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Kissimmee Vacation Rental Listings

Our Kissimmee Vacation Rentals selection includes only the best Kissimmee homes, condos, villas, hotels, bed & breakfasts, cabins, and cottages.

Listed below, you will find numerous Kissimmee lodging and accommodations to suit your needs. Click on the view details button to explore any of the Kissimmee rentals you see listed for more information. Disney Area, Kissimmee Vacation Rentals are continuously added and modified, so if you do not find what you are looking for in our Kissimmee Vacation rental inventory, make sure you bookmark us and come back frequently.

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Windsor Hills LAKE FRONT Disney Vacation Rental - Vacation Rental in Kissimmee

Windsor Hills LAKE FRONT Disney Vacation Rental - Kissimmee

3 Bedrooms
Sleeps 10
From USD115.0 nt

• Pool
• Jacuzzi/Hot Tub
• BBQ
• Utensils
• Stove - Electric
• Refrigerator

This 1500 sq ft beautiful 3 bedroom 2 bath condo has a great screened in lani with a lake front view next to the pool and Jacuzzi. Next to an elevator, very convenient for luggage transportation, children, the elderly.High speed Internet. Windsor Hill
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A Disney Vacation Home - Kissimmee Vacation Rental - Vacation Rental in Kissimmee

A Disney Vacation Home - Kissimmee Vacation Rental - Kissimmee

7 Bedrooms
Sleeps 16
 

• Pool
• Garage
• Utensils
• Stove - Electric
• Refrigerator
• Microwave

Rental homes in Kissimmee, Clermont and Davenport in Florida. 3, 4, 5, 6 & 7 bed villas with private pools close to all Attractions. All villas are fully equipped and furnished to a high standard. All villas have their own private pools and some have
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DISNEY! WELCOME TO SIMBA'S PRIDE! - Vacation Rental in Kissimmee

DISNEY! WELCOME TO SIMBA'S PRIDE! - Kissimmee

3 Bedrooms
Sleeps 8
From USD99.0 nt

• Pool
• Jacuzzi/Hot Tub
• BBQ
• Utensils
• Stove - Electric
• Refrigerator

WELCOME TO “SIMBA’S PRIDE!” “Really and truly unbelievable!” “Too good to be true” “The most beautiful home I’ve ever seen” “How can the price be so low for a home like this?” “Who designed and decorated it – are they available to do my home?” These a
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Closest to Disney New Windsor Hills Luxury Condo - Vacation Rental in Kissimmee

Closest to Disney New Windsor Hills Luxury Condo - Kissimmee

3 Bedrooms
Sleeps 8
From USD75.0 nt

• Pool
• Jacuzzi/Hot Tub
• Utensils
• Stove - Electric
• Refrigerator
• Microwave

Our 3 bed/2 bath (1 king, 1 queen, 2 twins and queen sleeper sofa in living room) corner luxury condo (in building 3) in the brand new popular Windsor Hills complex which is only 1 1/2 miles from Disney. Nicely decorated with all amenities and all new
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The Grand Emerald II - Disney Area FL - Vacation Rental in Kissimmee

The Grand Emerald II - Disney Area FL - Kissimmee

6 Bedrooms
Sleeps 14
From USD289.0 nt


This vacation rental home is located so close to Disney and you'll think you need a Park Pass! Less than 2 miles and only 5 minutes away! This 6 BEDROOM vacation resort home features 5.5 BATH and has the features that experienced visitors require. FOU
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Villas of Somerset - Vacation Rental in Kissimmee

Villas of Somerset - Kissimmee

3 Bedrooms
Sleeps 8
From USD89.0 nt

• Pool
• Jacuzzi/Hot Tub
• BBQ
• Utensils
• Stove - Electric
• Refrigerator

Our privately owned spacious, luxury, 3 bed 2 bath villa sleeps 8 and is perfect for your family vacation to the Disney area. Centrally located near all the attractions and restaurants. Just bring clothes and sunscreen. Everything you need is in the v
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Beautiful Condo (2004 built) - Vacation Rental in Kissimmee

Beautiful Condo (2004 built) - Kissimmee

3 Bedrooms
Sleeps 8
From USD70.0 nt

• Pool
• Jacuzzi/Hot Tub
• Utensils
• Stove - Electric
• Refrigerator
• Microwave

This is a beautiful 3 bedroom 2 bathroom condominium located only 5 miles from the entrance of Disney. The master bedroom has a king-size bed, TV, and private full bathroom and hair dryer. The #2 bedroom has a queen-sized bed. The #3 bedroom has 2 twi
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4 BED 3 BATH PRIVATE POOL & SPA ON INDIAN CREEK - Vacation Rental in Kissimmee

4 BED 3 BATH PRIVATE POOL & SPA ON INDIAN CREEK - Kissimmee

4 Bedrooms
Sleeps 10
From USD95.0 nt

• Pool
• Jacuzzi/Hot Tub
• BBQ
• Utensils
• Stove - Electric
• Refrigerator

This is a brand new 4 bedroom 3 bathroom ( two with master suites) air conditioned villa with a screened private heated pool and spa, backing onto a conservation area. Set in the up-market community of Indian Creek, Kissimmee, the villa is only 5 mil
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Celebration Villa At Kissimmee - Disney Area - Vacation Rental in Kissimmee

Celebration Villa At Kissimmee - Disney Area - Kissimmee

4 Bedrooms
Sleeps 8
From USD935.0 wk

• Air Conditioning
• Cable/Satellite TV
• High Speed Internet
• TV/VCR
• Coffee Maker
• Dishwasher

Orlando Florida Vacation Home! Hi we are Brian and Margaret and we want to welcome you to your fabulous Florida holiday in this brand new, air-conditioned Disney Area vacation villa right in the heart of the magic! To fully enjoy your holiday vacation
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Fairfield Star Island Vacation Condo rental - Vacation Rental in Kissimmee

Fairfield Star Island Vacation Condo rental - Kissimmee

2 Bedrooms
Sleeps 8
From USD79.0 nt

• Sauna
• Pool
• Jacuzzi/Hot Tub
• BBQ
• Utensils
• Stove - Electric

Finest in Orlando area. Spacious, over 1200 sq ft 5-STAR furnished 1-Bd Dlx Available: w/ 2 pers jacuzzi, W/D, (K,2 DB & 1 QSS), Full Kit./dining, 3 TVs-VCR/CD entertain ctr,2 full bath, w/balcony. Experience on-site: heated I /D, O/D & Child pool & H
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Disney 5-Star Tropical Resort Condo. Big Screen TV - Vacation Rental in Kissimmee

Disney 5-Star Tropical Resort Condo. Big Screen TV - Kissimmee

3 Bedrooms
Sleeps 8
From USD115.0 nt

• Sauna
• Pool
• Jacuzzi/Hot Tub
• Utensils
• Stove - Electric
• Refrigerator

Just minutes to Disney World! Our new 3 Bedroom Condo has 2 Full Baths and sleeps up to 8 people. It is on the first floor and handicap accessible. A full size swimming pool is directly behind the condo with a nice view from the living room and master
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SPECIAL OFFER
Seasons, an Orlando Vacation Home - Vacation Rental in Kissimmee
10% OFF
From: Jul 28, 2008
To: Aug 02, 2008

Seasons, an Orlando Vacation Home - Kissimmee

4 Bedrooms
Sleeps 10
From USD720.0 wk

• Pool
• Garage
• BBQ
• Utensils
• Stove - Electric
• Refrigerator

Welcome to our beautiful new home where you can enjoy a magical Disney-style vacation. Constructed in 2005 this brand new house offers all the latest features in vacation rentals. Our Villa comprises of 4 bedrooms including 2 master en-suites plus 2 t
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Enchanted Vacation Getaways, Inc - Vacation Rental in Kissimmee

Enchanted Vacation Getaways, Inc - Kissimmee

Studio
Sleeps 10
 

• Pool
• Jacuzzi/Hot Tub
• BBQ
• Utensils
• Stove - Electric
• Refrigerator

30% DISCOUNT, $49/NIGHT APPLIES TO THE 2 BED/2 BATHS VILLA AND 28% DISCOUNT $59 PER NIGHT APPLIES TO THE 2 BED/2 BATHS CONDO. 2 and 4 bedroom Villas and Condos either 7 miles from Disney or 30 minutes away on a 3,800 acre natural lake and nature prese
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Disney Vacation Condo - Vacation Rental in Kissimmee

Disney Vacation Condo - Kissimmee

3 Bedrooms
Sleeps 8
 

• Sauna
• Pool
• Utensils
• Stove - Electric
• Refrigerator
• Microwave

Relax in the comfort of our resort condos! This is the only way to enjoy a vacation to Disney World and all the attractions in the Central Florida area. Not only do we have the closest vacation condos to Disney World Resorts, we also have the best pri
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Villa in Kissimmee - Vacation Rental in Kissimmee

Villa in Kissimmee - Kissimmee

3 Bedrooms
Sleeps 8
From USD49.0 nt

• Pool
• Jacuzzi/Hot Tub
• Utensils
• Microwave
• Ice Maker
• Coffee Maker

This 1,285 square-foot, three-bedroom/two-bath Kissimmee vacation rental condo is fully furnished, and ready for you and your family to have the vacation of a lifetime! Just bring your clothes and sunscreen. Everything you need is in the Kissimmee vac
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Great 2 BR or 3 BR , 2 BA Villa in Mickey's Yard! - Vacation Rental in Kissimmee

Great 2 BR or 3 BR , 2 BA Villa in Mickey's Yard! - Kissimmee

2 Bedrooms
Sleeps 6
From USD79.0 nt

• Sauna
• Pool
• Jacuzzi/Hot Tub
• Utensils
• Stove - Electric
• Refrigerator

Everything is BRAND NEW in this spacious second floor Disney Area vacation rental unit features two Bedrooms, two Baths, Living Room, Dining Room comes complete with a Brand New Kitchen, ceramic tile throughout, new carpeting, new furniture throughout
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Kissimmee Vacation Rental 15 mins to Disney - Vacation Rental in Kissimmee

Kissimmee Vacation Rental 15 mins to Disney - Kissimmee

3 Bedrooms
Sleeps 6
From USD65.0 nt

• Pool
• Utensils
• Stove - Electric
• Refrigerator
• Microwave
• Full Kitchen

Well Maintained 2nd Floor condo in Beautiful Shadow Bay. Quiet development, 15 minutes to Disney World and Attractions. Near major restaurants, Pool Access. Located off of 192. Right in the middle of all the Florida fun....Towels and Linens are provid
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41 Royal Palm Bay - Vacation Rental in Kissimmee

41 Royal Palm Bay - Kissimmee

3 Bedrooms
Sleeps 8
From USD60.0 nt

• Sauna
• Pool
• Jacuzzi/Hot Tub
• BBQ
• Utensils
• Stove - Electric

This Kissimme Orlando vacation rental villa is on a quiet cul-de-sac called Royal Bay Boulevard. Its' location is off Poinciana Blvd. which is approximately 1 mile south of highway 192. From the 192, disney world orlando and all the other major attrac
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Laguna Bay Villas Vacation Condo - Vacation Rental in Kissimmee

Laguna Bay Villas Vacation Condo - Kissimmee

3 Bedrooms
Sleeps 8
From USD99.0 nt

• Pool
• Jacuzzi/Hot Tub
• BBQ
• Utensils
• Stove - Electric
• Refrigerator

Kissimmee Area Condo rental with 3 Bedrooms, 2 full Bathrooms, Kitchen, large Dining/Living area, full size Washer and Dryer, and Free Shuttle to the Disney Parks. Amenities include on site community pool and hottub, tennis courts, play area, weight r
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Grand Palms, Kissimmee, Central-Disney-Orlando Are - Vacation Rental in Kissimmee

Grand Palms, Kissimmee, Central-Disney-Orlando Are - Kissimmee

2 Bedrooms
Sleeps 8
From USD60.0 nt

• Air Conditioning
• Cable/Satellite TV
• CD Player
• High Speed Internet
• Linens provided
• Phone

Let the magic begin in this Disney-themed condo. This beautiful, two bedroom, two-bath condominium with excellent amenities will provide a relaxing and rejuvenated vacation. This unit provides a Disney theme kitchen, bedroom and bathroom for both youn
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Caitlins Disney Condo - Vacation Rental in Kissimmee

Caitlins Disney Condo - Kissimmee

3 Bedrooms
Sleeps 8
From USD75.0 nt

• Air Conditioning
• Cable/Satellite TV
• CD Player
• High Speed Internet
• Linens provided
• Phone

This fantastic property is the ideal location from which to visit the Disney theme parks and beyond. Situated in a select and quiet location, yet only minutes from all the shopping, eating and entertainment you would need on your vacation. The propert
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Windsor Palms condo - Vacation Rental in Kissimmee

Windsor Palms condo - Kissimmee

3 Bedrooms
Sleeps 8
From USD50.0 nt

• Air Conditioning
• Cable/Satellite TV
• Linens provided
• Phone
• Coffee Maker
• Dishwasher

Windsor Palms offers the highest level of comfort for your vacation dollar. The security gated Windsor Palms Resort Community caters to the vacationers every need! The homes and condos surround the 7500 square foot clubhouse consisting of the 25m hea
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Disney Condo Rental 407-791-7714 - Vacation Rental in Kissimmee

Disney Condo Rental 407-791-7714 - Kissimmee

2 Bedrooms
Sleeps 6
From USD99.0 nt

• Pool
• Stove - Electric
• Refrigerator
• Microwave
• Ice Maker
• Full Kitchen

Located just minutes from Disney World and all other major Orlando attractions. The condo is situated just steps away from the pool area. The residential area of Villas at Shadow Bay is very quiet and provide a calm haven after a thrilling day at area
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Windsor Hills Condo - Vacation Rental in Kissimmee

Windsor Hills Condo - Kissimmee

3 Bedrooms
Sleeps 8
 

• Linens provided
• CD Player
• Cable/Satellite TV
• Air Conditioning
• Stereo
• TV/VCR

BE OUR GUEST AT WINDSOR HILLS RESORT, A 5 STAR GATED COMMUNITY 1 1/2 MILES FROM DISNEY AND CLOSE TO OTHER ATTRACTIONS. iF YOU WANT PEACE AND QUIET, RETURN TO OUR 3 BEDROOM 2 BATH CONDO WITH A BEAUTIFUL MASTER SUITE THAT HAS A QUEEN SIZE BED, TV, AND D
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Vacation Condo at Disney - Vacation Rental in Kissimmee

Vacation Condo at Disney - Kissimmee

3 Bedrooms
Sleeps 8
From USD99.0 nt

• Pool
• Jacuzzi/Hot Tub
• Utensils
• Stove - Electric
• Refrigerator
• Microwave

In sunny Orlando/Kissimmee Florida, location is everything.....and we are located the very closest to Disney......less than two miles to the main entrance! Each evening, you may enjoy the breath taking view of Disney Fireworks from the Windsor Hills R
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Beautiful Condo - Just 7 Miles from Disney! - Vacation Rental in Kissimmee

Beautiful Condo - Just 7 Miles from Disney! - Kissimmee

2 Bedrooms
Sleeps 6
 

• Pool
• Jacuzzi/Hot Tub
• BBQ
• Utensils
• Refrigerator
• Microwave

Gorgeous two bedroom, two bath condo on first floor! Everything is brand new! Just seven miles from Disney and just two blocks off of 192. Perfect location, near all major parks, Epcot, Animal Kingdom, MGM, Universal Studios, Island of Adventures, etc
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