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Winter Haven Holiday Rentals

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50 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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Private Pool Paradise -  2.5 miles to Legoland & close to Disney!  Contactless E, holiday rental in Winter Haven

Private Pool Paradise - 2.5 miles to Legoland & close to Disney! Contactless E

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Special 10% Discount~ Lakeviews, Legoland, Foosball & Kayaks ~ Family Fun!, holiday rental in Winter Haven

Special 10% Discount~ Lakeviews, Legoland, Foosball & Kayaks ~ Family Fun!

5 bedrooms
3 bathrooms
Sleeps 11
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 Listing ~Chain of Lakes w Dock~Sunrise on Lake Idylwild~ Legoland  7.5 mi~Di, holiday rental in Winter Haven

New Listing ~Chain of Lakes w Dock~Sunrise on Lake Idylwild~ Legoland 7.5 mi~Di

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Lake Silver Retreat III * Lakeviews~Legoland~Foosball & Kayaks ~ Family Fun, holiday rental in Winter Haven

Lake Silver Retreat III * Lakeviews~Legoland~Foosball & Kayaks ~ Family Fun

3 bedrooms
2 bathrooms
Sleeps 7
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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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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Sailors Loch, holiday rental in Winter Haven

Sailors Loch

4 bedrooms
3 bathrooms
Sleeps 8
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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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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Lakefront Grove House, holiday rental in Winter Haven

Lakefront Grove House

1 bedroom
2 bathrooms
Sleeps 3
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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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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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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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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☀️ 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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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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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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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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No Contact Check in, Relax by your Private Pool, Stay With Us!,, holiday rental in Winter Haven

No Contact Check in, Relax by your Private Pool, Stay With Us!,

4 bedrooms
3 bathrooms
Sleeps 6
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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Captivating 4 bed. home w/south facing pool 1108MC, holiday rental in Winter Haven

Captivating 4 bed. home w/south facing pool 1108MC

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lovely, upgraded 3 bedroom home with a lake view, holiday rental in Winter Haven

Lovely, upgraded 3 bedroom home with a lake view

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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1104MCD - Family getaway overlooking Lake Joe!, holiday rental in Winter Haven

1104MCD - Family getaway overlooking Lake Joe!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Southern Dunes Home Lake Views!, holiday rental in Winter Haven

Southern Dunes Home Lake Views!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Golfer's Delight With Amazing Views Southern Dunes, holiday rental in Winter Haven

Golfer's Delight With Amazing Views Southern Dunes

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Winter Haven hideaway, holiday rental in Winter Haven

Tentrr Signature Site - Winter Haven hideaway

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - LazyRanch, holiday rental in Winter Haven

Tentrr Signature Site - LazyRanch

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Southern Charm /Southern Dunes Home, holiday rental in Winter Haven

Southern Charm /Southern Dunes Home

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Southern Dunes Home Lake Views!, holiday rental in Winter Haven

Southern Dunes Home Lake Views!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Golfer's Delight With Amazing Views Southern Dunes, holiday rental in Winter Haven

Golfer's Delight With Amazing Views Southern Dunes

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Auburndale House w/ Private Porch & Gas Grill, holiday rental in Winter Haven

NEW! Auburndale House w/ Private Porch & Gas Grill

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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