Lakeland - Winter Haven Holiday Rentals - Holiday Homes in Lakeland - Winter Haven

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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

Orlando

Julie

RM511 total

includes taxes & fees

16 Nov - 17 Nov

A large hotel complex with multiple high-rise buildings, a central swimming pool, and surrounding greenery.

2. Vacation Village Orlando, Celebration

Kissimmee

Richard Allen

RM437 total

includes taxes & fees

8 Nov - 9 Nov

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

Kissimmee

Cadine

RM2,019 total

includes taxes & fees

27 Oct - 28 Oct

A swimming pool with lounge chairs and umbrellas, a covered seating area, and a building with a balcony in the background.

4. Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Davenport

Rob

RM620 total

includes taxes & fees

27 Oct - 28 Oct

A riverside cabin with a dock, surrounded by lush greenery and a cloudy sky.

5. Camp Mack Lodge, Marina & RV Resort

Lake Wales

Terri

RM489 total

includes taxes & fees

27 Oct - 28 Oct

6. WorldQuest Orlando Resort

Orlando

Jodi

RM1,276 total

includes taxes & fees

27 Oct - 28 Oct

A two-story house with a porch, surrounded by palm trees and greenery.

7. Barefoot'n Resort Kissimmee Orlando

Kissimmee

James

RM526 total

includes taxes & fees

30 Oct - 31 Oct

A resort with a central swimming pool, lounge areas, and a landscaped garden.

8. Marriott's Royal Palms

Orlando

Ernie

RM809 total

includes taxes & fees

18 Nov - 19 Nov

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

9. BlockHaven near Legoland & Disney

Winter Haven

Yuliett

RM955 total

includes taxes & fees

12 Nov - 13 Nov

An aerial view of a resort with two large swimming pools, a tennis court, and a small playground.

10. Barefoot Suites

Kissimmee

Mary

RM592 total

includes taxes & fees

27 Oct - 28 Oct

A spacious lobby with modern furniture, large windows, and a grand piano.

11. Marriott's Sabal Palms

Orlando

Marco

RM814 total

includes taxes & fees

22 Nov - 23 Nov

A resort with a large central pool, multiple guest villas, and a scenic view of the surrounding landscape.

12. Regal Oaks Resort Vacation Townhomes by IDILIQ

Kissimmee

Tina

A spacious lobby with a grand chandelier, large windows offering a view of a pool, and a second-floor balcony with a railing.

13. The Berkley, Orlando

Kissimmee

Kristyn

RM626 total

includes taxes & fees

15 Nov - 16 Nov

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

14. Lake Ida Beach Resort

Winter Haven

Heather

RM288 total

includes taxes & fees

29 Oct - 30 Oct

A wooden dock leading to a calm lake with a 'NO SWIMMING' sign, surrounded by trees and a clear sky.

15. Grand Lake Resort

Kissimmee

Leslie

RM409 total

includes taxes & fees

8 Nov - 9 Nov

An aerial view of a resort with multiple swimming pools, lounge areas, and palm trees.

16. Reunion Resort & Golf Club

Reunion

Karen G

RM1,567 total

includes taxes & fees

29 Oct - 30 Oct

A thatched-roof gazebo with a wooden fence, surrounded by white lounge chairs on a sandy area.

17. Lifetime of Vacations Resort

Kissimmee

Alena

RM442 total

includes taxes & fees

8 Nov - 9 Nov

18. Bahama Bay Resort

Bahama Bay

Kavya

RM1,859 total

includes taxes & fees

30 Oct - 31 Oct

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Top Lakeland - Winter Haven Hotel Reviews

The Berkley, Orlando

8/10 Good

"Great staff. Beautiful property and only about 15 minutes from property. My place was huge with 2 masters both with jetted tubs and another bedroom with bath. I am booking again for the next trip."

Quality Inn & Suites By the Parks

8/10 Good

"Solo traveler here. This is my first time staying at this property. The bed was very comfortable, A/C ice cold, room was spacious. Microwave and fridge are in the room. Shower pressure was good. Several big chain restaurants are in easy driving distance, as well as some shopping and the Disney parks (Animal Kingdom is about 3 miles away). I would probably stay here again. Front desk staff was friendly. I did have a problem with the key not working initially, after I had toted all my luggage up 3 flights of stairs. So I had to take it all down again, walk to the front desk, and get a new key. Second time was the charm. Then I wanted ice to fill my mini cooler. The only machines were by the 3rd floor elevator, which was the same level as my room, but it ran out of ice before I could fill the cooler; so I took the elevator down to the machine by the pool, and it also ran empty before I could finish filling it. Got back to the room with just a little bit of ice in the cooler. It was already late and I had worked all day and then driven up from Miami. I was exhausted. I did not partake in the free breakfast so cannot provide a review about that. I will say the it was very noisy outside and I could hear it inside my room. Fire trucks, police cars, traffic from W-192. As I wrote above, I might stay here again."

Find out more about Lakeland - Winter Haven

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Check prices for these dates

Our top choices for Lakeland - Winter Haven holiday rentals

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

2. Vacation Village Orlando, Celebration

3. Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

4. Holiday Inn Club Vacations Orlando Breeze Resort by IHG

5. Camp Mack Lodge, Marina & RV Resort

6. WorldQuest Orlando Resort

7. Barefoot'n Resort Kissimmee Orlando

8. Marriott's Royal Palms

9. BlockHaven near Legoland & Disney

10. Barefoot Suites

11. Marriott's Sabal Palms

12. Regal Oaks Resort Vacation Townhomes by IDILIQ

13. The Berkley, Orlando

14. Lake Ida Beach Resort

15. Grand Lake Resort

16. Reunion Resort & Golf Club

17. Lifetime of Vacations Resort

18. Bahama Bay Resort

Find holiday rentals that suit your style

Top Lakeland - Winter Haven Hotel Reviews

The Berkley, Orlando

The Grove Resort & Water Park Orlando

Margaritaville Resort Orlando with H2O Waterpark

Westgate Town Center Resort

Meliá Orlando Celebration

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Westgate Vacation Villas Resort

Hilton Vacation Club Aqua Sol Orlando West

Quality Inn & Suites By the Parks

Find out more about Lakeland - Winter Haven

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Lakeland - Winter Haven Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Lakeland - Winter Haven holiday rentals

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

2. Vacation Village Orlando, Celebration

3. Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

4. Holiday Inn Club Vacations Orlando Breeze Resort by IHG

5. Camp Mack Lodge, Marina & RV Resort

6. WorldQuest Orlando Resort

7. Barefoot'n Resort Kissimmee Orlando

8. Marriott's Royal Palms

9. BlockHaven near Legoland & Disney

10. Barefoot Suites

11. Marriott's Sabal Palms

12. Regal Oaks Resort Vacation Townhomes by IDILIQ

13. The Berkley, Orlando

14. Lake Ida Beach Resort

15. Grand Lake Resort

16. Reunion Resort & Golf Club

17. Lifetime of Vacations Resort

18. Bahama Bay Resort

Find holiday rentals that suit your style

Top Lakeland - Winter Haven Hotel Reviews

The Berkley, Orlando

Find out more about Lakeland - Winter Haven

Explore a world of travel with Expedia

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