Safari Bowling Villa, 14 bedrooms/14.5 baths
Safari Bowling Villa, 14 bedrooms/14.5 baths
Safari Bowling Villa, 14 bedrooms/14.5 baths
Safari Bowling Villa, 14 bedrooms/14.5 baths
Safari Bowling Villa, 14 bedrooms/14.5 baths

Safari Bowling Villa, 14 bedrooms/14.5 baths

10 bedrooms·10 baths
Kissimmee • Florida
4.9(10 reviews)

$6,110.84 USD total for 3 nights

Oct 18 – 21, 2026

Sports Bowling Villa, 14 bedrooms/14.5 baths
Sports Bowling Villa, 14 bedrooms/14.5 baths
Sports Bowling Villa, 14 bedrooms/14.5 baths
Sports Bowling Villa, 14 bedrooms/14.5 baths
Sports Bowling Villa, 14 bedrooms/14.5 baths

Sports Bowling Villa, 14 bedrooms/14.5 baths

10 bedrooms·10 baths
Kissimmee • Florida
5(16 reviews)

$6,110.84 USD total for 3 nights

Oct 13 – 16, 2026

Wonder World Bowling Villa, 14 bedrooms/14.5 baths
Wonder World Bowling Villa, 14 bedrooms/14.5 baths
Wonder World Bowling Villa, 14 bedrooms/14.5 baths
wall-to-wall TV in living room
Wonder World Bowling Villa, 14 bedrooms/14.5 baths

Wonder World Bowling Villa, 14 bedrooms/14.5 baths

10 bedrooms·10 baths
Kissimmee • Florida
4.86(7 reviews)

$6,110.84 USD total for 3 nights

Oct 13 – 16, 2026

Elegant Luxury Villa Movie Game Room Private Pool
Elegant Dining Room. Seats 10 comfortably. (Nearby Breakfast bar seats 5. Outside Patio Seats an additional 8).
Back yard overlooks a peaceful forest conservation preserve. (Does not backup to another house like many listings).
Elegant Luxury Villa Movie Game Room Private Pool
Elegant Luxury Villa Movie Game Room Private Pool

Elegant Luxury Villa Movie Game Room Private Pool

9 bedrooms·5 baths
Kissimmee • Florida
4.93(15 reviews)

$2,236.60 USD total for 4 nights

Oct 18 – 22, 2026

2817 Storey Lake
2817 Storey Lake
2817 Storey Lake
2817 Storey Lake
2817 Storey Lake

2817 Storey Lake

5 bedrooms·5 baths
Kissimmee • Florida

$1,700.23 USD total for 3 nights

Oct 18 – 21, 2026

Arcade games, pool table, Airhockey
Outdoor area
Comfortable Living area furniture
Your very own private movie theatre
Private villa in Storey Lake community close to major Disney attractions, shopping etc.

The Magical Mansion

8 bedrooms·5 baths
Kissimmee • Florida
5(5 reviews)

$1,823.08 USD $1,689.57 USD total for 4 nights

Oct 18 – 22, 2026

Elegant Blue Moon House - TOP Stay 10 Minutes from Disney
Elegant Blue Moon House - TOP Stay 10 Minutes from Disney
Elegant Blue Moon House - TOP Stay 10 Minutes from Disney
Elegant Blue Moon House - TOP Stay 10 Minutes from Disney
Elegant Blue Moon House - TOP Stay 10 Minutes from Disney

Elegant Blue Moon House - TOP Stay 10 Minutes from Disney

5 bedrooms·5 baths
Kissimmee • Florida
4.73(85 reviews)
33 Disney Villa ★ GameRoom ★ Movie Theater ★ Pool
Private Heated Pool and Jacuzzi
Avengers Game Room with Xbox and Nintendo Switch Stations. Pool Table, Video Arcade Game, Twin Bunk Bed.
Club House Waterpark Slide
Bedroom #7. Mickey Room. 2 Full Beds. Smart TV.

33 Disney Villa ★ GameRoom ★ Movie Theater ★ Pool

9 bedrooms·5 baths
Kissimmee • Florida
4.92(39 reviews)

$1,688.68 USD total for 3 nights

Oct 13 – 16, 2026

The Villa
kitchen bar
Shaboo's Villa
Shaboo's Villa
kitchen

Shaboo's Villa

4 bedrooms·4 baths
Davenport • Florida
4.67(3 reviews)

$970.98 USD total for 4 nights

Oct 13 – 17, 2026

Enjoy the imported Italian loungers on our expanded pool deck and catch the sun!
Relax in the Comfort of Your Professionally Decorated Vacation Retreat!
The fully-equipped Kitchen with seating for eight overlooks the pool & lanai.
Quality furnishings, comfort and luxury await you in the master suite!
The MasterBath with its own access to the pool area, kept meticulously clean!

Pleasant Oak Villa

4 bedrooms·2 baths
Loughman • Florida
4.82(44 reviews)

$1,097.60 USD total for 5 nights

Mar 6 – 11, 2027

Your VERY Private Pool - Maintained & heated to 89° just for you! Photo June2017
Relax in the Comfort of Your Professionally Decorated Vacation Retreat!
The secluded & private Breezy Oak Villa, surrounded by tropical Florida forest.
Your King MasterBedroom awaits. Linens are replaced annually to ensure quality.
Master ensuite with large shower and direct pool access - brand new June 2017!

Breezy Oak Villa

4 bedrooms·2 baths
Loughman • Florida
4.87(63 reviews)

$901.60 USD total for 5 nights

Oct 25 – 30, 2026

Your wonderful pool & hot tub. Catch some Florida sun in comfortable loungers!
There's plenty of room for the entire family to relax! Photo January 2023
The master bedroom features a Queen sleigh bed that will carry you off to sleep.
The peaceful and relaxing Happy Oak Villa. Where you want to be in Florida!
Meal prep is easy in our well stocked kitchen! Photo January 2023.

Happy Oak Villa

4 bedrooms·2 baths
Loughman • Florida
5(3 reviews)

$1,002.40 USD total for 5 nights

Oct 27 – Nov 1, 2026

Aerial view of Sunset Palm Villa surrounded by conservation woodland and lake.
Extended pool and spa deck, south/south-west facing, with views onto conservation woodland and lake.
Large full-width lanai (patio) with ample seating for dining and relaxing, complete with outdoor corner shower for guests enjoying the pool and spa.
Family Lounge (Ground Floor) with warm decor
Marvel and DC Themed Games Room with 7.5ft Pool Table, Basketball Hoops, Dart Board and Corn Hole, for wholesome family fun.

Sunset Palm Villa at Watersong Resort near Disney

5 bedrooms·4½ baths
Davenport • Florida

$1,426.20 USD total for 5 nights

Nov 2 – 7, 2026

Rear view of villa showing deck area
Drone view showing lake proximity to villa
Drive will take 4 cars for parking
Aerial view of villa pool area
Aerial view of pool and furniture

Florida Delight @ Watersong Resort, Davenport, Fl

6 bedrooms·5 baths
Davenport • Florida
4.9(89 reviews)

$1,490.00 USD total for 5 nights

Oct 13 – 18, 2026

VillaMaggiore,Watersong, Disney, SW pool,free view
VillaMaggiore,Watersong, Disney, SW pool,free view
VillaMaggiore,Watersong, Disney, SW pool,free view
VillaMaggiore,Watersong, Disney, SW pool,free view
Floor plan of the entire Villa

VillaMaggiore,Watersong, Disney, SW pool,free view

5 bedrooms·4½ baths
Davenport • Florida
4.94(48 reviews)

$1,425.00 USD $1,362.50 USD total for 5 nights

Oct 13 – 18, 2026

TIger-Villa @ Watersong Resort, Davenport, FL
TIger-Villa @ Watersong Resort, Davenport, FL
Beautiful one story villa
Modern & Spacious Foyer
Open floor plan

TIger-Villa @ Watersong Resort, Davenport, FL

4 bedrooms·3 baths
Davenport • Florida
5(24 reviews)

$977.60 USD total for 4 nights

Oct 15 – 19, 2026

Crush's favorite way to sleep.
relaxation after walking all day!
Crush Crash Pad WDW Vacation Villa
Crush Crash Pad WDW Vacation Villa
Relaxing Lakeview pool with hand- rails

Crush Crash Pad WDW Vacation Villa

6 bedrooms·4 baths
Kissimmee • Florida
5(1 review)

$1,660.23 USD total for 3 nights

Oct 13 – 16, 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

Oct 18 – 21, 2026

Mickey's pool & spa
Beautiful lake view from the pool
Handrails for easy entry
Windsor Hills Resort
Conservation pond out back

Chilllax Inn Daulby

6 bedrooms·4 baths
Kissimmee • Florida

$1,471.59 USD $1,359.98 USD total for 3 nights

Oct 17 – 20, 2026

Pool
Front of house
Entry
Open area
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

Welcome to Chillax Inn Teascone Arcade
Free Arcade in the garage!
Chill on the couch
Windsor Hills amenities
Brrr!

Chillax Inn Teascone Arcade

5 bedrooms·5 baths
Kissimmee • Florida

$1,036.69 USD $954.95 USD total for 3 nights

Oct 17 – 20, 2026

Family Room with comfy couch and 70" TV with Cable
Free Heat Salt Water Pool & Spa
Star Wars Game Room with Pool, Foosball and PS5 with Games
Stocked Kitchen with Quartz Counter and stainless steel appliances
Free Access to the Windsor Hills Resort's community pool, dueling slides and splash pad play area!

Central Breeze Villa

6 bedrooms·4 baths
Kissimmee • Florida

$1,330.44 USD total for 3 nights

Oct 13 – 16, 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

$818.55 USD total for 3 nights

Nov 2 – 5, 2026

Welcome to Chillax Inn Pawnall
Pool and spa
Toy Story upstairs bedroom
Windsor Hills water slides
Star Wars upstairs bedroom

Chillax Inn Pawnall

5 bedrooms·5 baths
Kissimmee • Florida

$950.84 USD total for 3 nights

Nov 1 – 4, 2026