Location

Dates

Guests

Vacation rentals in Kissimmee, Florida, United States

CASA AMARELA

3 bedrooms·2½ baths

Kissimmee • Florida

$720.80 USD total for 3 nights

Oct 6 – 9, 2026

Sunset views nightly

Eat as the sunsets over the lake

Anyone for some night swimming?

Now this feels like vacation!

Outdoor Dining for 8

Sunset Magic Villa

8 bedrooms·6 baths

Four Corners • Florida

5(14 reviews)

$1,498.20 USD total for 3 nights

Oct 5 – 8, 2026

6 Lounge chairs, 6 burner BBQ grill, enclosed heated salt water pool and spa, overlooking the golf course

Movie theater seats 10, 4K Laser Projector, 150" screen and Dolby Atmos Surround sound, cable TV and a Roku to Stream all your Apps

Covered lanai, Outdoor dining table seats 8, outdoor sectional & 6 lounge chairs and that fantastic view!

There's a Pool Safety Fence to keep the little ones safely away from the pool when you need to. :)

Game Room with 8 foot pool table, 8 foot air hockey, 9 foot shuffle board table and foosball

Feels Like Funshine - Championsgate

8 bedrooms·5 baths

Kissimmee • Florida

5(60 reviews)

$3,155.30 USD total for 3 nights

Sep 29 – Oct 2, 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 – $1,034/ night(excl. fees & taxes)

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)

$1,020.37 USD $990.29 USD total for 3 nights

Sep 29 – Oct 2, 2026

Magic Home w/ Private Pool, Spa, Resort & Golf

Magic Home w/ Private Pool, Spa, Resort & Golf

Magic Home w/ Private Pool, Spa, Resort & Golf

Magic Home w/ Private Pool, Spa, Resort & Golf

Magic Home w/ Private Pool, Spa, Resort & Golf

Magic Home w/ Private Pool, Spa, Resort & Golf

9 bedrooms·5 baths

Davenport • Florida

4.75(4 reviews)

$1,000/ night(excl. fees & taxes)

Solara Resort is in a prime location with amazing pools, next to resorts such as Windsor at Westside, Windsor Island and only minutes to Disney World, Universal Studios, Sea World & other major theme parks. You will enjoy Kissimmee, Florida.

Solara Resort offers beautiful views all around. Fall into vacation mode as palm trees, water views and sunshine fill your time. Rated as one of the best resorts in Kissimmee, Florida.

The fabulous Finding Nemo room is located to the left at the top of the staircase. Adults & kids alike will be amazed at the lifelike Finding Nemo wall that is backlit to bring it to life. It has 2 double beds, a full length mirror, and a Smart TV.

The home is located inside the luxurious Solara Resort & is just steps away from the expansive water complex with a pool bar, zero depth entry splash pad, cabanas, fitness center, fire pits, bars, restaurant, coffee shop, walking paths, & Flowrider!

The home is located inside the luxurious Solara Resort & is just steps away from the expansive water complex with a pool bar, zero depth entry splash pad, cabanas, fitness center, fire pits, bars, restaurant, coffee shop, walking paths, & Flowrider!

SOLARA RESORT!! Sleeps 13 W/ Pool near Disney! 🎢

5 bedrooms·4½ baths

Kissimmee • Florida

5(63 reviews)

$986.97 USD total for 3 nights

Oct 4 – 7, 2026

Soak up the sunshine!

You've arrived!

Relax in your covered lanai with safety pool gate

Together is our favorite place to be!

Wide open floor plan for entertaining

Magical Retreat - Near Disney Heated Pool & Spa

5 bedrooms·5 baths

Davenport • Florida

5(32 reviews)

$1,156.79 USD total for 4 nights

Sep 29 – Oct 3, 2026

Welcome to the Marvelous Magical House

Settle in on the couch while watching the kids swim in the pool.

Paradise Palms Resort amenities. NO RESORT FEES :)

Hang out like Harry Potter and his gang in the Gryffindor Common Room. Complete with a fireplace, Roku TV, foosball table, and board games.

Curl up next to the fireplace with a good read, "Harry Potter and the Sorcerer's Stone".

5mi Disney* Immersive Themes* Outdoor Pool & Movie

6 bedrooms·5 baths

Kissimmee • Florida

5(80 reviews)

$1,167.03 USD total for 3 nights

Sep 29 – Oct 2, 2026

The pristine water of the resort pool invites you in! The water slide and splash pad are perfect for the youngest, or young at heart!

Ahhh, breakfast on the lanai. The sandhill cranes may even visit or just enjoy the peacefulness of the lake.

Friendly pirates invite the kids along for adventure.

Enough space for the whole family to play games, watch TV or relax after a day in the parks.

Kitchen with Breakfast Bar

CR Getaway

4 bedrooms·3 baths

Kissimmee • Florida

4.94(96 reviews)

$806.99 USD total for 4 nights

Sep 30 – Oct 4, 2026

Orlando Resort Home✦Sleeps 20

Orlando Resort Home✦Sleeps 20

Orlando Resort Home✦Sleeps 20

Orlando Resort Home✦Sleeps 20

Orlando Resort Home✦Sleeps 20

Orlando Resort Home✦Sleeps 20

9 bedrooms·6½ baths

Kissimmee • Florida

4.98(136 reviews)

$1,099.88 USD total for 4 nights

Oct 11 – 15, 2026

1b Disney Adventures Start at This Cozy Suite

1b Disney Adventures Start at This Cozy Suite

1b Disney Adventures Start at This Cozy Suite

1b Disney Adventures Start at This Cozy Suite

1b Disney Adventures Start at This Cozy Suite

1b Disney Adventures Start at This Cozy Suite

2 bedrooms·1 bath

Kissimmee • Florida

4.67(69 reviews)

$275.15 USD total for 3 nights

Sep 29 – Oct 2, 2026

1D Disney Fun Steps Away – Pool & Kids’ Activities

1D Disney Fun Steps Away – Pool & Kids’ Activities

1D Disney Fun Steps Away – Pool & Kids’ Activities

1D Disney Fun Steps Away – Pool & Kids’ Activities

1D Disney Fun Steps Away – Pool & Kids’ Activities

1D Disney Fun Steps Away – Pool & Kids’ Activities

2 bedrooms·1 bath

Kissimmee • Florida

4.65(79 reviews)

$293.08 USD total for 3 nights

Oct 15 – 18, 2026

Experience why kids, and grandkids love our year-round heated pool!

Aerial View of The Oasis Club

Enjoy the sunny, open floor plan with comfy seating!

Watch a movie in the newly themed Hogwarts Movie Theater Room.

3 XBox Ones, Air Hockey, and Connect Four, Oh My!! PS 4 coming soon.

Sun Gathering House

6 bedrooms·6 baths

Davenport • Florida

$1,810.03 USD total for 5 nights

Nov 2 – 7, 2026

Luxury 9BR Solara Pool Villa | Sleeps 20 | Disney

Solara Resort playground & sports courts — Sawyer Palm villa FL

Luxury 9BR Solara Pool Villa | Sleeps 20 | Disney

King bedroom with ensuite — Sawyer Palm 9BR villa, Solara Resort

Luxury 9BR Solara Pool Villa | Sleeps 20 | Disney

Luxury 9BR Solara Pool Villa | Sleeps 20 | Disney

9 bedrooms·6½ baths

Kissimmee • Florida

5(15 reviews)

$1,236.97 USD total for 3 nights

Sep 29 – Oct 2, 2026

4 Bedroom ChampionsGate Home with private pool

4 Bedroom ChampionsGate Home with private pool

4 Bedroom ChampionsGate Home with private pool

4 Bedroom ChampionsGate Home with private pool

4 Bedroom ChampionsGate Home with private pool

4 bedrooms·3 baths

Davenport • Florida

5(87 reviews)

$542.78 USD $490.00 USD total for 3 nights

Sep 29 – Oct 2, 2026

Den with wall mounted TV

Ample seating in the Den

Open concept living area

Kitchen with granite counter tops and stainless steel appliances.

Seating at breakfast bar in kitchen

Palm Tree Paradise

4 bedrooms·3 baths

Kissimmee • Florida

5(28 reviews)

$719.25 USD $668.89 USD total for 3 nights

Sep 29 – Oct 2, 2026

Disney Villa | Resort Amenities

Disney Villa | Resort Amenities

Disney Villa | Resort Amenities

Disney Villa | Resort Amenities

Disney Villa | Resort Amenities

Disney Villa | Resort Amenities

4 bedrooms·3 baths

Kissimmee • Florida

4.92(24 reviews)

$1,196.50 USD total for 3 nights

Sep 29 – Oct 2, 2026

Orlando Resort Home✦Sleeps 21

Orlando Resort Home✦Sleeps 21

Orlando Resort Home✦Sleeps 21

Orlando Resort Home✦Sleeps 21

Orlando Resort Home✦Sleeps 21

Orlando Resort Home✦Sleeps 21

7 bedrooms·6½ baths

Kissimmee • Florida

4.98(109 reviews)

$814.51 USD total for 3 nights

Oct 4 – 7, 2026

Poolside Paradise | Chic Retreat | Epic Lux Resort

Poolside Paradise | Chic Retreat | Epic Lux Resort

Poolside Paradise | Chic Retreat | Epic Lux Resort

Poolside Paradise | Chic Retreat | Epic Lux Resort

Poolside Paradise | Chic Retreat | Epic Lux Resort

Poolside Paradise | Chic Retreat | Epic Lux Resort

4 bedrooms·3 baths

Four Corners • Florida

5(6 reviews)

$811.33 USD $761.33 USD total for 3 nights

Sep 29 – Oct 2, 2026

Orlando Resort Home✦Sleeps 24

Orlando Resort Home✦Sleeps 24

Orlando Resort Home✦Sleeps 24

Orlando Resort Home✦Sleeps 24

Orlando Resort Home✦Sleeps 24

Orlando Resort Home✦Sleeps 24

9 bedrooms·6½ baths

Kissimmee • Florida

4.99(154 reviews)

$1,230.44 USD total for 3 nights

Nov 2 – 5, 2026

Upstairs Beedroom 2 Double Beds

Kitchen and Breakfast Bar

Sun n Serenity in Kissimmee Florida Near Disney

4 bedrooms·3 baths

Kissimmee • Florida

5(5 reviews)

$748.85 USD total for 3 nights

Sep 29 – Oct 2, 2026

South facing sun deck with screen to keep bugs out and let sunshine in

Rattan Patio Set and dining table, sun chairs and lounger. It's so peaceful!

Living area with 65 inch HDTV, Bose cinema sound, upgraded cable and Netflix

Soft leather seating with 2 recliners & rocking, reclining chair. Lots of DVD

Open plan aspect and lots of natural lighting. Remote control ceiling fans

Sleepy at Vista

3 bedrooms·2 baths

Kissimmee • Florida

4.94(88 reviews)

$1,575.00 USD total for 7 nights

Sep 29 – Oct 6, 2026

Your Dream Escape

Your Dream Escape

Your Dream Escape

You can walk out back and you are just behind the clubhouse, and the pools!

Your Dream Escape

Your Dream Escape

8 bedrooms·5 baths

Four Corners • Florida

4.95(19 reviews)

$2,145.00 USD total for 4 nights

Jan 1 – 5, 2027