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Lakeland - Winter Haven Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Lakeland - Winter Haven vacation rentals

A swimming pool with a fence, lounge chairs, and a palm tree.

1. 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
$70 nightly
The price is $79
Nov 29 - Nov 30
Total with taxes and fees
Lake Ida Beach 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.

2. 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
$211 nightly
The price is $237
Nov 12 - Nov 13
Total with taxes and fees
BlockHaven near Legoland & Disney
A swimming pool with a waterfall feature, lounge chairs, and a gazebo.

3. 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, (7,203 reviews)
"great place to stay!"
United States
Julie
$111 nightly
The price is $125
Nov 30 - Dec 1
Total with taxes and fees
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
A swimming pool with lounge chairs, surrounded by palm trees and a dock extending into a body of water, during sunset.

4. The Russell Lake House

The Russell Lake House
Winter Haven
9.8 out of 10, Exceptional, (25 reviews)
"Nice place!"
United States
Jake D.
$190 nightly
The price is $210
Oct 31 - Nov 1
Total with taxes and fees
The Russell Lake House
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, Excellent, (5,252 reviews)
"Great place to stay at a great place."
United States
Desiree
$104 nightly
The price is $118
Nov 29 - Nov 30
Total with taxes and fees
Vacation Village Orlando, Celebration
A two-story house with a porch, surrounded by palm trees and greenery.

6. Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (383 reviews)
"My favorite place to stay in Kissimmee"
United States
James
$127 nightly
The price is $144
Nov 20 - Nov 21
Total with taxes and fees
Barefoot'n Resort Kissimmee Orlando
A riverside cabin with a dock, surrounded by lush greenery and a cloudy sky.

7. 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
$108 nightly
The price is $121
Nov 9 - Nov 10
Total with taxes and fees
Camp Mack Lodge, Marina & RV Resort
A swimming pool with lounge chairs and umbrellas, a covered seating area, and a building with a balcony in the background.

8. 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, (584 reviews)
"Great place to stay. Large rooms. Had two bedrooms/bathrooms with king size bed in each room. Lots of things to do. Even had 18 hole Putt Putt course to enjoy for free."
United States
Lynn
$118 nightly
The price is $132
Nov 1 - Nov 2
Total with taxes and fees
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
A spacious lobby with a seating area, a counter with a menu board, and a kitchen area in the background.

9. Dundee | King Bed Non Smoking

Dundee | King Bed Non Smoking
Dundee FL
10.0 out of 10, Exceptional, (122 reviews)
"Comfy beds really helped recharge after busy days at nearby attractions."
United States
Anonymous traveler
$79 nightly
The price is $87
Oct 31 - Nov 1
Total with taxes and fees
Dundee | King Bed Non Smoking
A bedroom with a bed, a ceiling fan, a desk, a chair, and a door.

10. THE SIGNATURE ORANGE GROVE KING SUITE

THE SIGNATURE ORANGE GROVE KING SUITE
Lake Alfred
9.6 out of 10, Exceptional, (27 reviews)
"Great place to stay while there on business by myself!"
United States
Don V.
$102 nightly
The price is $112
Nov 1 - Nov 2
Total with taxes and fees
THE SIGNATURE ORANGE GROVE KING SUITE
A hotel room with a bed, a framed picture on the wall, and a view of the outside.

11. 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
$111 nightly
The price is $123
Nov 3 - Nov 4
Total with taxes and fees
King Bed|Non smoking
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.

12. Tiny Paradise

Tiny Paradise
Winter Haven
9.6 out of 10, Exceptional, (17 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
Nov 1 - Nov 2
Total with taxes and fees
Tiny Paradise
A cozy cabin-style bedroom with a large bed, a sitting area with a couch, and a kitchenette.

13. The Lake Alfred Citrus Wood Guest Cabin

The Lake Alfred Citrus Wood Guest Cabin
Lake Alfred
9.6 out of 10, Exceptional, (63 reviews)
"Very peaceful and clean place to stay. Easy to find and in a great location."
United States
Teresa
$119 nightly
The price is $131
Nov 1 - Nov 2
Total with taxes and fees
The Lake Alfred Citrus Wood Guest Cabin
Interior

14. Upstay 3BR Condo w Pool & Patio Near Disney

Upstay 3BR Condo w Pool & Patio Near Disney
4.0 star property
Winter Garden
$207 nightly
The price is $232
Nov 2 - Nov 3
Total with taxes and fees
Upstay 3BR Condo w Pool & Patio Near Disney
A modern living room with a TV, bookshelves, a dining area with chairs and a table, and a kitchen with a microwave.

15. Charming Suite In The Heart Of Lakeland

Charming Suite In The Heart Of Lakeland
Lakeland
9.0 out of 10, Wonderful, (79 reviews)
"very nice place"
United States
Benjamin P.
$129 nightly
The price is $142
Nov 5 - Nov 6
Total with taxes and fees
Charming Suite In The Heart Of Lakeland
A modern kitchen with stainless steel appliances, a microwave, and a refrigerator.

16. Studio Signature

Studio Signature
Lakeland
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful apartment in a quiet neighborhood, close to my event. Exceptionally clean, comfortable bed, everything I could have possibly needed in the kitchen. Easy check in and out. Highly recommend and I will be booking this property in the future."
United States
Juanita
$158 nightly
The price is $174
Oct 31 - Nov 1
Total with taxes and fees
Studio Signature
A residential driveway leading to a garage with a white garage door, surrounded by lush greenery and trees.

17. Private Studio Suite

Private Studio Suite
Lakeland
9.6 out of 10, Exceptional, (20 reviews)
"Excellent stay. Would definitely book again."
United States
Heather
$111 nightly
The price is $121
Nov 8 - Nov 9
Total with taxes and fees
Private Studio Suite
A living room with a sofa, a kitchen area with a counter and chairs, and a TV mounted on the wall.

18. RED DOOR HOUSE!

RED DOOR HOUSE!
South Lake Morton
9.6 out of 10, Exceptional, (70 reviews)
"Conveniently located and clean"
United States
Rachel
$253 nightly
The price is $280
Nov 19 - Nov 20
Total with taxes and fees
RED DOOR HOUSE!
A thatched-roof gazebo with a wooden fence, surrounded by white lounge chairs on a sandy area.

19. Lifetime of Vacations Resort

Lifetime of Vacations Resort
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (186 reviews)
"We absolutely love coming to lifetime and grand lake resort. This is our favorite place to stay!!"
United States
Alena
$105 nightly
The price is $117
Nov 29 - Nov 30
Total with taxes and fees
Lifetime of Vacations Resort
A reception area with a check-in counter, two red chairs, and a tiled floor.

20. 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
$123 nightly
The price is $137
Oct 31 - Nov 1
Total with taxes and fees
2 Full Beds|Non-Smoking
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 Berkley, Orlando

The Berkley, Orlando

10/10 Excellent
"Can’t fault anything. Room fantastic and well equipped with everything required. Really family friendly. Staff really helpful."
Andrew 1-night trip
Posted 2 hours ago
The Berkley, 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 $103 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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