Location

Dates

Guests

Vacation rentals in Loughman, Florida, United States

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 total for 3 nights

Nov 11 – 14, 2026

CASA AMARELA

3 bedrooms·2½ baths

Kissimmee • Florida

$720.80 USD total for 3 nights

Nov 11 – 14, 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

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

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

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

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

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

New exterior paint as of May 2023.

Resident mascots Flynn and Mingo overlook the pool.

Villa entrance, post May 2023 new paint.

More formal living room as entering the villa.

Flamingo Oasis at HR

4 bedrooms·3 baths

Polk County • Florida

4.92(79 reviews)

$1,232.00 USD total for 5 nights

Oct 27 – Nov 1, 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

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)

$1,693.48 USD total for 3 nights

Oct 30 – Nov 2, 2026

Private Pool Area

4BR 2.5BA Pool Home

open Living Area

open, equipped Kitchen

BASS LAKE - Spacious 4BR 2.5BA Pool Home

4 bedrooms·2½ baths

Kissimmee • Florida

$709.21 USD $689.70 USD total for 3 nights

Oct 27 – 30, 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

Mickey's Lakefront Escape

Mickey's Lakefront Escape

Mickey's Lakefront Escape

Mickey's Lakefront Escape

Mickey's Lakefront Escape

Mickey's Lakefront Escape

4 bedrooms·3 baths

Kissimmee • Florida

5(1 review)

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

$1,933.02 USD total for 3 nights

Oct 27 – 30, 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

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 27 – 30, 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

"Mahalo Magical" mit Whirlpool

Kitchen / Dining Room

"Mahalo Magical" mit Whirlpool

10 bedrooms·7 baths

Orlando • Florida

$444/ night(excl. fees & taxes)

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

$1,692.32 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 $942.94 USD total for 3 nights

Oct 27 – 30, 2026

᯽ Aurora Villa Palms

᯽ Aurora Villa Palms

᯽ Aurora Villa Palms

᯽ Aurora Villa Palms

᯽ Aurora Villa Palms

᯽ Aurora Villa Palms

5 bedrooms·3 baths

Davenport • Florida

$1,890.53 USD total for 3 nights

Nov 20 – 23, 2026

Secret Resort | Kissimmee Lakeview Condo

Secret Resort | Kissimmee Lakeview Condo

Secret Resort | Kissimmee Lakeview Condo

Secret Resort | Kissimmee Lakeview Condo

Secret Resort | Kissimmee Lakeview Condo

Secret Resort | Kissimmee Lakeview Condo

2 bedrooms·2 baths

Kissimmee • Florida

$441.79 USD total for 3 nights

Oct 27 – 30, 2026

Andy's Hideaway

Woody theme on the bottom bunk and Buzz Lightyear theme on the top. The bunk bed also has a pullout trundle for extra sleeping and a bean bag for watching TV!

Master bedroom has a king sized bed

There is a pool and hot tub right behind the condo!

Kids will love the splash pad and pools!

Andy's Hideaway

3 bedrooms·2 baths

Davenport • Florida

$456.62 USD total for 3 nights

Nov 10 – 13, 2026