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Vacation rentals in Winter Haven, Florida, United States

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 |Spacious 4BR Retreat | Full Kitchen

4 bedrooms·3 baths

Winter Haven • Florida

$143 – $675/ Nacht(zzgl. Gebühren & Steuern)

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

700,00 $ USD gesamt für 3 Nächte

26.–29. Okt. 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

698,85 $ USD gesamt für 3 Nächte

26.–29. Okt. 2026

Front of the house

Front of the house

Newly remodeled Vacation Home with Saltwater Pool

3 bedrooms·2 baths

Winter Haven • Florida

1.075,20 $ USD gesamt für 4 Nächte

1.–5. Apr. 2027

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

905,73 $ USD gesamt für 3 Nächte

22.–25. Nov. 2026

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

444,16 $ USD gesamt für 3 Nächte

26.–29. Okt. 2026

•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

3.424,50 $ USD gesamt für 10 Nächte

26. Okt. – 5. Nov. 2026

Magnolia House

3 bedrooms·2 baths

Davenport • Florida

485,00 $ USD gesamt für 3 Nächte

26.–29. Okt. 2026

MID CENTURY TINY HOUSE

MID CENTURY TINY HOUSE

MID CENTURY TINY HOUSE

MID CENTURY TINY HOUSE

MID CENTURY TINY HOUSE

MID CENTURY TINY HOUSE

1 bedroom·1 bath

Davenport • Florida

320,00 $ USD gesamt für 3 Nächte

26.–29. Okt. 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

1.550,00 $ USD gesamt für 4 Nächte

26.–30. Okt. 2026

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

1.632,80 $ USD gesamt für 4 Nächte

26.–30. Okt. 2026

Private kitchen

443 Excellent House Near Disney parks

4 bedrooms·2 baths

Davenport • Florida

5(12 reviews)

525,00 $ USD gesamt für 3 Nächte

1.–4. Dez. 2026

The Cozy Cottage image 1

The Cozy Cottage image 2

The Cozy Cottage image 3

The Cozy Cottage image 4

The Cozy Cottage image 5

The Cozy Cottage

1 bedroom·2 baths

Lakeland • Florida

5(28 reviews)

312,00 $ USD gesamt für 3 Nächte

26.–29. Okt. 2026

Master Bathroom

Charming Duplex in Lakeland!

1 bedroom·1 bath

Lakeland • Florida

Cozy porch

2 bedrooms·1 bath

Lakeland • Florida

750,00 $ USD gesamt für 3 Nächte

26.–29. Okt. 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

761,49 $ USD gesamt für 3 Nächte

26.–29. Okt. 2026

Kitchen / Dining Room

mit Terrasse

4 bedrooms·3 baths

Orlando • Florida

Ruhiger 4BR Rückzug in der Nähe von Orlando Parks

Kitchen / Dining Room

Kitchen / Dining Room

Ruhiger 4BR Rückzug in der Nähe von Orlando Parks

4 bedrooms·3 baths

Orlando • Florida

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 gesamt für 3 Nächte

31. Dez. 2026 – 3. Jan. 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)

594,00 $ USD gesamt für 3 Nächte

4.–7. Nov. 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

579,99 $ USD gesamt für 3 Nächte

26.–29. Okt. 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 gesamt für 3 Nächte

26.–29. Okt. 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 gesamt für 3 Nächte

27.–30. Okt. 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)

737,80 $ USD gesamt für 3 Nächte

26.–29. Okt. 2026