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8,129 apartment rentals
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
Responds fast!
avg. 2 hours 16 minutes
Price per night from
$121
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
Responds fast!
avg. 2 hours 16 minutes
Price per night from
$138
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 4 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
$257
Price per night from
$257
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
$90
Price per night from
$90
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
Responds fast!
avg. 2 hours 16 minutes
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. 2 hours 59 minutes
Price per night from
$75
Snowbird - Central Florida - Waterfront / Bord de lac
Central Florida / Winter Haven
2 5 90 nights min
- 2 bedrooms
- sleeps 5
- 90 nights min
- Air conditioning
- Pet Friendly
- Private garden
Map
Price per night from
$71
Responds fast!
avg. 1 hour 32 minutes
Price per night from
$71
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
Responds fast!
avg. 2 hours 16 minutes
Price per night from
$138
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
Responds fast!
avg. 2 hours 16 minutes
Price per night from
$138
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
Responds fast!
avg. 2 hours 16 minutes
Price per night from
$121
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
$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
Pool Home near Disney | FREE WiFi, Parking, Cable, Tennis and Water-park | Golf
Central Florida / Orlando
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
Gated Resort, Gorgeous 7BR(3Kings)/Pool/SPA/Game Rm - two 7BR HOMES SIDE-BY-SIDE
Central Florida / Orlando
7 16 min stay varies
- 7 bedrooms
- sleeps 16
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$172
Price per night from
$172
Distance approx 17.55 km from Winter Haven
3250sqft 5BR/4BA Luxury Home, close to Disney
Central Florida / Davenport
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
Certificate of Excellence
Luxurious 8 Bedroom Pool Villa with Movie Theater
Central Florida / Orlando
8 18 4 nights min
- 8 bedrooms
- sleeps 18
- 4 nights min
- Swimming pool
- Child Friendly
- Car not necessary
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
The Retreat - Champions Gate from $235/night
Central Florida / ChampionsGate
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
4 Bedroom Villa on Gated Community *611
Central Florida / Orlando
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
Luxurious Villa at Calabay Parc, Haines City, FL
Central Florida / Haines City
5 10 3 nights min
- 5 bedrooms
- sleeps 10
- 3 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Map
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
⭐Premium Villa+Spacious Theatre Room+Relaxing Pool+Amazing Golf Resort⭐
Central Florida / Davenport
8 20 min stay varies
- 8 bedrooms
- sleeps 20
- min stay varies
- Nearest beach 90 mi
- Swimming pool
- Child Friendly
Price per night from
$199
Responds fast!
avg. 49 minutes
Price per night from
$199
Distance approx 16.87 km from Winter Haven
Casa Mass
Central Florida / Davenport
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
Stunning 4 bed villa with south west facing pool and spa overlooking conservatio
Central Florida / Davenport
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
Private Thousand Oaks Villa close to the action
Central Florida / Davenport
3 7 5 nights min
- 3 bedrooms
- sleeps 7
- 5 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$126
Price per night from
$126
Distance approx 9.94 km from Winter Haven Show on Map
Villa 513 - 4 bed 3 bath villa not overlooked with private north facing Pool/spa
Central Florida / Haines City
4 8 min stay varies
- 4 bedrooms
- sleeps 8
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Map
Price per night from
$144
Price per night from
$144
Distance approx 17.52 km from Winter Haven
5* Devine Villa Private Pool, free WIFI & calls
Central Florida / Davenport
4 8 min stay varies
- 4 bedrooms
- sleeps 8
- min stay varies
- Nearest beach 97 mi
- Swimming pool
- Child Friendly
Price per night from
$177
Price per night from
$177
Distance approx 17.09 km from Winter Haven
9 bedroom for 24 people! Champions Gate 1478MVCG
Central Florida / ChampionsGate
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
Florida Vacation Rental Home | Play Under the Palm
Central Florida / Haines City
3 6 5 nights min
- 3 bedrooms
- sleeps 6
- 5 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Map
Price per night from
$138
Price per night from
$138
Distance approx 16.8 km from Winter Haven
Casa Bonita Great Larges Families
Central Florida / ChampionsGate
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
Solterra - 5369 Oakbourne Ave
Central Florida / Davenport
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
Remodeled 3 bed / 2 bath villa & pool in gated community, 10 mins to Disney
Central Florida / Four Corners
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
419 Fox Loop GAMES ROOM
Central Florida / Davenport
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
Beautiful 6 Bedroom Villa with South Facing Pool Overlooking Conservation Area
Florida / Sand Lake
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
701 SANDY RIDGE DRIVE
Central Florida / Loughman
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
Most private backyard in Orlando! Minutes 2 Disney
Central Florida / Loughman
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
Certificate of Excellence
New Vacation Pool Home Orlando Area West Haven
Central Florida / Davenport
4 10 3 nights min
- 4 bedrooms
- sleeps 10
- 3 nights min
- Swimming pool
- Child Friendly
- Air conditioning
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
Certificate of Excellence
7 Dwarfs Hideaway-S. Pool & Spa-2 masters 12 min Disney-Game Room-conservation
Central Florida / Four Corners
4 11 min stay varies
- 4 bedrooms
- sleeps 11
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
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
TRANQUILITY AT REUNION RESORT- OFFERING FANTASTIC AMENITIES
Central Florida / Reunion
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
Lovely secluded villa, near Disney& Golf, Huge SW facing pool, Games Room, WiFi
Central Florida / ChampionsGate
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!
What is Certificate of Excellence?
TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travelers.