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Lakeland - Winter Haven Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Lakeland - Winter Haven vacation rentals

A living room with a large mural of marine life, a ceiling fan, a flat-screen TV, and a dining area in the background.

1. BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
10.0 out of 10, Exceptional, (6 reviews)
"We loved this place! It was perfect for all of us! It was nice and clean as well!"
United States
Ericka
$230 nightly
The price is $258
Sep 9 - Sep 10
Total with taxes and fees
BlockHaven near Legoland & Disney
A swimming pool with a waterfall feature, lounge chairs, and a gazebo.

2. 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, (6,706 reviews)
"Great resort"
United States
christina
$123 nightly
The price is $139
Sep 29 - Sep 30
Total with taxes and fees
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
A hotel room with a bed, a framed picture on the wall, and a view of the outside.

3. 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
$84 nightly
The price is $93
Sep 9 - Sep 10
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.

4. Tiny Paradise

Tiny Paradise
Winter Haven
9.6 out of 10, Exceptional, (14 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.
$113 nightly
The price is $124
Sep 9 - Sep 10
Total with taxes and fees
Tiny Paradise
A riverside cabin with a dock, surrounded by lush greenery and a cloudy sky.

5. Camp Mack Lodge, Marina & RV Resort

Camp Mack Lodge, Marina & RV Resort
3.0 star property
Lake Wales
9.0 out of 10, Wonderful, (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
$119 nightly
The price is $133
Sep 9 - Sep 10
Total with taxes and fees
Camp Mack Lodge, Marina & RV Resort
A swimming pool with a fence, lounge chairs, and a palm tree.

6. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (194 reviews)
"The cabins were great loved it there"
United States
Jennifer
$77 nightly
The price is $86
Oct 9 - Oct 10
Total with taxes and fees
Lake Ida Beach Resort
A reception area with a check-in counter, two red chairs, and a tiled floor.

7. 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
$88 nightly
The price is $97
Sep 9 - Sep 10
Total with taxes and fees
2 Full Beds|Non-Smoking
A modern living room with a TV, bookshelves, a dining area with chairs and a table, and a kitchen with a microwave.

8. Charming Suite In The Heart Of Lakeland

Charming Suite In The Heart Of Lakeland
Lakeland
8.8 out of 10, Excellent, (78 reviews)
"very nice place"
United States
Benjamin P.
$129 nightly
The price is $142
Sep 10 - Sep 11
Total with taxes and fees
Charming Suite In The Heart Of Lakeland
A large hotel complex with multiple high-rise buildings, a central swimming pool, and surrounding greenery.

9. Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (4,995 reviews)
"It's is a very nice resort my family enjoyed it and use way they rooms are designed is awesome you can get a little privacy from your kids and love ones at the same time."
United States
Vernon
$97 nightly
The price is $110
Sep 9 - Sep 10
Total with taxes and fees
Vacation Village Orlando, Celebration
A cozy cabin-style bedroom with a large bed, a sitting area with a couch, and a kitchenette.

10. The Lake Alfred Citrus Wood Guest Cabin

The Lake Alfred Citrus Wood Guest Cabin
Lake Alfred
9.6 out of 10, Exceptional, (59 reviews)
"Wonderful little cabin perfect for a getaway. Quiet and cozy!"
United States
Sarah P.
$119 nightly
The price is $131
Sep 9 - Sep 10
Total with taxes and fees
The Lake Alfred Citrus Wood Guest Cabin
A spacious lobby with a seating area, a counter with a menu board, and a kitchen area in the background.

11. 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
$96 nightly
The price is $107
Sep 9 - Sep 10
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.

12. THE SIGNATURE ORANGE GROVE KING SUITE

THE SIGNATURE ORANGE GROVE KING SUITE
Lake Alfred
9.6 out of 10, Exceptional, (24 reviews)
"Great place to stay while there on business by myself!"
United States
Don V.
$102 nightly
The price is $112
Sep 9 - Sep 10
Total with taxes and fees
THE SIGNATURE ORANGE GROVE KING SUITE
A living room with a sofa, a kitchen area with a counter and chairs, and a TV mounted on the wall.

13. RED DOOR HOUSE!

RED DOOR HOUSE!
South Lake Morton
9.6 out of 10, Exceptional, (66 reviews)
"Conveniently located and clean"
United States
Rachel
$189 nightly
The price is $208
Sep 9 - Sep 10
Total with taxes and fees
RED DOOR HOUSE!
A modern living room with a grey sofa, a dining area with a round table and chairs, a kitchen with white cabinets, a clock, and a decorative wall piece.

14. Cozy 1 bedroom home in Winter Haven perfect for your getaway.

Cozy 1 bedroom home in Winter Haven perfect for your getaway.
Winter Haven
10.0 out of 10, Exceptional, (4 reviews)
"This is such a cozy 1 bedroom unit and the side yard was such a great bonus amenity."
United States
Christopher V.
$170 nightly
The price is $188
Sep 10 - Sep 11
Total with taxes and fees
Cozy 1 bedroom home in Winter Haven perfect for your getaway.
A compact living space with a loft bed, a TV mounted on the wall displaying streaming services, a small bathroom, and a wooden floor.

15. Lakefront Tiny Cottage 4 Miles to LEGOLAND.

Lakefront Tiny Cottage 4 Miles to LEGOLAND.
winter have
9.0 out of 10, Wonderful, (42 reviews)
"Awesome location, very nice"
United States
Kyle P.
$135 nightly
The price is $149
Sep 9 - Sep 10
Total with taxes and fees
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
A residential driveway leading to a garage with a white garage door, surrounded by lush greenery and trees.

16. Private Studio Suite

Private Studio Suite
Lakeland
9.6 out of 10, Exceptional, (19 reviews)
"Excellent stay. Would definitely book again."
United States
Heather
$115 nightly
The price is $126
Sep 23 - Sep 24
Total with taxes and fees
Private Studio Suite
A golf course with a large rock formation, palm trees, and a well-maintained green.

17. 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, (578 reviews)
"First time experience. The stay was pretty good."
United States
Anquanice
$118 nightly
The price is $132
Sep 10 - Sep 11
Total with taxes and fees
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
An outdoor hot tub area with a pool, surrounded by chairs and a table.

18. Legoland Splash Escape with pool and hot tub!

Legoland Splash Escape with pool and hot tub!
Winter Haven
10.0 out of 10, Exceptional, (71 reviews)
"We had a great time staying here. The house was well maintained. The kids enjoyed the pool."
United States
Amy
$306 nightly
The price is $338
Sep 9 - Sep 10
Total with taxes and fees
Legoland Splash Escape with pool and hot tub!
A modern kitchen with stainless steel appliances, a microwave, and a refrigerator.

19. Studio Signature

Studio Signature
Lakeland
10.0 out of 10, Exceptional, (11 reviews)
"Clean cute friendly quiet neighborhood really enjoyed this stay and will likely stay again in future"
United States
Mel B.
$158 nightly
The price is $174
Sep 17 - Sep 18
Total with taxes and fees
Studio Signature
A grassy area with a view of the sunset over a body of water, a covered structure, and a palm tree.

20. Cozy 1 Bedroom home on Beautiful Lake Alfred

Cozy 1 Bedroom home on Beautiful Lake Alfred
Lake Alfred
8.6 out of 10, Excellent, (38 reviews)
"Nice, older lake house with a great location. The sunsets are exceptional."
United States
Rob G.
$176 nightly
The price is $195
Sep 9 - Sep 10
Total with taxes and fees
Cozy 1 Bedroom home on Beautiful Lake Alfred
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

Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

10/10 Excellent
"Aside from enjoying the property amenities, having the adjacent Sunset Walk was great!"
Orlando 3-night trip
Posted 1 hour ago
Margaritaville Resort Orlando with H2O Waterpark

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 $101 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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