Florida Vacations: 6 Kissimmee Vacation Rentals with Private Pool

Between theme park jaunts, live like a local and experience the best of Orlando's indoor-outdoor lifestyle

We’ve all been there. By the time you rent hotel rooms for four separate couples, or parents/ grandparents/cousins, or a bunch of guys or ladies out for a grand time at Orlando’s theme parks—poof! Your budget is dented. Here’s an idea that can cost less and be a whole lot of fun: renting a vacation house that has its own private pool in a very good location.

The city of Kissimmee is just south of Disney World, and the sprawling destination is loaded with 50,000 private rental homes—from apartments and cottages to villas and mansions. Most have all the amenities and space a bunch of you will need for a week, month or season of relaxing. Live like a local, in other words.

Choose an individual home rented to vacationers by the owner and expect what you’re used to in your own residence: a living room, a kitchen, cable, WiFi and family-friendly amenities like a washer-dryer. Only here, a sparkling swimming pool for splashing in the sunshine is all but a must. Or choose a location within a resort; then besides your own home and pool you’ll get access to hotel-like amenities elsewhere on the property.

Whether you want two bedrooms or 22, seclusion or a social scene, you’ll have a treat of a retreat for your Orlando-area holiday!

A High-End Home With a Hint of Hogwarts


Gather your gang—friends, famil,y or adventure seekers, up to 22 in all—and settle into the Ec076. This space is so well-designed for your ladies’ bonding week or extended family holiday that everyone will put on a happy face. With 10 bedrooms (and 10 bathrooms) including five king suites, this villa also caters to a crowd with two refrigerators and two dishwashers.

The pool with its paver deck and expansive view is open-air—not screened in—so swimming in the stylish square, or lounging beside it, feels like a true resort experience. The spillover spa can be heated as an add-on. Set up in the shaded area for dinner alfresco. When you’ve had your fill of sunshine, head inside the two-story house to its loft entertainment area with a foosball table, Xbox game system, and large-screen TV.

Ec076- 10 Bedroom Villa With Private Pool

9.6 Excellent (35 reviews)

An Elegant Vacation Rental With Pool and Air-Conditioned Game Room


With snazzy upscale furnishings and a sparkling private pool, the two-story Mediterranean-style Disney Windsor Hills! is a pampering vacation home. Hole up here whether you’re a few families together or a clutch of friends seeking a sophisticated space for a holiday near the Walt Disney World Resort.

You’ll linger by the pool. Mostly oval, it has a separate spa and is surrounded by pavers, not to mention dining and lounge seating on the spacious deck. A child fence assures safety. Stay seven nights or more to qualify for free pool heating, and rent a grill if you like to barbecue.

Indoors, an open floor plan lets the living, dining, and cooking area—with granite countertops—intertwine naturally. Fun is easy to find, as the garage is air-conditioned and filled with air hockey, foosball, and pool tables. The family room has a PlayStation 4 game console and free Netflix. All bedrooms include high-definition TVs with DVD players and ceilings fans.

Tots through tweens will enjoy the children’s bedrooms, one with extensive Mickey Mouse accents, the others Disney princess-themed. Many baby extras like a stair gate and stroller are included, while others including a full-size crib and bed guard are available for rental.

Disney Windsor Hills! Mickey! Heated Pools+Games Room! Up to 50\ OFF

9.1 Excellent (66 reviews)

A Green Weekend Getaway Spot for Family Fun


Only few miles from Disney World and loaded with Disney® theming, Cap’n Jack Sparrow’s Hideaway, also known as this Large 5 Bedroom 3 Bath Pool Home caters to families. It’s a 2,700-square-foot five-bedroom pool house that has all the comforts grown-ups like—comfy sofas, a well-equipped kitchen, cable TV—yet also a crib, a highchair, and a two-twin bedroom that will win you over with Winnie the Pooh accents.

The other room with two twins, a king, and the two queen bedrooms all have more generic decors. After a day of wizards or princesses, unwind in and around the screened-in rectangular pool and spa that is bordered by trees. In chillier weather, splurge on pool and spa heating. A child safety fence is included. Located in a quiet neighborhood, this Kissimmee vacation rental with private pool also has a billiards table, a Wii console, and easy access to a community tennis court and major roads.

Large 5 Bedroom 3 Bath Pool Home - 3 Miles From Disney Entrance

8.5 Excellent (7 reviews)

A Light, Bright and Elegant Pool Home in Kissimee


Be among the first to enjoy this 4 Bed Pool Home,

where up to 10 of you can sleep in the four-bedroom, two-story home. With three-and-a-half bathrooms, there’ll be no battles about who showers next. You’ll all chill in or around the splash pool (add on a gas grill or heat in winter for a surcharge), a clear blue oasis with a screened-in paved deck.

With an array of whites and creams set against dark cabinets, the open-plan kitchen and living room is pampering enough for a bridal party and spacious enough for a multigenerational family. While adults will be comfy staying in the sophisticated king and two queen bedrooms with pillowtop mattresses, they might envy the kids. Their bunkbed room is decorated with whimsical Mickey Mouse touches. Don’t expect the little ones to spend too much time there, as the a pool table, a dart board, and a TV room with games will keep them happily entertained.

$195 Fall Special, also Drone Video - Scroll Down, Brand New Resort and 4 Bed Pool Home!

9.3 Excellent (29 reviews)

A Peaceful and Quiet Vacation Rental Near Disney Attractions


Going by the name Isle of Tranquility, this Ultimate 4 Bedroom is all about being a serene escape from the theme park hubbub. This cheerful freestanding house with a private pool easily allows a family or two, or several adults, to toast their time off indoors and out. You’ll gather around the lagoon-style pool with its cobalt tiling touches.

A raised spa is just the place for a satisfying soak. Or sun yourselves on the extended pool deck’s lounge chairs followed by a cold one at the covered lanai’s dining table. The screened enclosure will keep bugs away. Prepare meals in a full-size kitchen. Unwind amid the contemporary and boldly colored living/dining area.

When it’s time to play, head to the garage, which is used as a family game room with a pool table, foosball table, and dart board. Like the living room, the game room has a Bluetooth soundbar so you can stream your favorite tunes. Both master bedrooms have en-suite bathrooms. One children’s room has a Minions theme, the other Peanuts.

Ultimate 4 Bedroom 3 Bathroom Pool Home Near To Disney Attractions, Themed Rooms

8.5 Excellent (49 reviews)

A Two-Story House in Kissimmee With a L-Shaped Pool


Up to 10 guests can stay at 3039 Pool Home, with a design so logical that five bedrooms and four bathrooms accommodate guests in 2,000 square feet. The tailored furnishings in neutral tones are universally appealing, yet the kids may need to pull straws to see which two get the twin beds in the room with a Harry Potter mural dominating one wall.

Quidditch aside, the real fun takes place out back, where a stucco fence makes the L-shaped pool quite private; heating is available as an add-on for three days or more. A screened ceiling provides views of clear blue sky. Simple loungers and a dining table allow sun-worshippers to stay dry. The common rooms are tiled, while the bedrooms including two king master suites carpeted.

3039 Beach Palm Avenue Pool Home

8.9 Excellent (65 reviews)

This article is an independent review of a popular destination proposed by trivago and is neither commanded nor applied by Disney.