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Vacation rentals in Winter Haven, Florida, United States

Fremhævet

Hand-painted creature-adventure kids' room with a giant sleepy-creature bed and murals on every wall, designed with love by the owner. A dream come true for young explorers!

Neon-lit Fortnite-style game room with arcade basketball, racing simulators, a Pac-Man air hockey table, and gaming screens. The ultimate hangout!

Sonic-themed kids room with a tiki-style loft bunk, stairs, twin bed, and vibrant hand-painted murals. Built for speed, fun, and plenty of sleepovers.

Covered summer kitchen with a stainless grill, range hood, sink, and mini fridge, set against green tile. Grill up dinner steps from the pool.

Roblox-themed bedroom with a vibrant blocky mural, plush queen bed, and cube nightstands. A fun, modern space for teens and gamers.

Gamer's Paradise

6 bedrooms·4 baths

Kissimmee • Florida

1.523,09 $ USD total for 3 nætter

15.–18. nov. 2026

Fremhævet

Sky Lantern Manor

Outdoor projector for those movie nights under the stars!

Rapunzel's castle with starry night lighting makes the perfect setting for our Princesses

Retreat Club and Water Park! Water Slides, Sprinklers, Zero Entry Pool and even Mini Golf!

Your own tropical paradise! Unwind on cozy outdoor sofas beneath twinkling lights, with a poolside movie, tiki bar, and plenty of space to relax.

Sky Lantern Manor

6 bedrooms·5 baths

Davenport • Florida

5(1 review)

1.842,42 $ USD total for 4 nætter

8.–12. dec. 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 |Spacious 4BR Retreat | Full Kitchen

4 bedrooms·3 baths

Winter Haven • Florida

1.187,42 $ USD total for 3 nætter

25.–28. nov. 2026

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

703,36 $ USD total for 3 nætter

15.–18. nov. 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 total for 3 nætter

16.–19. nov. 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 total for 4 nætter

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

750,74 $ USD total for 3 nætter

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

526,01 $ USD total for 3 nætter

16.–19. jan. 2027

Calm, spacious home with sensory‑friendly design

Calm, spacious home with sensory‑friendly design

Calm, spacious home with sensory‑friendly design

Calm, spacious home with sensory‑friendly design

Calm, spacious home with sensory‑friendly design

Calm, spacious home with sensory‑friendly design

4 bedrooms·3 baths

Haines City • Florida

718,36 $ USD total for 3 nætter

15.–18. nov. 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

3.457,50 $ USD total for 10 nætter

15.–25. nov. 2026

Oasis 15 minutes from Disney

Oasis 15 minutes from Disney

Oasis 15 minutes from Disney

Oasis 15 minutes from Disney

Oasis 15 minutes from Disney

Oasis 15 minutes from Disney

3 bedrooms·2 baths

Davenport • Florida

544,53 $ USD total for 3 nætter

1.–4. apr. 2027

Magnolia House

3 bedrooms·2 baths

Davenport • Florida

485,00 $ USD total for 3 nætter

15.–18. nov. 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 total for 3 nætter

15.–18. nov. 2026

The Champions Gate Grand Villa

The Champions Gate Grand Villa

The Champions Gate Grand Villa

The Champions Gate Grand Villa

The Champions Gate Grand Villa

The Champions Gate Grand Villa

9 bedrooms·5 baths

Davenport • Florida

1.550,00 $ USD total for 4 nætter

15.–19. nov. 2026

The Backswing Way Pool Villa

The Backswing Way Pool Villa

The Backswing Way Pool Villa

The Backswing Way Pool Villa

The Backswing Way Pool Villa

The Backswing Way Pool Villa

5 bedrooms·5 baths

Davenport • Florida

1.406,00 $ USD total for 4 nætter

15.–19. nov. 2026

Private kitchen

443 Excellent House Near Disney parks

4 bedrooms·2 baths

Davenport • Florida

5(12 reviews)

525,00 $ USD total for 3 nætter

1.–4. dec. 2026

The Cozy Cottage image 1

The Cozy Cottage image 2

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The Cozy Cottage

1 bedroom·2 baths

Lakeland • Florida

5(28 reviews)

312,00 $ USD total for 3 nætter

15.–18. nov. 2026

Cozy porch

2 bedrooms·1 bath

Lakeland • Florida

750,00 $ USD total for 3 nætter

15.–18. nov. 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 total for 3 nætter

15.–18. nov. 2026

Kitchen / Dining Room

mit Terrasse

4 bedrooms·3 baths

Orlando • Florida

$197/ nat(exkl. gebyrer & skatter)

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

$225/ nat(exkl. gebyrer & skatter)

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 for 3 nætter

31. dec. 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 total for 3 nætter

15.–18. nov. 2026

Pool Area w/No Rear Neighbors

Lower Level Front Suite - King Bed

Lower Level Front Suite - King Bed

Lower Level Front En Suite

Lower Level Rear Suite - King Bed

Solterra Sunny Oasis

6 bedrooms·5½ baths

Davenport • Florida

5(30 reviews)

1.271,08 $ USD total for 4 nætter

28. nov.–2. dec. 2026