10, Exceptional, (266 reviews)
"Great stay in Bartow."
United States
Anonymous traveler
$91 nightly
The price is $101
Oct 16 - Oct 17
Total with taxes and fees
2 Full Beds|Non-Smoking
A spacious lobby with a grand chandelier, large windows offering a view of a pool, and a second-floor balcony with a railing.

19. The Berkley, Orlando

The Berkley, Orlando
4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (2,454 reviews)
"Clean rooms, great pool area, reasonably priced"
United States
Dean
$122 nightly
The price is $137
Nov 1 - Nov 2
Total with taxes and fees
The Berkley, Orlando
A bedroom with a bed, a ceiling fan, a desk, a chair, and a door.

20. THE SIGNATURE ORANGE GROVE KING SUITE

THE SIGNATURE ORANGE GROVE KING SUITE
Lake Alfred
9.6 out of 10, Exceptional, (26 reviews)
"Great place to stay while there on business by myself!"
United States
Don V.
$102 nightly
The price is $112
Oct 16 - Oct 17
Total with taxes and fees
THE SIGNATURE ORANGE GROVE KING SUITE
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

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Excellent very spacious, great for large families. Fees will catch you at the end. Paid about 400 for the weekend then Monday I got another charge of 300 no one can explain."
Luis 2-night trip
Posted 6 hours ago
The Grove Resort & Water Park Orlando

Find out more about Lakeland - Winter Haven

Everything you need to know about Lakeland - Winter Haven vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Lakeland - Winter Haven vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Lakeland - Winter Haven vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Lakeland - Winter Haven vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Lakeland - Winter Haven. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Lakeland - Winter Haven in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $105 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Lakeland - Winter Haven rentals

At Expedia, we put the best Lakeland - Winter Haven vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Lakeland - Winter Haven rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Lakeland - Winter Haven vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Lakeland - Winter Haven. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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