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Holiday homes in Winter Haven You’ll Love

Top-Rated Winter Haven Holiday homes for Every Budget and Style!

Looking for a holiday home in Winter Haven (Florida)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $50.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Winter Haven.

We found 45 Holiday-homes in Winter Haven and the surrounding area (within 20 miles)

Walk to LEGOLAND Heated Pool Putting Green Beach Sunsets Boat Dock in Winter Haven, USA

Walk to LEGOLAND Heated Pool Putting Gre...

Villa in Winter Haven, Florida , 2511 Cypress Gardens Boulevard
Walk to LEGOLAND Heated Pool Putting Green Beach Sunsets Boat Dock offers accommodations in Winter Haven, 0.9 miles from Legoland Florida and 12 miles...
  • Parking
  • Family rooms
  • Outdoor pool
  • Swimming Pool

Exceptional 2 Reviews 10.0

from $98.00 Show details »

Getaway Clubhouse 5 mil Legoland & .5 mil Downtown in Winter Haven, USA

Getaway Clubhouse 5 mil Legoland & .5 mi...

Villa in Winter Haven, Florida , 144 Avenue East Southeast
Getaway Clubhouse 5 mil Legoland &.5 mil Downtown offers accommodations in Winter Haven, 4.1 miles from Legoland Florida and 11 miles from Dearborn Ra...
  • Parking
  • Family rooms
  • Kids' outdoor play equipment

no reviews

from $52.00 Show details »

Lakeside Lofts at Lake Martha in Winter Haven, USA

Lakeside Lofts at Lake Martha

Villa in Winter Haven, Florida , 433 Ave C NE
Lakeside Lofts at Lake Martha is located in Winter Haven, just 4.2 miles from Legoland Florida and 12 miles from Dearborn Railroad Station.
  • Parking
  • Family rooms

Superb 22 Reviews 9.2

from $218.59 Show details »

The Luxury Lakehouse in Winter Haven, USA

The Luxury Lakehouse

Holiday home in Winter Haven, Florida
The Luxury Lakehouse offers accommodations in Winter Haven, 14 miles from Dearborn Railroad Station and 16 miles from Morris Mine Railroad Station.
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Good 3 Reviews 7.7

from $469.43 Show details »

Family-Friendly Eagle Lake Home, 7 Mi to Legoland! in Winter Haven, USA

Family-Friendly Eagle Lake Home, 7 Mi to...

Holiday home in Winter Haven, Florida
Family-Friendly Eagle Lake Home, 7 Mi to Legoland! is located in Winter Haven, just 6 miles from Legoland Florida and 8.5 miles from Dearborn Railroad...
  • Parking
  • Outdoor pool
  • Swimming Pool

no reviews

from $71.00 Show details »

146 Florida 3BR Home close to Legoland Park 12ppl in Winter Haven, USA

146 Florida 3BR Home close to Legoland P...

Holiday home in Winter Haven, Florida , 146 Brad Circle
146 Florida 3BR Home close to Legoland Park 12ppl is located in Winter Haven, just 7.7 miles from Legoland Florida and 9.3 miles from Morris Mine Rail...

no reviews

from $414.17 Show details »

Family-Friendly Winter Haven Home with Pool! in Winter Haven, USA

Family-Friendly Winter Haven Home with P...

Holiday home in Winter Haven, Florida
Family-Friendly Winter Haven Home with Pool! is located in Winter Haven, just 7.9 miles from Dearborn Railroad Station and 9.1 miles from Legoland Flo...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Superb 6 Reviews 9.2

from $213.92 Show details »

Winter Haven Retreat with Private Pool! in Winter Haven, USA

Winter Haven Retreat with Private Pool!

Holiday home in Winter Haven, Florida
Winter Haven Retreat with Private Pool! offers accommodations in Winter Haven, 1.8 miles from Legoland Florida and 12 miles from Dearborn Railroad Sta...
  • Parking
  • Outdoor pool
  • Swimming Pool

Good 6 Reviews 7.8

from $362.08 Show details »

Winter Haven Home with Pool Near Legoland! in Winter Haven, USA

Winter Haven Home with Pool Near Legolan...

Holiday home in Winter Haven, Florida
Featuring a garden, Winter Haven Home with Pool Near Legoland! offers accommodations in Winter Haven.
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Fabulous 13 Reviews 9.0

from $202.72 Show details »

Bagonia Home in Winter Haven, USA

Bagonia Home

Holiday home in Winter Haven, Florida , 1536 Axel Circle
Bagonia Home offers accommodations in Winter Haven, 7.3 miles from Legoland Florida and 10 miles from Dearborn Railroad Station.
  • Parking
  • Pets allowed
  • Family rooms

Exceptional 17 Reviews 9.9

from $271.94 Show details »

The Imperious Home in Winter Haven, USA

The Imperious Home

Holiday home in Winter Haven, Florida , 1532 Axel Circle
The Imperious Home is located in Winter Haven, just 7.3 miles from Legoland Florida and 10 miles from Dearborn Railroad Station.
  • Parking
  • Pets allowed
  • Family rooms

Exceptional 3 Reviews 9.7

from $413.35 Show details »

Stylish-N-Private 1BR Retreat 2 Miles to LegoLand in Winter Haven, USA

Stylish-N-Private 1BR Retreat 2 Miles to...

Holiday home in Winter Haven, Florida , 806 Wakulla Drive
Stylish-N-Private 1BR Retreat 2 Miles to LegoLand offers accommodations in Winter Haven, 15 miles from Morris Mine Railroad Station and 15 miles from ...
  • Parking
  • Pets allowed

Good 24 Reviews 7.9

from $104.53 Show details »

Bright Cypress Gardens Home Near Legoland! in Cypress Gardens, USA

Bright Cypress Gardens Home Near Legolan...

Holiday home in Cypress Gardens near Winter Haven, Florida
Bright Cypress Gardens Home Near Legoland! offers accommodations in Cypress Gardens, 12 miles from Dearborn Railroad Station and 17 miles from Elmer R...
  • Parking

Exceptional 7 Reviews 9.8

from $173.28 Show details »

Groovy Funhouse Getaway - 4 bdrm near Legoland in Winter Haven, USA

Groovy Funhouse Getaway - 4 bdrm near Le...

Holiday home in Winter Haven, Florida , 3357 Timberline Road West
Groovy Funhouse Getaway - 4 bdrm near Legoland is a recently renovated vacation home in Winter Haven where guests can make the most of its outdoor swi...
  • Parking
  • Allergy-free room
  • Outdoor pool
  • Kids' pool
  • Swimming Pool

Good 32 Reviews 7.6

from $295.98 Show details »

Cozy Lakefront Home w/ Pool -7 mins from Legoland in Winter Haven, USA

Cozy Lakefront Home w/ Pool -7 mins from...

Holiday home in Winter Haven, Florida , 104 Lake Ring Drive
Cozy Lakefront Home w/ Pool -7 mins from Legoland is located in Winter Haven, just 2 miles from Legoland Florida and 12 miles from Dearborn Railroad S...
  • Parking
  • Family rooms
  • Outdoor pool
  • Swimming Pool

Good 8 Reviews 7.8

from $301.66 Show details »

Spacious 4-bedroom 2-bath Abode in Winter Haven, USA

Spacious 4-bedroom 2-bath Abode

Holiday home in Winter Haven, Florida , 1216 Lysiloma Avenue
Spacious 4-bedroom 2-bath Abode is located in Winter Haven, just 10 miles from Dearborn Railroad Station and 12 miles from Elmer Railroad Station.
  • Parking
  • Family rooms

Good 14 Reviews 7.1

from $312.01 Show details »

Stylish Lake home with HEATED POOL, Arcade with PS5,and Theater Just 5 min from Legoland in Winter Haven, USA

Stylish Lake home with HEATED POOL, Arca...

Holiday home in Winter Haven, Florida , 120 Lake Ring Drive
Stylish Lake home with HEATED POOL, Arcade with PS5, and Theater Just 5 min from Legoland offers accommodations in Winter Haven, 2 miles from Legoland...
  • Parking
  • Pets allowed
  • Family rooms
  • Outdoor pool
  • Swimming pool

Very good 7 Reviews 8.0

from $483.12 Show details »

Large 3Bedrooms 1 Bath Near DownTown Dining in Winter Haven, USA

Large 3Bedrooms 1 Bath Near DownTown Din...

Holiday home in Winter Haven, Florida , 677 Ave F SE
Large 3Bedrooms 1 Bath Near DownTown Dining is located in Winter Haven, just 3.5 miles from Legoland Florida and 11 miles from Dearborn Railroad Stati...
  • Parking
  • Pets allowed
  • Family rooms

Fabulous 18 Reviews 8.8

from $146.93 Show details »

Cozy Bungalow 5 mi Legoland and 0.5 mi Dwntwn in Winter Haven, USA

Cozy Bungalow 5 mi Legoland and 0.5 mi D...

Holiday home in Winter Haven, Florida , 138 Avenue East Southeast
Cozy Bungalow 5 mi Legoland and 0.5 mi Dwntwn offers accommodations in Winter Haven, 11 miles from Dearborn Railroad Station and 13 miles from Elmer R...

Exceptional 2 Reviews 10.0

from $160.43 Show details »

Getaway Clubhouse 5 mil Legoland .5 mil Downtown in Winter Haven, USA

Getaway Clubhouse 5 mil Legoland .5 mil...

Holiday home in Winter Haven, Florida , 144 Avenue East Southeast
Getaway Clubhouse 5 mil Legoland.5 mil Downtown is located in Winter Haven, just 11 miles from Dearborn Railroad Station and 13 miles from Elmer Railr...

Exceptional 13 Reviews 9.5

from $184.67 Show details »

Winter Haven Vacation Rental about 1 Mi to Downtown! in Winter Haven, USA

Winter Haven Vacation Rental about 1 Mi...

Holiday home in Winter Haven, Florida
Winter Haven Vacation Rental about 1 Mi to Downtown! is located in Winter Haven, just 12 miles from Dearborn Railroad Station and 13 miles from Elmer ...
  • Parking

no reviews

from $74.00 Show details »

The Old Haven - An Enduring Piece of Nostalgia in Winter Haven, USA

The Old Haven - An Enduring Piece of Nos...

Holiday home in Winter Haven, Florida , 718 Carroll Avenue Southwest
The Old Haven - An Enduring Piece of Nostalgia is located in Winter Haven, just 4.6 miles from Legoland Florida and 11 miles from Tanco Railroad Stati...
  • Fitness centre

Superb 5 Reviews 9.2

from $178.00 Show details »

Winter Haven Abode Near Lakes and Attractions in Winter Haven, USA

Winter Haven Abode Near Lakes and Attrac...

Holiday home in Winter Haven, Florida
Winter Haven Abode Near Lakes and Attractions offers accommodations in Winter Haven, 12 miles from Dearborn Railroad Station and 13 miles from Elmer R...
  • Parking
  • Spa and wellness centre

Superb 16 Reviews 9.4

from $57.00 Show details »

3Bed 2 Bath Spacious Lake Home Ace Location4Miles2 Legoland in Winter Haven, USA

3Bed 2 Bath Spacious Lake Home Ace Locat...

Holiday home in Winter Haven, Florida , 1724 Lake Mariam Drive
3Bed 2 Bath Spacious Lake Home Ace Location4Miles2 Legoland is located in Winter Haven, just 13 miles from Dearborn Railroad Station and 14 miles from...
  • Parking
  • Pets allowed

Very good 4 Reviews 8.3

from $235.87 Show details »

Modern Cottage Tiny-Home 4miles to LEGOLAND in Cypress Gardens, USA

Modern Cottage Tiny-Home 4miles to LEGOL...

Holiday home in Cypress Gardens near Winter Haven, Florida , 1722 Lake Mariam Drive
Modern Cottage Tiny-Home 4miles to LEGOLAND offers accommodations in Cypress Gardens, 13 miles from Dearborn Railroad Station and 14 miles from Elmer ...
  • Parking
  • Pets allowed

Fabulous 7 Reviews 8.8

from $133.97 Show details »

Number of Holiday homes in Winter Haven 45
Number of guest ratings 5,303
Average price per night $214.00
Lowest price per night $50,00
Highest price per night $487,73

Top 10 Cheapest Holiday-homes in Winter Haven

Discover the Cheapest Holiday-homes in Winter Haven – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Winter Haven

Check out the Most Booked Holiday-homes in Winter Haven – Based on Guest Popularity.

Holiday homes in Winter Haven (Florida), comfortable and familiar

Staying in a holiday or vacation home in Winter Haven can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Winter Haven for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Winter Haven should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com