Location

Dates

Guests

Vacation rentals in Winter Haven, Florida, United States

Waterslide - don't you wish you were here!

Resort pool - shallow section

Separate heated pool at sunset

Pool in the evening with heavy clouds.

Resort entrance

Townhouse at the Regal Palms resort near Disney

4 bedrooms·3 baths

Davenport • Florida

4.87(110 reviews)

$847.55 USD total for 4 nights

Oct 27 – 31, 2026

Regal Palms Getaway

Regal Palms Getaway

Regal Palms Getaway

Regal Palms Getaway

Regal Palms Getaway

Regal Palms Getaway

4 bedrooms·3 baths

Davenport • Florida

$410.09 USD total for 3 nights

Oct 27 – 30, 2026

Hogwarts Express House

Hogwarts Express House

Hogwarts Express House

Hogwarts Express House

Hogwarts Express House

Hogwarts Express House

3 bedrooms·3 baths

Davenport • Florida

$517.29 USD total for 3 nights

Oct 27 – 30, 2026

Sunset views nightly

Eat as the sunsets over the lake

Anyone for some night swimming?

Now this feels like vacation!

Outdoor Dining for 8

Sunset Magic Villa

8 bedrooms·6 baths

Four Corners • Florida

5(15 reviews)

$1,437.50 USD total for 3 nights

Oct 28 – 31, 2026

Orlando Resort Home✦Sleeps 21

Orlando Resort Home✦Sleeps 21

Orlando Resort Home✦Sleeps 21

Orlando Resort Home✦Sleeps 21

Orlando Resort Home✦Sleeps 21

Orlando Resort Home✦Sleeps 21

7 bedrooms·6½ baths

Kissimmee • Florida

4.98(109 reviews)

$915.13 USD total for 3 nights

Oct 27 – 30, 2026

Regal palms home, gated community ,pool (712CAL)

Island Getaway Villa Welcomes You

alternate view of kitchen

Regal palms home, gated community ,pool (712CAL)

4 bedrooms·3 baths

Davenport • Florida

4.6(5 reviews)

$623.60 USD total for 3 nights

Oct 27 – 30, 2026

Waterside Resort Villa112, Disney 9mi/14km, Gym

Waterside Resort Villa112, Disney 9mi/14km, Gym

Lazy river use included with your resort fee. Floats are not included

Waterside Resort Villa112, Disney 9mi/14km, Gym

Waterside Resort Villa112, Disney 9mi/14km, Gym

Waterside Resort Villa112, Disney 9mi/14km, Gym

4 bedrooms·1 bath

Davenport • Florida

4.7(10 reviews)

$492.54 USD total for 3 nights

Oct 27 – 30, 2026

Luxury 9BR Solara Pool Villa | Sleeps 20 | Disney

Solara Resort playground & sports courts — Sawyer Palm villa FL

Luxury 9BR Solara Pool Villa | Sleeps 20 | Disney

King bedroom with ensuite — Sawyer Palm 9BR villa, Solara Resort

Luxury 9BR Solara Pool Villa | Sleeps 20 | Disney

Luxury 9BR Solara Pool Villa | Sleeps 20 | Disney

9 bedrooms·6½ baths

Kissimmee • Florida

5(15 reviews)

$964.58 USD total for 3 nights

Oct 27 – 30, 2026

Private back yard pool and Hot tub

8mi to Disney: themed kids' rooms, pool, 9BR

8mi to Disney: themed kids' rooms, pool, 9BR

Solara Resort Solstice Bar & Grill

8mi to Disney: themed kids' rooms, pool, 9BR

8mi to Disney: themed kids' rooms, pool, 9BR

9 bedrooms·6 baths

Kissimmee • Florida

5(1 review)

$1,072.33 USD total for 3 nights

Nov 1 – 4, 2026

Resort Amenities,

Living Room - Dining room Combo

Dining Room/Living Room Combo

Primary King bedroom with private bath, located downstairs, with its own entry

Cozy Retreat w/ Fireplace 12 miles to Disney

Cozy Retreat w/ Fireplace 12 miles to Disney

4 bedrooms·3½ baths

Davenport • Florida

5(1 review)

$587.00 USD total for 3 nights

Oct 27 – 30, 2026

Regal Palms 4BR w/ lake view & waterpark

Regal Palms 4BR w/ lake view & waterpark

Regal Palms 4BR w/ lake view & waterpark

Regal Palms 4BR w/ lake view & waterpark

Regal Palms 4BR w/ lake view & waterpark

Regal Palms 4BR w/ lake view & waterpark

4 bedrooms·3½ baths

Davenport • Florida

5(2 reviews)

$502.84 USD total for 3 nights

Oct 28 – 31, 2026

Ideal Vacation Getaway for Families close 2 Disney

Ideal Vacation Getaway for Families close 2 Disney

Ideal Vacation Getaway for Families close 2 Disney

Ideal Vacation Getaway for Families close 2 Disney

Ideal Vacation Getaway for Families close 2 Disney

Ideal Vacation Getaway for Families close 2 Disney

3 bedrooms·3 baths

Davenport • Florida

4.87(15 reviews)

$656.00 USD total for 3 nights

Oct 31 – Nov 3, 2026

Fabulous 5Bd Family Townhome with Splash Pool-726G

Fabulous 5Bd Family Townhome with Splash Pool-726G

Fabulous 5Bd Family Townhome with Splash Pool-726G

Fabulous 5Bd Family Townhome with Splash Pool-726G

Fabulous 5Bd Family Townhome with Splash Pool-726G

Fabulous 5Bd Family Townhome with Splash Pool-726G

5 bedrooms·4 baths

Four Corners • Florida

$1,267.73 USD total for 4 nights

Nov 1 – 5, 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!

Watch the sunset under the all-inclusive amenities to you!

This is a bird's eye view of the main clubhouse. It is walking distance from your resort stay. This includes water park, tennis courts, lounge areas, arcade area and so much more!

Magic is calling!

The south facing pool gives you an extended abundance of sunlight to enjoy and relax poolside.

Windsor's Avengers Villa, SF Pool, 6mi to Disney!

5 bedrooms·5 baths

Kissimmee • Florida

4.7(166 reviews)

$623.30 USD total for 3 nights

Oct 29 – Nov 1, 2026

Toy Story double single bunk

Lounge by the pool

Chillax with Mickey and friends

Windsor Island Resort lazy river & slides

Chillax Inn the living room

Chillax Inn Jetty Way

5 bedrooms·4½ baths

Davenport • Florida

$747.16 USD total for 3 nights

Nov 9 – 12, 2026

Harry Potter House

If you're loyal, hardworking, and have a love all living things, you might be a Hufflepuff.

Green lights and silver decor symbolize the Slytherin colors. You might also notice the snakes placed throughout both the bedroom and bathroom. This room features a Queen sized bed with velvet bedding.

The kitchen and main living area is themed as The Leaky Cauldron just like the movies/books and Universal Studios!

Inside the Gryffindor bedroom, for our young guests, there are Harry Potter toys to play with, books to read, their own large Television, even a snitch nightlight! It really can't get any better. Two twin bunk beds sleep 4 in this room.

Harry Potter House

4 bedrooms·3½ baths

Davenport • Florida

$592.18 USD total for 3 nights

Nov 2 – 5, 2026

1C Magical Family Stay Near Disney 8mi/Pool/Resort

1C Magical Family Stay Near Disney 8mi/Pool/Resort

1C Magical Family Stay Near Disney 8mi/Pool/Resort

1C Magical Family Stay Near Disney 8mi/Pool/Resort

1C Magical Family Stay Near Disney 8mi/Pool/Resort

1C Magical Family Stay Near Disney 8mi/Pool/Resort

2 bedrooms·1 bath

Kissimmee • Florida

4.41(22 reviews)

$282.84 USD total for 3 nights

Oct 27 – 30, 2026

Orlando Resort Home✦Sleeps 24

Orlando Resort Home✦Sleeps 24

Orlando Resort Home✦Sleeps 24

Orlando Resort Home✦Sleeps 24

Orlando Resort Home✦Sleeps 24

Orlando Resort Home✦Sleeps 24

9 bedrooms·6½ baths

Kissimmee • Florida

4.99(154 reviews)

$1,230.44 USD total for 3 nights

Nov 2 – 5, 2026

Mickey & Minnie

Windsor Island water slides

Chillax Inn Jasmine

5 bedrooms·4½ baths

Davenport • Florida

$686.97 USD total for 3 nights

Nov 14 – 17, 2026

1A Magical Disney Getaway in Gated Community 8mi

1A Magical Disney Getaway in Gated Community 8mi

1A Magical Disney Getaway in Gated Community 8mi

1A Magical Disney Getaway in Gated Community 8mi

1A Magical Disney Getaway in Gated Community 8mi

1A Magical Disney Getaway in Gated Community 8mi

1 bedroom·1 bath

Kissimmee • Florida

4.9(29 reviews)

$212.04 USD total for 3 nights

Oct 27 – 30, 2026

1b Disney Adventures Start at This Cozy Suite

1b Disney Adventures Start at This Cozy Suite

1b Disney Adventures Start at This Cozy Suite

1b Disney Adventures Start at This Cozy Suite

1b Disney Adventures Start at This Cozy Suite

1b Disney Adventures Start at This Cozy Suite

2 bedrooms·1 bath

Kissimmee • Florida

4.67(69 reviews)

$300.79 USD total for 3 nights

Oct 27 – 30, 2026

1D Disney Fun Steps Away – Pool & Kids’ Activities

1D Disney Fun Steps Away – Pool & Kids’ Activities

1D Disney Fun Steps Away – Pool & Kids’ Activities

1D Disney Fun Steps Away – Pool & Kids’ Activities

1D Disney Fun Steps Away – Pool & Kids’ Activities

1D Disney Fun Steps Away – Pool & Kids’ Activities

2 bedrooms·1 bath

Kissimmee • Florida

4.65(79 reviews)

$316.74 USD total for 3 nights

Nov 1 – 4, 2026

Kitchen / Dining Room

Kitchen / Dining Room

Kitchen / Dining Room

Kitchen / Dining Room

Kitchen / Dining Room

Nur wenige Minuten von Disney Pool, Spa und Seeblick

3 bedrooms·2 baths

Kissimmee • Florida

GemStone Retreat image 1

GemStone Retreat

GemStone Retreat

GemStone Retreat

GemStone Retreat

GemStone Retreat

11 bedrooms·11 baths

Kissimmee • Florida

5(3 reviews)

$2,973.70 USD total for 3 nights

Oct 27 – 30, 2026