Holiday homes in Winter Haven You’ll Love (Page 2)

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)

Serene, Cozy, Lakefront home

Holiday home in Winter Haven, Florida , 134 Lake Howard Drive Southwest

Serene, Cozy, Lakefront home offers accommodations in Winter Haven, 5.7 miles from Legoland Florida and 9.4 miles from Tanco Railroad Station.

no reviews

from $301.50 Show details »

Peaceful Lakeside Retreat

Holiday home in Winter Haven, Florida , 46 Lake Howard Drive Southwest

Providing a garden, Peaceful Lakeside Retreat provides accommodations in Winter Haven.

Parking
Family rooms

Exceptional 10 Reviews 9.8

from $261.68 Show details »

Bungalow Haven

Holiday home in Winter Haven, Florida , 317 8th Street Northeast

Bungalow Haven is located in Winter Haven, just 4.2 miles from Legoland Florida and 12 miles from Dearborn Railroad Station.

Parking
Family rooms

Exceptional 15 Reviews 9.5

from $78.00 Show details »

Lake Silver Retreat lll

Holiday home in Winter Haven, Florida , 111 S. Lake Silver Drive NW

Lake Silver Retreat lll offers accommodations in Winter Haven, 12 miles from Dearborn Railroad Station and 12 miles from Tanco Railroad Station.

no reviews

from $312.38 Show details »

Emerald Anchor Escape

Holiday home in Winter Haven, Florida , 1521 North Lake Howard

Emerald Anchor Escape offers accommodations in Winter Haven, 5.8 miles from Legoland Florida and 9.4 miles from Tanco Railroad Station.

Exceptional 1 Reviews 10.0

from $465.59 Show details »

341 Legoland Shermans Antiques Lake Silv...

Holiday home in Winter Haven, Florida , 341 Avenue L Northeast

341 Legoland Shermans Antiques Lake Silver offers accommodations in Winter Haven, 12 miles from Elmer Railroad Station and 12 miles from Allied Railro...

Parking

no reviews

from $403.28 Show details »

Lake Hamilton III Pool and Backyard Oasi...

Holiday home in Winter Haven, Florida , 2950 Crump Rd

Lake Hamilton III Pool and Backyard Oasis with Kayaks Lake Access Theater offers accommodations in Winter Haven, 5.7 miles from Legoland Florida and 1...

no reviews

from $362.13 Show details »

Historic home lake access, near parks an...

Holiday home in Winter Haven, Florida , 404 Ave O NE

Historic home lake access, near parks and venues offers accommodations in Winter Haven, 12 miles from Allied Railroad Station and 12 miles from Tanco ...

Parking
Family rooms

Exceptional 3 Reviews 10.0

from $143.32 Show details »

My place near Legoland

Holiday home in Winter Haven, Florida , 2805 Ave M NW

My place near Legoland is located in Winter Haven, just 10 miles from Allied Railroad Station and 10 miles from Tanco Railroad Station.

Parking
Allergy-free room

Superb 5 Reviews 9.2

from $280.81 Show details »

Lakefront Winter Haven Retreat Hot Tub a...

Holiday home in Winter Haven, Florida

Lakefront Winter Haven Retreat Hot Tub and Patio! is located in Winter Haven, just 10 miles from Elmer Railroad Station and 10 miles from Allied Railr...

Parking
Pets allowed

Exceptional 2 Reviews 10.0

from $409.17 Show details »

Waterfront Vacation Rental on Lake Mirro...

Holiday home in Winter Haven, Florida

Waterfront Vacation Rental on Lake Mirror! offers accommodations in Winter Haven, 6.5 miles from Legoland Florida and 10 miles from Elmer Railroad Sta...

Parking

no reviews

from $65.00 Show details »

Lakefront Home with Screened Porch and G...

Holiday home in Winter Haven, Florida

Lakefront Home with Screened Porch and Grill is located in Winter Haven, just 5.7 miles from Legoland Florida and 11 miles from Elmer Railroad Station...

Parking

Exceptional 9 Reviews 10.0

from $238.56 Show details »

The Cozy Nook

Holiday home in Winter Haven, Florida , 2037 Canton Park Drive

The Cozy Nook enjoys a location in Winter Haven, 5.9 miles from Legoland Florida and 12 miles from Elmer Railroad Station.

Parking
Pets allowed
Family rooms

Exceptional 8 Reviews 9.7

from $385.87 Show details »

Sunrise on Lake Idylwild

Holiday home in Winter Haven, Florida , 1076 Idylwild Dr NW

Sunrise on Lake Idylwild offers accommodations in Winter Haven, 8 miles from Legoland Florida and 9 miles from Elmer Railroad Station.

no reviews

from $261.03 Show details »

Auburndale Vacation Rental with Yard and...

Holiday home in Auburndale near Winter Haven, Florida

Auburndale Vacation Rental with Yard and Lake Views offers accommodations in Auburndale, 6.7 miles from Allied Railroad Station and 6.8 miles from Tan...

Parking

Superb 3 Reviews 9.3

from $158.56 Show details »

Pet-Friendly Auburndale House with Lake...

Holiday home in Auburndale near Winter Haven, Florida

Pet-Friendly Auburndale House with Lake Views! is located in Auburndale, just 7.8 miles from Elmer Railroad Station and 7.8 miles from Allied Railroad...

Parking
Pets allowed

Superb 7 Reviews 9.2

from $157.44 Show details »

Serene Lakeside Retreat- 3 Bdr Romantic...

Holiday home in Winter Haven, Florida , 4840 Old Lucerne Park Road

Serene Lakeside Retreat- 3 Bdr Romantic Getaway offers accommodations in Winter Haven, 10 miles from Legoland Florida and 15 miles from Elmer Railroad...

Parking
Family rooms
Kids' outdoor play equipment

Fabulous 7 Reviews 8.8

from $181.00 Show details »

Adams Estate

Holiday home in Lake Alfred near Winter Haven, Florida , 2222 West Pierce Street Unit #9

Offering pool with a view, Adams Estate provides accommodations in Lake Alfred.

Parking
Outdoor pool
Swimming pool
Swimming Pool

Superb 10 Reviews 9.2

from $409.98 Show details »

Sweet Cottage 5 mi to Legoland and 0.5 m...

Country house in Winter Haven, Florida , 137 Avenue East Southeast

Sweet Cottage 5 mi to Legoland and 0.5 mi to dwntwn offers accommodations in Winter Haven, 4.1 miles from Legoland Florida and 11 miles from Dearborn ...

Exceptional 1 Reviews 10.0

from $168.67 Show details »

1Bed 1Bath Container Home Centrally Loca...

Chalet in Cypress Gardens near Winter Haven, Florida , 1724 Lake Mariam Drive

1Bed 1Bath Container Home Centrally Located is located in Cypress Gardens, just 14 miles from Elmer Railroad Station and 14 miles from Allied Railroad...

Parking
Pets allowed

Very good 13 Reviews 8.4

from $104.77 Show details »

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Holiday homes in Winter Haven You’ll Love (Page 2)

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

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