Find Romantic Hotels in Winter Haven, FL

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Check availability on Winter Haven Romantic Hotels

Our top choices for Winter Haven romantic hotels

Upstay: 3BR Condo w Pool, Sauna—Near Disney

Upstay: 3BR Condo w Pool, Sauna—Near Disney
Winter Garden
The price is ¥17,348
¥50,613 total
includes taxes & fees
Mar 19 - Mar 20
Upstay: 3BR Condo w Pool, Sauna—Near Disney

Crystal 3 BR TH Gated Resort Close to Disney

Crystal 3 BR TH Gated Resort Close to Disney
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Nice and clean house patio chairs were broken blinds were broken beds were not comfortable make noises, right beside highway too much traffic noise, saw a lizard and cockraches in the kitchen. Lot of parking"
Canada
Mohammad zaki A.
The price is ¥13,381
¥79,752 total
includes taxes & fees
Mar 25 - Mar 26
Crystal 3 BR TH Gated Resort Close to Disney

Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney

Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
Kissimmee
9.2 out of 10, Wonderful, (159 reviews)
"Excellent accommodations."
United States
Raychelle
The price is ¥15,134
¥38,444 total
includes taxes & fees
Apr 12 - Apr 13
Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney

*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works

*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works
Kissimmee
9.6 out of 10, Exceptional, (142 reviews)
"The pool was great for the whole family, and everything worked and matched the listing "
United States
Robert S.
The price is ¥27,878
¥73,960 total
includes taxes & fees
Apr 13 - Apr 14
*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works

7 BDRM, Private Pool, Hot Tub, Games, New Decor, New Mgmt., 10 min to parks!

7 BDRM, Private Pool, Hot Tub, Games, New Decor, New Mgmt., 10 min to parks!
Kissimmee
9.0 out of 10, Wonderful, (62 reviews)
"Property was well kept and it was a quiet safe neighborhood with a beautiful pool."
United States
Amanda D.
The price is ¥29,888
¥88,343 total
includes taxes & fees
Mar 16 - Mar 17
7 BDRM, Private Pool, Hot Tub, Games, New Decor, New Mgmt., 10 min to parks!

Incredible Renovated home located near all !!

Incredible Renovated home located near all !!
Champions Gate
6.4 out of 10, (5 reviews)
"We really enjoyed Melissa’s condo Deja Blue. Quite pretty inside and quiet surroundings. Beds are comfortable, plenty of towels available, most things you need for a stay are provided. A few things in the condo could be updated but overall we had a great month in this unit and love the Champions Gate area for walking and dining."
United States
Susan K.
The price is ¥14,337
¥37,225 total
includes taxes & fees
Mar 15 - Mar 16
Incredible Renovated home located near all !!

3 Bedrooms / 2 Bathrooms / Storey Lake (4751-308 CT)

3 Bedrooms / 2 Bathrooms / Storey Lake (4751-308 CT)
Kissimmee
9.6 out of 10, Exceptional, (4 reviews)
"This property was a great size for our family and we thoroughly enjoyed our stay. My boys loved the Minion themed room. Everything was clean and the kitchen was well stocked with dishes. Excellent stay! "
United States
Luke W.
The price is ¥30,226
¥80,339 total
includes taxes & fees
Mar 22 - Mar 23
3 Bedrooms / 2 Bathrooms / Storey Lake (4751-308 CT)

MAGIC 5* LAKE VIEW VILLA HEATED POOL&HOT SPA, near DISNEY, 10 Guests

MAGIC 5* LAKE VIEW VILLA HEATED POOL&HOT SPA, near DISNEY, 10 Guests
Lake Berkley
8.6 out of 10, Excellent, (34 reviews)
"Host was very helpful and responsive. The view of the pond behind the house was the best part. Got to watch the wildlife come and go throughout the day including a pair of bald eagles.The house was clean and spacious. The pool is a bit on the small side. Just a heads up. We did have aomeniasues with the pool and hot tub, but Claire offered free pool heat for our troubles. Though the heat did shut off one day so we had a cold pool for a day. I was excited that there was an onsite gym at the...
United States
Stephanie B.
The price is ¥31,860
¥91,558 total
includes taxes & fees
Mar 27 - Mar 28
MAGIC 5* LAKE VIEW VILLA HEATED POOL&HOT SPA, near DISNEY, 10 Guests

LUXURY RESORT & GOLF CONDO MIN CLOSE TO DISNEY

LUXURY RESORT & GOLF CONDO MIN CLOSE TO DISNEY
Four Corners
10.0 out of 10, Exceptional, (7 reviews)
"Relaxing getaway from everyday stressors. Very clean and comfortable property "
United States
Odell M.
The price is ¥21,506
¥61,975 total
includes taxes & fees
Mar 25 - Mar 26
LUXURY RESORT & GOLF CONDO MIN CLOSE TO DISNEY

ON SALE! 4BD 3BTH 1.5 MILES TO DISNEY!

ON SALE! 4BD 3BTH 1.5 MILES TO DISNEY!
Kissimmee
9.6 out of 10, Exceptional, (118 reviews)
"Very comfortable stay for our day at Epcot. It was a quick, easy Uber ride to the park. The home was very clean and comfortable. The host was very nice and responsive. I will stay here again for our next Disney adventure."
United States
Sharlene G.
The price is ¥25,576
¥68,315 total
includes taxes & fees
Mar 15 - Mar 16
ON SALE! 4BD 3BTH 1.5 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.

Top Winter Haven Hotel Reviews

Frequently asked questions

Searching for romantic hotels in Winter Haven?
Are you looking for a romantic vacation? Our guests also love Winter Haven for its array of dining options, sporting events, and beautiful lakeside setting. You might consider checking out some of the nearby sights and attractions such as LEGOLAND® Florida, Theatre Winter Haven, or Chain of Lakes Park. If you're interested in staying close to a certain attraction, you can sort properties by neighborhood and proximity to top sights, so you and your partner will get to see everything on your list.
When is the best time of year for a romantic getaway to Winter Haven?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Winter Haven: The hottest months are usually August and July with an average temp of 81°F, while the coldest months are January and February with an average of 64°F. The rainiest months in Winter Haven are August, July, September, and June, with each month seeing an average of 8 inches of rainfall.
What is there to do in Winter Haven?
There's nothing better than seeing a new place with your sweetheart, so consider taking time to discover all that Winter Haven has to offer. Couples looking for a little of everything will enjoy Winter Haven for its lakeside setting, gardens, and restaurants. LEGOLAND® Florida, Theatre Winter Haven, and Chain of Lakes Park are worth a stop when you're out and about.
What's the best way to get to Winter Haven and around town during my romantic getaway?
These transportation options in Winter Haven might help your romantic trip get off to a smooth start: To get to Winter Haven, book a flight to Lakeland Intl. Airport (LAL), which is the closest major airport, located 17.3 mi (27.8 km) from the city center. To see more of the larger area, ride aboard one of the trains from Winter Haven Station.