Location

Dates

Guests

Vacation rentals in Winter Haven, Florida, United States

Neverland Escape

Neverland Escape

Neverland Escape

Neverland Escape

Neverland Escape

Neverland Escape

3 bedrooms·2½ baths

Davenport • Florida

$461.70 USD total for 3 nights

Oct 27 – 30, 2026

WI927- ♥LUXURY BRAND NEW Cozy Pool Townhouse near to Disney♥

5 bedrooms·4½ baths

Davenport • Florida

$1,106.51 USD total for 4 nights

Oct 27 – 31, 2026

Stunning Themed 7 Bed Pool Home with Theater-3229L

Stunning Themed 7 Bed Pool Home with Theater-3229L

Stunning Themed 7 Bed Pool Home with Theater-3229L

Stunning Themed 7 Bed Pool Home with Theater-3229L

Stunning Themed 7 Bed Pool Home with Theater-3229L

Stunning Themed 7 Bed Pool Home with Theater-3229L

7 bedrooms·6 baths

Four Corners • Florida

$2,370.38 USD total for 3 nights

Oct 27 – 30, 2026

Keep everyone occupied!

Mickey & Minnie double and single

Windsor at Westside lazy river and splash area

Chillax Inn the spa

Chillax Inn Qin Loop

8 bedrooms·6 baths

Kissimmee • Florida

$1,170.78 USD total for 3 nights

Nov 8 – 11, 2026

Swift BnB - Taylor themed rooms - Pool - sleeps 16

Swift BnB - Taylor themed rooms - Pool - sleeps 16

Swift BnB - Taylor themed rooms - Pool - sleeps 16

Swift BnB - Taylor themed rooms - Pool - sleeps 16

Swift BnB - Taylor themed rooms - Pool - sleeps 16

Swift BnB - Taylor themed rooms - Pool - sleeps 16

8 bedrooms·7 baths

Kissimmee • Florida

5(10 reviews)

$1,461.31 USD $1,303.50 USD total for 3 nights

Oct 27 – 30, 2026

Poolside Cinema: Dive into relaxation while enjoying movies under stunning sunset skies!

Circus Playroom: Dive into fun with arcade games, ping pong, and vibrant circus-themed decor!

Home Theater Oasis: Experience cinematic bliss in plush red recliners and a giant screen!

Living Room: Bright and airy space with modern decor, perfect for relaxation and fun gatherings!

Pool Hall: Play your best shot in style with a vibrant pool table and sleek bar seating!

Big Top Family Vacation Villa

9 bedrooms·6½ baths

Kissimmee • Florida

5(95 reviews)

$1,462.33 USD total for 3 nights

Nov 1 – 4, 2026

Star wars twins bedroom #8

Game room in air conditioned garage

The force is strong in this one!

Windsor Island water slides

Shoot some pool and chillax

Chillax Inn Lilac

10 bedrooms·8 baths

Davenport • Florida

$2,339.77 USD $2,122.17 USD total for 4 nights

Oct 27 – 31, 2026

"Mahalo Magical" mit Whirlpool

Kitchen / Dining Room

"Mahalo Magical" mit Whirlpool

10 bedrooms·7 baths

Orlando • Florida

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 4Bd TH Pool Windsor at Westside-2018WW

Gorgeous 4Bd TH Pool Windsor at Westside-2018WW

Gorgeous 4Bd TH Pool Windsor at Westside-2018WW

Gorgeous 4Bd TH Pool Windsor at Westside-2018WW

Gorgeous 4Bd TH Pool Windsor at Westside-2018WW

Gorgeous 4Bd TH Pool Windsor at Westside-2018WW

4 bedrooms·3 baths

Four Corners • Florida

$1,153.62 USD total for 3 nights

Oct 27 – 30, 2026

Living room area

Front of the house

Amazing Pool and View with no neighbors in the back

Harry potter room, game room, upstairs movie/gathering room, mickey room

Mickey mouse themed room

Brand New 7BR Home in Windsor Island Resort

7 bedrooms·5½ baths

Davenport • Florida

4.9(52 reviews)

$1,130.08 USD total for 3 nights

Nov 8 – 11, 2026

Smart phone room

Windsor Island Resort

Upstairs livingroom

Chillax Inn Summer 2

5 bedrooms·5½ baths

Davenport • Florida

$791.39 USD total for 3 nights

Nov 15 – 18, 2026

Chillax by the pool

Frozen twin with trundle

Chillax Inn Aloha

5 bedrooms·4 baths

Davenport • Florida

$776.65 USD $720.63 USD total for 3 nights

Nov 3 – 6, 2026

Car pool table and movie room

Free arcade garage conversion

Chillax at night

Windsor Island slides

Home theater area with 85" TV

Chillax Inn Lana

8 bedrooms·6 baths

Davenport • Florida

$1,321.81 USD $1,204.61 USD total for 3 nights

Oct 27 – 30, 2026

Aloha Club at Windsor Island

Mickey and Minnie relaxing after a day at the parks

Watch your favorite movies on the 85 inch 4k TV

Game room with ample seating for players and observers

Open view from lanai pool side.

Ohana Gathering House

7 bedrooms·5½ baths

Davenport • Florida

5(5 reviews)

$1,197.05 USD total for 3 nights

Nov 2 – 5, 2026

Avengers has two twin beds

Plenty of sun with west facing pool and south exposure

Windsor Island water slides

Night swimming!

Chillax Inn Summer

5 bedrooms·4 baths

Davenport • Florida

$903.19 USD total for 3 nights

Nov 17 – 20, 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

$1,004.96 USD total for 4 nights

Oct 27 – 31, 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

$790.90 USD total for 3 nights

Oct 27 – 30, 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

$618.32 USD total for 3 nights

Oct 27 – 30, 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

Disney Area Attractive house with private pool

Disney Area Attractive house with private pool

Disney Area Attractive house with private pool

Living room / dining room

Dining room area

Disney Area Attractive house with private pool

4 bedrooms·3 baths

Davenport • Florida

4.74(39 reviews)

$737.80 USD total for 3 nights

Oct 27 – 30, 2026

Lovely New Pool Home at Windsor at Westside-2167TC

Lovely New Pool Home at Windsor at Westside-2167TC

Lovely New Pool Home at Windsor at Westside-2167TC

Lovely New Pool Home at Windsor at Westside-2167TC

Lovely New Pool Home at Windsor at Westside-2167TC

Lovely New Pool Home at Windsor at Westside-2167TC

8 bedrooms·6 baths

Four Corners • Florida

$1,284.71 USD total for 3 nights

Nov 4 – 7, 2026

2312045

6 bedrooms·4 baths

Orlando • Florida

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