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Vacation rentals in Winter Haven, Florida, United States

Cute & Cozy in Winter Haven, Florida image 1

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Cute & Cozy Guesthouse in Winter Haven

1 bedroom·1 bath

Winter Haven • Florida

4.79(42 reviews)

$ 295,68 USD total por 3 noites

29 de set. – 2 de out. de 2026

Refresh, reset, and relax: A space that feels as good as it looks.

Fresh spaces, peaceful moments: Where comfort begins and stress fades away.

Fun-filled game room with pool table and bar area – perfect for family entertainment at Oh Winter Heaven, Winter Haven FL

Crystal-clear private pool with sun loungers and lush tropical landscaping – Oh Winter Heaven's resort-style backyard

Open-concept kitchen, dining and game room view – fully equipped for your perfect Florida vacation at Oh Winter Heaven

Private Pool | Game Room Fun | Fenced Yard

4 bedrooms·3 baths

Winter Haven • Florida

$152 – $667/ noite(excl. taxas & impostos)

Sunset Lakefront Home | Hot Tub, Private Dock

Sunset Lakefront Home | Hot Tub, Private Dock

Sunset Lakefront Home | Hot Tub, Private Dock

Sunset Lakefront Home | Hot Tub, Private Dock

Sunset Lakefront Home | Hot Tub, Private Dock

Sunset Lakefront Home | Hot Tub, Private Dock

3 bedrooms·2 baths

Eagle Lake • Florida

$ 734,72 USD total por 3 noites

23 – 26 de set. de 2026

Serene Cabin Escape- Lakeside Romantic Getaway

Serene Cabin Escape- Lakeside Romantic Getaway

Serene Cabin Escape- Lakeside Romantic Getaway

Serene Cabin Escape- Lakeside Romantic Getaway

Serene Cabin Escape- Lakeside Romantic Getaway

Serene Cabin Escape- Lakeside Romantic Getaway

3 bedrooms·2 baths

Winter Haven • Florida

$145 – $522/ noite(excl. taxas & impostos)

Front of the house

Front of the house

Newly remodeled Vacation Home with Saltwater Pool

3 bedrooms·2 baths

Winter Haven • Florida

$195/ noite(excl. taxas & impostos)

Game night in Lakeland, Florida! This vibrant rec room with a pool table, cozy seating & beach-view TV is perfect for families, friends, or long-term guests seeking entertainment, relaxation, and unforgettable indoor fun.

Cook, dine, and unwind in style! This sleek Lakeland, Florida, home features a fully equipped kitchen, and a cozy dining space bathed in natural light. Perfect for families, couples, and remote workers looking for comfort near Lakeland & Clearwater.

Recharge in style! This cozy Lakeland, Florida, bedroom features bold navy and sunny yellow accents, plush linens, and warm lighting—perfect for unwinding after a day of exploring Lakeland or Clearwater. Comfort meets charm in every corner.

Family comfort in Lakeland, Florida! This bright bunk-bed room with striped bedding, soft towels & playful accents is perfect for kids, friends, or long-term guests seeking a clean, cheerful space to relax and recharge.

Cozy curb appeal in Lakeland, Florida! This single-story home with a shaded patio, stylish facade & peaceful yard is perfect for couples, solo travelers, or long-term guests seeking comfort, privacy, and a relaxing stay near nature.

Pool table | University nearby | Fenced yard.

3 bedrooms·1 bath

Lakeland • Florida

$88 – $467/ noite(excl. taxas & impostos)

Relaxation meets vibrancy: Natural light and sleek design make this bedroom ideal for unwinding, with vibrant touches that inspire and refresh

An inviting atmosphere and modern touches make this space ideal for both cooking and sharing special moments

Cozy and stylish: A mix of comfort and aesthetics makes this patio the perfect spot to unwind and enjoy peaceful moments

Elevate your stay: Enjoy beachy vibes and sophisticated design in a bedroom that embodies comfort and elegance your perfect getaway awaits

Luxury and elegance: Elegant marble and modern design create a bathroom that’s both inviting and stylish—perfect for relaxation

Charming in Lakeland | Quiet Patio | Free Parking.

1 bedroom·1 bath

Lakeland • Florida

$54 – $279/ noite(excl. taxas & impostos)

•Private 3 Acre Estate W/ Home Theater & Jacuzzi• 𝙗𝙮 𝙎𝙏𝘼𝙔-𝙏𝙊𝘿𝘼𝙔 | Casa Tallman

•Private 3 Acre Estate W/ Home Theater & Jacuzzi• 𝙗𝙮 𝙎𝙏𝘼𝙔-𝙏𝙊𝘿𝘼𝙔 | Casa Tallman

•Private 3 Acre Estate W/ Home Theater & Jacuzzi• 𝙗𝙮 𝙎𝙏𝘼𝙔-𝙏𝙊𝘿𝘼𝙔 | Casa Tallman

•Private 3 Acre Estate W/ Home Theater & Jacuzzi• 𝙗𝙮 𝙎𝙏𝘼𝙔-𝙏𝙊𝘿𝘼𝙔 | Casa Tallman

•Private 3 Acre Estate W/ Home Theater & Jacuzzi• 𝙗𝙮 𝙎𝙏𝘼𝙔-𝙏𝙊𝘿𝘼𝙔 | Casa Tallman

•Private 3 Acre Estate W/ Home Theater & Jacuzzi• 𝙗𝙮 𝙎𝙏𝘼𝙔-𝙏𝙊𝘿𝘼𝙔 | Casa Tallman

5 bedrooms·3 baths

Haines City • Florida

$ 3.346,50 USD total por 10 noites

23 de set. – 3 de out. de 2026

601 PBD, Champions Gate

601 PBD, Champions Gate

601 PBD, Champions Gate

601 PBD, Champions Gate

601 PBD, Champions Gate

601 PBD, Champions Gate

9 bedrooms·5 baths

Davenport • Florida

$250/ noite(excl. taxas & impostos)

8975 BSW, Champions Gate

8975 BSW, Champions Gate

8975 BSW, Champions Gate

8975 BSW, Champions Gate

8975 BSW, Champions Gate

8975 BSW, Champions Gate

5 bedrooms·5 baths

Davenport • Florida

$220 – $283/ noite(excl. taxas & impostos)

Private kitchen

443 Excellent House Near Disney parks

4 bedrooms·2 baths

Davenport • Florida

5(12 reviews)

$170/ noite(excl. taxas & impostos)

Master Bathroom

Charming Duplex in Lakeland!

1 bedroom·1 bath

Lakeland • Florida

Cozy porch

2 bedrooms·1 bath

Lakeland • Florida

$ 775,00 USD total por 3 noites

23 – 26 de set. de 2026

Peaceful Escape- Tivoli Manor

Peaceful Escape- Tivoli Manor

Peaceful Escape- Tivoli Manor

Peaceful Escape- Tivoli Manor

Peaceful Escape- Tivoli Manor

Peaceful Escape- Tivoli Manor

4 bedrooms·3 baths

Davenport • Florida

$ 749,32 USD total por 3 noites

23 – 26 de set. de 2026

Beautiful Mid-Century Bungalow

Beautiful Mid-Century Bungalow

Beautiful Mid-Century Bungalow

Beautiful Mid-Century Bungalow

Beautiful Mid-Century Bungalow

Beautiful Mid-Century Bungalow

2 bedrooms·1 bath

Lakeland • Florida

5(8 reviews)

$ 492,20 USD total por 3 noites

31 de dez. de 2026 – 3 de jan. de 2027

Lakefront Stay in Central Lakeland - Sleeps 11

Lakefront Stay in Central Lakeland - Sleeps 11

Lakefront Stay in Central Lakeland - Sleeps 11

Lakefront Stay in Central Lakeland - Sleeps 11

Lakefront Stay in Central Lakeland - Sleeps 11

Lakefront Stay in Central Lakeland - Sleeps 11

3 bedrooms·2 baths

Lakeland • Florida

4.75(24 reviews)

$ 564,00 USD total por 3 noites

23 – 26 de set. de 2026

3BR Game Room Home - 20min Disney + Pool

3BR Game Room Home - 20min Disney + Pool

3BR Game Room Home - 20min Disney + Pool

3BR Game Room Home - 20min Disney + Pool

3BR Game Room Home - 20min Disney + Pool

3BR Game Room Home - 20min Disney + Pool

3 bedrooms·2 baths

Davenport • Florida

$ 559,56 USD total por 3 noites

23 – 26 de set. de 2026

Famous Bowling House

Famous Bowling House

Famous Bowling House

Famous Bowling House

Famous Bowling House

Famous Bowling House

10 bedrooms·10 baths

Davenport • Florida

5(6 reviews)

$ 5.918,08 USD total por 3 noites

23 – 26 de set. de 2026

New Build - Cozy House & Game Room

New Build - Cozy House & Game Room

2260 Derwent Dr Davenport FL-35

festival 2021 - 1001

2260 Derwent Dr Davenport FL-16

New Build - Cozy House & Game Room

4 bedrooms·3 baths

Davenport • Florida

$ 591,34 USD total por 3 noites

27 – 30 de set. de 2026

Disney Area Charming house with private pool

Disney Area Charming house with private pool

Disney Area Charming house with private pool

Disney Area Charming house with private pool

4 bedrooms·3 baths

Davenport • Florida

4.93(107 reviews)

$ 748,50 USD total por 3 noites

23 – 26 de set. de 2026

z King Bed Escape-Desk/400MB/Kitchen/Disney RmF

z King Bed Escape-Desk/400MB/Kitchen/Disney RmF

z King Bed Escape-Desk/400MB/Kitchen/Disney RmF

z King Bed Escape-Desk/400MB/Kitchen/Disney RmF

z King Bed Escape-Desk/400MB/Kitchen/Disney RmF

z King Bed Escape-Desk/400MB/Kitchen/Disney RmF

1 bedroom·1 bath

Davenport • Florida

$43/ noite(excl. taxas & impostos)

Test Listing not real

Test Listing not real

Test Listing not real

Test Listing not real

Test Listing not real

Test Listing not real

1 bedroom·1 bath

Davenport • Florida

$57/ noite(excl. taxas & impostos)

Große, luxuriöse Ferienvilla mit Pool und Spieleraum, in ruhiger Umgebung in de

Große, luxuriöse Ferienvilla mit Pool und Spieleraum, in ruhiger Umgebung in de

Große, luxuriöse Ferienvilla mit Pool und Spieleraum, in ruhiger Umgebung in de

Große, luxuriöse Ferienvilla mit Pool und Spieleraum, in ruhiger Umgebung in de

Große, luxuriöse Ferienvilla mit Pool und Spieleraum, in ruhiger Umgebung in de

Große, luxuriöse Ferienvilla mit Pool und Spieleraum, in ruhiger Umgebung in de

4 bedrooms·4 baths

Orlando • Florida

SUNNY SOUTH-FACING POOL HOME WITH GAME ROOM

Beautiful south-facing pool with spa

Master Bedroom / 1
Ground Floor En-suite

Master En-Suite

Master Bedroom 1

SUNNY SOUTH-FACING POOL HOME WITH GAME ROOM

5 bedrooms·5 baths

Davenport • Florida

5(6 reviews)

$ 1.795,32 USD $ 1.686,66 USD total por 7 noites

23 – 30 de set. de 2026