Lakeland - Winter Haven Vacation Rentals

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Check prices for these dates

In two weeks
Sep 12 - Sep 14
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23
In four months
Dec 19 - Dec 21

Browse Select Lakeland - Winter Haven Vacation Homes

Our top choices for Lakeland - Winter Haven vacation homes

The Berkley, Orlando
Lobby

The Berkley, Orlando

4.0 star property
9.6 out of 10, Exceptional, (1890)
"Beautiful, perfect for a family getaway"
The price is CA $135
CA $168 total
includes taxes & fees
Aug 28 - Aug 29
The Berkley, Orlando
Formosa Valley Resort by UNE Homes
Private pool

Formosa Valley Resort by UNE Homes

4.0 star property
9.4 out of 10, Exceptional, (168)
"My children and I enjoyed our stay. This place is close to everything. The property managers responds within minutes for any inquires. You can also reach someone by phone at any hour. The home was very clean with everything you need! I would definitely recommend!"
The price is CA $211
CA $681 total
includes taxes & fees
Aug 28 - Aug 29
Formosa Valley Resort by UNE Homes
Amazing, Brand New 10BD/8BR for Up to 28 Guests
10 bedrooms, iron/ironing board, travel crib, free WiFi

Amazing, Brand New 10BD/8BR for Up to 28 Guests

3.0 star property
10.0 out of 10, Exceptional, (5)
"My family and I enjoyed this property so much! It was clean, decorated nicely and comfy. The rooms were spacious and the pool/jacuzzi/grill was an extra nice touch. The hosts were responsive and accommodating. I will definitely book again. "
Amazing, Brand New 10BD/8BR for Up to 28 Guests
Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5
Outdoor pool, a heated pool

Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5

10.0 out of 10, Exceptional, (68)
"Very happy with our stay here and hope to return."
Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5
Uncover One-of-a-Kind Wonderland! Themed Rooms + Free Pool Heat & Magical Perks!
Outdoor pool, a heated pool

Uncover One-of-a-Kind Wonderland! Themed Rooms + Free Pool Heat & Magical Perks!

10.0 out of 10, Exceptional, (108)
"We had such a wonderful stay and can’t wait to come back next year! This house was a dream for all 4 families!"
Uncover One-of-a-Kind Wonderland! Themed Rooms + Free Pool Heat & Magical Perks!
The Grand Village 4BR Pool Home near Disney Parks
Interior

The Grand Village 4BR Pool Home near Disney Parks

The Grand Village 4BR Pool Home near Disney Parks
6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
Pool

6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ

9.4 out of 10, Exceptional, (240)
"We were there for my brother's surprise 60th birthday "
6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
Luxury 6BR near Disney, Pool, Jacuzzi, Game & Theme Room
Outdoor pool, a heated pool

Luxury 6BR near Disney, Pool, Jacuzzi, Game & Theme Room

9.8 out of 10, Exceptional, (22)
"This place is everything you want. Easy to find and got everything you need to make your vacation a dream. Close to the parks, places to eat and shop. Uber-eats is also an option. I had a great time! "
Luxury 6BR near Disney, Pool, Jacuzzi, Game & Theme Room
Spectacular 5⭐Villa -⛳Golf Course View, Salt💧Pool/Spa, Game Room, BBQ & Theater
Outdoor pool, a heated pool

Spectacular 5⭐Villa -⛳Golf Course View, Salt💧Pool/Spa, Game Room, BBQ & Theater

10.0 out of 10, Exceptional, (47)
"We really enjoyed this home! Plenty of space for us to work and play while here for a convention!!! "
Spectacular 5⭐Villa -⛳Golf Course View, Salt💧Pool/Spa, Game Room, BBQ & Theater
Every Amenity! 2 Theaters, Private Gym, Pool, Baby Equip FREE, Outdoor Grill
Outdoor dining

Every Amenity! 2 Theaters, Private Gym, Pool, Baby Equip FREE, Outdoor Grill

9.4 out of 10, Exceptional, (50)
"We had a great stay, the host was responsive and everything was as expected."
Every Amenity! 2 Theaters, Private Gym, Pool, Baby Equip FREE, Outdoor Grill
Newly Renovated 8BR Villa equipped with a heated pool / Spa Located near Disney
Indoor pool, outdoor pool

Newly Renovated 8BR Villa equipped with a heated pool / Spa Located near Disney

9.6 out of 10, Exceptional, (107)
"Everything was as pictured! The host was helpful and quick to answer any questions! We loved this house and everything about it. It was beautiful and perfect for our family. "
Newly Renovated 8BR Villa equipped with a heated pool / Spa Located near Disney
Disney Area – Heated Pool/Spa, Outdoor TV, Walk to Resort Amenities
Outdoor pool, a heated pool

Disney Area – Heated Pool/Spa, Outdoor TV, Walk to Resort Amenities

10.0 out of 10, Exceptional, (65)
"We had a wonderful vacation staying at this beautiful home! Everything was exactly as pictured and described. Susan was a wonderful host and was an amazing communicator! "
Disney Area – Heated Pool/Spa, Outdoor TV, Walk to Resort Amenities
Extended Stay Retreat – Private Pool, Spa & Space for Everyone
Terrace/patio

Extended Stay Retreat – Private Pool, Spa & Space for Everyone

9.8 out of 10, Exceptional, (60)
"The property was clean, and the host was always accessible and friendly. Quiet neighborhood with easy access to everything "
Extended Stay Retreat – Private Pool, Spa & Space for Everyone
3 Miles to Disney! Themed Home FREE Heated Pool & Spa Theater Grill & 7 Bedrooms
Outdoor pool, a heated pool

3 Miles to Disney! Themed Home FREE Heated Pool & Spa Theater Grill & 7 Bedrooms

10.0 out of 10, Exceptional, (184)
"Loved staying at this home again!"
3 Miles to Disney! Themed Home FREE Heated Pool & Spa Theater Grill & 7 Bedrooms
Disney Area Villa, 5 BDRM in Gated Aviana Resort with Pool, Spa, Wi-Fi
A heated pool

Disney Area Villa, 5 BDRM in Gated Aviana Resort with Pool, Spa, Wi-Fi

9.4 out of 10, Exceptional, (130)
"Great host, smooth checkin, comfortable and safe neighborhood "
Disney Area Villa, 5 BDRM in Gated Aviana Resort with Pool, Spa, Wi-Fi
ChampionsGate, 9 Bed Luxury Spacious Villa, Sleeps 30+2, West Facing Pool & Spa
Outdoor pool, a heated pool

ChampionsGate, 9 Bed Luxury Spacious Villa, Sleeps 30+2, West Facing Pool & Spa

9.4 out of 10, Exceptional, (147)
"Absolutely one of the best experiences i have had in renting a vacation home. No issues at all. Great location, helpful employees at gate that were always smiling, and everything listed was readily available at the property. 5 star rating!!! "
ChampionsGate, 9 Bed Luxury Spacious Villa, Sleeps 30+2, West Facing Pool & Spa
Luxury 10 Bed w/Pool, Home Theater, & Gameroom!
Outdoor pool, a heated pool

Luxury 10 Bed w/Pool, Home Theater, & Gameroom!

9.8 out of 10, Exceptional, (9)
"Very nice and comfortable enjoyed our time there, pool was great for the kids, will rent again."
Luxury 10 Bed w/Pool, Home Theater, & Gameroom!
Great quiet and comfortable, South Central Lakeland location.
Outdoor pool

Great quiet and comfortable, South Central Lakeland location.

9.8 out of 10, Exceptional, (163)
"The property is awesome, great location and very quiet. Will stay there again. "
The price is CA $105
CA $145 total
includes taxes & fees
Sep 7 - Sep 8
Great quiet and comfortable, South Central Lakeland location.
Minutes from Disney! Clean family size Townhouse with a private pool.
Outdoor pool, a heated pool

Minutes from Disney! Clean family size Townhouse with a private pool.

9.2 out of 10, Wonderful, (77)
"2 families stayed here and the size of the house was enough for all of us to be together when we want and to have our separate area to decompress after a full day at the park. Communicating with the owner was prompt and very easy. Would definitely stay here again!"
Minutes from Disney! Clean family size Townhouse with a private pool.
🌴 2023 Fabulous 5BD - Tiki Bar | Private Pool | 8 Miles to Disney! 🌴
A heated pool

🌴 2023 Fabulous 5BD - Tiki Bar | Private Pool | 8 Miles to Disney! 🌴

5.0 out of 10, (2)
"The rental unit was good and as advertised. We had issues with the door lock beeping during our entire stay despite asking to have it fixed, it was very loud. The check in process was difficult and the waiting to get into the community was chaotic, taking over 45 minutes to get through the front gate and register. Communication with the property manager was ok. They were very nice but seemed reactive. I asked to rent the golf cart ahead of our stay but that was never set up. The community...
🌴 2023 Fabulous 5BD - Tiki Bar | Private Pool | 8 Miles to Disney! 🌴
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

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent
"The staff was very helpful. Plenty of things to do "
lynnette 7-night trip
Posted 2 days ago
Hilton Vacation Club Aqua Sol Orlando West

Find out more about Lakeland - Winter Haven

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Vacation Homes information

Number of reviews
3,403
Accommodation
1326 Vacation Homes
Lowest Price
CA $105
Highest Price
CA $211

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