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Vacation Rentals & Apartment Rentals in Winter Haven

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2,090 apartment rentals

Disney 45 minutes away! LegoLand 10 minutes away!!!

Winter Haven house

3 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$138

Chain of Lakes w Dock & Kayaks ~Sunrise on Lake Idylwild~Legoland 7.5 mi~Disney

Winter Haven house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 1 hour 48 minutes

Price per night from

$229

Dock! Lakehouse Getaway with your Family and Enjoy this Spacious Home!

Winter Haven house

5 bedrooms / 3 bathrooms / sleeps 11

Responds fast! avg. 1 hour 48 minutes

Price per night from

$306

Dock!!! Time to Go Lakeside, Great for Families & Close to Lego Land!

Winter Haven house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 1 hour 48 minutes

Price per night from

$261

Family Fun Times ~ Pet Friendly - 45 minutes to Disney

Winter Haven house

3 bedrooms / 1 bathroom / sleeps 9

Responds fast! avg. 1 hour 48 minutes

Price per night from

$105

Great rentals within 20 miles that match your search

Pluto's Palace Disney Villa

Davenport villa

3 bedrooms / 8 bathrooms / sleeps 8

Price per night from

$241

KYLEMORE

Davenport villa

5 bedrooms / 3 bathrooms / sleeps 11

Responds fast! avg. 3 hours 52 minutes

Price per night from

$184

Exceptional Villa Large Private South Facing Pool

Haines City villa

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$277

Jasmine Villa

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 17 minutes

Price per night from

$179

Woodview

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

“Absolutely Perfect” Our Experience in this home was magnificent!! The home is beautiful both inside and out the pictures does not do this house justice!! It was fully equipped with everything you can imagine and more. The owner Julie Southern is terrific, she was always available and answered any questions. If you are looking for a beautiful home in a great location to enjoy with family and friends look no further.

Price per night from

$139

Charming, captivating & inviting home from home villa

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 9 minutes

Price per night from

$194

Lovely 5 Bedroom Home Close To Disney

Davenport villa

5 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$194

Palm View

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

“Very nice unit.” Would give it a 8 out of 10 review. A few minor thing would make it nicer. Fix rollers on patio doors. Latch sets do not lock on some bedroom and bathroom doors. Garage door is very heavy, and doesn't lock easily, power operator would be nice. Light over kitchen table needs a higher out put bulb.

Responds fast! avg. 1 hour 56 minutes

Price per night from

$111

Disney Villa

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

“Fab villa” A beautiful villa with lots of entertaining room, additional games room and large pool area .. had a lovely 2 week stay and hope to go again soon ..

Responds fast! avg. 2 hours 44 minutes

Price per night from

$129

249 Scrub Jay Way - Sandy Ridge, Davenport 5 Bedroom, 3 Bathrooms, private pool.

Davenport villa

5 bedrooms / 3 bathrooms / sleeps 10

“Great vacation spot” I rented this home for a Disney getaway with my husband and our toddler. The home was located in a very pleasant and quiet neighborhood. The backyard and pool area was very relaxing and peaceful which is exactly what you need after a day at the theme parks. The home itself was very spacious and had all the amenities we needed and much more. Everything was pretty much in order and if we had any issue or concern the owner was always readily available via email. Additionally within a few days after our departure, we received our deposit refund as promised. We were content with our stay at this home and look forward to staying there again in the near future.

Responds fast! avg. 2 hours 22 minutes

Price per night from

$184

Florida villa

ChampionsGate villa

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 12 minutes

Price per night from

$166

Bienvenue

Davenport villa

6 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$227

Magic@Marbella

Davenport villa

5 bedrooms / 4 bathrooms / sleeps 10

“You have to see it...to believe it!!!! :)” My family and I had an AWESOME time at Marbella resorts!!! This was my first time booking through TripAdvsior and I must admit that I was a little skeptical at first (because I was paying an "unknown source!" I even called TripAdvisor to reassure myself that it wan't a scam! John (the owner of the unit) also reassured me that everything was fine! :) Upon arriving at our unit we were blown away with the neighborhood My kids couldn't wait for me to unlock the door and turn off the alarm!!! Their eyes glisten with excitement!!! The unit was GORGEOUS!!! Everyone scrambled to "find their room" while we toured the rest of the house! It was EVERYTHING (and more) that the site listed!!! The pictures did it no justice!!! Although we went to go to Disney the kids felt like staying at the house with their private pool was more enjoyable (and less crowded) ;) I can't thank John and his TripAdvisor for making our 1st family vacation a HUGE SUCCESS!!! We're DEFINITELY gonna make this a yearly thing!! Thanks again!!!

Responds fast! avg. 28 minutes

Price per night from

$125

6 bedroom, Private Villa, Kissimmee, Private Pool

Davenport house

6 bedrooms / 3 bathrooms / sleeps 12

“Perfect house” The house was great. The location was convenient to relatives,Disney and shopping. Would stay again.

Responds fast! avg. 3 hours 30 minutes

Price per night from

$133

Tilys

Davenport villa

5 bedrooms / 4 bathrooms / sleeps 14

Responds fast! avg. 3 hours 40 minutes

Price per night from

$201

My-Villa-in-Florida

Davenport villa

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$190

Villa Sunnyside

Orlando villa

3 bedrooms / 3 bathrooms / sleeps 6

“Excellent!” Very nice clean house in very quiet location. Nice view of lake from the pool deck. Lots of wildlife to view around the lake too!

Price per night from

$230

Hampton Lakes 6 bedroom 4 bathroom detached Villa.

Davenport villa

6 bedrooms / 4 bathrooms / sleeps 14

Responds fast! avg. 1 hour 22 minutes

Price per night from

$224

Only 20min to Disney Parks - This villa has it all for the whole family to enjoy

Davenport villa

5 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$222

Upscale Condo Near Disney

Davenport apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$90

Spencer's Belle Vue Villa - with lake & conservation views

Davenport villa

6 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$208

Golfview Florida Villa, Southern Dunes

Haines City villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 39 minutes

Price per night from

$153

Sandy Ridge Villa

Davenport villa

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$137

Cocoa Villa

Haines City villa

4 bedrooms / 3 bathrooms / sleeps 10

“Vacation to remember” beautiful home, beautiful neighborhood, security guards were very nice, always smiling and greeting us as we enter and exit, The pest control guy was very informative and nice, seems to love his job. The maintenance guy answer questions and followed up on our concerns immediately. Overall I enjoyed our home and would be interested in leasing property out there. Very convenient to all stores and dinning areas

Price per night from

$97

Emerald Villas

Davenport villa

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$172

Golf Resort Private Pool Golf Tennis SPA Villa

Davenport house

12 bedrooms / 6 bathrooms / sleeps 24

Price per night from

$883

Villa by Disney

Davenport villa

3 bedrooms / 2 bathrooms / sleeps 7

“idilic location/ perfect for visiting theme parks” Service from owners fist class. House was exactly as described. Ideal location for theme parks and shopping and eating. Could not get grandkids out the pool they absolutely loved it. 2nd time we have stayed there and will have no hesitation booking again should we go back to Florida.

Price per night from

$125

Highlands Reserve villa :South facing private Pool

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 14 minutes

Price per night from

$201

Beautiful Villa (featuring secluded pool area)

Davenport villa

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$104

The Orlando Lodge

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

“Fun in the sun” Very nice- with 2 masters, and a nice layout. Clean home with nice pool- the kitchen had only the basics and you will need to provide dish soap, cleaners, TP and garbage bags. Our only issue was parking- be warned, if you have more than one car, you will need to find parking- we had a travel trailer, and didn't know we would not be able to park on the street- we ended up renting a storage space down the road. The neighbors were not very nice about it. Gary was great, and so was his rental management.

Responds fast! avg. 3 hours 25 minutes

Price per night from

$89

Davenport Villa Rental Florida

Davenport villa

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 2 minutes

Price per night from

$119

Highlands Reserve Golf Villa

Davenport villa

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$173

Keyvilla-The Disney Retreat. Free Spa Heat!

Davenport villa

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$180

Viewing 38 of 2,090
rentals in Winter Haven

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About Winter Haven

Whether you're in Winter Haven because of the kids (hello, Legoland!) or flying solo, there is something for everyone in this city! Why not visit FlipKey for the perfect Winter Haven vacation rental that you can relax in when you're done exploring?

About Winter Haven

The earliest people known to what is now Winter Haven were the Timucua and the Calusa. In the 1860s, the first settlers came to Winter Haven and it wasn't named Winter Haven until 1885 by P.D. Eycleshimer.

Winter Haven has a myriad of interconnected lakes. Started in 1915 and completed by the early 1920s, be sure to check out the Chain of Lakes!

Winter Haven has a long history which you can find out about at the Museum of Winter Haven.

The second largest city in Polk County, Winter Haven is home to a variety of cultural experiences. Located between Tampa and Orlando, there is plenty to do in this fabulous city!

Whether you want to discover your inner water baby by checking out the watersports Winter Haven has to offer, or you'd rather just relax and enjoy the eclectic food scene, Winter Haven is for everybody!

What to do

Why not start your day off by exploring Downtown Winter Haven? Full of great shops and restaurants, you will really get a feel of Winter Haven here!

When you're done exploring, head on over to The Chain of Lakes so you can take part in a spot of fishing. Too boring? Then there are many watersports you can enjoy, such as jet skiing, water tubing, and boating.

Make sure to check out the fountain in Central Park, which changes its colors during holidays!

Winter Haven holds many events throughout the year. Enjoy local musicians at Pickin in the Park held the first Friday of the month.

Check out the local produce at the Farmer's Market, which is held every Thursday 8 am - 5 pm.

Last but not least, be sure to check out Legoland which is the second-largest Legoland in the world. The kids will be sure to enjoy it!

Top Winter Haven travel tips

Winter Haven enjoys a mild climate throughout most of the year, so you can mostly get away with a light sweater. Be aware of the occasional shower during the summer months, though!

You'll be able to get to Winter Haven quite easily from Orlando. Orlando International Airport is only 45 minutes away. You can also access Winter Haven via Tampa International Airport. However, this is slightly further away.

You can easily get around Winter Haven by bus using the two bus services on offer: Winter Haven Area Transit and Citrus connection.

Winter Haven is the perfect vacation spot as there are so many things to do! Whether you're an art lover or a watersports enthusiast, Winter Haven doesn't turn anybody away. Find the perfect Winter Haven vacation rental FlipKey!

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