Location

Dates

Guests

Vacation rentals in Winter Haven, Florida, United States

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

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

Beautiful private pool deck with spa, shaded dining area, pool fence for families with children (pool/spa heat is a pre-bookable paid optional extra to be requested before check-in)

Front of this beautiful pool home with parking for two vehicles on the paved driveway (please no oversized/long-bed vehicles, no street parking)

Beautiful private pool deck with spa, shaded dining area, pool fence for families with children (pool/spa heat is a pre-bookable paid optional extra to be requested before check-in)

Family room with Smart TV, fan and views out to the pool deck

Formal dining area

Lovely 4 Bed Pool Home, Games Room, Disney 8 miles

4 bedrooms·3 baths

Davenport • Florida

4.83(47 reviews)

$750.00 USD total for 3 nights

Oct 27 – 30, 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

Downstairs Living Area

Resort Water Park

Saleda at Windsor

7 bedrooms·5½ baths

Kissimmee • Florida

$1,015.71 USD total for 3 nights

Nov 1 – 4, 2026

Twin Palms Family Vacation Villa

Twin Palms Family Vacation Villa

Twin Palms Family Vacation Villa

Twin Palms Family Vacation Villa

Twin Palms Family Vacation Villa

9 bedrooms·6 baths

Kissimmee • Florida

5(84 reviews)

$1,409.89 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

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

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

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)

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

Kingswood

5 bedrooms·4½ baths

Davenport • Florida

4.64(88 reviews)

$755.04 USD total for 3 nights

Oct 27 – 30, 2026

Turtley Awesome - Heated Spa - Themed Bedrooms - BBQ Grill

Turtley Awesome - Heated Spa - Themed Bedrooms - BBQ Grill

Turtley Awesome - Heated Spa - Themed Bedrooms - BBQ Grill

Turtley Awesome - Heated Spa - Themed Bedrooms - BBQ Grill

Turtley Awesome - Heated Spa - Themed Bedrooms - BBQ Grill

Turtley Awesome - Heated Spa - Themed Bedrooms - BBQ Grill

5 bedrooms·3 baths

Davenport • Florida

$780.99 USD total for 3 nights

Nov 29 – Dec 2, 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

$1,287.82 USD total for 3 nights

Oct 27 – 30, 2026

Themed (Star Wars & Frozen) family-friendly villa with both a private and a community pool with a gorgeous view!

1 outdoor table, lounge chairs, and an outdoor shower in the pool area. The pool area has colored LED lights for night-time use.

The formal dining room has seating for 8 (there is another informal dining room)

Master bedroom with a king-size bed and a 50-inch Roku Smart TV.

Sit back and relax in the new massage chair after a long but rewarding day at the theme park!

Disney 5 mile Private Pool, Massage Chair, Tennis!

6 bedrooms·3 baths

Kissimmee • Florida

5(36 reviews)

$1,061.23 USD total for 3 nights

Oct 27 – 30, 2026

Vista Home near Disney - NEW heated hot tub - games room

Welcome to Vista

Pool view dining

Vista Home near Disney - NEW heated hot tub - games room

Vista Home near Disney - NEW heated hot tub - games room

Vista Home near Disney - NEW heated hot tub - games room

5 bedrooms·4 baths

Davenport • Florida

$835.09 USD total for 3 nights

Nov 30 – Dec 3, 2026

Impressive curb appeal

mcinema (4).jpg

Movie room,5 bed, Pool , Spa, Pickleball close by

5 bedrooms·3 baths

Kissimmee • Florida

4.6(53 reviews)

$1,000.00 USD total for 3 nights

Oct 27 – 30, 2026

The Grand Village 4BR Pool Home near Disney Parks image 1

The Grand Village 4BR Pool Home near Disney Parks image 2

The Grand Village 4BR Pool Home near Disney Parks image 3

The Grand Village 4BR Pool Home near Disney Parks image 4

The Grand Village 4BR Pool Home near Disney Parks image 5

The Grand Village 4BR Pool Home near Disney Parks

4 bedrooms·4 baths

Davenport • Florida

$629.77 USD total for 3 nights

Oct 27 – 30, 2026

in Davenport mit großem Pool

in Davenport mit großem Pool

in Davenport mit großem Pool

in Davenport mit großem Pool

4 bedrooms·3 baths

Orlando • Florida

Front of our beautiful home

even when the sun goes down, our house keeps his beauty

Hillcrest Villa

Hillcrest Villa

4 bedrooms·2 baths

Davenport • Florida

4.8(69 reviews)

$1,257.42 USD total for 7 nights

Nov 21 – 28, 2026

Home, but Away! image 1

Home, but Away! image 2

Home, but Away! image 3

Home, but Away! image 4

Home, but Away! image 5

Home, but Away!

5 bedrooms·4 baths

Davenport • Florida

4.32(34 reviews)

$984.00 USD total for 3 nights

Oct 27 – 30, 2026

Sunny Oaks Poolside, pool spa games,4m to Disney

Sunny Oaks Poolside, pool spa games,4m to Disney

Sunny Oaks Poolside, pool spa games,4m to Disney

Sunny Oaks Poolside, pool spa games,4m to Disney

Sunny Oaks Poolside, pool spa games,4m to Disney

Sunny Oaks Poolside, pool spa games,4m to Disney

4 bedrooms·2 baths

Kissimmee • Florida

$833.55 USD total for 3 nights

Oct 31 – Nov 3, 2026