Location

Dates

Guests

Vacation rentals in Lakeland, Florida, United States

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 total for 5 nights

Nov 7 – 12, 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

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

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

Spacious Family Pool Home with Game Room-588OCB

Spacious Family Pool Home with Game Room-588OCB

Spacious Family Pool Home with Game Room-588OCB

Spacious Family Pool Home with Game Room-588OCB

Spacious Family Pool Home with Game Room-588OCB

Spacious Family Pool Home with Game Room-588OCB

4 bedrooms·3 baths

Davenport • Florida

$1,009.01 USD total for 3 nights

Oct 26 – 29, 2026

2312045

6 bedrooms·4 baths

Orlando • Florida

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

Dec 6 – 11, 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

$448.18 USD total for 3 nights

Nov 10 – 13, 2026

Windsor at Westside 7Bd Hm Pool-2112MW

Windsor at Westside 7Bd Hm Pool-2112MW

Windsor at Westside 7Bd Hm Pool-2112MW

Windsor at Westside 7Bd Hm Pool-2112MW

Windsor at Westside 7Bd Hm Pool-2112MW

Windsor at Westside 7Bd Hm Pool-2112MW

7 bedrooms·5 baths

Four Corners • Florida

$1,322.17 USD total for 3 nights

Nov 6 – 9, 2026

Oasis Villa with Pool overlooking Pond

Oasis Villa with Pool overlooking Pond

Oasis Villa with Pool overlooking Pond

Oasis Villa with Pool overlooking Pond

Oasis Villa with Pool overlooking Pond

Oasis Villa with Pool overlooking Pond

5 bedrooms·4 baths

Davenport • Florida

$1,215.25 USD total for 5 nights

Oct 27 – Nov 1, 2026

Fairview at Reunion - Games Room

Fairview at Reunion - Games Room

Fairview at Reunion - Games Room

Fairview at Reunion - Games Room

Fairview at Reunion - Games Room

Fairview at Reunion - Games Room

6 bedrooms·6 baths

Kissimmee • Florida

$942.97 USD total for 3 nights

Nov 3 – 6, 2026

Vacation Rental Villa House of Orange at Watersong Resort

Master bedroom Vacation Rental Villa House of Orange at Watersong Resort

Front of Vacation Rental Villa House of Orange at Watersong Resort

Pool at night Vacation Rental Villa House of Orange at Watersong Resort

Entrance Vacation Rental Villa House of Orange at Watersong Resort

House of Orange at Watersong Resort, Davenport FL

4 bedrooms·3½ baths

Davenport • Florida

4.93(14 reviews)

$1,030.00 USD total for 5 nights

Nov 21 – 26, 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 $1,367.40 USD total for 5 nights

Nov 2 – 7, 2026

Watersong Resort 6Bd Pool Hm,2 Master Suites-956OC

Watersong Resort 6Bd Pool Hm,2 Master Suites-956OC

Watersong Resort 6Bd Pool Hm,2 Master Suites-956OC

Watersong Resort 6Bd Pool Hm,2 Master Suites-956OC

Watersong Resort 6Bd Pool Hm,2 Master Suites-956OC

Watersong Resort 6Bd Pool Hm,2 Master Suites-956OC

6 bedrooms·4 baths

Davenport • Florida

$1,236.94 USD total for 3 nights

Oct 26 – 29, 2026

New Elegant House Gateaway - Close to Parks

New Elegant House Gateaway - Close to Parks

New Elegant House Gateaway - Close to Parks

New Elegant House Gateaway - Close to Parks

New Elegant House Gateaway - Close to Parks

New Elegant House Gateaway - Close to Parks

3 bedrooms·2 baths

Kissimmee • Florida

$602.69 USD total for 3 nights

Oct 27 – 30, 2026

3 Bedroom Luxury Resort Condo 10 Min. From Disney! - Apartment

3 Bedroom Luxury Resort Condo 10 Min. From Disney! - Apartment

3 Bedroom Luxury Resort Condo 10 Min. From Disney! - Apartment

3 Bedroom Luxury Resort Condo 10 Min. From Disney! - Apartment

3 Bedroom Luxury Resort Condo 10 Min. From Disney! - Apartment

3 Bedroom Luxury Resort Condo 10 Min. From Disney! - Apartment

3 bedrooms·2 baths

Kissimmee • Florida

$499.60 USD total for 3 nights

Oct 27 – 30, 2026

Downstairs Living Area

Resort Water Park

Saleda at Windsor

7 bedrooms·5½ baths

Kissimmee • Florida

$1,007.29 USD total for 3 nights

Nov 1 – 4, 2026

Lakeside 5Bd Pool Hm Spa Gm Watersng-237YS

Lakeside 5Bd Pool Hm Spa Gm Watersng-237YS

Lakeside 5Bd Pool Hm Spa Gm Watersng-237YS

Lakeside 5Bd Pool Hm Spa Gm Watersng-237YS

Lakeside 5Bd Pool Hm Spa Gm Watersng-237YS

Lakeside 5Bd Pool Hm Spa Gm Watersng-237YS

5 bedrooms·4 baths

Davenport • Florida

$1,181.49 USD total for 3 nights

Oct 26 – 29, 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

Cozy Family Friendly Pool Home with Game Room-227Y

Cozy Family Friendly Pool Home with Game Room-227Y

Cozy Family Friendly Pool Home with Game Room-227Y

Cozy Family Friendly Pool Home with Game Room-227Y

Cozy Family Friendly Pool Home with Game Room-227Y

Cozy Family Friendly Pool Home with Game Room-227Y

5 bedrooms·4 baths

Davenport • Florida

$1,163.02 USD total for 3 nights

Oct 26 – 29, 2026

Something for Everyone!

X Wing Twin/Full Bunk Bed

South Facing Pool and Spa

Star Wars Theater

Disney Magic

7 bedrooms·5½ baths

Four Corners • Florida

5(1 review)

$1,449.40 USD total for 3 nights

Nov 19 – 22, 2026

7BR Themed Villa | Private Pool & Games | Disney

7BR Themed Villa | Private Pool & Games | Disney

Minions-themed bedroom with bunk beds—kids will love this playful yellow paradise!

Finding Nemo room with sea turtles—dive into this magical underwater adventure!

Windsor at Westside splash pad—colorful water fun just steps from your villa!

7BR Themed Villa | Private Pool & Games | Disney

7 bedrooms·5½ baths

Kissimmee • Florida

$1,253.60 USD total for 3 nights

Oct 26 – 29, 2026

Orlando Resort Home✦Sleeps 19

Orlando Resort Home✦Sleeps 19

Orlando Resort Home✦Sleeps 19

Orlando Resort Home✦Sleeps 19

Orlando Resort Home✦Sleeps 19

Orlando Resort Home✦Sleeps 19

8 bedrooms·6 baths

Kissimmee • Florida

4.96(217 reviews)

$119 – $989/ night(excl. fees & taxes)

Lakefront | Pool+Game Room | 6 BR | Near Disney

Enjoy complete privacy with a fully fenced pool-your own oasis! Backs onto small lake for relaxation and fun. Enjoy the floaties and pool while having a BBQ on the patio! We love our "Lakeside Villa".

Lakefront | Pool+Game Room | 6 BR | Near Disney

Lakefront | Pool+Game Room | 6 BR | Near Disney

Lakefront | Pool+Game Room | 6 BR | Near Disney

Lakefront | Pool+Game Room | 6 BR | Near Disney

6 bedrooms·5 baths

Davenport • Florida

5(4 reviews)

$658.15 USD total for 3 nights

Nov 2 – 5, 2026