Ready to kick back and enjoy a much needed family holiday or a great getaway with your friends? If you’re ready to feel stress-free and want to soak up the sunny rays take a look at our list of the best of the best Kissimmee Florida vacation rentals with private pools. Let’s dive into it!
Kissimmee is a fabulous gateway to theme parks, golf courses, shopping and world-class dining found in the Orlando-Disney area. A fab holiday is within reach so pack your swim trunks and suntan lotion with this many options available you’ll definitely find your dream Kissimmee vacation rental in a snap.
Kissimmee Florida Vacation Rentals – What Do You Need To Know?
Renting a Kissimmee vacation rental in Florida
Travel to Florida vacation rentals is surging. You can rent one of the best Kissimmee Florida vacation rentals with a private pool to stay close with your family. Vacation rentals are one of the most popular budget friendly and self isolating ways to vacation with family and friends together.
A few traveler tips before you search:
- Area – Kissimmee is close to Disney, Universal Studios and the Orlando airport
- Do your homework on average Kissimmee vacation rental rates and your budget
- Find out if Kissimmee is geared towards your needs (ie: family friendly, snowbird friendly, large groups, etc…)
Choose one of our Kissimmee Florida Vacation Rentals
What cities are close to Kissimmee?
The following cities are also great choices if you can’t find a your ideal vacation rental in Kissimmee;
- Babson Park
- Davenport
- Doctor Philips
- Haines City
- Lake Buena Vista
- Lake Wales
- Lakeland
- Loughman
- Maitland
- Ocala
- The Villages
Amazing Kissimmee Vacation Rentals with Private Pools in FL
- Emerald Island Resort – 7 Bedroom Vacation Rental
- Elite Disney Home – 5 Bedroom Vacation Rental
- Windsor Hills – 6 Bedroom Vacation Rental
- Bungalow Villa – 4 Bedroom Vacation Rental
- Pure Luxury – 6 Bedroom Vacation Rental
- Paradise Villa – 4 Bedroom Vacation Rental
- Affordable Lake View Villa – 4 Bedroom Vacation Rental
- Modern Luxury – 8 Bedroom Vacation Rental
- Encore Resort – 6 Bedroom Vacation Rental
- 551-Luxury Villa – 8 Bedroom Vacation Rental
Emerald Island Resort – 7 Bedroom Kissimmee Vacation Rental with Private Pool
Kissimmee Florida vacation rentals with Private Pool – FLARBO Listing #1091
Bring the entire extended family or large friend group to this beautifully furnished 7 bedroom villa which is the perfect vacation getaway. Snuggled in Emerald Island Resort, a gated community boasting basketball courts, sauna volleyball, pools, and tennis. One of the best Florida Kissimmee vacation rentals with private pool that you can find.
This vacation home has a games room complete with a pool table in addition to the expansive private pool and hot tub to enjoy al fresco meals and creating memories. The extended patio provides plenty of room for your party to relax in and enjoy the quiet cul-de-sac location. The large shaded lanai area with fans and an outside shower is truly indoor-outdoor living.
Elite Disney Home – 5 Bedroom Kissimmee Vacation Rental with Private Pool
Best Kissimmee Florida vacation rentals with Private Pool – FLARBO Listing #254
Check out this award-winning Kissimmee Vacation Rental with private pool and hot tub which has won Book.com’s Guest Review awards 2 consecutive years! The city of Kissimmee has also recognized Elite Disney Home for being the best vacation rental home in the city. These accolades represent the owner’s dedication to making sure every guest is completely satisfied. A benefit of renting a Florida vacation rental by the owner.
Savour plenty of privacy in the backyard with the southern facing pool with full sunshine and warmth throughout the year. You’ll love spending time in the private pool area featuring an over-sized deck, large swimming pool with underwater lighting, and an in-ground spa. There are plenty of tables, chairs and loungers for everyone to relax and enjoy themselves outside. If you need a break from the sun there’s a covered lanai to provide shade as well as a ceiling fan to cool you off. Also in the pool area is a gas grill perfect for cooking up for your group. This very spacious villa that can comfortably accommodate up to 10 guests.
Windsor Hills – 6 Bedroom Kissimmee Vacation Rental with Private Pool
Best Kissimmee Vacation Rentals with Private Pool – FLARBO Listing #1089
Windsor Hills resort is only 1.5 mile to Disney World! Proximity to everything you need, this Kissimmee vacation rental with private pool and hot tub allows you to walk to dining, shopping and a view of the fireworks. Dip into the private pools and hang out in the game rooms. Some special perks include baby and handicap equipment that are also available! Vacation stress-free… groceries can ordered online and stocked in the home prior to your arrival. Wholesale tickets & corporate rate car rentals will save you hundreds!
The themed playground is found just down the street and offers a short walk to clubhouse where the larger resort pool and waterslide, movie theater, poolside cafe & grill, sundry shop, game room, and the fitness center can be enjoyed! The recreation amenities include tennis, basketball, volleyball, putting green, BBQ and picnic areas and much more! This home is the bomb of Kissimmee vacation rentals with a private pool.
Bungalow Villa – 4 Bedroom Kissimmee Vacation Rental with Private Pool
Best Kissimmee Vacation Rentals with Private Pool – FLARBO Listing #630
This Kissimmee vacation rental villa with private pool is a beautiful professionally decorated 4 bedroom bungalow that sleeps up to 8 guests in comfortable accommodations. This luxury vacation home is equipped with all the amenities to make you stay relaxing and pleasurable.
Step into sunshine and slide into the private pool right out your backdoor paradise. Not only is this home fully outfitted but guests can enjoy more amenities at the larger resort pool nearby. The perfect spot to grab a getaway to the Disney-Florida area.
Pure Luxury – 6 Bedroom Kissimmee Vacation Rental with Private Pool
Best Kissimmee Vacation Rentals with Private Pool – FLARBO Listing #1030
When only the best will do, this luxurious 6 bedroom villa makes it one of the best Kissimmee vacation rentals with a private pool. Bring the entire gang to this large villa that sleeps up to 14 with an expansive 3,500 sq ft of comfort that you would expect from a 5 star resort.
The south-facing private saltwater pool with spillover hot tub spa is a dream overlooking the lush tropical landscape. Truly an escape within itself, guests enjoy a games room, 10 television, karaoke, air hockey, foosball, pool table, a theater room, themed bedrooms, and baby equipment. Definitely one of the most luxurious and best outfitted villas found in Windsor Hills resort.
Don’t forget to check out the Mystic Dunes golf course, the resort’s massive double Olympic size lagoon-style pool with water chute, jacuzzi spa, clubhouse, movie theatre, video arcade, tennis and basketball courts, sand volleyball and putting greens and gym. The children’s playground is not to be missed including a castle with drawbridge, climbing frame, giant chess, dragons, swings, and picnic area.
Paradise Villa – 4 Bedroom Kissimmee Vacation Rental with Private Pool
Best Kissimmee Vacation Rentals with Private Pool – FLARBO Listing #234
If you’re looking for the perfect Kissimmee vacation rental with private pool look no further. This bright, airy villa is found in the desirable 5-star Emerald Island Resort. A fantastic home base that’s conveniently close to theme parks, restaurants, and shopping, but tucked away enough to offer peace and quiet when you need it most.
Tropical Paradise Villa is found snuggled inside the gated Emerald Island Resort located just 2.5 miles from Disney’s doorstep. Showcasing a bright and sunny private screened-in private pool area replete with pool toys, cushy sun loungers and dining area. The game room with pool table, foosball table, dart board, and basketball hoop.
Whether you take the day off from the theme parks or come back late after the fireworks, the private pool means it’s always open and no crowds to contend with. Sit by the pool and read a book, watch the kids play, or have a romantic candlelight dinner. A retractable safety fence is provided to keep the kiddos safe. The lanai backs up to a beautiful 11-acre conservation land.
A short one-minute walk from Tropical Paradise Villa provides all the resort amenities that guests can utilize. They include clubhouse sauna, fitness center, games arcade, Internet cafe, free Wifi around the pool areas, Tiki-bar, heated community pools and spa, volleyball court, tennis courts, basketball facilities, kiddie play areas and walking trails. A short drive from the Magic Kingdom and the other Disney Parks, it’s also just minutes away from loads of shopping and dining
Affordable Lake View Villa – 4 Bedroom Kissimmee Vacation Rental with Private Pool
Best Kissimmee Vacation Rentals with Private Pool – FLARBO Listing #2349
Modern Luxury – 5 Bedroom Kissimmee Vacation Rental with Private Pool
Beautiful modern grey and white coastal living room – FLARBO Listing #2175
The GroovyMouseHouse is an amazing 8-bedroom modern, luxury Kissimmee villa with private pool and spa, located at The Encore Resort in Reunion. It’s the perfect vacation rental for families wanting an unforgettable stay in the Orlando-Disney area boasting a convenient location close to Disney, restaurants, supermarkets and golf courses
Amazing amenities abound at the Encore Resort such as their state-of-the-art aqua park with 50 ft water slides & spectacular Splash Zone, Kids Club, Arcade Zone, family friendly restaurants, as well as all the other conveniences and amenities within Reunion itself such as Golf courses and restaurants. Complimentary shuttle service to the parks On-site Concierge Service to assist with tickets to shows and theme parks.
This stunning Kissimmee vacation rental with private pool is beautifully furnished to high standards and a delightful haven of peace and serenity while offering comfort and entertainment in a luxurious setting. The outdoor living showcases a private swimming pool and spa. A quiet pool deck with unblocked vistas, sun loungers and a 6 seat patio table with an optional pool safety fence for young children.
Entertainment is found throughout the home with TVs in every bedroom, a loft with: PS4, Air hockey, comfortable leather sofa, 2 bean bags, 50s diner themed Games room with a ping-pong table and a foosball table.
Encore Resort – 6 Bedroom Kissimmee Vacation Rental with Private Pool
Incredible resort setting in Kissimmee – FLARBO Listing #2152
This Orlando – Kissimmee vacation rental with private pool is the perfect home for families and friends in search of a large 6 bedroom luxury pool home in the guarded, gated community of Encore Resort near Walt Disney World! Accommodating up to 12 guests this holiday home is perfect for a multi-family vacation that includes grandma and grandpa!
The west facing pool deck, spa and lanai, the home is perfect for theme park fans that love to keep driving to a minimum and enjoy evening relaxation at a maximum! The private swimming pool and spillover spa is the perfect backdrop to the pool deck with patio dining table and sun loungers.
Best of all, a truly professional clubhouse, concierge desk, water park and fabulous food and drink are all there for our guests without restrictions. The 10 acre water park includes multiple water slides, a calm adult pool, a side by side multi-lane mat racer, a two person inner-tube slide and a thrilling aqua drop with a trap door aqua launch.
Enjoy “Room Service” by having the restaurant’s affordable casual cuisine delivered right to your vacation home. There is a Grab and Go convenience store for drinks, snacks and necessary items. An arcade room with air hockey, video games and basketball machine. A Soccer pitch, beach volleyball, basketball and tennis courts A Private room to accommodate business meetings, small weddings or reunions. Stay fit in the state of the art gym.
551-Luxury Villa – 6 Bedroom Kissimmee Vacation Rental with Private Pool
Top 10 Kissimmee Florida vacation rentals with private pool
Need a super large Kissimmee vacation rental with private pool that sleeps up to 18 guests? This home is it! Showcasing Star War’s and Frozen themed bedrooms, as well as an upstairs loft area with a movie theater with video game console for hours of entertainment!
This short term rental house has a private swimming pool and hot tub spa located right outside where you and your family can experience Florida’s sunshine and warm weather. A tropical paradise perfectly outfitted for large groups to vacation together.
Relish the unbelievable sunrises over the Atlantic ocean! Watch the dolphins and shrimp boats right from your balcony! Let the sound of the ocean lull you to sleep! Enjoy oceanfront dining right from the beachfront balcony. There are miles of idyllic beach to walk and shell.
Work while on vacation with free password protected wifi to access your computer or smartphone network. This gated community is found just south of the Ritz Carlton hotel. The community offers four clay tennis courts at your disposal day or night; two pools to enjoy as well. Lush bike and running paths. Find your happy in this 1 bedroom condo that sleeps 2.
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Kissimmee Florida Vacation Rentals with private pools for those that love the privacy after a long day at the theme parks! There is a FLARBO, Florida Rental By Owners Kissimmee area vacation rental for you.
Anytime you are looking for a breezy Orlando – Kissimmee area rental with a private pool, Florida Rental By Owners has an excellent selection to accommodate your specific vacation needs. Click here to look for your next Kissimmee Florida vacation rental with private pool!
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