Location

Dates

Guests

Vacation rentals in Haines City, Florida, United States

Luxurious Pool Home with Private Pool-2061LC

Luxurious Pool Home with Private Pool-2061LC

Luxurious Pool Home with Private Pool-2061LC

Luxurious Pool Home with Private Pool-2061LC

Luxurious Pool Home with Private Pool-2061LC

Luxurious Pool Home with Private Pool-2061LC

8 bedrooms·6 baths

Four Corners • Florida

$1,489.50 USD total for 3 nights

Nov 4 – 7, 2026

Enjoy a beautiful sunset from your private pool with no rear neighbors and a view of the nightly fireworks from Disney. Bistro lights, palm trees, outdoor games, outdoor seating, sofa, TV and mini fridge complete this outdoor oasis!

SEEN ON TV | Themed Rooms | Arcade, Pool & Resort

professionally designed open concept living and dining room with spacious kitchen, 75" Smart TV, Nintendo switch, karaoke, and ample comfortable seating for a comfortable and fun experience.

Game room with 9 Arcade Games, a pool table, TV, full size Darth Vader and glow in the dark Custom Murals.

Windsor Island Resort & Aloha Clubhouse amenities included with your stay!

SEEN ON TV | Themed Rooms | Arcade, Pool & Resort

9 bedrooms·8 baths

Davenport • Florida

$1,420.00 USD total for 3 nights

Nov 15 – 18, 2026

Aloha Oasis- Windsor Island Resort

Downstairs Living Room

Aloha Oasis- Windsor Island Resort

5 bedrooms·5½ baths

Davenport • Florida

5(9 reviews)

$1,284.68 USD total for 4 nights

Nov 1 – 5, 2026

Largest private pool and pool deck in Windsor Island Resort

Largest private pool and pool deck in Windsor Island Resort! The neighbors are jealous!

Windsor Island slides

Complete relaxation all day!

Chillax Inn Kaipo

7 bedrooms·5½ baths

Davenport • Florida

$1,203.88 USD $1,118.01 USD total for 3 nights

Nov 1 – 4, 2026

Gorgeous 8BR/8Bath Windsor Island Dry Sauna

Gorgeous 8BR/8Bath Windsor Island Dry Sauna

16 seater dining room table

Living Room w/ fireplace

Gorgeous 8BR/8Bath Windsor Island Dry Sauna

8 bedrooms·8 baths

Davenport • Florida

4.87(60 reviews)

$1,580.43 USD total for 3 nights

Oct 31 – Nov 3, 2026

Even tooth-brushing is an adventure in this custom Minion bathroom! A hit with the little ones, it features a tub / shower combo—perfect for easy bath times after a long day at Disney.

Welcome to Magical Magnolia Manor! Our modern, bright home features a keyless entry for a seamless 'self-check-in' experience after your flight or drive and easy parking right outside your door.

The adventure starts here! This custom movie-scene niche sits right between the kitchen and living room, serving as your family's gateway to our immersive themed bedrooms and the playful Minion bathroom.

Climb into Rafiki's Treehouse (twin-over-double bunk) under a glowing sunset mural with Simba and friends.

Ultimate pool privacy! Tall hedges and a protected nature reserve ensure a peaceful stay with no rear neighbors. Relax in your private sanctuary and enjoy the Florida sun in total seclusion. A magical escape for every guest!

Disney, Toy Story, Minions, Pool+Gameroom and more

4 bedrooms·3 baths

Kissimmee • Florida

5(109 reviews)

$1,814.86 USD total for 6 nights

Jan 6 – 12, 2027

Beautiful Sunset Villa by Disney w/many amenities!

Private pool setting with fantastic sunset views!

Beautiful Sunset Villa by Disney w/many amenities!

Beautiful Sunset Villa by Disney w/many amenities!

Beautiful Sunset Villa by Disney w/many amenities!

Beautiful Sunset Villa by Disney w/many amenities!

5 bedrooms·5 baths

Four Corners • Florida

5(5 reviews)

$1,554.00 USD total for 5 nights

Oct 31 – Nov 5, 2026

A Date With Disney image 1

A Date With Disney image 2

A Date With Disney image 3

A Date With Disney image 4

A Date With Disney image 5

A Date With Disney

3 bedrooms·3 baths

Kissimmee • Florida

4.78(67 reviews)

$624.25 USD total for 4 nights

Oct 31 – Nov 4, 2026

Dreams Come True Villa LLC

Dreams Come True Villa LLC

5 bedrooms·5 baths

Kissimmee • Florida

4.93(27 reviews)

$1,897.54 USD total for 5 nights

Nov 11 – 16, 2026

Pool and Patio Area

Our Windsor Hills Water Park!

Welcome to Windsor Hills!

Layout of our 6BR 4 BA Disney Villa

Air-Conditioned Game room with air hockey, two video games, Basketball and fun for kids and teenagers!

Waterpark! 5 Star 6BR4BA Pool/Game Room/Disney

6 bedrooms·4 baths

Kissimmee • Florida

4.84(122 reviews)

$1,332.85 USD $1,137.40 USD total for 3 nights

Oct 31 – Nov 3, 2026

Queen Bed suitable for your princesses!

Toys, sleeping bags, costumes in all sizes.

Toy Story, sleeps 3, truck bed doors open and close, dress ups in closet

Woody, Jessie, Buzz dress ups included. Toy Story and vintage toys ready to play

Step into Andy's room with all his favorite toys!

Be Our Guest Vacation Villa

6 bedrooms·4 baths

Kissimmee • Florida

4.94(185 reviews)

$1,850.05 USD $1,691.60 USD total for 4 nights

Oct 31 – Nov 4, 2026

New Listing! Windsor Island-2166 8BR · Disney

New Listing! Windsor Island-2166 8BR · Disney

New Listing! Windsor Island-2166 8BR · Disney

New Listing! Windsor Island-2166 8BR · Disney

New Listing! Windsor Island-2166 8BR · Disney

New Listing! Windsor Island-2166 8BR · Disney

8 bedrooms·6 baths

Four Corners • Florida

$1,735.90 USD total for 3 nights

Oct 31 – Nov 3, 2026

Sleeps 28 | Game & Themed Rooms | Heated Pool

Sleeps 28 | Game & Themed Rooms | Heated Pool

Sleeps 28 | Game & Themed Rooms | Heated Pool

Sleeps 28 | Game & Themed Rooms | Heated Pool

Sleeps 28 | Game & Themed Rooms | Heated Pool

Sleeps 28 | Game & Themed Rooms | Heated Pool

10 bedrooms·8 baths

Davenport • Florida

$1,345.00 USD total for 3 nights

Oct 31 – Nov 3, 2026

Close to the parks! 5bd/4ba home & pool in resort

Close to the parks! 5bd/4ba home & pool in resort

Close to the parks! 5bd/4ba home & pool in resort

Close to the parks! 5bd/4ba home & pool in resort

Close to the parks! 5bd/4ba home & pool in resort

Close to the parks! 5bd/4ba home & pool in resort

5 bedrooms·4½ baths

Davenport • Florida

$1,112.24 USD total for 4 nights

Nov 7 – 11, 2026

Private pool 5bd home in resort close to parks

Private pool 5bd home in resort close to parks

Private pool 5bd home in resort close to parks

Private pool 5bd home in resort close to parks

Private pool 5bd home in resort close to parks

Private pool 5bd home in resort close to parks

5 bedrooms·4½ baths

Davenport • Florida

$909.32 USD total for 3 nights

Nov 7 – 10, 2026

Close to the parks! 5bd/4ba home & pool in resort

Close to the parks! 5bd/4ba home & pool in resort

Close to the parks! 5bd/4ba home & pool in resort

Close to the parks! 5bd/4ba home & pool in resort

Close to the parks! 5bd/4ba home & pool in resort

Close to the parks! 5bd/4ba home & pool in resort

5 bedrooms·4½ baths

Davenport • Florida

$1,028.40 USD total for 3 nights

Nov 21 – 24, 2026

Themed 5bd home w/ private Pool & Arcade in Resort

Themed 5bd home w/ private Pool & Arcade in Resort

Themed 5bd home w/ private Pool & Arcade in Resort

Themed 5bd home w/ private Pool & Arcade in Resort

Themed 5bd home w/ private Pool & Arcade in Resort

Themed 5bd home w/ private Pool & Arcade in Resort

5 bedrooms·4½ baths

Davenport • Florida

$1,133.75 USD total for 3 nights

Nov 21 – 24, 2026

Welcome to Chillax Inn Teascone Arcade

Free Arcade in the garage!

Chill on the couch

Windsor Hills amenities

Chillax Inn Teascone Arcade

5 bedrooms·5 baths

Kissimmee • Florida

$2,238.65 USD $2,036.71 USD total for 3 nights

Dec 20 – 23, 2026

Welcome to Ohana House

Favorite Place!

Ohana House at Windsor Island Resort

Fully Equipped Kitchen with a Patio Door to the Pool Area

Beautifully Decorated

Ohana House at Windsor Island Resort

5 bedrooms·5½ baths

Davenport • Florida

$1,694.56 USD total for 6 nights

Dec 12 – 18, 2026

Free arcade in the garage

Mickey and friends queen ensuite

Windsor Island slides

Toy story queen ensuite

Chillax Inn Lil Lana

5 bedrooms·5½ baths

Davenport • Florida

$1,042.00 USD total for 3 nights

Nov 10 – 13, 2026

Chillax Inn the pool area under the big lanai

Frozen Bedroom with double

Welcome to Chillax Inn Teascone

Windsor Hills Slides

Star Wars Bedroom with two doubles

Chillax Inn Teascone

4 bedrooms·4 baths

Kissimmee • Florida

$812.32 USD $748.87 USD total for 3 nights

Nov 2 – 5, 2026

Townhouse near Disney w/ pool & game room

Townhouse near Disney w/ pool & game room

Townhouse near Disney w/ pool & game room

Townhouse near Disney w/ pool & game room

Townhouse near Disney w/ pool & game room

Townhouse near Disney w/ pool & game room

3 bedrooms·3 baths

Kissimmee • Florida

$945.90 USD total for 3 nights

Oct 31 – Nov 3, 2026

Princess castle

View to the pool

Windsor Hills Resort amenities free with your stay!

Chillax by the pool

Chillax Inn Fitzclarence

3 bedrooms·3 baths

Kissimmee • Florida

$773.75 USD total for 3 nights

Nov 19 – 22, 2026

The lanai has a table that seats 8, privacy bushes, 4 lounge chairs & BBQ

The outdoor table under the lanai seats 8 and the pool has a security fence

The Game room has a pool table, air hockey, foosball, & Air Conditioning

Private screened in, heated salt water pool and spa with oversized pool deck

The covered lanai, lounge chairs & basketball hoop, salt water pool & spa

Villa By The Castle

6 bedrooms·4 baths

Kissimmee • Florida

5(385 reviews)

$2,298.38 USD total for 3 nights

Nov 11 – 14, 2026