Book a Lakeland - Winter Haven Resort

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Check prices for these dates

Next weekend
May 2 - May 4
In two weeks
May 9 - May 11
In one month
May 23 - May 25
In two months
Jun 20 - Jun 22

Compare 29 Resorts in Lakeland - Winter Haven with updated reviews, rates, and availability.

The Grove Resort & Water Park Orlando
Aerial view

The Grove Resort & Water Park Orlando

4.0 star property
8.0 out of 10, Very Good, (7511)
"Na"
The price is ￥24,455
￥35,510 total
includes taxes & fees
May 12 - May 13
The Grove Resort & Water Park Orlando
Holiday Inn Club Vacations at Orange Lake Resort by IHG
Exterior

Holiday Inn Club Vacations at Orange Lake Resort by IHG

4.0 star property
8.6 out of 10, Excellent, (1927)
"Loved it"
The price is ￥19,763
￥28,489 total
includes taxes & fees
Apr 29 - Apr 30
Holiday Inn Club Vacations at Orange Lake Resort by IHG
Margaritaville Resort Orlando with H2O Waterpark
Lobby

Margaritaville Resort Orlando with H2O Waterpark

4.0 star property
9.0 out of 10, Wonderful, (3376)
"Stay was great besides the two times the front desk ignored and skipped me while was in line . I don't know if was a racist thing or not , no apology and I'm sure camera will show I waited and was next both times "
The price is ￥23,484
￥33,754 total
includes taxes & fees
May 14 - May 15
Margaritaville Resort Orlando with H2O Waterpark
Westgate Town Center Resort
Water park

Westgate Town Center Resort

4.0 star property
7.8 out of 10, Good, (1240)
"Love love love this resort will definitely be back great for people with kids so much to do from swimming to arts and crafts to paddle boating and more. This is definitely a must do"
The price is ￥12,642
￥19,186 total
includes taxes & fees
Apr 27 - Apr 28
Westgate Town Center Resort
Westgate Vacation Villas Resort
Water park

Westgate Vacation Villas Resort

4.0 star property
7.8 out of 10, Good, (1551)
"Everything great minus the selling of the timeshare. "
The price is ￥12,076
￥18,546 total
includes taxes & fees
Apr 27 - Apr 28
Westgate Vacation Villas Resort
Encore Resort and Water Park At Reunion by Rentyl
Outdoor pool, a heated pool, cabanas (surcharge), pool umbrellas

Encore Resort and Water Park At Reunion by Rentyl

5.0 star property
8.4 out of 10, Very Good, (963)
"The stay was enjoyable although there were some items at the house broken or dirty of use but I reported and it went great."
Encore Resort and Water Park At Reunion by Rentyl
Embassy Suites By Hilton Orlando Sunset Walk
Egyptian cotton sheets, premium bedding, down comforters, in-room safe

Embassy Suites By Hilton Orlando Sunset Walk

3.5 star property
9.2 out of 10, Wonderful, (169)
"Incredible. Loved every bit of it. Will be back"
The price is ￥15,191
￥23,698 total
includes taxes & fees
Apr 27 - Apr 28
Embassy Suites By Hilton Orlando Sunset Walk
Westgate River Ranch Resort & Rodeo
Horseback riding

Westgate River Ranch Resort & Rodeo

3.5 star property
8.0 out of 10, Very Good, (339)
"Austin my bartender was amazing and alway greeted me with a smile and was very attentive and responsive to all my needs. Good service was amazing and customer service from Austin was out of this world also"
The price is ￥13,867
￥19,509 total
includes taxes & fees
May 4 - May 5
Westgate River Ranch Resort & Rodeo
AMAZING STUDIO AT WESTGATE TOWN CENTER RESORT & SPA NEAR DISNEY
Outdoor pool, a heated pool

AMAZING STUDIO AT WESTGATE TOWN CENTER RESORT & SPA NEAR DISNEY

9.0 out of 10, Wonderful, (90)
"Excellent stay all the every "
AMAZING STUDIO AT WESTGATE TOWN CENTER RESORT & SPA NEAR DISNEY
Designer Renovated Condo in Gorgeous Tropical Setting
Outdoor pool, a heated pool

Designer Renovated Condo in Gorgeous Tropical Setting

9.6 out of 10, Exceptional, (155)
"great property, relatively quiet…it is a gated property and super well kept…This rental is right next to the activity court…Basketball, pickleball, yoga…all things court associated…the water feature shown in the description is not by this unit"
Designer Renovated Condo in Gorgeous Tropical Setting
Magical Newly Renovated 10 minutes to Disney 2Bed,2Bath
Outdoor pool, a heated pool

Magical Newly Renovated 10 minutes to Disney 2Bed,2Bath

9.6 out of 10, Exceptional, (52)
"The place was beautifully decorated and very clean. Great location with lots of places to eat nearby. Beautiful pool. Bathrooms were a little worn and water. Pressure was not great. Communication with owner wasn’t great either."
The price is ￥9,953
￥31,370 total
includes taxes & fees
Apr 27 - Apr 28
Magical Newly Renovated 10 minutes to Disney 2Bed,2Bath
Spacious upgraded 1st floor condo w/ Resort Amenities. Disney, less than 15 mins
Pool

Spacious upgraded 1st floor condo w/ Resort Amenities. Disney, less than 15 mins

10.0 out of 10, Exceptional, (28)
"We stayed from April 1- April 12, 2025. The place is beautiful inside and out. I would definitely recommend it. The host was great and returned messages within minutes. Looking forward to another stay in the future."
Spacious upgraded 1st floor condo w/ Resort Amenities. Disney, less than 15 mins
Disney 2 miles w/Heated Pool, water park, basketball tennis courts, game room
Outdoor pool, a heated pool

Disney 2 miles w/Heated Pool, water park, basketball tennis courts, game room

8.8 out of 10, Excellent, (15)
"Time to enjoy FL sunshine"
Disney 2 miles w/Heated Pool, water park, basketball tennis courts, game room
Spacious 2 Bedroom 2 Bathroom, Family Friendly Resort Condo, Near Disney ++++++
Outdoor pool, a heated pool

Spacious 2 Bedroom 2 Bathroom, Family Friendly Resort Condo, Near Disney ++++++

10.0 out of 10, Exceptional, (17)
"Great location and accommodations. Condo was wonderful and ground very well kept. The pool can’t be beat. Minimal issues but Louie made sure everything was quickly taken care off. We’re coming back next year. "
Spacious 2 Bedroom 2 Bathroom, Family Friendly Resort Condo, Near Disney ++++++
Alhambra Villas
Pool

Alhambra Villas

2.0 star property
8.4 out of 10, Very Good, (11)
"Very nice property! Rooms were clean and fully stocked with everything one needs, Very quiet. Pool was crystal clear and warm considering the chilly weather that popped up out of nowhere. It’s a great location for day trips to both sides of the peninsula! 2 hours to St. Pete on the Gulf, 2 hours to Cocoa Beach on the Atlantic! I also recommend Jetty Park for an Atlantic day trip! I’ll definitely stay here again! "
Alhambra Villas
GREAT TWO BEDROOM RESORT CONDO MINUTES FROM DISNEY
Outdoor pool, a heated pool

GREAT TWO BEDROOM RESORT CONDO MINUTES FROM DISNEY

9.2 out of 10, Wonderful, (62)
"Loved cant wait to come back"
GREAT TWO BEDROOM RESORT CONDO MINUTES FROM DISNEY
Luxury Resort Villa. Fun, family style!
Terrace/patio

Luxury Resort Villa. Fun, family style!

2.0 out of 10, (2)
"It was infested with bed bugs and we were not able to find another house last minute because they were all booked. The owner is not replying about refunding my money anymore and blaming it on the cleaning company. "
Luxury Resort Villa. Fun, family style!
PROMO 10% WEEKLY DISCOUNT! Fun-Filled Family Getaways Near the Magic of Disney
Outdoor pool

PROMO 10% WEEKLY DISCOUNT! Fun-Filled Family Getaways Near the Magic of Disney

9.6 out of 10, Exceptional, (26)
"First time renting from Vrbo, we enjoyed our stay the house was clean and comfortable, we felt very safe in the gated community. My granddaughter enjoyed the pool and lazy river. We will definitely be back."
PROMO 10% WEEKLY DISCOUNT! Fun-Filled Family Getaways Near the Magic of Disney
STUNNING 2 BEDROOM AT THE TOWN CENTER RESORT NEAR DISNEY
Fridge, microwave, oven, stovetop

STUNNING 2 BEDROOM AT THE TOWN CENTER RESORT NEAR DISNEY

8.6 out of 10, Excellent, (45)
"All overall great stay"
STUNNING 2 BEDROOM AT THE TOWN CENTER RESORT NEAR DISNEY
AMAZING 2 BEDROOM AT WESTGATE TOWN CENTER & SPA RESORT NEAR DISNEY
Exterior

AMAZING 2 BEDROOM AT WESTGATE TOWN CENTER & SPA RESORT NEAR DISNEY

9.0 out of 10, Wonderful, (91)
"We love Westgate Town Center! It's convenient, centrally located, staff is friendly ...is always great when we stay here."
AMAZING 2 BEDROOM AT WESTGATE TOWN CENTER & SPA RESORT NEAR 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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Other property types in Lakeland - Winter Haven

Summer Bay Orlando by Exploria Resorts
5 outdoor pools

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very Good, (5359)
"First time taking my daughter out of country as a single mom. There is so much to do on resort, transportation to the theme parks, hospitable, clean, excellent communication and overall exceptional service. The staff here go above and beyond, will be rebooking in the future"
The price is ￥15,995
￥22,490 total
includes taxes & fees
Apr 27 - Apr 28
Summer Bay Orlando by Exploria Resorts
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Interior

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1343)
"I like the multi level and the property is well kept. "
The price is ￥83,744
￥130,782 total
includes taxes & fees
May 10 - May 11
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
The Berkley, Orlando
Lobby sitting area

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1745)
"As always, we had a great stay and will return next year "
The price is ￥16,748
￥20,456 total
includes taxes & fees
May 4 - May 5
The Berkley, Orlando
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.

Frequently asked questions

What can I expect from a resort vacation in Lakeland - Winter Haven?
Longing for a relaxing escape? Indulge in all the comforts of a resort, where you can find everything you need for your stay—from convenient food and drink options to activities and entertainment. Pick from 22 resorts in Lakeland - Winter Haven and discover the one that’s best for you, whether you envision yourself sitting down to fine dining or heading to the spa for a deep-tissue massage.
What's a top resort for my stay in Lakeland - Winter Haven?
Westgate River Ranch Resort & Rodeo - Family-friendly property with a 3.5-star rating. Features a marina, an outdoor pool, and a restaurant. Room enough for everyone! Steps from LEGOLAND, Free Breakfast & Parking - Located just 10 minutes from Legoland Florida. Has a water park, free breakfast, and concierge services. Steps From Legoland, Free Breakfast & Parking - Situated just 10 minutes away from Legoland Florida. Enjoy the water park and concierge services. Fun Filled Vacation! Multiple Units, Pool, Play Areas, LEGOLAND, Golf nearby - Situated just 10 minutes away from Legoland Florida. Amenities include a water park, free breakfast, and concierge services. Room enough for everyone! Steps from LEGOLAND, Free Breakfast & Parking - Situated just 10 minutes away from Legoland Florida. Access to a water park, free breakfast, and concierge services.
What can I do in Lakeland - Winter Haven?
Travelers come to Lakeland - Winter Haven for shopping and other popular activities, and say that there are lots of great restaurants here. Grab your golf clubs for a game at Southern Dunes Golf and Country Club and City of Bartow Golf Course, or take the whole family to Legoland Florida and Safari Wilderness. Other top attractions you can add to your list are Bok Tower Gardens and Lakeside Village.
What's the seasonal weather like in Lakeland - Winter Haven?
The hottest months are usually July and August with an average temp of 82°F, while the coldest months are January and December with an average of 65°F. The rainiest months in Lakeland - Winter Haven are July, August, June, and September, with each month seeing an average of 8 inches of rainfall.
What's the best way to get to and around Lakeland - Winter Haven?
Fly into Tampa Intl. Airport (TPA), which is located 52.1 mi (83.9 km) away. You can also search for flights into Tampa, FL (TPF-Peter O. Knight), which is 46.5 mi (74.8 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.