Winter Haven Vacation Rentals

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Vacation Rentals in Winter Haven

Lake Ida Beach Resort

Lake Ida Beach Resort

3 out of 5
2524 Lake Alfred Rd, Winter Haven, FL
The price is $75 per night from Oct 29 to Oct 29
Situated on a lake, this cottage is 0.1 mi (0.1 km) from Lake Conine and within 3 mi (5 km) of Winter Haven Hospital and Indigo's Family Fun Center. Baycare ...
4/5 Very Good! (64 reviews)
"I liked that the owner was caring about her guests and concerned. Everyday checking what was needed. The only thing there is an older looking mobile rusted home that if removed the place would look nicer. And the lagoon in the back people should not be throwing garbage in the lagoon it makes it look ..."

Reviewed on Aug 27, 2021

Lake Ida Beach Resort
Private Pool Paradise -  2.5 miles to Legoland & close to Disney!  Contactless Entry!

Private Pool Paradise - 2.5 miles to Legoland & close to Disney! Contactless Entry!

Winter Haven, FL
Situated in Winter Haven, this vacation home is within 3 mi (5 km) of LEGOLAND® Florida, Chain of Lakes Park, and Winter Haven Women's Hospital. Baycare Womens ...
4.4/5 Wonderful! (9 reviews)
Just outside Legoland.
"Pool was nice."

Reviewed on Aug 4, 2021

Private Pool Paradise - 2.5 miles to Legoland & close to Disney! Contactless Entry!
Modern HouseBoat*AceLoca*4Miles*LegoLand*

Modern HouseBoat*AceLoca*4Miles*LegoLand*

Winter Haven, FL
Situated on the waterfront, this houseboat is within 3 mi (5 km) of Winter Haven Hospital, Baycare Womens Hospital, and Winter Haven Women's Hospital. Indigo's ...
4.8/5 Exceptional! (6 reviews)
We loved the houseboat.
"We loved the getaway. It was the first time we stayed on a houseboat. Great views and many nearby activities. The houseboat was clean and well prepared for us."

Reviewed on Sep 12, 2021

Modern HouseBoat*AceLoca*4Miles*LegoLand*
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*Modern Tiny Lake Cottage*AceLoc*4miles*LEGOLAND*

*Modern Tiny Lake Cottage*AceLoc*4miles*LEGOLAND*

Winter Haven, FL
Situated on a lake, this cottage is within 3 mi (5 km) of Winter Haven Hospital, Baycare Womens Hospital, and Winter Haven Women's Hospital. Indigo's Family ...
4.8/5 Exceptional! (12 reviews)
Thank you!
"Everything was clean, well placed and easy to find. Neighbors minded our privacy, and I really enjoyed the set up outside on the porch."

Reviewed on Sep 15, 2021

*Modern Tiny Lake Cottage*AceLoc*4miles*LEGOLAND*
Conveniently located 10 minutes from Legoland!

Conveniently located 10 minutes from Legoland!

Winter Haven, FL
This family-friendly Winter Haven vacation home is within a 15-minute walk of Winter Haven Women's Hospital and Baycare Womens Hospital. Indigo's Family Fun ...
4.9/5 Exceptional! (20 reviews)
Great Location
"The house was very clean and pretty much as stated on VRBO. The location was very close to many attractions and restaurants."

Reviewed on Sep 17, 2021

Conveniently located 10 minutes from Legoland!
Confidently Clean, Quint & Cozy Apartment

Confidently Clean, Quint & Cozy Apartment

Winter Haven, FL
Located in the heart of Winter Haven, this apartment building is 0.7 mi (1.1 km) from Lake Conine and within 3 mi (5 km) of Winter Haven Hospital and Indigo's ...
4.9/5 Exceptional! (10 reviews)
Highly Recommend
"This small, adorable apartment was exactly what we needed for our visit in Winter Haven! It was very clean, in a quiet neighborhood and very close to restaurants and shopping! Check in was so easy and any questions we had were responded to quickly! We will definitely stay here again on other trips ..."

Reviewed on Oct 1, 2021

Confidently Clean, Quint & Cozy Apartment
Serenity Retreat, Confidently Clean

Serenity Retreat, Confidently Clean

Winter Haven, FL
Located in the heart of Winter Haven, this historic apartment building is 0.7 mi (1.1 km) from Lake Conine and within 3 mi (5 km) of Winter Haven Hospital and ...
5/5 Exceptional! (3 reviews)
10 out of 10 stars. !
"The place was amazing & very quiet! Had anything you could possibly even think of . Great location, not far from food , quiet neighborhood with a nice dock and a lake within a 2 min walk . Nice and convenient for a couple or more ! Will definitely keep in mind for a second visit"

Reviewed on Sep 15, 2021

Serenity Retreat, Confidently Clean
Soak up the charm of this cozy, recently  remodel studio.

Soak up the charm of this cozy, recently remodel studio.

Winter Haven, FL
Situated by the sea, this apartment building is 0.7 mi (1.1 km) from Lake Conine and within 3 mi (5 km) of Winter Haven Hospital and Indigo's Family Fun Center. ...
5/5 Exceptional! (5 reviews)
Cozy
"It a very nice studio and really close to both Winter Haven and Auburndale."

Reviewed on Aug 12, 2021

Soak up the charm of this cozy, recently remodel studio.
Awesome Lake House With Private Dock, Canoe, Kayaks, Game-Room, & Lots To Do!!!

Awesome Lake House With Private Dock, Canoe, Kayaks, Game-Room, & Lots To Do!!!

Winter Haven, FL
The price is $128 per night from Nov 9 to Nov 9
This family-friendly Winter Haven vacation home is located on the waterfront, within 2 mi (3 km) of Winter Haven Hospital, Lake Conine, and Winter Haven Women's ...
4.4/5 Excellent! (8 reviews)
Quaint Lake House
"We had a great two night stay at Jenny’s lake house! The back yard on the water is amazing! We had a wonderful time using the fire pit to cook dinner and s’mores! The kids also loved the game room! Jenny was very warm, helpful and responsive!"

Reviewed on Aug 4, 2021

Awesome Lake House With Private Dock, Canoe, Kayaks, Game-Room, & Lots To Do!!!
Relaxing 3 Bedroom Home with an Amazing Pool!

Relaxing 3 Bedroom Home with an Amazing Pool!

Winter Haven, FL
Set in Winter Haven, this family-friendly vacation home is within 6 mi (10 km) of LEGOLAND® Florida, Indigo's Family Fun Center, and Eagle Ridge Mall. Chain ...
Relaxing 3 Bedroom Home with an Amazing Pool!
Private Entrance Suite near State Farm & Legoland

Private Entrance Suite near State Farm & Legoland

Winter Haven, FL
Situated in Winter Haven, this apartment building is 1.1 mi (1.8 km) from LEGOLAND® Florida and within 6 mi (10 km) of Chain of Lakes Park and Winter Haven Women's ...
5/5 Exceptional! (3 reviews)
Much better than expected! Clean, comfy and well-equiped!
"Nestled in a quiet, upscale neighborhood, Steven's place is thoughtfully equipped with anything we might have needed. The bed was comfortable and the room felt spacious. Great shower! Microwave, fridge, printer, hair dryer, coffeemaker were nice touches. We'll definitely stay here again!"

Reviewed on Oct 18, 2021

Private Entrance Suite near State Farm & Legoland
Winter Haven Home with Dock & Hot Tub!

Winter Haven Home with Dock & Hot Tub!

Winter Haven, FL
This family-friendly Winter Haven vacation home is located on the waterfront, within 1 mi (2 km) of Winter Haven Women's Hospital and Chain of Lakes Park. Indigo's ...
5/5 Exceptional! (31 reviews)
Great house
"The house was wonderful and the amenities including the pool and the game room were also great. The lake view was beautiful and we were easily able to rent a pontoon to enjoy the surrounding lakes. Overall was a great stay and we would go back again!"

Reviewed on Aug 24, 2021

Winter Haven Home with Dock & Hot Tub!
Lake Silver Retreat III * Lakeviews~Legoland~Foosball & Kayaks ~ Family Fun

Lake Silver Retreat III * Lakeviews~Legoland~Foosball & Kayaks ~ Family Fun

Winter Haven, FL
Situated on the waterfront, this vacation home is within 2 mi (3 km) of Winter Haven Hospital, Winter Haven Women's Hospital, and Baycare Womens Hospital. Indigo's ...
Lake Silver Retreat III * Lakeviews~Legoland~Foosball & Kayaks ~ Family Fun
Charming Lakefront Pool Home - 5 Min to Legoland!

Charming Lakefront Pool Home - 5 Min to Legoland!

Winter Haven, FL
Situated in Winter Haven, this vacation home is within 3 mi (5 km) of Winter Haven Women's Hospital, Chain of Lakes Park, and Baycare Womens Hospital. Indigo's ...
4.3/5 Excellent! (9 reviews)
Cozy Stay
"While the home is an older property, it was perfect for our family vacation. There is a private pool and located right on the lake. It sits back off the main road which lends to feeling like you’re in a bit of a secluded section, but close enough to stores and shops."

Reviewed on Oct 4, 2021

Charming Lakefront Pool Home - 5 Min to Legoland!
New Listing ~Chain of Lakes w Dock~Sunrise on Lake Idylwild~ Legoland  7.5 mi~Disney 30 mi.

New Listing ~Chain of Lakes w Dock~Sunrise on Lake Idylwild~ Legoland 7.5 mi~Disney 30 mi.

Winter Haven, FL
Situated on the waterfront, this vacation home is 2.3 mi (3.7 km) from Lake Conine and within 6 mi (10 km) of Winter Haven Hospital and Indigo's Family Fun Center. ...
New Listing ~Chain of Lakes w Dock~Sunrise on Lake Idylwild~ Legoland 7.5 mi~Disney 30 mi.
Lake Lucerne way villa

Lake Lucerne way villa

Winter Haven, FL
Situated in Winter Haven, this vacation home is 1 mi (1.6 km) from Lake Henry Golf Club and within 3 mi (5 km) of Willowbrook Golf Course and Lake Conine. Winter ...
Lake Lucerne way villa
FALL/WINTER SPECIAL RATES Mid-century Mod w/ Fireplaces - Downtown Near Legoland

FALL/WINTER SPECIAL RATES Mid-century Mod w/ Fireplaces - Downtown Near Legoland

Winter Haven, FL
This family-friendly Winter Haven vacation home is located on a lake, within 1 mi (2 km) of Winter Haven Hospital and Indigo's Family Fun Center. Winter Haven ...
4.6/5 Wonderful! (39 reviews)
Month of March
"We had beautiful weather While we were there. Walking distance to walk around Lake Howard."

Reviewed on Apr 11, 2020

FALL/WINTER SPECIAL RATES Mid-century Mod w/ Fireplaces - Downtown Near Legoland
Fantastic Water Front Home on the Chain of Lakes

Fantastic Water Front Home on the Chain of Lakes

Winter Haven, FL
Situated on the waterfront, this vacation home is within 3 mi (5 km) of Winter Haven Hospital, Lake Conine, and Indigo's Family Fun Center. Baycare Womens Hospital ...
5/5 Exceptional! (6 reviews)
Great stay
"The owner of this property is the absolute best and easiest to communicate with before and during the stay. You will feel like a family friend staying at this home. The house has everything you would need or want for a comfortable stay. The house has lots of space. The view from the house of the ..."

Reviewed on May 31, 2021

Fantastic Water Front Home on the Chain of Lakes
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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.

Large Group Rentals Winter Haven

3 bedroom, 2 bathroom Bahama Bay Resort Villa near all of Orlando's magic!

3 bedroom, 2 bathroom Bahama Bay Resort Villa near all of Orlando's magic!

Davenport, FL
3 bedroom, 2 bathroom Bahama Bay Resort Villa near all of Orlando's magic!
Super Nice and Spacious Home for Your Disney Vacation

Super Nice and Spacious Home for Your Disney Vacation

1240 Challenge Dr, Kissimmee, FL
Super Nice and Spacious Home for Your Disney Vacation
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.

Large Group Cabins Winter Haven

Camp Mack, a Guy Harvey Lodge, Marina & RV Resort

Camp Mack, a Guy Harvey Lodge, Marina & RV Resort

3 out of 5
14900 Camp Mack Rd, Lake Wales, FL
Fully refundableReserve now, pay when you stay
The price is $103 per night from Oct 28 to Oct 28
Camp Mack, a Guy Harvey Lodge, Marina & RV Resort
Paradise Palms 2933

Paradise Palms 2933

3.5 out of 5
2933 Banana Palm Drive, Kissimmee, FL
Paradise Palms 2933
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.

Everything you need to know about 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 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 Winter Haven vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winter Haven vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winter Haven. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year. is the cheapest month to visit, with the most expensive. 

Your chosen location, property type, and amenities will impact the cost of your trip, too. Right now, Winter Haven vacation rentals range between $75 per night and $128 per night.

How to find incredible deals on Winter Haven rentals

At Expedia, we put the best 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 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 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 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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