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Top Holiday Rentals in Winter Haven

Ramada by Wyndham Kissimmee Gateway
3.0 star property
7.2 out of 10, Good, (5840)
"We have stayed the last 3 years. We like that there is a Walmart, a Starbucks, souvenir shop, liquor store and Black Angus steak restaurant within walking distance. Pool is wonderful. Wish we had a newer room like we had in the past. Great hotel to stay at! Free coffee and water always available!!"
The price is £70
per night
16 May - 17 May
Ramada by Wyndham Kissimmee Gateway
Summer Bay Orlando by Exploria Resorts
3.5 star property
8.4 out of 10, Very good, (4679)
"Summer bay was great although the furniture was a little dated and it had a funny smell the entire stay. My children enjoyed themselves."
The price is £141
per night
12 May - 13 May
Summer Bay Orlando by Exploria Resorts
Seralago Hotel & Suites Main Gate East
3.0 star property
5.2 out of 10, (5217)
"Roaches, lights didn’t work, big deposit I was unaware. Good points air was great water temp/pressure great, they accepted being a few minutes late as we were unaware of the 10 am checkout….?? Which is another bummer! The lace is really really old….. and repaired a lot…. You can tell ever place it’s been repaired….. "
The price is £51
per night
12 May - 13 May
Seralago Hotel & Suites Main Gate East
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Holiday Inn & Suites Orlando SW - Celebration Area, an IHG Hotel
3.0 star property
7.8 out of 10, Good, (1419)
"Good. Breakfast really good, worth to pay the extra."
The price is £78
per night
14 May - 15 May
Holiday Inn & Suites Orlando SW - Celebration Area, an IHG Hotel
Margaritaville Resort Orlando Cottages by Rentyl
4.0 star property
8.8 out of 10, Excellent, (820)
"Excellent stay! "
Margaritaville Resort Orlando Cottages by Rentyl
Vacation Village at Parkway
3.0 star property
8.2 out of 10, Very good, (1247)
"Second room was a separate apartment."
Vacation Village at Parkway
Regal Oaks Resort Vacation Townhomes by IDILIQ
4.0 star property
8.4 out of 10, Very good, (2657)
"We had a very good experience. The localization is great, near to Disney, Walmart, Walgreens and Old Town. The house is very functional and the full kitchen was essential for a trip with children. Only the shower could be better, because in all the bathrooms there was little water in the showers."
The price is £245
per night
5 May - 6 May
Regal Oaks Resort Vacation Townhomes by IDILIQ
The Berkley, Orlando
4.0 star property
9.4 out of 10, Exceptional, (1402)
"Very quiet "
The Berkley, Orlando
Spectrum Resort Orlando
4.0 star property
9.4 out of 10, Exceptional, (184)
"Front desk/Danay or Danae is very accommodating. A good face of the company. Knows the needs of a client. We badly needed elevator for our 90 yr old mother. Pictures shown a townhouse with ground level accomodation. But the one we chose upon check out was located at the 2nd floor w/o elevator (not deluxe). Expedia cannot help due to protection coverage. Anyway, she find a way for us to be upgraded. If not for her I regret that I chose spectrum. I highly recommend this beatiful resort. Worth...
Spectrum Resort Orlando
Encantada Resort Vacation Townhomes by IDILIQ
3.0 star property
8.6 out of 10, Excellent, (1249)
"Having a heated pool just outside your backdoor was fantastic. It was just the right size."
The price is £215
per night
6 May - 7 May
Encantada Resort Vacation Townhomes by IDILIQ
Reunion Resort & Golf Club
5.0 star property
8.6 out of 10, Excellent, (1118)
"Great hotel "
Reunion Resort & Golf Club
Magic Village Yards, Trademark Collection by Wyndham
4.0 star property
9.2 out of 10, Wonderful, (1065)
"We stayed here because it is close to all the parks. Pleasantly surprised with the unit too. All new!"
Magic Village Yards, Trademark Collection by Wyndham
Upstay - Theme Rooms|Movie Theatre|Pool|Sleeps 18
10.0 out of 10, Exceptional, (1)
"This is a very beautiful home. I only have two small regrets. (1) I didn’t book for a longer stay (2) No puck for the air hockey game. However, my family thoroughly enjoyed our time here and have already asked if we can come back again next summer!"
Upstay - Theme Rooms|Movie Theatre|Pool|Sleeps 18
Lifetime of Vacations Resort
3.0 star property
9.0 out of 10, Wonderful, (77)
"Everything good for the low price, smelled a little like humidity. Overall 4 star"
Lifetime of Vacations Resort
Champions Gate!*Disney Themes!*4 Bedrooms!*Private Pool!*
9.8 out of 10, Exceptional, (9)
"Great location awesome home Great for the kids"
Champions Gate!*Disney Themes!*4 Bedrooms!*Private Pool!*
Home w/ Pool, Hot Tub & Game Room, 6 Mi to Disney!
9.8 out of 10, Exceptional, (9)
"First of all I have to say the property manager was super attentive and always at the end of a text message for issues and sorted them straight away. Positives. The property manager. The cleanliness inside the villa. The space The pool (generally) The hottub. Didn't use the games room but it looked great. Negatives. Unless you are going upstairs (we were only 2 so didn't) the thermostat goes into ECO mode and doesn't cool the house. Daily text message to have to get it set remotely. The pool...
Home w/ Pool, Hot Tub & Game Room, 6 Mi to Disney!
Villas At Regal Palms
4.0 star property
8.4 out of 10, Very good, (459)
"This is a great place to stay. This was second time staying and definitely not my last. Can’t wait to come back. "
Villas At Regal Palms
Family house / 4 BD-2Baths (August promotion!! low rates for this month)
9.2 out of 10, Wonderful, (10)
"House was beautiful and everything needed for a good stay. Property was very nice and surprisingly quiet. Be advised though that traffic getting to and from Orlando is absolutely terrible. An hour to an hour and a half just for a 19 mile drive and it didn't seem to matter the time of day. I realize owners have no control over that. Communication was a little sketchy but overall a great home and good stay."
Family house / 4 BD-2Baths (August promotion!! low rates for this month)
Grand Lake Resort
3.0 star property
9.0 out of 10, Wonderful, (84)
"nd quiet. Nobody bothering you the pool was amazing and heated the jacuzzi whew amazing lol. I will definitely book again when I visit. The view is also so nice in the backyard seeing the water. Option to even use the boat but I was scared of alligators lol so I stayed on shore. It’s an amazing quiet place. Even slept in a couple times due to the quietness and not knowing it was day time lol. Definitely an amazing birthday trip"
Grand Lake Resort
MISSION TO MARS EXTREME PRIVATE ATTRACTION VACATION HOME
MISSION TO MARS EXTREME PRIVATE ATTRACTION VACATION HOME
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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.

Winter Haven Holiday Rental Travel Info

Other types of properties in Winter Haven you may be interested in

Holiday Inn Winter Haven, an IHG Hotel
3.0 star property
8.8 out of 10, Excellent, (942)
"Verónica was awesome took care of everything right away she made me smile she has awesome attitude and very nice woman "
The price is £105
per night
8 May - 9 May
Holiday Inn Winter Haven, an IHG Hotel
Howard Johnson by Wyndham Winter Haven FL
2.0 star property
7.0 out of 10, Good, (1001)
"To Much Noise At Night 🌙 "
The price is £84
per night
6 May - 7 May
Howard Johnson by Wyndham Winter Haven FL
Best Western Plus Winter Haven Inn & Suites 
2.5 star property
9.4 out of 10, Exceptional, (311)
"Very cleaned the room."
The price is £118
per night
9 May - 10 May
Best Western Plus Winter Haven Inn & Suites 
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Haven holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winter Haven holiday 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 and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winter Haven holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winter Haven holiday rentals we have selected for you start as low as £51 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winter Haven rentals

At Expedia, we put the best Winter Haven holiday 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 holiday.

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. 

Frequently asked questions

Can I find a holiday rental in Winter Haven?

Yes, there are holiday rentals in Winter Haven close to LEGOLAND® Florida, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Winter Haven speak positively about the scenic lakeside and top-notch restaurants in this destination. Leave time to check out the gardens and entertainment venues during your visit.

What are some of the best holiday rentals that Winter Haven has to offer?

The Berkley, Orlando: This holiday home rental outside of Winter Haven offers a furnished patio, a terrace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a microwave and a coffee maker. You can relax into your holiday with an arcade/games room and 1 hot tub.

How many holiday rentals are there in Winter Haven?

Choose from 102 Expedia holiday rentals in Winter Haven for a memorable holiday.

What can I see and do in Winter Haven?

Family-friendly attractions include LEGOLAND® Florida and Indigo's Family Fun Center, whereas The Circle B Bar Reserve and Rotary Park are a couple of great spots to enjoy the outdoors. Theatre Winter Haven and Chain of Lakes Park are other places to visit while you're in town.

What are holiday rentals like in Winter Haven?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winter Haven. Holiday rentals offer amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for a family trip.

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