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8,391 apartment rentals
Lake house #10
Central Florida / Winter Haven
2 7 min stay varies
- 2 bedrooms
- sleeps 7
- min stay varies
- Child Friendly
- Air conditioning
Map
Price per night from
$138
Price per night from
$138
Lake house #18
Central Florida / Winter Haven
1 4 min stay varies
- 1 bedroom
- sleeps 4
- min stay varies
- Child Friendly
- Air conditioning
Map
Price per night from
$121
Price per night from
$121
Saltwater Pool Villa Next to Legoland and Near All Disney Attractions
Central Florida / Winter Haven
3 6 4 nights min
- 3 bedrooms
- sleeps 6
- 4 nights min
- Nearest beach 126 mi
- Swimming pool
- Child Friendly
Map
Price per night from
$142
Responds fast!
avg. 3 hours 27 minutes
Price per night from
$142
45 Min to Disney 15 Min to Legoland on chain of la
Central Florida / Winter Haven
3 10 3 nights min
- 3 bedrooms
- sleeps 10
- 3 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Map
Price per night from
$258
Price per night from
$258
Vacation home 3 Bedroom Next to LEGOLAND
Central Florida / Winter Haven
3 6 1 night min
- 3 bedrooms
- sleeps 6
- 1 night min
- Child Friendly
- Air conditioning
- Private garden
Map
Price per night from
$91
Price per night from
$91
Lake house #13
Central Florida / Winter Haven
1 4 min stay varies
- 1 bedroom
- sleeps 4
- min stay varies
- Child Friendly
- Air conditioning
Map
Price per night from
$121
Price per night from
$121
Lakeview Tiny Home by Legoland/Disney w/ boats!
Central Florida / Winter Haven
1 3 1 night min
- 1 bedroom
- sleeps 3
- 1 night min
- Child Friendly
- Air conditioning
- Ask about pets
Map
Price per night from
$75
Responds fast!
avg. 3 hours 54 minutes
Price per night from
$75
Lake house #15
Central Florida / Winter Haven
1 4 min stay varies
- 1 bedroom
- sleeps 4
- min stay varies
- Child Friendly
- Air conditioning
Map
Price per night from
$121
Price per night from
$121
Snowbird - Central Florida - Waterfront / Bord de lac
Central Florida / Winter Haven
2 5 120 nights min
- 2 bedrooms
- sleeps 5
- 120 nights min
- Air conditioning
- Pet Friendly
- Private garden
Map
Price per night from
$71
Price per night from
$71
Lake house #17
Central Florida / Winter Haven
2 7 min stay varies
- 2 bedrooms
- sleeps 7
- min stay varies
- Child Friendly
- Air conditioning
Map
Price per night from
$138
Price per night from
$138
Lake house #9
Central Florida / Winter Haven
2 6 min stay varies
- 2 bedrooms
- sleeps 6
- min stay varies
- Child Friendly
- Air conditioning
Map
Price per night from
$138
Price per night from
$138
NEW! Lakefront Vacation Home with Pool & Boatdock!
Central Florida / Winter Haven
3 6 3 nights min
- 3 bedrooms
- sleeps 6
- 3 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Map
Price per night from
$144
Responds fast!
avg. 3 hours 59 minutes
Price per night from
$144
Livin the Dream
Central Florida / Winter Haven
3 6 min stay varies
- 3 bedrooms
- sleeps 6
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Map
Price per night from
$125
Price per night from
$125
Great rentals within 20 miles that match your search
Distance approx 18.5 km from Winter Haven
Certificate of Excellence
Disney Area Villa with Pool
Central Florida / Davenport
4 9 min stay varies
- 4 bedrooms
- sleeps 9
- min stay varies
- Beach / lakeside relaxation
- Nearest beach 75 mi
- Swimming pool
Certificate of Excellence
Price per night from
$106
Responds fast!
avg. 3 hours 7 minutes
Price per night from
$106
Distance approx 19.23 km from Winter Haven
Davenport Holiday Villa 27724
Central Florida / Loughman
5 10 7 nights min
- 5 bedrooms
- sleeps 10
- 7 nights min
- Swimming pool
- Air conditioning
Price per night from
$302
Price per night from
$302
Distance approx 16.77 km from Winter Haven
Watersong Resort-406AOCJGI
Central Florida / Davenport
6 12 6 nights min
- 6 bedrooms
- sleeps 12
- 6 nights min
- Swimming pool
- Child Friendly
- Car not necessary
Price per night from
$446
Price per night from
$446
Distance approx 13.19 km from Winter Haven
Golf Lovers Paradise
Central Florida / Davenport
5 12 min stay varies
- 5 bedrooms
- sleeps 12
- min stay varies
- Child Friendly
Price per night from
$160
Responds fast!
avg. 1 hour 42 minutes
Price per night from
$160
Distance approx 17.02 km from Winter Haven
★ SUMMER VACATION AT DISNEY 5BEDRM/4BATH AT SOLTERRA RESORT
Central Florida / Loughman
5 16 min stay varies
- 5 bedrooms
- sleeps 16
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$265
Price per night from
$265
Distance approx 19.41 km from Winter Haven
Calusa Villa is a 6 bedroom 4 bathroom detached Villa.
Davenport / Hampton Lakes
6 14 5 nights min
- 6 bedrooms
- sleeps 14
- 5 nights min
- Beach / lakeside relaxation
- Nearest beach 100 mi
- Swimming pool
Price per night from
$228
Price per night from
$228
Distance approx 17.07 km from Winter Haven
The Sanctuary at West Haven Luxury
Central Florida / Davenport
4 8 7 nights min
- 4 bedrooms
- sleeps 8
- 7 nights min
- Nearest beach 97 mi
- Swimming pool
- Air conditioning
Price per night from
$171
Price per night from
$171
Distance approx 17.95 km from Winter Haven
**Cinema Room***Elegant Champion Gates Cozy Escape Sleep 17 FREE Water Park
Central Florida / ChampionsGate
8 17 min stay varies
- 8 bedrooms
- sleeps 17
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$388
Responds fast!
avg. 2 hours 10 minutes
Price per night from
$388
Distance approx 19.11 km from Winter Haven
KYLEMORE
Davenport / The Manors North at Westridge
5 11 7 nights min
- 5 bedrooms
- sleeps 11
- 7 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$142
Responds fast!
avg. 3 hours 3 minutes
Price per night from
$142
Distance approx 18 km from Winter Haven
Private one bedroom apartment at a great price
Central Florida / Lakeland
1 4 2 nights min
- 1 bedroom
- sleeps 4
- 2 nights min
- Child Friendly
- Car not necessary
- Air conditioning
Price per night from
$89
Responds fast!
avg. 3 hours 31 minutes
Price per night from
$89
Distance approx 17 km from Winter Haven
5 star luxury Florida home - close to Disney
Central Florida / Davenport
4 8 min stay varies
- 4 bedrooms
- sleeps 8
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$171
Price per night from
$171
Distance approx 18.24 km from Winter Haven
Lake facing five bedroom property in Davenport, Florida
Central Florida / Davenport
5 8 3 nights min
- 5 bedrooms
- sleeps 8
- 3 nights min
- Child Friendly
Price per night from
$149
Price per night from
$149
Distance approx 18.07 km from Winter Haven
Your Villa in Florida
Central Florida / Davenport
4 10 3 nights min
- 4 bedrooms
- sleeps 10
- 3 nights min
- Child Friendly
Price per night from
$129
Responds fast!
avg. 1 hour 25 minutes
Price per night from
$129
Distance approx 16.97 km from Winter Haven
Solterra Resort 6 Bedroom 4 Bath Villa 5340OA
Central Florida / Davenport
6 12 min stay varies
- 6 bedrooms
- sleeps 12
- min stay varies
- Swimming pool
- Child Friendly
- Car not necessary
Price per night from
$255
Price per night from
$255
Distance approx 18.29 km from Winter Haven
StaySmooth Retreat- Near Disney!!!
Central Florida / Four Corners
3 7 min stay varies
- 3 bedrooms
- sleeps 7
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$125
Price per night from
$125
Distance approx 17.26 km from Winter Haven
At Last You can Rent the Perfect Luxury Villa on Champions Gate Resort, minutes
Central Florida / ChampionsGate
9 18 min stay varies
- 9 bedrooms
- sleeps 18
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$382
Price per night from
$382
Distance approx 17.39 km from Winter Haven
4 bedroom pool homes near Disney
Central Florida / Davenport
4 8 min stay varies
- 4 bedrooms
- sleeps 8
- min stay varies
- Nearest beach 80 mi
- Swimming pool
- Child Friendly
Price per night from
$143
Price per night from
$143
Distance approx 12.26 km from Winter Haven
Lakeside Villa
Central Florida / Davenport
6 12 7 nights min
- 6 bedrooms
- sleeps 12
- 7 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$224
Price per night from
$224
Distance approx 16.91 km from Winter Haven
Luxury 5 Star Villa on Solterra Resort,Minutes from Disney World, Orlando Villa
Central Florida / Loughman
15 26 min stay varies
- 15 bedrooms
- sleeps 26
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$679
Price per night from
$679
Distance approx 19.27 km from Winter Haven
'Lake View Dream Villa' 5BR Davenport Home w/Pool!
Central Florida / Davenport
5 10 5 nights min
- 5 bedrooms
- sleeps 10
- 5 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$125
Responds fast!
avg. 40 minutes
Price per night from
$125
Distance approx 16.52 km from Winter Haven
H6112 Beautiful 14 Bedroom 11 Bathroom Resoret
Central Florida / Loughman
14 28 min stay varies
- 14 bedrooms
- sleeps 28
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$834
Price per night from
$834
Distance approx 17.26 km from Winter Haven
Beautiful 5 Star Villa with Private Pool on the Prestigious Champions Gate
Central Florida / ChampionsGate
5 16 min stay varies
- 5 bedrooms
- sleeps 16
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$314
Price per night from
$314
Distance approx 18.74 km from Winter Haven
3BR Reunion Condo w/10 Pools - 4 Miles from Disney
Central Florida / Reunion
3 8 3 nights min
- 3 bedrooms
- sleeps 8
- 3 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$143
Responds fast!
avg. 14 minutes
Price per night from
$143
Distance approx 17.25 km from Winter Haven
The Secret to Enjoying Your Luxury Home Holiday on Champions Gate Resort
Central Florida / ChampionsGate
4 8 min stay varies
- 4 bedrooms
- sleeps 8
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$162
Price per night from
$162
Distance approx 17.71 km from Winter Haven
Luxury 6 bed new villa ,pool , hot tub , games rooms , home cinema
Central Florida / Davenport
6 13 7 nights min
- 6 bedrooms
- sleeps 13
- 7 nights min
- Nearest beach 80 mi
- Swimming pool
- Child Friendly
Price per night from
$224
Responds fast!
avg. 42 minutes
Price per night from
$224
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!
What is Certificate of Excellence?
TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travelers.