Location

Dates

Guests

Vacation rentals in Winter Haven, Florida, United States

Lots of comfortable seating for everyone and 70 inch HDTV, Netflix & HD Cable

You'll spend hours out here! Luxurious rattan loungers & recliners to relax

Poolside patio area with 42 inch Smart TV

Kick back in the poolside living area with padded rattan seating and 42 inch tv

The bubbling jets of the hot tub will rejuvenate those aching legs!

Serendipity at Indian Creek

5 bedrooms·4 baths

Kissimmee • Florida

4.98(172 reviews)

$285 – $300/ night(excl. fees & taxes)

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

Spa And Pool Lounge Area

Sleep Like A Princess!

’Til The Last Petal Falls…

To Infinity & Beyond!

Wish Upon A Star

5 bedrooms·5 baths

Kissimmee • Florida

$825.15 USD total for 3 nights

Oct 31 – Nov 3, 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 27 – 30, 2026

Luxuriöse 4-Bett-Villa in Disney

Luxuriöse 4-Bett-Villa in Disney

Luxuriöse 4-Bett-Villa in Disney

Luxuriöse 4-Bett-Villa in Disney

Luxuriöse 4-Bett-Villa in Disney

Luxuriöse 4-Bett-Villa in Disney

4 bedrooms·3 baths

Orlando • Florida

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

$2,180.17 USD $1,984.07 USD total for 3 nights

Dec 20 – 23, 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

Splish Splash at your own pool

Open Entry area

Mickey Hideaway Villa

Mickey Hideaway Villa

6 bedrooms·4 baths

Kissimmee • Florida

5(71 reviews)

$1,936.26 USD total for 5 nights

Oct 27 – Nov 1, 2026

Magical Mickey Villa LLC

Gorgeous Sunset

Beautiful overlook No rear neighbors

Relax and enjoy

Magical Mickey Villa LLC

5 bedrooms·5 baths

Kissimmee • Florida

5(52 reviews)

$2,323.59 USD total for 5 nights

Nov 22 – 27, 2026

ENJOY THE SUN FLORIDA IN YOUR PRIVATE POOL

PRIVATE POOL WITH SUNSHINE

YOU CAN ENJOY THE POOL AFTER THE PARKS

BEAUTIFUL RESORT

CLUBHOUSE WITH CONCIERGE SERVICE

THE HAVEN IN EMERALD ISLAND

4 bedrooms·3 baths

Kissimmee • Florida

4.73(51 reviews)

$1,078.25 USD total for 5 nights

Oct 27 – Nov 1, 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 27 – 31, 2026

Upstairs Beedroom 2 Double Beds

Kitchen and Breakfast Bar

Sun n Serenity in Kissimmee Florida Near Disney

4 bedrooms·3 baths

Kissimmee • Florida

5(5 reviews)

$748.85 USD total for 3 nights

Oct 27 – 30, 2026

Queen's Fun Spot

Queen's Fun Spot

Beautiful and spacious lanai

Seating for all

Queen's Fun Spot

7 bedrooms·4½ baths

Kissimmee • Florida

5(12 reviews)

$2,179.20 USD total for 5 nights

Oct 27 – Nov 1, 2026

Lilo's Paradise in Windsor Hills is the perfect vacation destination!

All of our guests have free access to the 5* amenities at Windsor Hills Resort in Kissimmee.

Jungle Cruise themed room has custom bunk beds, fun mural and reading "cave" under the bed.

The cozy living room is the perfect place to enjoy family time

Location! Location! Location! Lilo’s Paradise is just minutes from the Disney theme parks!

Lilo's Paradise in Windsor Hills Resort - Near Walt Disney World

5 bedrooms·5 baths

Kissimmee • Florida

4.89(35 reviews)

$1,117.98 USD total for 3 nights

Oct 27 – 30, 2026

Little Mermaid twins

Windsor Hills Resort

Mandalorian twins

Chillax Inn Archfeld

5 bedrooms·5 baths

Kissimmee • Florida

$965.78 USD $876.19 USD total for 3 nights

Oct 27 – 30, 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

Master bedroom King bed

Toy story 2-twin room

Slide into vacation mode !

Community pool with beach entry,slide and kiddie area

Majesty Family Villa sleeps 8

4 bedrooms·3 baths

Kissimmee • Florida

4.91(107 reviews)

$649.65 USD total for 3 nights

Dec 5 – 8, 2026

Welcome to Chillax Inn Pawnall

Toy Story upstairs bedroom

Windsor Hills water slides

Star Wars upstairs bedroom

Chillax Inn Pawnall

5 bedrooms·5 baths

Kissimmee • Florida

$950.84 USD $877.68 USD total for 3 nights

Nov 1 – 4, 2026

Grand Superior 3BD Townhouse near Disney image 1

Grand Superior 3BD Townhouse near Disney image 2

Grand Superior 3BD Townhouse near Disney image 3

Grand Superior 3BD Townhouse near Disney image 4

Grand Superior 3BD Townhouse near Disney image 5

Grand Superior 3BD Townhouse near Disney

3 bedrooms·2 baths

Kissimmee • Florida

$604.67 USD total for 3 nights

Oct 27 – 30, 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

$819.81 USD total for 3 nights

Oct 27 – 30, 2026

Kitchen Coffee Station

Magic Holiday House

3 bedrooms·3 baths

Kissimmee • Florida

$662.84 USD total for 3 nights

Oct 27 – 30, 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

$845.91 USD total for 3 nights

Nov 19 – 22, 2026

Relax on our extended screened pool deck that allows for full sunshine all day year round!

Enjoy endless game night possibilities in the Star Wars themed game room.

Experience a true home away from home in retreat in our first floor primary bedroom boasting a view of the pool and a tranquil ensuite bathroom for the ultimate comfort.

The Force is strong in the Star Wars themed hall, bathroom and bedroom.

Windsor Hills is Minutes From the Magic of Disney World

Pooh's Palace in Windsor Hills, Near Walt Disney World

5 bedrooms·5 baths

Kissimmee • Florida

$1,083.93 USD total for 3 nights

Oct 27 – 30, 2026

Hours of family fun in the arcade!

Frozen bedroom upstairs. It even looks cold!

Night swimming!

A view from the top of water slides

Ratatouille themed kitchen

Chillax Inn Beechfield

5 bedrooms·5 baths

Kissimmee • Florida

$1,050.38 USD total for 3 nights

Nov 4 – 7, 2026