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Resort holiday rentals in Kissimmee

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Top-rated resort rentals in Kissimmee

Guests agree: these resort rentals are highly rated for location, cleanliness and more.

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Resort in Kissimmee

4.67 out of 5 average rating, 3 reviews

Vacation Villas at Fantasy World (by Disney World)

The resort is located about 10 minutes (4 miles) Disney World. This two-story, Mediterranean townhouse features 2-bedrooms, one with a queen-sized bed and the second with two twin-sized beds, two full baths and a fully equipped kitchen, sitting area with pull sofa, dining area, breakfast bar and screened-in patio. Amenities include: 3 swimming pools, 2 lighted tennis courts, an activities center, business center, exercise room, and a pool bar. Complimentary transportation to theme parks.

Private room in Orange County

5 out of 5 average rating, 3 reviews

Club Wyndham Bonnet Creek, 1 BR Deluxe

Club Wyndham Bonnet Creek offers fantastic family fun on the doorsteps of the Walt Disney World Resort. Nestled right next to Magic Kingdom, your family will be mere minutes away from making memories that last a lifetime. Children and adults alike will be swept away by the extravagant swimming pools, splash pads, lazy rivers and hot tubs found at Club Wyndham Bonnet Creek. Multiple on-site restaurants and pizza delivery service means delicious meals are only a short walk or call away.

Guest favourite

Private room in Orange County

5 out of 5 average rating, 25 reviews

Cozy Orlando Condo 4Mi from Disney

Get ready for a memorable vacation when you stay at this 2-bedroom, 2-bathroom rental on Floridays Resort Drive. This condo is located in a beautiful 4.5 star rated resort community where you experience upscale living at its finest. Spend your days visiting local attractions like Universal Studios, Walt Disney World, Sea World, and many more. After a day of fun, return home to hang by the pool, have a family game night in the arcade, or enjoy the Florida scenery from your balcony.

Private room in Orlando

4.67 out of 5 average rating, 6 reviews

Hogwarts Secret Bunkhouse

Relaxation Pool View! Enjoy Orlando in a beautiful, updated 3Br 2Ba condo with close proximity to Disney World! There are many on-site amenities including our popular pirate ship pool/slide, restaurants, arcade, bars, spa, and gym. Outlet shops and convenience store are only a short walk away. On-site parking and shuttle service to Disney World available. This great location is 20min from Universal Studios, 5 min from Disney, and 7min from Orlando World Center Marriott. Book now!

Private room in Kissimmee

4.86 out of 5 average rating, 7 reviews

Fantasyworld Resort 2BR Townhouse

PLEASE READ I want to make the booking experience as efficient as possible. Therefore, the pricing/payment structure requires a separate charge for the booking cost thru my resort membership. Please send me your dates. I'll respond with availability and the amount of the additional booking cost that can fall between $400- $1,950 USD based on resort category and dates (season/holidays). This resort charges resort fees that are included in the rate you see. Parking is free.

Guest favourite

Private room in Florida Center

4.8 out of 5 average rating, 5 reviews

Updated Suite Near Universal Studios

You really can't beat the location of The Enclave Resort and Suites with good amenities and easy access to local hot spots from this newly owned unit. Your stay includes a step-out balcony, onsite breakfast and lunch restaurant, convenience store and gift shop from 7 am to 2 pm., Indoor heated pool and jacuzzi, two outdoor pools and whirlpools, fitness room and laundry facilities right around the corner of your suite plus a tennis court.

Resort in Kissimmee

4.9 out of 5 average rating, 10 reviews

Westgate Town Center Studio One-Bedroom Deluxe

Property is located just a mile from Walt Disney World. Start with 14 heated outdoor swimming pools and hot tubs, arcade, paddle boats, a Disney movie theater, miniature golf, playgrounds, tennis, basketball, sand volleyball, a fitness center, and scheduled activities. Ship Wreck Island water park featuring multiple slides, tunnel slides, fountains, play areas and a lazy river is available for $25 dollars a day per person.

Private room in Kissimmee

4.8 out of 5 average rating, 5 reviews

Holiday Inn Club Vacations at Orange Lake Resort

Please arrange the room at least 7 days before. Available floor-plans: 1Bedroom(King)1Bath/2Bedroom(King+2Queen)2Bath/3Bedroom(King+Queen+2Queen)3Bath. PRICE VARIES FROM FLOORPLANS AND DATES. LISTING PRICE IS FOR A 3BEDROOM UNIT. Perfect for a large group/groups of families and friends. Please MESSAGE FIRST to CONFIRM AVAILABILITY before making an reservation. Thanks for the cooperation and understanding.

Resort in Orlando

5 out of 5 average rating, 5 reviews

Three-Bedroom Villa, Westgate Lakes Resort and Spa

*Available weekly only from Dec 21-28, 2024, available for the entire week only* The wonderfully decorated and spacious Three-Bedroom Villa at Westgate Resorts in Orlando offers astonishing spaciousness – 1,690 square feet of space and room for up to 12 guests. The Three-Bedroom Villa gives families plenty of room to spread out and enjoy the space. Relax and unwind on your private balcony or patio!

Private room in Kissimmee

4.92 out of 5 average rating, 13 reviews

Celebration Suites - 2 Miles from Disney - For 4

1-bedroom PRIVATE apartment suite with a full kitchen including all cookware/utensils, and 2 TVs in this suite in total. The room includes 1 king-sized bed and 1 full-sized bed. We also offer a great fitness center and guest laundry rooms so you can wash/dry clothing. You can pick up keys easily as our Front desk staff is on-site 24-hours per day and speaks English, Spanish, and Portuguese.

Resort in Orlando

5 out of 5 average rating, 3 reviews

Disney-Wyndham Bonnet Creek Resort

Closest to Disney Magic! Located in Lake Buena Vista, Wyndham Bonnet Creek Resort is mere minutes from the gates of Walt Disney World®. You’ll will enjoy a very rewarding stay on site. From the full activities calendar to special touches like the tranquil Lazy River, beautiful pool and private lake, this is no ordinary stay. Shuttle available directly to Disney World for a fee.

Private room in Celebration

5 out of 5 average rating, 3 reviews

Perfect Sanctuary in Orlando 2-BR

This unit is located within a resort, just five miles from the entrance to Walt Disney World. Celebration Town Center is seven miles away, and SeaWorld and Universal Orlando are within 20 miles. Enjoy one- to three-bedroom suites, each with a kitchenette or full kitchen and living area. Cool off in the pool complex with a water slide.

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space that's all yours, with room for everyone

Flats

Convenient locations with everyday essentials

Popular amenities for resort rentals in Kissimmee

Free parking on premises

Air conditioning

Family-friendly resort rentals

Private room in Kissimmee

4.93 out of 5 average rating, 27 reviews

Westgate Town Center Resort & Spa

Resort in Orlando

Book your next family vacation at Westgate Resorts

Private room in Kissimmee

KING - SUITE STYLE - ORLANDO AREA VACATION GETAWAY

Private room in Celebration

4.6 out of 5 average rating, 5 reviews

MYSTIC DUNES RESORT & GOLF CLUB 1bd

Private room in Kissimmee

Star Island Resort- 1 bedroom

Private room in Kissimmee

5 out of 5 average rating, 9 reviews

2BR Resort Villa 1 mile from Disney

Private room in Kissimmee

5 out of 5 average rating, 5 reviews

Orlando FL Orange Lake Resort 2BR Close to Disney

Private room in Kissimmee

4.72 out of 5 average rating, 299 reviews

WorldMark Reunion Three Bedroom

Resort rentals with a pool

Private room in Orlando

4.67 out of 5 average rating, 3 reviews

Westgate lake resort & spa sleep up to 12 people

Private room in Davenport

4.87 out of 5 average rating, 62 reviews

Near all Disney Parks. Condo 204 Rum Run.

Private room in Orlando

5 out of 5 average rating, 3 reviews

Wyndham Bonnet Creek 2 BD/2 BA inside Disney World

Private room in Lake Buena Vista

4.94 out of 5 average rating, 33 reviews

Wyndham Bonnet Creek - 2 Bedroom Condo

Private room in Orange County

5 out of 5 average rating, 3 reviews

Club Wyndham Bonnet Creek, 2 BR Deluxe

Private room in Lake Buena Vista

5 out of 5 average rating, 19 reviews

Wyndham Bonnet Creek - 2 Bedroom Condo

Private room in Lake Buena Vista

5 out of 5 average rating, 3 reviews

Wyndham Bonnet Creek - 1 Bedroom Suite

Private room in Orlando

4.8 out of 5 average rating, 5 reviews

4 Bedroom Westgate Lakes Resort & Spa

Resort rentals with a gym

Private room in Kissimmee

5 out of 5 average rating, 3 reviews

Christmas in Resort close to Disney theme parks

Private room in Kissimmee

4.83 out of 5 average rating, 6 reviews

Celebration Suites - 2 Miles from Disney - For 4

Private room in Lake Buena Vista

5 out of 5 average rating, 3 reviews

Wyndham Bonnet Creek - 2 Bedroom Condo

Guest favourite

Private room in Lake Buena Vista

4.79 out of 5 average rating, 66 reviews

Wyndham Bonnet Creek - 2 Bedroom Condo

Private room in Lake Buena Vista

5 out of 5 average rating, 3 reviews

Wyndham Bonnet Creek - 2 Bedroom Condo

Private room in Lake Buena Vista

5 out of 5 average rating, 7 reviews

Wyndham Bonnet Creek - 1 Bedroom Suite

Private room in Kissimmee

4.8 out of 5 average rating, 5 reviews

Celebration Suites - 2 Miles from Disney - For 4

Private room in Kissimmee

5 out of 5 average rating, 7 reviews

Celebration Suites - 2 Miles from Disney - For 6

Quick stats about resort rentals in Kissimmee

Total rentals
50 properties
Nightly prices starting at
₹848 before taxes and fees
Total number of reviews
30 reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
30 properties have a dedicated workspace

Destinations to explore