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Winter Haven Holiday Apartments

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49 rentals in Winter Haven.
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Are you ready to get back to Living?  This is a GREAT place to start. Come!, holiday rental in Winter Haven

Are you ready to get back to Living? This is a GREAT place to start. Come!

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Spectacular Waterfront Home in Winter Haven, holiday rental in Winter Haven

Spectacular Waterfront Home in Winter Haven

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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FALL/WINTER SPECIAL RATES Mid-century Mod w/ Fireplaces - Downtown Near Legoland, holiday rental in Winter Haven

FALL/WINTER SPECIAL RATES Mid-century Mod w/ Fireplaces - Downtown Near Legoland

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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College Students! Off Campus Life!, holiday rental in Winter Haven

College Students! Off Campus Life!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Disney 45 minutes away! LegoLand 10 minutes away!!!, holiday rental in Winter Haven

Disney 45 minutes away! LegoLand 10 minutes away!!!

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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NEW! Winter Haven Home: Near Fishing & Family Fun!, holiday rental in Winter Haven

NEW! Winter Haven Home: Near Fishing & Family Fun!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private Pool Paradise with Outdoor TV  2.5 miles to Legoland & close to Disney!, holiday rental in Winter Haven

Private Pool Paradise with Outdoor TV 2.5 miles to Legoland & close to Disney!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Snowbird - Central Florida - Waterfront / Bord de lac, holiday rental in Winter Haven

Snowbird - Central Florida - Waterfront / Bord de lac

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Modern Home w/Porch & Private Canal to Lake Eloise, holiday rental in Winter Haven

Modern Home w/Porch & Private Canal to Lake Eloise

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Lake Eloise Home w/Boat Ramp Access!, holiday rental in Winter Haven

Charming Lake Eloise Home w/Boat Ramp Access!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Stylish Home w/ Private Canal Access to Lake Eloise, holiday rental in Winter Haven

Stylish Home w/ Private Canal Access to Lake Eloise

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Upscale modern  2 Bedrooms Condo On Southern Dunes Golf Gated Community., holiday rental in Winter Haven

Upscale modern 2 Bedrooms Condo On Southern Dunes Golf Gated Community.

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Low Cost Vacation/Holiday Home Near Golf Courses/Lakes, Nr Disney Orlando  and Tampa, holiday rental in Winter Haven

Low Cost Vacation/Holiday Home Near Golf Courses/Lakes, Nr Disney Orlando and Tampa

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Sailors Loch, holiday rental in Winter Haven

Sailors Loch

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lake Home with 4 Bed/4 Bath & Pool with Diving Board, holiday rental in Winter Haven

Lake Home with 4 Bed/4 Bath & Pool with Diving Board

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Mariner Cay Villa at Southern Dunes Golf and Country Club, holiday rental in Winter Haven

Mariner Cay Villa at Southern Dunes Golf and Country Club

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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1628 Forest Hills Lane, holiday rental in Winter Haven

1628 Forest Hills Lane

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Spacious farmhouse in 100 acres of ranch close to Legoland, holiday rental in Winter Haven

Spacious farmhouse in 100 acres of ranch close to Legoland

4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Just Bring Your Toothbrush, holiday rental in Winter Haven

Just Bring Your Toothbrush

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Lakefront Grove House, holiday rental in Winter Haven

Lakefront Grove House

1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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KISSIMMEE'S KNIGHT CASTLE, holiday rental in Winter Haven

KISSIMMEE'S KNIGHT CASTLE

7 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
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Winter Haven Home with Dock & Hot Tub!, holiday rental in Winter Haven

Winter Haven Home with Dock & Hot Tub!

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Golf Course and Disney World, Legoland, holiday rental in Winter Haven

Golf Course and Disney World, Legoland

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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☀️ UNIQUE SCANDINAVIAN LUXURY VILLA ☀️ Exclusive with Private Pool & Golf View, holiday rental in Winter Haven

☀️ UNIQUE SCANDINAVIAN LUXURY VILLA ☀️ Exclusive with Private Pool & Golf View

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Lakefront Hideaway on Private Lake, holiday rental in Winter Haven

Lakefront Hideaway on Private Lake

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful vacation home, holiday rental in Winter Haven

Beautiful vacation home

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stunning Over 50 Gated Golf and Modular Home Community, holiday rental in Winter Haven

Stunning Over 50 Gated Golf and Modular Home Community

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Perfect Home For Your Florida Vacation!, holiday rental in Winter Haven

Perfect Home For Your Florida Vacation!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Pool Home!, holiday rental in Winter Haven

Private Pool Home!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Citrus Sun Private Pool Home & Game Room, holiday rental in Winter Haven

Citrus Sun Private Pool Home & Game Room

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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South Facing Pool/Spa in Southern Dunes!, holiday rental in Winter Haven

South Facing Pool/Spa in Southern Dunes!

6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Belle's Southern Dream in Southern Dunes, holiday rental in Winter Haven

Belle's Southern Dream in Southern Dunes

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront Auburndale Home w/ Resort Amenities, holiday rental in Winter Haven

Lakefront Auburndale Home w/ Resort Amenities

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Farm House Stay 5 Miles to Legoland!, holiday rental in Winter Haven

Farm House Stay 5 Miles to Legoland!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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55+ community, Sleeps 6-8, Minimum monthly rental, Pets Considered, holiday rental in Winter Haven

55+ community, Sleeps 6-8, Minimum monthly rental, Pets Considered

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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55 Plus Golf Community 2 Bed/Den, Lanai, Backyard Deck, Grill, Golf, Pool, holiday rental in Winter Haven

55 Plus Golf Community 2 Bed/Den, Lanai, Backyard Deck, Grill, Golf, Pool

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Citrus Sun Private Pool Home & Game Room, holiday rental in Winter Haven

Citrus Sun Private Pool Home & Game Room

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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South Facing Pool/Spa in Southern Dunes!, holiday rental in Winter Haven

South Facing Pool/Spa in Southern Dunes!

6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Belle's Southern Dream in Southern Dunes, holiday rental in Winter Haven

Belle's Southern Dream in Southern Dunes

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Perfect Home For Your Florida Vacation!, holiday rental in Winter Haven

Perfect Home For Your Florida Vacation!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Scenic View From Your Private Pool!, holiday rental in Winter Haven

Scenic View From Your Private Pool!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Pool Home!, holiday rental in Winter Haven

Private Pool Home!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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SD5016HC - 2 beds condo - Gated resort, holiday rental in Winter Haven

SD5016HC - 2 beds condo - Gated resort

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Safe and Clean, We Utilize CDC Approved Products and Standards, Stay With Us!,, holiday rental in Winter Haven

Safe and Clean, We Utilize CDC Approved Products and Standards, Stay With Us!,

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Winter Haven Getaway w/ Direct Lake Access!, holiday rental in Winter Haven

NEW! Winter Haven Getaway w/ Direct Lake Access!

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Stunning 4 Bd Single Family w/ Pool & Lake View 175, holiday rental in Winter Haven

Stunning 4 Bd Single Family w/ Pool & Lake View 175

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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1122MCD, holiday rental in Winter Haven

1122MCD

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful 4 Bed Home With South Facing Pool 1108MC, holiday rental in Winter Haven

Beautiful 4 Bed Home With South Facing Pool 1108MC

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Impressive 4BR Private Pool Gated Golf Community, holiday rental in Winter Haven

Impressive 4BR Private Pool Gated Golf Community

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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