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2026-11-03
2026-11-04
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Holiday Homes in Winter Haven

Groovy Funhouse Getaway - 4 Bdrm Near Legoland

3357 Timberline Road West, Winter Haven, United States Show map

Hosting up to 10 guests, the 4-bedroom Groovy Funhouse Getaway - 4 Bdrm Near Legoland Villa Winter Haven offers a convenient location within a 6-km distance of sports attractions such as Chain of… More

From US$ 233 Book Now

Large 3Bedrooms 1 Bath Near Downtown Dining

677 Ave F Se, Winter Haven, United States Show map

Situated around 500 metres from A Personal Touch, Large 3Bedrooms 1 Bath Near Downtown Dining Winter Haven villa offers easy access to numerous tourist spots in the area. More

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Peaceful Lakeside Retreat

46 Lake Howard Drive Southwest, Winter Haven, United States Show map

Offering a terrace and a patio for guests' leisure, Peaceful Lakeside Retreat Winter Haven villa is situated a 10-minute ride from Simmers-Young Park. Located 4.9 km from the natural freshwater Lake… More

From US$ 155 Book Now

Cozy Lakefront Home W/ Pool -7 Mins From Legoland

104 Lake Ring Drive, Winter Haven, United States Show map

Nestled 6 km from Lake Region Baptist Church, Cozy Lakefront Home W/ Pool -7 Mins From Legoland Winter Haven entices guests to explore various tourist destinations nearby. More

From US$ 204 Book Now

The Old Haven - An Enduring Piece Of Nostalgia

718 Carroll Avenue Southwest, Winter Haven, United States Show map

The 4-bedroom The Old Haven - An Enduring Piece Of Nostalgia Villa Winter Haven entices active guests with access to a fitness suite and is located about a 15-minute stroll from Beymer United… More

From US$ 242 Book Now

The Cozy Nook

2037 Canton Park Drive, Winter Haven, United States Show map

The Cozy Nook Villa Winter Haven is located 4.3 km from Lake Region Golf Club and offers guests to enjoy their evening on a patio with outdoor dining areas. More

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The Luxury Lakehouse

9640 W Lake Ruby Dr, Winter Haven, United States Show map

Located 10 minutes' drive from the 150-acre interactive theme park "Legoland Florida Resort", The Luxury Lakehouse Winter Haven villa gives access to various tourist sites in the vicinity. More

From US$ 309 Book Now

Winter Haven Retreat W/ Private Pool!

154 Lake Roy Dr, Winter Haven, United States Show map

Along with access to such natural sites as Lego City Rescue Academy Theme Park, 2.5 km away, the 3-bedroom Winter Haven Retreat W/ Private Pool! Villa offers an outdoor swimming pool. Providing… More

From US$ 343 Book Now

Blockhaven Near Legoland, Disney

404 Red Hawk Loop, Winter Haven, United States Show map

During the stay at Blockhaven Near Legoland, Disney Winter Haven villa, guests can indulge in billiard or visit Simmers-Young Park, located 4.2 km away. More

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Waterfront Winter Haven Home With Dock & Hot Tub!

Winter Haven, FL, 33880, Winter Haven, United States Show map

Situated within a 3-km distance of The Garden Ballroom Event Venue, the 4-bedroom Waterfront Winter Haven Home With Dock & Hot Tub! includes a heated pool, as well as a Jacuzzi to relax in. More

From US$ 664 Book Now

Cozy Bungalow

138 Avenue East Southeast, Winter Haven, United States Show map

The 3-bedroom Cozy Bungalow Winter Haven offers easy access to such tourist spots as First Baptist Church, located only a 6-minute walk away. Providing guests with Wi-Fi and parking, this Winter… More

From US$ 143 Book Now

Promise Land Manor Historic Home Lake Access, Near Parks And Venues

404 Ave O Ne, Winter Haven, United States Show map

Located about a 10-minute drive from Lake Rochelle, the 2-room Promise Land Manor Historic Home Lake Access, Near Parks And Venues Winter Haven provides access to various tourist attractions in the… More

From US$ 259 Book Now

Modern 3 Bed 2 Bath Home 3 Minutes From Legoland

522 Lake Dexter Boulevard, Winter Haven, United States Show map

Nestled a 10-minute drive from the round Lake Fox, Modern 3 Bed 2 Bath Home 3 Minutes From Legoland Winter Haven entices guests to explore various tourist destinations nearby. More

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Chain Of Lakes Cottage

2140 West Central Avenue, Winter Haven, United States Show map

Located 25 minutes' walk from Lake Shipp Park, Chain Of Lakes Cottage Winter Haven offers a games room for guests' leisure. Located 7 km from Lego Ninjago World, this holiday home provides Wi-Fi and… More

From US$ 217 Book Now

6 Mi To Legoland: Retreat W/ Pool & Fenced Yard

832 Howard Terrace Nw, Winter Haven, United States Show map

Located about 25 minutes' walk from Rotary Park, 6 Mi To Legoland: Retreat W/ Pool & Fenced Yard Villa Winter Haven has a heated pool and is ideal for up to 6 guests. More

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Peaceful Waterfront Home Minutes From Legoland, Fl

115 North Lake Florence Drive, Winter Haven, United States Show map

Located nearly a 25-minute walk from Legoland, Peaceful Waterfront Home Minutes From Legoland, Fl Winter Haven has an outdoor swimming pool and is ideal for up to 12 guests. Guests can enjoy… More

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Lake, Pool, Hottub, Game Room, 8 Beds, Sleeps 17

108 North Lake Howard Drive, Winter Haven, United States Show map

Situated nearly a 10-minute ride from Simmers-Young Park, the 4-bedroom Lake, Pool, Hottub, Game Room, 8 Beds, Sleeps 17 Winter Haven villa includes an outdoor swimming pool, as well as a Jacuzzi to… More

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Getaway Clubhouse

144 Avenue East Southeast, Winter Haven, United States Show map

The 3-bedroom Getaway Clubhouse Villa Winter Haven offers swift access to various city sites, such as First Baptist Church, situated merely 6 minutes' walk away. Providing guests with Wi-Fi and… More

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Large Family Home, Legoland, Pet Friendly, 7 Beds

2140 West Central Avenue, Winter Haven, United States Show map

Situated about a 25-minute walk from The Garden Ballroom Event Venue, the 4-bedroom Large Family Home, Legoland, Pet Friendly, 7 Beds Winter Haven entices guests to explore various tourist… More

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5 Bedroom Home With Pool And Outdoor Fun

120 Lincoln Rd, Winter Haven, United States Show map

Staying at the 5-bedroom 5 Bedroom Home With Pool And Outdoor Fun Winter Haven, guests can visit Lego Ninjago World, which is just 1.8 km away. The Winter Haven villa is suitable for up to 10 guests… More

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Serene Lakeside Cottage Retreat

4840 Old Lucerne Park Road, Winter Haven, United States Show map

Nestled 3.2 km from Lake Henry Golf Club, Serene Lakeside Cottage Retreat Winter Haven entices guests to explore various tourist destinations nearby. This 3-bedroom holiday home can host up to 6… More

From US$ 206 Book Now

Lakefront Winter Haven Retreat: Hot Tub & Patio!

1700 S Lake Mirror Dr Nw, Winter Haven, United States Show map

Ensuring a relaxing stay with a Jacuzzi, the 4-bedroom Lakefront Winter Haven Retreat: Hot Tub & Patio! villa is situated approximately a 10-minute drive from the 200-acre Simmers Park and can… More

From US$ 330 Book Now

8 Mi To Legoland: Winter Haven Home W/ Lanai!

469 Adriel Ave, Winter Haven, United States Show map

Situated about 7 km from the 150-acre interactive theme park "Legoland Florida Resort", the 3-bedroom 8 Mi To Legoland: Winter Haven Home W/ Lanai! entices guests to explore various tourist… More

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Legoland & Downtown Getaway - Pool, Jacuzzi, Theater, Game Room, And Lego Theme Room

814 Sunset Cove Drive, Winter Haven, United States Show map

Located 6 km from Village Square, Legoland & Downtown Getaway - Pool, Jacuzzi, Theater, Game Room, And Lego Theme Room Winter Haven villa gives access to various tourist sites in the vicinity. More

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3Br 2Ba Modern Spacious Lake Home 4Miles Legoland - 1724

1724 Lake Mariam Dr, Winter Haven, United States Show map

The 3-bedroom 3Br 2Ba Modern Spacious Lake Home 4Miles Legoland - 1724 Winter Haven accommodates up to 7 guests and offers a convenient location nearly a 10-minute drive from such places of worship… More

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Chain Of Lakes - Sunrise On Lake Idylwild - Tiki Bar, Dock & Kayaks - Legoland

1076 Idylwild Dr Nw, Winter Haven, United States Show map

During the stay at Chain Of Lakes - Sunrise On Lake Idylwild - Tiki Bar, Dock & Kayaks - Legoland Winter Haven villa, guests can indulge in canyoning, billiard, and fisheries or visit the 200-acre… More

From US$ 254 Book Now

Kid-Friendly Home W Pool & Bbq

2414 West Central Avenue, Winter Haven, United States Show map

Featuring an outdoor swimming pool, the 3-bedroom Kid-Friendly Home W Pool & Bbq Winter Haven is suitable for up to 7 people and is located about 25 minutes' walk from Simmers-Young Park. Providing… More

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Lakefront Vibes W/ Lanai! Bird-Watching Paradise

510 Sears Ave Ne, Winter Haven, United States Show map

Situated 3.9 km from Willowbrook Golf Course, Lakefront Vibes W/ Lanai! Bird-Watching Paradise Winter Haven villa provides access to numerous tourist attractions in the area. The 3-bedroom holiday… More

From US$ 232 Book Now

Nice Little Get-Away

7109 Summit Drive, Winter Haven, United States Show map

The 3-bedroom Nice Little Get-Away Winter Haven villa hosts up to 6 guests and is nestled within 3 km of natural sites such as the large natural Lake Winterset. Located around a 10-minute drive from… More

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Luxury 3Br With Heated Private Pool & Game Room, Only 4 Min To Legoland

910 East Heron Circle, Winter Haven, United States Show map

Situated 1.6 km from the round Lake Fox, Luxury 3Br With Heated Private Pool & Game Room, Only 4 Min To Legoland Winter Haven villa is suitable for 8 guests and provides an outdoor swimming pool for… More

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Lake Hamilton VI ~ Pool And Backyard Oasis

2950 Crump Road, Winter Haven, United States Show map

The 6-bedroom Lake Hamilton VI ~ Pool And Backyard Oasis Winter Haven villa is located within 7 km of the 150-acre interactive theme park "Legoland Florida Resort" and provides canyoning and… More

From US$ 443 Book Now

9 Mi To Legoland: Family Gem W/ Games Galore!

3357 Timberline Rd W, Winter Haven, United States Show map

Located around 10 minutes' drive from Lake Shipp Park, the 4-bedroom 9 Mi To Legoland: Family Gem W/ Games Galore! Winter Haven villa provides access to various tourist attractions in the vicinity. More

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Spacious 4-Bedroom 2-Bath Abode

1216 Lysiloma Avenue, Winter Haven, United States Show map

Offering a location 4.8 km from Inman Park, the 4-bedroom Spacious 4-Bedroom 2-Bath Abode Winter Haven villa gives access to various tourist spots in the area. The holiday home hosts up to 10 guests… More

From US$ 265 Book Now

Legoland Pool Home With Private Suite

622 Avenue D Southeast, Winter Haven, United States Show map

Situated nearly a 20-minute walk from First Baptist Church, the historical Legoland Pool Home With Private Suite Winter Haven provides access to numerous tourist attractions in the area. More

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Stylish-N-Private 1Br Retreat 2 Miles To Legoland

806 Wakulla Drive, Winter Haven, United States Show map

Staying at Stylish-N-Private 1Br Retreat 2 Miles To Legoland Villa Winter Haven, guests can visit the large natural Lake Eloise, which is approximately a 10-minute ride away. More

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My Place Near Legoland

2805 Ave M Nw, Winter Haven, United States Show map

Nestled 10 minutes' drive from The Historic Baynard House Museum, My Place Near Legoland Winter Haven villa entices guests to explore various tourist destinations nearby. More

From US$ 135 Book Now

Winter Haven Home With Pool Near Legoland!

919 Ave S Se, Winter Haven, United States Show map

Winter Haven Home With Pool Near Legoland! offers proximity to nearby tourist spots, such as Lake Region Baptist Church, situated around 10 minutes away by car. More

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Sleeps 16+, Sports Team Friendly, Pet Friendly

2140 West Central Avenue, Winter Haven, United States Show map

Nestled a 25-minute walk from Lake Shipp Park, Sleeps 16+, Sports Team Friendly, Pet Friendly Villa Winter Haven entices guests to explore various tourist destinations nearby. The 6-bedroom villa… More

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3Br Private Pool Legoland, Disney & Universal

919 Avenue South Southeast, Winter Haven, United States Show map

Located nearly 25 minutes' walk from Lego City Rescue Academy Theme Park, the 3-bedroom 3Br Private Pool Legoland, Disney & Universal Winter Haven villa provides access to various tourist attractions… More

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Waterfront Vacation Rental On Lake Mirror!

1630 17Th St Nw, Winter Haven, United States Show map

Offering access to entertainment venues such as The Garden Ballroom Event Venue, situated nearly a 25-minute walk away, the 2-bedroom Waterfront Vacation Rental On Lake Mirror! Winter Haven villa can… More

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Family-Friendly Winter Haven Home With Pool!

3520 Majesty Loop, Winter Haven, United States Show map

Nestled a 10-minute drive from the 200-acre Simmers Park, Family-Friendly Winter Haven Home With Pool! entices guests to explore various tourist destinations nearby. More

From US$ 101 Book Now

White Door House!

2073 9Th Lane Northeast, Winter Haven, United States Show map

The 1-bedroom White Door House! Villa Winter Haven offers proximity to nearby tourist spots, such as the natural freshwater Lake Conine, situated approximately 25 minutes' walk away. With a maximum… More

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Your Vibrant Winter Haven Oasis Awaits

252 Sunfish Drive, Winter Haven, United States Show map

The 1-bedroom Your Vibrant Winter Haven Oasis Awaits villa can host up to 6 guests, boasting a convenient location 4.2 km from iconic cultural attractions such as Fort Cummings Museum. Located within… More

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The Imperious One

1532 Axel Circle, Winter Haven, United States Show map

Offering a location 4.2 km from The Garden Ballroom Event Venue, The Imperious One Villa Winter Haven gives access to various tourist spots in the area. More

From US$ 297 Book Now

Bungalow Haven

317 8Th Street Northeast, Winter Haven, United States Show map

Located a 5-minute ride from The Garden Ballroom Event Venue, Bungalow Haven Winter Haven gives access to various tourist sites in the vicinity. More

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Lake Lulu Escape

900 Ave Z Se Unit G7, Winter Haven, United States Show map

Located within 25 minutes' walk of the 150-acre interactive theme park "Legoland Florida Resort", the 2-bedroom Lake Lulu Escape Winter Haven villa provides access to various tourist attractions in… More

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John Shirleys Retreat

1037 Mockingbird Circle, Winter Haven, United States Show map

Located within a 10-minute drive of Lake Region Yacht & Country Club, the 3-bedroom John Shirleys Retreat Villa Winter Haven provides access to various tourist attractions in the vicinity. More

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Serene, Cozy, Lakefront Home

134 Lake Howard Drive Southwest, Winter Haven, United States Show map

Located 3 km from Chain of Lakes Park Florida Baseball Field, Serene, Cozy, Lakefront Home Winter Haven gives access to various tourist sites in the vicinity. The 2-bedroom holiday home hosts up to 7… More

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Winter Haven Chain Of Lakes Getaway Near Legoland

3721 Conine Dr E, Winter Haven, United States Show map

Offering a terrace and a patio for guests' leisure, the welcoming Winter Haven Chain Of Lakes Getaway Near Legoland villa is situated a 10-minute drive from Fort Cummings Museum. Located 2.7 km from… More

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Central Florida Vacation Home

3783 Fieldstone Circle, Winter Haven, United States Show map

Staying at the 4-bedroom Central Florida Vacation Home Winter Haven, guests can visit Calvary Baptist Church, which is nearly a 25-minute walk away. The Winter Haven villa accommodates up to 12… More

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