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Resort vacation rentals near Old Town Kissimmee

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Top-rated resort rentals near Old Town Kissimmee

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A large swimming pool is framed by palm trees and lounge chairs, with umbrellas providing shade. Colorful water slides are visible in the background, adjacent to a spacious area for sunbathing. Clear blue skies enhance the inviting atmosphere of the resort's outdoor space.

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.

Top guest favorite

A resort pool area features a large, curving swimming pool surrounded by palm trees and lounge chairs. A pirate ship play structure is positioned nearby, complemented by a lake view in the background. The scene is set against a backdrop of resort buildings.

Resort in Orlando

5 out of 5 average rating, 11 reviews

Wyndham Bonnet Creek Resort: 2-Bedroom Deluxe

Experience the ultimate Orlando getaway at Club Wyndham Bonnet Creek's 2-bedroom suite, accommodating up to eight guests. The master bedroom features a king bed, the second bedroom offers two double beds, and a queen sleeper sofa is in the living area. Enjoy a fully equipped kitchen, two bathrooms, and a private balcony. Resort amenities include five outdoor pools, two lazy rivers, six hot tubs, and a fitness center. It is adjacent to Disney World, minutes from Orlando's top attractions.

A resort-style pool area is surrounded by lush palm trees and tropical landscaping. Lounge chairs are positioned around the pool, with a fountain adding a serene element. The building in the background features a Mediterranean-inspired design.

Resort in Orange County

5 out of 5 average rating, 33 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.

An outdoor swimming pool is surrounded by palm trees and lounge chairs under a clear blue sky. Water cascades gently from stone structures into the pool, which features a gradual entry. The resort building stands in the background, complementing the tranquil scenery.

Resort in Orlando

4.85 out of 5 average rating, 47 reviews

By Universal Orlando Marriott Grande Vista studio

Explore popular attractions, including Walt Disney World®, Universal Orlando and SeaWorld®, Start your day with a few swings at the Grande Vista Golf Club or a lesson from the experts at Marriott Golf Academy. Refresh yourself in the outdoor swimming pools and reenergize at our fitness center. Find tasty American cuisine at The Grill at Grande Vista and delectable poolside fare at Copa Loca Bar & GrilL. 8 miles to Disney World 8.3 miles to Universal Orlando 2.4 miles to Sea World

A spacious studio suite features a king-size bed and a comfortable couch, complemented by large sliding glass doors opening to a private balcony. Natural light filters through the windows, highlighting a minimalist aesthetic with light wood flooring and subtle decor.

Resort in Orlando

4.83 out of 5 average rating, 46 reviews

Updated Suite Near Universal Studios

Guests 21+ Only. 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 to 11 a.m., 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.

A scenic view of a tranquil fountain lake is captured at dusk, reflecting the surrounding architecture. Spacious balconies overlook the water, surrounded by lush greenery and palm trees. The soft glow of evening lights enhances the serene atmosphere.

Resort in Kissimmee

4.93 out of 5 average rating, 14 reviews

Wyndham Star Island

Two-bedroom Lockout. A 10-minute drive from a Walt Disney World. Set alongside a scenic fountain lake, there are two pools, one with a waterfall, and indoor and outdoor hot tubs. Jet Ski and paddle boat rentals available. A spa providing massages and a sauna are onsite. There are nine tennis courts, a basketball and volleyball court, a putting green, and golf and tennis pro are available for lessons. A game room and arcade are available for children.

The resort's exterior showcases a three-story building surrounded by lush palm trees and vibrant greenery, enhancing the tropical atmosphere. Curved pathways lead through manicured lawns, connecting the various sections of the property. A clear blue sky provides a bright backdrop to the inviting facade.

Resort in Kissimmee

4.69 out of 5 average rating, 330 reviews

Club Wyndham Cypress Palms One Bedroom

This spacious one-bedroom resort suite measures approximately 513 square feet. You will enjoy a king bed in the master bedroom and one queen sleeper sofa in the living room. Additional amenities include a kitchenette and dining area. Unwind in one of the two outdoor heated swimming pools or squeeze in a morning workout at the fitness center. Discover a host of activities like golf, tennis, water skiing and boating right at their doorstep.

Top guest favorite

A winding pool flows through lush tropical landscaping, featuring palm trees and vibrant plants. Yellow flotation devices rest on the water's edge, inviting leisure. The backdrop includes colorful resort buildings, with gentle sunlight casting soft reflections on the water.

Resort in Lake Buena Vista

5 out of 5 average rating, 28 reviews

1 Bedroom at Bonnet Creek Resort Near Disney!

Note: Kindly submit an inquiry prior to making a reservation request, so I can check the availability of dates at the resort. Club Wyndham Bonnet Creek is the perfect home-base for easy access to Central Florida's most popular attractions. The magic of Disney. The thrills of Universal Studios. The aquatic animals of SeaWorld. Plus, hang out at the shops and restaurants at Disney Springs, Universal CityWalk, Mall at Millenia, and more.

An aerial view captures an expansive resort area featuring a large water park with multiple slides, a lazy river, and vibrant play areas. Surrounding lounging chairs in various colors provide ample seating. The warm tones of the buildings complement the sunlit pool areas.

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.

A sprawling resort area is presented, featuring multiple pools and lounging areas surrounded by lush greenery. Palm trees and bright umbrellas offer shade, while guests can be seen enjoying the outdoors. A manicured landscape extends in the background, with hints of nearby attractions visible.

Resort 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.

The hotel exterior is showcased under a colorful sunset, highlighting the welcoming entrance with a registration area. Outdoor seating with tables and chairs is visible, creating an inviting atmosphere. The structure is designed with an accessible layout, blending functionality with a family-friendly approach.

Resort in Kissimmee

5 out of 5 average rating, 7 reviews

Celebration Suites - 2 Miles from Disney - For 6

1-bedroom PRIVATE apartment suite with poolview, has a full kitchen including all cookware/utensils, and 2 TVs in this suite in total. The room includes 3 full-sized beds. 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.

A bird's-eye view showcases the sprawling Wyndham Bonnet Creek Resort, featuring a tranquil lake surrounded by palm trees. The surrounding high-rise buildings reflect the warm hues of sunset against a clear sky, creating a harmonious blend of nature and architecture.

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.

Popular amenities for resort rentals near Old Town Kissimmee

Free parking on premises

Air conditioning

Family-friendly resort rentals

A detailed map of the resort is displayed, highlighting various amenities and layouts. Key features include pools, playgrounds, dining options, and activity areas. Landmarks are marked for easy navigation, emphasizing the resort's layout and nearby attractions.

Resort in Kissimmee

4.75 out of 5 average rating, 8 reviews

Timeshare at Westgate town center

The inviting bedroom features a spacious bed adorned with plush pillows and decorative throws. Framed ocean-themed artwork hangs above the headboard. Soft lighting from the bedside lamps complements the warm curtains, creating a comfortable atmosphere. A seating area is visible next to the bed.

Resort in Kissimmee

4.93 out of 5 average rating, 27 reviews

Westgate Town Center Resort & Spa

A spacious outdoor swimming pool is surrounded by palm trees and sun loungers. The pool features a waterfall structure and a gentle slope, leading to a relaxing area. Nearby, a shaded pavilion provides additional seating, enhancing the tranquil environment.

Resort in Kissimmee

4.8 out of 5 average rating, 5 reviews

Star Island Resort - 2 Bedroom Condo

A tranquil pool area is surrounded by palm trees and green vegetation. Lounge chairs are arranged along the deck, and a water slide is visible adjacent to the pool. The sky features a warm sunset, creating a peaceful setting.

Resort in Orlando

5 out of 5 average rating, 4 reviews

Harbour Lake - Studio

A spacious bedroom features a large bed adorned with white pillows and a decorative red runner. Light-colored walls are complemented by framed nautical artwork. An ensuite bathroom with a soaking tub is partially visible, showcasing elegant columns and a vanity area.

Resort in Orlando

4.86 out of 5 average rating, 7 reviews

Best Resort for Family Vacation in the Nation

Aerial view of a resort set alongside a waterfront area, surrounded by lush greenery. Mediterranean-style buildings are visible, with multiple pools and lounge areas nestled among palm trees. The pathway along the water leads to a serene outdoor seating area, inviting relaxation.

Resort in Orlando

5 out of 5 average rating, 7 reviews

Luxury Studio at Marriott's Grande

A spacious kitchen and dining area are showcased, featuring a large wooden table surrounded by six upholstered chairs. A breakfast bar with four high stools is positioned next to a well-equipped kitchen, complete with light wooden cabinets and modern appliances, all illuminated by soft overhead lighting.

Resort in Lake Buena Vista

4.67 out of 5 average rating, 3 reviews

Bonnet Creek Disney Golf and more 2 BR/2 BA Deluxe

A spacious bedroom features a large bed with multiple pillows and a decorative red throw. Natural light enters through the sliding glass door, revealing a view of a balcony with seating overlooking the water. A flat-screen TV and desk are positioned for convenience.

Resort in Orlando

5 out of 5 average rating, 3 reviews

Spacious unit w/access to 7 pools

Resort rentals with a pool

An expansive pool area features vibrant water slides, a children's play zone, and numerous lounge chairs arranged around the pool. The surrounding buildings are designed in a Spanish-inspired style, providing a lively atmosphere for family-friendly activities.

Resort in Kissimmee

5 out of 5 average rating, 3 reviews

Christmas in Resort close to Disney theme parks

An aerial view captures a resort area featuring a heated outdoor swimming pool surrounded by palm trees and lounge chairs. The layout of the buildings reflects a relaxed tropical ambiance, with lush green vegetation visible in the background.

Resort in Kissimmee

4.77 out of 5 average rating, 13 reviews

Wyndham Cypress Palms | 1BR/1BA King Bed Suite

Resort in Orlando

4.8 out of 5 average rating, 5 reviews

Sheraton Vistana - Sleeps 8 -Disney & Universal

A welcoming entrance to Westgate Lakes Resort & Spa is surrounded by vibrant flower beds in various colors. Lush palm trees and tropical plants frame the resort's sign, contributing to a serene and inviting atmosphere for guests arriving at the property.

Resort in Orlando

5 out of 5 average rating, 3 reviews

Stay in Resort Christmas @ Disney! 3 bedroom Villa

An aerial view of the resort showcases a large, curvy swimming pool surrounded by palm trees and lounge chairs. Nearby, well-maintained gardens and pathways enhance the outdoor space, complementing the surrounding buildings with a warm color palette and balconies overlooking the pool area.

Resort in Kissimmee

4.86 out of 5 average rating, 7 reviews

Wyndham Cypress Palms | 1BR/1BA King Bed Suite

An aerial view captures the expansive resort complex surrounded by lush landscaping and a serene lake. Multiple buildings with terracotta roofs are visible, reflecting sunlight. The area is dotted with palm trees and features ample parking spaces, creating a welcoming atmosphere for guests.

Resort in Orlando

5 out of 5 average rating, 3 reviews

Wyndham Bonnet Creek 2 BD/2 BA inside Disney World

A lagoon-style pool area is surrounded by lush tropical plants and palm trees. Yellow inner tubes float gently in the water, while a multicolored building rises in the background under a clear sky.

Resort in Lake Buena Vista

4.91 out of 5 average rating, 23 reviews

Wyndham Bonnet Creek Resort | 1BR/1BA King Suite

A spacious pool area is surrounded by palm trees and lounge chairs. The clear water of the pool reflects the bright sky, while an adjacent building with a mix of yellow and red facades presents multiple stories and balconies overlooking the outdoor space.

Resort in Orlando

4.78 out of 5 average rating, 23 reviews

Orlando's Sunshine Resort - 2 Bedroom Condo

Resort rentals with a gym

The resort building is showcased from an elevated perspective, featuring a vibrant exterior with multiple stories, turrets, and palm trees lining the walkway. A lush green area is seen in the foreground, complementing the colorful facade under a partly cloudy sky.

Resort in Osceola County

5 out of 5 average rating, 3 reviews

3 Bedroom Deluxe Suite on Beautiful Florida Resort

An outdoor area featuring a large, lagoon-style pool surrounded by tropical palm trees and lounge chairs. A pirate ship-themed playground is present in the background, overlooking a serene lake with lush greenery. Multiple buildings are visible across the water, showcasing a vibrant resort environment.

Resort in Lake Buena Vista

5 out of 5 average rating, 12 reviews

Wyndham Bonnet Creek Resort | 2BR/2BA King Bed

A spacious bedroom features a large bed with decorative pillows and a maroon bed skirt. Warm lighting is provided by overhead fixtures, and a ceiling fan adds to the comfort. Optional balcony doors reveal a view of the outdoors, framed by elegant curtains.

Resort in Orlando

4.67 out of 5 average rating, 3 reviews

Luxurious Westgate Lake Resort suite in Orlando

A large multi-story building is surrounded by lush palm trees and well-maintained landscaping. A peaceful lake, featuring a fountain, is positioned in the foreground, reflecting the blue sky and scattered clouds above.

Resort in Celebration

4.6 out of 5 average rating, 5 reviews

MYSTIC DUNES RESORT & GOLF CLUB 1bd

Top guest favorite

A large outdoor pool area features a sandy beach entrance, surrounded by tropical landscaping and lounge chairs. A pirate ship decoration is visible nearby, alongside a lake reflecting the surrounding resort buildings. Palm trees and shaded seating areas enhance the inviting setting.

Resort in Lake Buena Vista

5 out of 5 average rating, 23 reviews

Wyndham Bonnet Creek Resort | 3BR/2BA King Suite

A spacious bedroom features a large bed with decorative pillows and a rich bedspread. Soft lighting from bedside lamps highlights the wood framing and warm tones throughout. An inviting seating area is visible, and an adjoining area is partially seen through a curtain.

Resort in Orlando

4.8 out of 5 average rating, 5 reviews

4 Bedroom Westgate Lakes Resort & Spa

An aerial view captures the resort's layout, showcasing a large, curvy outdoor swimming pool surrounded by palm trees. Lounge chairs line the pool's edge, while further greenery provides a natural backdrop for the buildings, enhancing the resort's tranquil environment.

Resort in Kissimmee

4.89 out of 5 average rating, 44 reviews

Wyndham Cypress Palms | 2BR/2BA King Bed Suite

A winding pool area is surrounded by lush greenery and palm trees, creating a tropical atmosphere. Floating loungers are positioned in the water, and a shaded seating area is visible on the pool's edge. Towering resort buildings provide a backdrop against the clear blue sky.

Resort in Lake Buena Vista

4.92 out of 5 average rating, 13 reviews

Wyndham Bonnet Creek Resort | 1BR/1BA King Suite

Other resort vacation rentals

An outdoor pool area is framed by lush palm trees and greenery, reflecting the sunlight on its calm surface. A poolside bar is visible, alongside rows of lounge chairs positioned for relaxation. The building's modern facade provides a backdrop to this inviting scene.

Resort in Orlando

5 out of 5 average rating, 4 reviews

Las Palmeras, Hilton - Studio Apartment

A resort pool area features a winding shape, surrounded by palm trees. Lounge chairs are arranged around the pool, and a pirate ship-themed play area is visible. The serene lake reflects the surrounding buildings and greenery, enhancing the tranquil ambiance.

Resort in Lake Buena Vista

5 out of 5 average rating, 3 reviews

Wyndham Bonnet Creek Resort | 2BR/2BA King Bed

An aerial view captures the resort grounds, featuring a serpentine swimming pool surrounded by lounge chairs and palm trees. The buildings are arranged around the pool area, and lush greenery can be seen in the background, creating a relaxing atmosphere.

Resort in Kissimmee

4.56 out of 5 average rating, 9 reviews

Wyndham Cypress Palms | 1BR/1BA King Bed Suite

A winding water feature is surrounded by lush tropical landscaping and palm trees. Yellow inner tubes float on the water, inviting relaxation. The backdrop includes a multi-story building, enhancing the resort's vibrant atmosphere.

Resort in Lake Buena Vista

5 out of 5 average rating, 8 reviews

Wyndham Bonnet Creek Resort | 1BR/1BA King Suite

An aerial view reveals a spacious outdoor swimming pool surrounded by tropical landscaping. Lounge chairs are arranged around the pool, while several umbrellas provide shade. The three-story building features large windows that overlook the inviting pool area.

Resort in Kissimmee

4.63 out of 5 average rating, 8 reviews

Wyndham Cypress Palms | 2BR/2BA King Bed Suite

Top guest favorite

A winding pool area is surrounded by lush greenery, featuring tropical plants and palm trees. Lounging floats are placed on the water, inviting relaxation. The buildings in the background are partially visible, providing a contrasting urban vibe to the natural landscape.

Resort in Lake Buena Vista

5 out of 5 average rating, 13 reviews

1 Bedroom at Bonnet Creek Resort Near Disney!

An expansive water area features a lagoon-style pool surrounded by palm trees, with a children's play area designed like a pirate ship visible in the background. A calm lake reflects the blue sky, offering a serene setting complemented by lounge chairs and shaded tables nearby.

Resort in Lake Buena Vista

5 out of 5 average rating, 3 reviews

Wyndham Bonnet Creek Resort | 2BR/2BA King Bed

A large outdoor pool is surrounded by palm trees and lounge chairs. A bar area is visible adjacent to the pool, with a shaded seating space. The multi-story building in the background features balconies and large windows, adding to the resort-like atmosphere.

Resort in Orlando

4.91 out of 5 average rating, 22 reviews

Las Palmeras, Hilton - Studio Apartment

Quick stats about resort rentals near Old Town Kissimmee

Total rentals
20 properties
Nightly prices starting at
R2,309 ZAR before taxes and fees
Total number of reviews
70 reviews
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Destinations to explore