Vacation Rentals & Apartment Rentals in Winter Haven

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8,129 apartment rentals

24

Lake house #18

Central Florida / Winter Haven

Winter Haven villa

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$121

Responds fast!
avg. 2 hours 16 minutes

Price per night from

$121

31

Lake house #10

Central Florida / Winter Haven

Winter Haven villa

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$138

Responds fast!
avg. 2 hours 16 minutes

Price per night from

$138

(3) Very Good 

22

Saltwater Pool Villa Next to Legoland and Near All Disney Attractions

Central Florida / Winter Haven

Winter Haven villa

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Nearest beach 126 mi
  • Swimming pool
  • Child Friendly

Price per night from

$142

Responds fast!
avg. 3 hours 4 minutes

Price per night from

$142

(3) Excellent 

20

45 Min to Disney 15 Min to Legoland on chain of la

Central Florida / Winter Haven

Winter Haven house

3 10 3 nights min

  • 3 bedrooms
  • sleeps 10
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$257

Price per night from

$257

(6) Excellent 

28

Vacation home 3 Bedroom Next to LEGOLAND

Central Florida / Winter Haven

Winter Haven house

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$90

Price per night from

$90

29

Lake house #13

Central Florida / Winter Haven

Winter Haven villa

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$121

Responds fast!
avg. 2 hours 16 minutes

Price per night from

$121

(2) Average 

12

Lakeview Tiny Home by Legoland/Disney w/ boats!

Central Florida / Winter Haven

Winter Haven house

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Ask about pets

Price per night from

$75

Responds fast!
avg. 2 hours 59 minutes

Price per night from

$75

10

Snowbird - Central Florida - Waterfront / Bord de lac

Central Florida / Winter Haven

Winter Haven house

2 5 90 nights min

  • 2 bedrooms
  • sleeps 5
  • 90 nights min
  • Air conditioning
  • Pet Friendly
  • Private garden

Price per night from

$71

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$71

34

Lake house #9

Central Florida / Winter Haven

Winter Haven villa

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$138

Responds fast!
avg. 2 hours 16 minutes

Price per night from

$138

33

Lake house #17

Central Florida / Winter Haven

Winter Haven villa

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$138

Responds fast!
avg. 2 hours 16 minutes

Price per night from

$138

28

Lake house #15

Central Florida / Winter Haven

Winter Haven villa

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$121

Responds fast!
avg. 2 hours 16 minutes

Price per night from

$121

15

NEW! Lakefront Vacation Home with Pool & Boatdock!

Central Florida / Winter Haven

Winter Haven house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$143

Responds fast!
avg. 1 hour 55 minutes

Price per night from

$143

Great rentals within 20 miles that match your search

Distance approx 17.37 km from Winter Haven

(8) Excellent 

71

Pool Home near Disney | FREE WiFi, Parking, Cable, Tennis and Water-park | Golf

Central Florida / Orlando

Orlando villa

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Nearest beach 75 mi
  • Swimming pool
  • Child Friendly

Price per night from

$209

Price per night from

$209

Distance approx 17.44 km from Winter Haven

(4) Very Good 

41

Gated Resort, Gorgeous 7BR(3Kings)/Pool/SPA/Game Rm - two 7BR HOMES SIDE-BY-SIDE

Central Florida / Orlando

Orlando villa

7 16 min stay varies

  • 7 bedrooms
  • sleeps 16
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Spacious and comfortable” Although this was not the home pictured in the photos of the home we chose and thought we were staying, it provided the same spacious and comfortable space needed for a family reunion. The lanai with the pool and hot tub was
…see more

Price per night from

$172

Price per night from

$172

Distance approx 17.55 km from Winter Haven

(1) Excellent 

56

3250sqft 5BR/4BA Luxury Home, close to Disney

Central Florida / Davenport

Davenport villa

5 10 4 nights min

  • 5 bedrooms
  • sleeps 10
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$201

Price per night from

$201

Distance approx 17.22 km from Winter Haven

(11) Very Good 

Certificate of Excellence

46

Luxurious 8 Bedroom Pool Villa with Movie Theater

Central Florida / Orlando

Orlando villa

8 18 4 nights min

  • 8 bedrooms
  • sleeps 18
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary
“Awesome” We arrived August 12th 2017 and enjoyed our stay even though it rained every day. We loved the Movie Theater room it was a very cozy room for watching movies, however the projector did not work 5 of the seven days we were there and even after
…see more

Certificate of Excellence

Price per night from

$447

Responds fast!
avg. 12 minutes

Price per night from

$447

Distance approx 17.09 km from Winter Haven

(1) Excellent 

33

The Retreat - Champions Gate from $235/night

Central Florida / ChampionsGate

ChampionsGate house

7 16 4 nights min

  • 7 bedrooms
  • sleeps 16
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$345

Price per night from

$345

Distance approx 18.85 km from Winter Haven

15

4 Bedroom Villa on Gated Community *611

Central Florida / Orlando

Orlando villa

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$132

Responds fast!
avg. 1 hour 55 minutes

Price per night from

$132

Distance approx 9.87 km from Winter Haven Show on Map

(1) Excellent 

36

Luxurious Villa at Calabay Parc, Haines City, FL

Central Florida / Haines City

Haines City villa

5 10 3 nights min

  • 5 bedrooms
  • sleeps 10
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$161

Responds fast!
avg. 1 hour 15 minutes

Price per night from

$161

Distance approx 17.27 km from Winter Haven

(4) Excellent 

76

⭐Premium Villa+Spacious Theatre Room+Relaxing Pool+Amazing Golf Resort⭐

Central Florida / Davenport

Davenport villa

8 20 min stay varies

  • 8 bedrooms
  • sleeps 20
  • min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child Friendly
“Perfect all around” My family and I has had a wonderful time in this vacation rental. The home was beautifully decorated and furnished and the pictures really didn't do the home justice. The pool was great and we loved using it every minute we were in
…see more

Price per night from

$199

Responds fast!
avg. 49 minutes

Price per night from

$199

Distance approx 16.87 km from Winter Haven

15

Casa Mass

Central Florida / Davenport

Davenport townhouse

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$190

Price per night from

$190

Distance approx 16.52 km from Winter Haven

8

Stunning 4 bed villa with south west facing pool and spa overlooking conservatio

Central Florida / Davenport

Davenport house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children

Price per night from

$138

Price per night from

$138

Distance approx 18.78 km from Winter Haven

(2) Excellent 

19

Private Thousand Oaks Villa close to the action

Central Florida / Davenport

Davenport villa

3 7 5 nights min

  • 3 bedrooms
  • sleeps 7
  • 5 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“We would have no hesitation in recommending your villa to anyone” We have just returned from a fantastic stay in Florida at your lovely villa. it was fully equipped with everything we could possibly need and it was lovely to return to the comfort and
…see more

Price per night from

$126

Price per night from

$126

Distance approx 9.94 km from Winter Haven Show on Map

12

Villa 513 - 4 bed 3 bath villa not overlooked with private north facing Pool/spa

Central Florida / Haines City

Haines City villa

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$144

Price per night from

$144

Distance approx 17.52 km from Winter Haven

(2) Excellent 

12

5* Devine Villa Private Pool, free WIFI & calls

Central Florida / Davenport

Davenport villa

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 97 mi
  • Swimming pool
  • Child Friendly
“Fantastic holiday” We booked this at the last minute and the owner was a real pleasure to deal with, this was my third time renting a villa in Florida, and this has been the best so far. It was very clean, with new furniture and was well-maintained. T
…see more

Price per night from

$177

Price per night from

$177

Distance approx 17.09 km from Winter Haven

36

9 bedroom for 24 people! Champions Gate 1478MVCG

Central Florida / ChampionsGate

ChampionsGate house

9 24 min stay varies

  • 9 bedrooms
  • sleeps 24
  • min stay varies
  • Child Friendly

Price per night from

$379

Price per night from

$379

Distance approx 9.93 km from Winter Haven Show on Map

23

Florida Vacation Rental Home | Play Under the Palm

Central Florida / Haines City

Haines City house

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$138

Price per night from

$138

Distance approx 16.8 km from Winter Haven

39

Casa Bonita Great Larges Families

Central Florida / ChampionsGate

ChampionsGate house

7 15 min stay varies

  • 7 bedrooms
  • sleeps 15
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$316

Responds fast!
avg. 2 hours 16 minutes

Price per night from

$316

Distance approx 16.86 km from Winter Haven

23

Solterra - 5369 Oakbourne Ave

Central Florida / Davenport

Davenport house

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • Swimming pool
  • Car not necessary

Price per night from

$266

Responds fast!
avg. 3 hours 24 minutes

Price per night from

$266

Distance approx 18.93 km from Winter Haven

27

Remodeled 3 bed / 2 bath villa & pool in gated community, 10 mins to Disney

Central Florida / Four Corners

Four Corners villa

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 110 mi
  • Swimming pool
  • Child Friendly

Price per night from

$97

Responds fast!
avg. 1 hour 42 minutes

Price per night from

$97

Distance approx 14.31 km from Winter Haven

(1) Excellent 

7

419 Fox Loop GAMES ROOM

Central Florida / Davenport

Davenport villa

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Pet Friendly

Price per night from

$121

Price per night from

$121

Distance approx 16.69 km from Winter Haven

39

Beautiful 6 Bedroom Villa with South Facing Pool Overlooking Conservation Area

Florida / Sand Lake

Sand Lake house

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$167

Price per night from

$167

Distance approx 19.05 km from Winter Haven

10

701 SANDY RIDGE DRIVE

Central Florida / Loughman

Loughman villa

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Pet Friendly

Price per night from

$106

Price per night from

$106

Distance approx 18.19 km from Winter Haven

(11) Excellent 

93

Most private backyard in Orlando! Minutes 2 Disney

Central Florida / Loughman

Loughman villa

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 126 mi
  • Swimming pool
  • Child Friendly

Price per night from

$171

Responds fast!
avg. 8 minutes

Price per night from

$171

Distance approx 16.79 km from Winter Haven

(6) Excellent 

Certificate of Excellence

39

New Vacation Pool Home Orlando Area West Haven

Central Florida / Davenport

Davenport house

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Perfect private pool home” Very close to Orlando. Disney parks. Beautiful clean house, wonderful private pool and awesome hot tub. House came with EVERYTHING we needed. kitchen utensils pots and pans, dishes and cups. Our kids loved the themed décor r
…see more

Certificate of Excellence

Price per night from

$132

Responds fast!
avg. 1 hour 27 minutes

Price per night from

$132

Distance approx 14.56 km from Winter Haven

(5) Excellent 

Certificate of Excellence

31

7 Dwarfs Hideaway-S. Pool & Spa-2 masters 12 min Disney-Game Room-conservation

Central Florida / Four Corners

Four Corners house

4 11 min stay varies

  • 4 bedrooms
  • sleeps 11
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Perfect retreat!” GREAT HOUSE in beautiful location and so close to everything! Kitchen has everything you need to cook for your family and even storage containers for left overs. Kids love the game room and private pool. Adults like the separate sea
…see more

Certificate of Excellence

Price per night from

$99

Responds fast!
avg. 23 minutes

Price per night from

$99

Distance approx 19.53 km from Winter Haven

71

TRANQUILITY AT REUNION RESORT- OFFERING FANTASTIC AMENITIES

Central Florida / Reunion

Reunion villa

12 28 7 nights min

  • 12 bedrooms
  • sleeps 28
  • 7 nights min
  • Child Friendly

Price per night from

$2,036

Price per night from

$2,036

Distance approx 16.74 km from Winter Haven

24

Lovely secluded villa, near Disney& Golf, Huge SW facing pool, Games Room, WiFi

Central Florida / ChampionsGate

ChampionsGate villa

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Nearest beach 100 mi
  • Swimming pool
  • Child Friendly

Price per night from

$137

Price per night from

$137

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!