Winter Haven Vacation Rentals

January 2025

SundayMondayTuesdayWednesdayThursdayFridaySaturday

February 2025

SundayMondayTuesdayWednesdayThursdayFridaySaturday
  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Winter Haven

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very Good, (5087)
"The property and staff were wonderful! If our plan was to stay at the resort the whole time, it would have been perfect! The pools were amazing and the food on-site was good! Our issue was that we were in Orlando to visit the Theme Parks and it took over 40 minutes to get to Universal Studios, SeaWorld, and Disney - not the 15-20 min as advertised. The shuttle offered by the resort operates on a very limited schedule, so we ended up taking an Uber every day which worked well but wasn't what...
The price is P7,091
P9,815 total
includes taxes & fees
Jan 26 - Jan 27
Summer Bay Orlando by Exploria Resorts

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1153)
"The unit was a townhouse style and was beautiful. It also appeared to be very new. The only complaint I had would be in the lower level shower. The water was hot and there was no way of making it cold. It was bearable for me and we were so busy at the resorts, that I never alerted the main office of this, so someone may want to look into that. Otherwise, it couldn't have been much better. Beautiful townhouse and I would absolutely stay here again."
Margaritaville Resort Orlando Cottages by Rentyl

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very Good, (1412)
"Great price and value for a family vacation! "
The price is P6,400
P8,139 total
includes taxes & fees
Jan 14 - Jan 15
Vacation Village at Parkway

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1637)
"All areas of the Berkeley were well maintained. The staff was warm and welcoming to us on arrival. There were a couple of minor issues in the unit and maintenance was there in just a few minutes of our request and fixed the issues. "
The Berkley, Orlando

Regal Oaks Resort Vacation Townhomes by IDILIQ

4.0 star property
8.4 out of 10, Very Good, (2825)
"I would recommend this property! Just be sure you townhome is not on the side close to Old Town. The townhouse was great and could easily have held 8. We were 6. But they definitely need attention. The carpet on the stairs and in the rooms is absolutely awful and must be replaced. The dryer vent was leaking into the house so the washer/dryer cabinet was filled with lint and hot moist air when you ran it. The a/c vent on the stairwell was so dusty and needed a good scrubbing. These are...
The price is P6,831
P19,280 total
includes taxes & fees
Jan 27 - Jan 28
Regal Oaks Resort Vacation Townhomes by IDILIQ

Reunion Resort & Golf Club

5.0 star property
8.6 out of 10, Excellent, (1208)
"So luxurious and very well decorated! We enjoyed feeling so comfortable and it was super clean! Staff was so knowledgeable and very accommodating. Definitely coming back!!!"
The price is P14,337
P19,039 total
includes taxes & fees
Jan 13 - Jan 14
Reunion Resort & Golf Club

Magic Village Yards, Trademark Collection by Wyndham

4.0 star property
9.2 out of 10, Wonderful, (1112)
"This is a nice, quiet, clean and convenient place to stay near Disney. It has plenty of room for a large family and more bathrooms than you could need! That said, the property is a bit tired and could use some updates and TLC. "
Magic Village Yards, Trademark Collection by Wyndham

Encantada Resort Vacation Townhomes by IDILIQ

3.0 star property
8.6 out of 10, Excellent, (1322)
"I recently stayed at Encantada Resort Vacation Townhomes by IDILIQ in Four Corners, Florida, from December 23 to January 2, and it was absolutely fantastic! The resort provided the perfect balance of relaxation and convenience. The townhome was spacious, clean, and well-maintained, with all the amenities we needed to feel at home. The fully equipped kitchen made it easy to prepare meals, and the private patio with a hot tub was an incredible touch for unwinding after a day of exploring. The...
Encantada Resort Vacation Townhomes by IDILIQ

Villas At Regal Palms

4.0 star property
8.4 out of 10, Very Good, (520)
"I would definitely recommend villas at regal palms because it was clean, cozy, well equipped and conveniently located to lots of shopping, things to do and eat. My family and I really enjoyed our stay. Only recommendation would be smart bigger tvs in the living room as well as in the master bedroom. Other than that everything was great"
Villas At Regal Palms

Bahama Bay Resort

3.5 star property
8.6 out of 10, Excellent, (2055)
"Todo dentro de.lo esperado. Excelente . Es la segunda vez que vamos y siemlre acorde a lo qie buscamos ."
Bahama Bay Resort

Lifetime of Vacations Resort

3.0 star property
9.2 out of 10, Wonderful, (115)
"Amazing for families. Great location and amenities. "
The price is P6,829
P8,743 total
includes taxes & fees
Jan 19 - Jan 20
Lifetime of Vacations Resort

Grand Lake Resort

3.0 star property
9.0 out of 10, Wonderful, (102)
"Only issue I had was that there wasn't a broom or many cleaning supplies located in the room"
The price is P9,192
P11,527 total
includes taxes & fees
Jan 26 - Jan 27
Grand Lake Resort

Formosa Valley Resort by UNE Homes

4.0 star property
9.4 out of 10, Exceptional, (133)
"Clean and comfortable, food and shopping close by"
Formosa Valley Resort by UNE Homes

The Azur Resort

4.0 star property
8.8 out of 10, Excellent, (23)
"Me in my family really enjoy our stay "
The Azur Resort

Caribe Cove Resort

3.5 star property
8.8 out of 10, Excellent, (2242)
"Condo is spacious, beds aren’t comfortable but for the price it’s understandable. If they could change the mattress would be amazing! Pool area is really nice. "
Caribe Cove Resort

High Point World Resort

3.5 star property
8.8 out of 10, Excellent, (169)
"Amazon quit friendly what I really enjoy is quick checking in "
High Point World Resort
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.
Don't see what you're looking for?
See all available properties in Winter Haven
Save an average of 15% on thousands of hotels when you're signed in

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

Best Western Plus Winter Haven Inn & Suites 

3.5 star property
9.4 out of 10, Exceptional, (664)
"Clean and nice hotel "
The price is P7,479
P8,376 total
includes taxes & fees
Jan 14 - Jan 15
Best Western Plus Winter Haven Inn & Suites 

Howard Johnson by Wyndham Winter Haven FL

2.0 star property
7.0 out of 10, Good, (1004)
"Nice hotel for a decent price. "
The price is P5,953
P6,668 total
includes taxes & fees
Jan 16 - Jan 17
Howard Johnson by Wyndham Winter Haven FL

Holiday Inn Winter Haven, an IHG Hotel

3.0 star property
9.0 out of 10, Wonderful, (1003)
"Liked the rooms were clean and friendly receptionist "
The price is P6,479
P7,256 total
includes taxes & fees
Jan 19 - Jan 20
Holiday Inn Winter Haven, an IHG Hotel
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

Can I find a vacation rental in Winter Haven?

Yes, there are vacation rentals in Winter Haven close to LEGOLAND® Florida, or you can choose a more secluded option if you'd like a relaxing place to 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's the top vacation rental that Winter Haven has to offer?

The Berkley, Orlando: This vacation home rental outside of Winter Haven offers a furnished patio, a terrace, and a barbecue grill 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 vacation with an arcade game room and a spa tub.

How many vacation rentals are there in Winter Haven?

Choose from 130 Expedia vacation rentals in Winter Haven for a memorable vacation.

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 vacation rentals like in Winter Haven?

Vacation rentals are private properties you can book for a few days or a quick weekend in Winter Haven. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a small group gathering.