Vacation rentals in Winter Haven, FL

Best vacation rentals and Airbnb offers in Winter Haven, FL

Winter Haven Apt: 1 Mi to Polk State College!

Apartment, Winter Haven

Winter Haven Apt: 1 Mi to Polk State College! is a apartment in Winter Haven, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Winter Haven Apt: 1 Mi to Polk State College!

Winter Haven Apt: 1 Mi to Polk State College! is a apartment in Winter Haven, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $728.

From$65/night

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Lake Ida Beach Resort

Cottage, Winter Haven

Lake Ida Beach Resort is a cottage in Winter Haven, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Lake Ida Beach Resort

Lake Ida Beach Resort is a cottage in Winter Haven, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $532.

From$68/night

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Studio Apartment in Winter Haven, FL

Apartment, Winter Haven

Studio Apartment in Winter Haven, FL is a apartment in Winter Haven, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Studio Apartment in Winter Haven, FL

Studio Apartment in Winter Haven, FL is a apartment in Winter Haven, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $494.

From$71/night

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Tiny Paradise

Apartment, Winter Haven

Tiny Paradise is a apartment in Winter Haven, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Tiny Paradise

Tiny Paradise is a apartment in Winter Haven, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $559.

From$80/night

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Vacation rentals with a pool in Winter Haven, FL

Add a pool to the search when you want an easy place to cool off between outings.

Stylish Lake home with HUGE POOL, Arcade with PS5,and Theater Just 5 min from Legoland

Holiday Home, Winter Haven

Stylish Lake home with HUGE POOL, Arcade with PS5,and Theater Just 5 min from Legoland is a holiday home in Winter Haven, with pet-friendly space and pool access. This stay gives travelers…

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About Stylish Lake home with HUGE POOL, Arcade with PS5,and Theater Just 5 min from Legoland

Stylish Lake home with HUGE POOL, Arcade with PS5,and Theater Just 5 min from Legoland is a holiday home in Winter Haven, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,332.

From$269/night

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Charming 1-bedroom guesthouse with pool view WiFi and AC in Winter Haven

Holiday Home, Winter Haven

Charming 1-bedroom guesthouse with pool view WiFi and AC in Winter Haven is a holiday home in Winter Haven, with pool access, parking, and kitchen access. This stay gives travelers a…

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About Charming 1-bedroom guesthouse with pool view WiFi and AC in Winter Haven

Charming 1-bedroom guesthouse with pool view WiFi and AC in Winter Haven is a holiday home in Winter Haven, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $981.

From$140/night

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Comfortable bedroom and house to stay in w/ swimming pool.

Holiday Home, Winter Haven

Comfortable bedroom and house to stay in w/ swimming pool. is a holiday home in Winter Haven, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Comfortable bedroom and house to stay in w/ swimming pool.

Comfortable bedroom and house to stay in w/ swimming pool. is a holiday home in Winter Haven, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,018.

From$145/night

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1/1 condo located on Lk Lulu. 7 minutes from Legoland. access to hwy 27, 17 & I4

Condo, Winter Haven

1/1 condo located on Lk Lulu. 7 minutes from Legoland. access to hwy 27, 17 & I4 is a condo in Winter Haven, with pet-friendly space and pool access. This stay gives travelers a comfortable…

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About 1/1 condo located on Lk Lulu. 7 minutes from Legoland. access to hwy 27, 17 & I4

1/1 condo located on Lk Lulu. 7 minutes from Legoland. access to hwy 27, 17 & I4 is a condo in Winter Haven, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,192.

From$170/night

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Vacation rentals with parking in Winter Haven, FL

Find vacation rentals that make arriving by car easier.

The Perfect Package of Space, Style and Comfort

Apartment, Winter Haven

The Perfect Package of Space, Style and Comfort is a apartment in Winter Haven, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About The Perfect Package of Space, Style and Comfort

The Perfect Package of Space, Style and Comfort is a apartment in Winter Haven, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and onsite parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $572.

From$82/night

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Bright Cypress Gardens Home Near Legoland!

Cottage, Winter Haven

Bright Cypress Gardens Home Near Legoland! is a cottage in Winter Haven, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Bright Cypress Gardens Home Near Legoland!

Bright Cypress Gardens Home Near Legoland! is a cottage in Winter Haven, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,274.

From$128/night

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Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn

Holiday Home, Winter Haven

Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn is a holiday home in Winter Haven, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn

Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn is a holiday home in Winter Haven, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,111.

From$159/night

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Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

Holiday Home, Winter Haven

Getaway Clubhouse 5 mil Legoland & .5 mil Downtown is a holiday home in Winter Haven, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

Getaway Clubhouse 5 mil Legoland & .5 mil Downtown is a holiday home in Winter Haven, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,122.

From$160/night

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Pet-friendly vacation rentals in Winter Haven, FL

Bring your pet along with stays that welcome four-legged travelers.

The Lake Alfred Citrus Wood Guest Cabin

Cabin, Winter Haven

The Lake Alfred Citrus Wood Guest Cabin is a cabin in Winter Haven, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About The Lake Alfred Citrus Wood Guest Cabin

The Lake Alfred Citrus Wood Guest Cabin is a cabin in Winter Haven, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, washer, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $695.

From$99/night

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The Lake Alfred Citruswood Cabin

B & B, Winter Haven

The Lake Alfred Citruswood Cabin is a b & b in Winter Haven, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About The Lake Alfred Citruswood Cabin

The Lake Alfred Citruswood Cabin is a b & b in Winter Haven, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,032.

From$115/night

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Charming 2-bedroom house with huge yard and firepit in Eagle Lake

Holiday Home, Winter Haven

Charming 2-bedroom house with huge yard and firepit in Eagle Lake is a holiday home in Winter Haven, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers…

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About Charming 2-bedroom house with huge yard and firepit in Eagle Lake

Charming 2-bedroom house with huge yard and firepit in Eagle Lake is a holiday home in Winter Haven, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $885.

From$126/night

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Modern Comfort, Pet Friendly, 2 King Beds

Holiday Home, Winter Haven

Modern Comfort, Pet Friendly, 2 King Beds is a holiday home in Winter Haven, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Modern Comfort, Pet Friendly, 2 King Beds

Modern Comfort, Pet Friendly, 2 King Beds is a holiday home in Winter Haven, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,091.

From$156/night

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Vacation rentals with a kitchen in Winter Haven, FL

Compare stays with kitchen access for longer trips and easier meals.

Family Fun Haven: 3 Bed/2 Bath/6 Mi to Legoland/Pet Friendly!

Holiday Home, Winter Haven

Family Fun Haven: 3 Bed/2 Bath/6 Mi to Legoland/Pet Friendly! is a holiday home in Winter Haven, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a…

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About Family Fun Haven: 3 Bed/2 Bath/6 Mi to Legoland/Pet Friendly!

Family Fun Haven: 3 Bed/2 Bath/6 Mi to Legoland/Pet Friendly! is a holiday home in Winter Haven, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,031.

From$147/night

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*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1722

Holiday Home, Winter Haven

*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1722 is a holiday home in Winter Haven, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About *3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1722

*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1722 is a holiday home in Winter Haven, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,065.

From$152/night

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The Old Haven - An Enduring Piece of Nostalgia

Holiday Home, Winter Haven

The Old Haven - An Enduring Piece of Nostalgia is a holiday home in Winter Haven, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About The Old Haven - An Enduring Piece of Nostalgia

The Old Haven - An Enduring Piece of Nostalgia is a holiday home in Winter Haven, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, gym, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,068.

From$153/night

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Ricks's Retreat - Downtown Winter Haven Getaway, Near Chain of Lakes

Holiday Home, Winter Haven

Ricks's Retreat - Downtown Winter Haven Getaway, Near Chain of Lakes is a holiday home in Winter Haven, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Ricks's Retreat - Downtown Winter Haven Getaway, Near Chain of Lakes

Ricks's Retreat - Downtown Winter Haven Getaway, Near Chain of Lakes is a holiday home in Winter Haven, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,196.

From$171/night

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Family-friendly vacation rentals in Winter Haven, FL

Plan a trip with stays that give families more room to spread out.

Luxury StayComfy at WinterHeaven

Holiday Home, Winter Haven

Luxury StayComfy at WinterHeaven is a holiday home in Winter Haven, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Luxury StayComfy at WinterHeaven

Luxury StayComfy at WinterHeaven is a holiday home in Winter Haven, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $847.

From$121/night

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3 Bedroom Cozy Home with the Perfect Patio

Holiday Home, Winter Haven

3 Bedroom Cozy Home with the Perfect Patio is a holiday home in Winter Haven, with outdoor space, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About 3 Bedroom Cozy Home with the Perfect Patio

3 Bedroom Cozy Home with the Perfect Patio is a holiday home in Winter Haven, with outdoor space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $856.

From$122/night

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Chain of Lakes Cottage

B & B, Winter Haven

Chain of Lakes Cottage is a b & b in Winter Haven, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Chain of Lakes Cottage

Chain of Lakes Cottage is a b & b in Winter Haven, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,103.

From$145/night

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Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Cottage, Winter Haven

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn is a cottage in Winter Haven, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn is a cottage in Winter Haven, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,025.

From$146/night

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