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Vacation rentals in Winter Haven, Florida, United States

Remarkable Themed Home with Resort Amenities

Remarkable Themed Home with Resort Amenities

Remarkable Themed Home with Resort Amenities

Remarkable Themed Home with Resort Amenities

Remarkable Themed Home with Resort Amenities

Remarkable Themed Home with Resort Amenities

6 bedrooms·4 baths

Kissimmee • Florida

1.379,53 $ USD gesamt für 3 Nächte

17.–20. Nov. 2026

Neon arcade game room

Arcade racing simulators

Private screened pool and spa at twilight

Front of home at twilight

Spacious living room

Magical Themed Home, Arcade, Private Pool/Spa, Resort Amenities

6 bedrooms·4 baths

Kissimmee • Florida

1.341,48 $ USD gesamt für 3 Nächte

3.–6. Nov. 2026

Twin Mansions: Both homes from the street

Twin Mansions: Aerial view of the homes and pools

Twin Mansions: Aerial of both homes and pools

Twin Mansions: Both homes and pools from the rear

Magical Home: Private screened pool and spa at twilight

The Windsor Hills Twin Mansions

12 bedrooms·8 baths

Kissimmee • Florida

3.361,33 $ USD gesamt für 3 Nächte

17.–20. Nov. 2026

Pool and Hot Tub

Cinema Movie Theater

Kids Theme Bedroom

Under the Sea room - 2 x Pirate Beds

Mickeys Sunrise South Facing Pool Hot Tub Splashpad Theater BBQ

7 bedrooms·6 baths

Kissimmee • Florida

5(8 reviews)

2.581,86 $ USD gesamt für 5 Nächte

3.–8. Nov. 2026

Private Epcot-Themed Near Disney image 1

Private Epcot-Themed Near Disney image 2

Private Epcot-Themed Near Disney image 3

Private Epcot-Themed Near Disney image 4

Private Epcot-Themed Near Disney image 5

Epcot-Themed Home Near Disney | Pool • Game Room

3 bedrooms·2 baths

Kissimmee • Florida

4.99(141 reviews)

864,14 $ USD gesamt für 3 Nächte

30. Okt. – 2. Nov. 2026

Wasserpark Fantastischer Pool Nur wenige Minuten von Disney Parks entfernt

Wasserpark Fantastischer Pool Nur wenige Minuten von Disney Parks entfernt

Wasserpark Fantastischer Pool Nur wenige Minuten von Disney Parks entfernt

Wasserpark Fantastischer Pool Nur wenige Minuten von Disney Parks entfernt

Wasserpark Fantastischer Pool Nur wenige Minuten von Disney Parks entfernt

Wasserpark Fantastischer Pool Nur wenige Minuten von Disney Parks entfernt

3 bedrooms·2 baths

Orlando • Florida

Private cul-de-sac.

Sparkling modern kitchen

clubhouse and main community pool

Spacious open floorplan with plenty of dining space.

King bed, en suite bath, balcony, TV

Disney Villa • resort pools • Near Margaritaville

3 bedrooms·2 baths

Kissimmee • Florida

4.84(100 reviews)

318,05 $ USD gesamt für 3 Nächte

1.–4. Nov. 2026

Disney Villa | Resort Amenities

Disney Villa | Resort Amenities

Disney Villa | Resort Amenities

Disney Villa | Resort Amenities

Disney Villa | Resort Amenities

Disney Villa | Resort Amenities

4 bedrooms·3 baths

Kissimmee • Florida

4.92(24 reviews)

1.196,50 $ USD gesamt für 3 Nächte

27.–30. Okt. 2026

EMERALD ISLAND (8409BL) - 3BR 2.5BA Townhome, Gated Resort

Emerald Island 3BR 25BA Townhome

Emerald Island Resort

Main Resort Pool and Clubhouse

Living Room, Sleeper Sofa, Smart TV

EMERALD ISLAND (8409BL) - 3BR 2.5BA Townhome, Gated Resort

3 bedrooms·2½ baths

Kissimmee • Florida

510,47 $ USD 497,97 $ USD gesamt für 3 Nächte

27.–30. Okt. 2026

Cinema Movie Theater

Kids Theme Bedroom

Lakeview Pool and Hot Tub

Master Bedroom Suites

Kids Theme Bedroom

Mickeys Escape Lakeview (4 Masters) Pool Hot Tub Cinema BBQ

7 bedrooms·6 baths

Kissimmee • Florida

4.99(101 reviews)

2.471,66 $ USD gesamt für 5 Nächte

30. Okt. – 4. Nov. 2026

Free Pool Heat | Hypoallergenic Private Villa | Lux Resort

Free Pool Heat | Hypoallergenic Private Villa | Lux Resort

Free Pool Heat | Hypoallergenic Private Villa | Lux Resort

Free Pool Heat | Hypoallergenic Private Villa | Lux Resort

Free Pool Heat | Hypoallergenic Private Villa | Lux Resort

Free Pool Heat | Hypoallergenic Private Villa | Lux Resort

4 bedrooms·3 baths

Four Corners • Florida

5(6 reviews)

703,07 $ USD gesamt für 3 Nächte

2.–5. Nov. 2026

Den with wall mounted TV

Ample seating in the Den

Open concept living area

Kitchen with granite counter tops and stainless steel appliances.

Seating at breakfast bar in kitchen

Palm Tree Paradise

4 bedrooms·3 baths

Kissimmee • Florida

5(28 reviews)

719,25 $ USD 668,89 $ USD gesamt für 3 Nächte

27.–30. Okt. 2026

Surprise your family with a trip to Disney and world class theme parks! ...while enjoying all the enormous amount of amenities that this resort offers!

One is faster, the other more adventurous!

Spend your best memories under amenities galore!

Magic is calling!

New! Windsor Hills Magical Retreat, 2mi to Disney!

3 bedrooms·2 baths

Kissimmee • Florida

5(12 reviews)

519,64 $ USD gesamt für 3 Nächte

3.–6. Nov. 2026

Large Stunning Pool with a real Hut Tub overlooking the lake

Amazing Disney Move Room

Disney Mickey Mouse Themed Bedroom

Luxury Large King Master Suites

Luxury King Master Suite

Mickeys Waterside SouthE Pool Hot Tub Cinema Outdoor Kitchen BBQ

9 bedrooms·8 baths

Kissimmee • Florida

5(20 reviews)

4.488,47 $ USD gesamt für 5 Nächte

31. Okt. – 5. Nov. 2026

Your Sun, Fun and Everything Disney Destination!

Your Sun, Fun and Everything Disney Destination!

Your Sun, Fun and Everything Disney Destination!

Your Sun, Fun and Everything Disney Destination!

Your Sun, Fun and Everything Disney Destination!

3 bedrooms·2 baths

Kissimmee • Florida

5(4 reviews)

635,60 $ USD gesamt für 3 Nächte

27.–30. Okt. 2026

Magical Adventure-Game Room-Skeeball-Free Waterpark

Immersive Toy Story Mania Experience

Access to the waterpark is included in your stay

Magical Adventure-Game Room-Skeeball-Free Waterpark

Double Olympic sized poolOn

Magical Adventure-Game Room-Skeeball-Free Waterpark

3 bedrooms·2 baths

Kissimmee • Florida

5(5 reviews)

758,18 $ USD gesamt für 3 Nächte

27.–30. Okt. 2026

Welcome to the Marvelous Magical House

Settle in on the couch while watching the kids swim in the pool.

Paradise Palms Resort amenities. NO RESORT FEES :)

Hang out like Harry Potter and his gang in the Gryffindor Common Room. Complete with a fireplace, Roku TV, foosball table, and board games.

Curl up next to the fireplace with a good read, "Harry Potter and the Sorcerer's Stone".

5mi Disney* Immersive Themes* Outdoor Pool & Movie

6 bedrooms·5 baths

Kissimmee • Florida

5(80 reviews)

1.167,03 $ USD gesamt für 3 Nächte

27.–30. Okt. 2026

Orlando Condo in der Nähe von Disney. Schläft 8

Orlando Condo in der Nähe von Disney. Schläft 8

Orlando Condo in der Nähe von Disney. Schläft 8

Orlando Condo in der Nähe von Disney. Schläft 8

Orlando Condo in der Nähe von Disney. Schläft 8

Orlando Condo in der Nähe von Disney. Schläft 8

4 bedrooms·2 baths

Orlando • Florida

Harry's Hangout

Harry's Hangout

Harry's Hangout

Harry's Hangout

Harry's Hangout

Harry's Hangout

1 bedroom·1 bath

Kissimmee • Florida

406,42 $ USD gesamt für 3 Nächte

31. Okt. – 3. Nov. 2026

Your Home Away From the Magic

Your Home Away From the Magic

Your Home Away From the Magic

Your Home Away From the Magic

Your Home Away From the Magic

Your Home Away From the Magic

2 bedrooms·2 baths

Kissimmee • Florida

300,00 $ USD gesamt für 3 Nächte

27.–30. Okt. 2026

CASA AMARELA

3 bedrooms·2½ baths

Kissimmee • Florida

720,80 $ USD gesamt für 3 Nächte

11.–14. Nov. 2026

Mickey's Oyster 9 Bedroom 8 Bathroom Sleeps 18 People 2 Miles to Disney Gorgeous large tropical pool area with spa, surrounded by palm trees and shrubs.

Mulan Suite (king bed) with french doors to pool, with Ensuite Bathroom

Star Wars room - desk with chair in the corner

Movie/ game room - with air hockey, table tennis 🏓, darts 🎯, karaoke 🎤 machine

Air hockey and table tennis 🏓 table. Karaoke 🎤 machine for kids in the corner

Mickeys Oyster Amazing Southeast Pool Hot Tub Cinema Game RM BBQ

9 bedrooms·8 baths

Kissimmee • Florida

5(45 reviews)

4.249,10 $ USD gesamt für 5 Nächte

17.–22. Nov. 2026

Spacious Kitchen

private screened private pool swim during the day or at night

private screened pool can be heated

Screened in private pool

Master bedroom on second floor Queen bed with ensuite

Bay Lilly sleeps 8 your home away from home

4 bedrooms·3 baths

Kissimmee • Florida

4.92(108 reviews)

646,46 $ USD gesamt für 3 Nächte

11.–14. Nov. 2026

Beautiful, spacious, well maintained home in a gated community

Beautiful, spacious, well maintained home in a gated community

Custom built pool / spa / kiddie pool

Luscious greenery from the conservation preserve is the backdrop

Our Blue Oasis

6 bedrooms·7 baths

Kissimmee • Florida

5(1 review)

1.546,88 $ USD gesamt für 3 Nächte

27.–30. Okt. 2026