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13 A-List Orlando Vacation Home Rentals with Private Pools

Orlando is a playground for all ages, located in the middle of sun-drenched Florida. It’s here travellers discover the magic of Walt Disney World, spot alligators in the Everglades and ride thrilling roller coasters at Universal’s Islands of Adventure. Orlando’s hot summers also make it perfect for water parks and pool games with the family.

The best way to experience Orlando is with one of the city’s luxurious vacation home rentals. Fit for A-list celebrities, these homes combine contemporary entertainment with flexibility and exclusivity. With more than 400 million annual visitors to HotelsCombined, we’ve tracked down the best Orlando vacation rentals, all of which have that crucial ingredient for a memorable Orlando holiday: a private pool.

Windsor Hills – Global Resort Homes

Windsor Hills – Global Resort Homes, Home rentals in Orlando

Photo| Windsor Hills – Global Resort Homes| Provided by BOOKING.COM

Windsor Hills – Global Resort Homes provides some of the closest vacation homes to Walt Disney World, placing you minutes from Disney’s Blizzard Beach Water Park and Disney’s Animal Kingdom Theme Park. This gated property boasts four, five and six-bedroom homes with alluring private pools. These enticing holiday homes also have king-size beds in the master bedrooms, spa baths and full kitchens.

The in-home washer and dryers provide valued convenience for long stays, while the game rooms in certain homes come with billiard tables, table tennis, air hockey and PlayStations. Take advantage of the property’s resort-style swimming pool, which has a water slide and hot tub. 

Why You Should Stay Here 

  • A wealth of leisure facilities, including a playground, tennis courts, 40-seat movie theatre and video arcade.
  • Large private homes with their own pools and full kitchens
  • Positioned on the picturesque Reedy Lake.

Star Rating: 4*
Price: USD 433 – USD 742
Guest Rating: 8.7
Address: 7600 Comrow street, Maingate West, Orlando, United States

Advantage Vacation Homes Orlando

You’re spoilt for choice with Advantage Vacation Homes Kissimmee, which boasts about 50 vacation homes with private screened-in pools perfect throughout the year. Almost all of these properties are located within six kilometres of Walt Disney World and offer a range of sizes, from three to seven bedrooms.

These holiday rentals all feature the comforts of home, including Wi-Fi, flat-screen TVs, fully-equipped kitchens, washer/dryers and game rooms with various table games. The Tuscan Ridge 7341, for instance, has an eight-seater dining table, a backyard and Jacuzzi, while the seven-bedroom Emerald Island 3855 has access to communal resort facilities, including a full-service pool bar and fitness centre. 

Why You Should Stay Here 

  • Around 50 vacation homes with private pools.
  • Excellent value for money for self-contained Orlando accommodation.
  • Certain homes also have access to resort facilities, including tennis courts and saunas.

Star Rating: 3*
Price: USD 99 – USD 299
Guest Rating: 7.7
Address: 7799 Styles Blvd, Four Corners, Orlando, United States

Magical Memories Villas

Magical Memories Villas, Orlando homes

Photo|Magical Memories Villas| Provided by BOOKING.COM

Magical Memories Villas offers a variety of 3-star holiday rentals with sun-drenched private pools. The five-bedroom Heathrow Home with pool at Windsor Hills also features a secure double garage, master suites with king-size beds and a game room with a billiards table, card table and air hockey. Alternatively, opt for the Southampton Vacation Home with Pool for four bedrooms, an indoor basketball court and a large kitchen.

Most of the vacation rentals at Magical Memories Villas are located within 15 minutes’ drive of the Walt Disney World theme parks, numerous golf courses and the Disney Springs shopping, dining and entertainment hub. You can also opt for holiday rentals in specific resorts, such as Encantada Resort, for access to communal game rooms, gyms and pools.

Why You Should Stay Here

  • Multiple holiday rentals with four to five bedrooms and game rooms.
  • A short drive from Walt Disney World.
  • Affordable prices for families on a budget.

Star Rating: 3*
Price: USD 99 – USD 238
Guest Rating: 7.1
Address: 2801 North Poinciana Boulevard, Maingate East, Orlando, United States

Paradise Palms by Orlando Fun Rentals

The four rental properties at Paradise Palms by Orlando Fun Rentals all feature private covered lanais with splash pools and poolside furnishings. They also feature full kitchens, king-size beds in the master bedrooms and a variety of in-home entertainment. All the rentals are adorned with modern furnishings, including washers and dryers, and also come with plush bedding and linen.

All guests at these vacation rentals have access to the property’s on-site facilities, such as the sprawling outdoor pool with waterfalls, palm trees and a playground. About 15 minutes’ drive away you’ll find Disney’s Hollywood Studios and the ESPN Wide World of Sports Complex. 

Why You Should Stay Here 

  • Multi-bedroom rentals with full kitchens, lanais and private pools.
  • About 15 minutes’ drive from Walt Disney World.
  • A large communal swimming pool.

Star Rating: 4*
Price: USD 3,267 – USD 3,626
Guest Rating: 9.4
Address: 8959 Candy Palm Road, Four Corners, Orlando, United States

Hapimag Resort Orlando

You’ll find everything you need at Hapimag Resort Orlando, a luxurious four-bedroom holiday home with three modern bathrooms, a fully-equipped kitchen, washer and dryer and a large backyard with a screened-in pool and patio. The pool also has a glass ceiling, making it accessible during those rainy days.

Don’t forget to also enjoy the resort’s communal facilities, including tennis and basketball courts, beach volleyball, table tennis, two sun-drenched pools and a hot tub. You can play billiards on the poolside table, fish in the catch-and-release lake or let the kids run wild on the splash pad or playground. 

Why You Should Stay Here 

  • A spacious four-bedroom house with a glass-ceiling pool.
  • More facilities than most resorts, including two pools, playgrounds and lake fishing.
  • About 10 minutes’ drive from over 400 vendors at 192 Flea Market.

Star Rating: 4*
Price: USD 458 – USD 816
Guest Rating: 9.2
Address: 1010 Park Ridge Circle, Kissimmee, Orlando, United States

Terra Verde Resort Kissimmee Orlando

Choose from the modern three, four, five, six and seven-bedroom rental homes at Terra Verde Resort Kissimmee Orlando. All of these, except for the three-bedroom home, feature private pools with enclosed decks, along with spacious dining and lounge rooms, gourmet kitchens and secure garages. You also have the option of adding a covered lanai and whirlpool.

You’ll find plenty of reasons to stay around the resort, from the game room, tiki bar and fitness centre in the Clubhouse to the resort’s large freeform pool with sun decks. You can also enjoy catch-and-release fishing on the neighbouring lake or play basketball, beach volleyball, tennis or miniature golf. 

Why You Should Stay Here 

  • Multiple homes with four to seven bedrooms and private pool decks.
  • Separate children play areas with swings, slides and a sandpit.
  • Cocktails, American fare and snacks at the poolside tiki bar.

Star Rating: 4*
Price: USD 698 – USD 1,366
Guest Rating: 9
Address: 109 Madiera Beach Blvd, Kissimmee, Orlando, United States

Starmark Vacation Homes Celebration

Starmark Vacation Homes Celebration offers a variety of vacation rentals with private pools, most of which are located within the centre of Kissimmee near the picturesque Lake Tohopekaliga. These properties offer a range of bedroom options to suit large groups and multiple families, along with modern amenities, including gourmet kitchens, state-of-the-art lounge room entertainment and backyards.

The prices vary depending on the property, with the 7 Bedroom Crystal Cove being one of the most lavish with its granite kitchen, heated and glass-enclosed pool and outdoor patio. You can splurge a little more on the 8 Bed Westside Resort Home, which boasts an enclosed pool overlooking the lake. It also has themed kids’ rooms, two living rooms and a game room. 

Why You Should Stay Here 

  • Multiple vacation rentals with pools, backyards, gourmet kitchens and luxe bedrooms.
  • Most of the homes are within 12 kilometres of the theme parks and outlet malls.
  • A range of prices to suit most holiday budgets.

Star Rating: 3*
Price: USD 171 – USD 501
Guest Rating: 7.8
Address: 715 Bloom Street Suite 200, Celebration, Orlando, United States

Nine Bedrooms with Private Pool Spa and Game Room 1818

Holidaying with multiple families? Nine Bedrooms with Private Pool, Spa and Game Room 1818, might be the perfect vacation rental property for you. Its nine bedrooms, including four with king-size beds, are complemented by eight bathrooms and a large open-plan living and dining area with comfy sofas and a Smart TV. The fully-equipped kitchen has two fridges and dishwashers, while the private pool, Jacuzzi and barbecue grill provide ample outdoor recreation.

Kick back on the house’s shady patio, dine around the 10-seater dining table or sunbathe on a deck chair. This property is under five minutes’ drive from Orlando Tree Trek Adventure Park Zip Line and about 20 minutes from the Orlando Vineland Premium Outlets. 

Why You Should Stay Here 

  • Enough space for multiple families with nine bedrooms and eight bathrooms.
  • Within easy driving distance of Orlando’s theme parks.
  • A private pool, Jacuzzi and barbecue grill.

Star Rating: 3*
Price: USD 140 – USD 224
Guest Rating: 7
Address: 2900 Parkway Boulevard, Maingate East, Orlando, United States

CLC Regal Oaks Resort Kissimmee Florida

CLC Regal Oaks Resort Kissimmee Florida, home rentals in Orlando

Photo|CLC Regal Oaks Resort Kissimmee Florida| Provided by BOOKING.COM

The 3-Bedroom Townhome and 4-Bedroom Townhome at CLC Regal Oaks Resort Kissimmee Florida come with private patios with small pools that double as spas for year-round pampering. These opulent homes also feature king-size beds in the master bedrooms, living rooms, full kitchens and washers and dryers.

Part of the exclusive Regal Oaks Resort, the Townhomes also grant access to inviting on-site facilities, from the sprawling swimming pool with sun loungers and water slides to the Jacuzzi and cocktail service at the Pool Bar. You can indulge in hearty meals at Regal Oaks Bar and Grill or pick up snacks and supplies from the on-site mini-market. 

Why You Should Stay Here 

  • A state-of-the-art fitness centre and Jacuzzi.
  • Fine dining at Regal Oaks Bar and Grill.
  • About 10 minutes’ walk from Fun Spot America Kissimmee and the surrounding restaurants.

Star Rating: 3*
Price: USD 342 – USD 363
Guest Rating: 8.9
Address: 5780 Golden Hawk Way, Maingate East, Orlando, United States

Premium Six Bedrooms with Private Pool Spa and Grill 1845

You’re spoilt for space and leisure facilities at the rental property, Premium Six Bedrooms with Private Pool Spa and Grill 1845. This two-storey house not only has six bedrooms, including four with king-size beds, but also features Mickey and Nemo-themed rooms, a kids’ room, a private patio and sprawling backyard.

Spend those sunny days swimming in the pool while the rest of the family chills out on the sun loungers or grills up a feast on the barbecue. Located in Kissimmee, this holiday home is just down the road from Orlando Tree Trek Adventure Park Zip Line and is within 20 minutes’ drive of Celebration Golf Club and Walt Disney World.

Why You Should Stay Here 

  • Six bedrooms, including Mickey and Nemo-themed rooms for the kids.
  • Ample outdoor entertaining, including a pool, deck chairs and barbecue.
  • Nestled in a quiet housing estate with limited vehicular traffic.

Star Rating: No Rating
Price: USD 1,141 – USD 1,633
Guest Rating: No Rating
Address: 791 Lasso Drive, Orlando, United States

Casiola Vacation Homes

Casiola Vacation Homes, Vacation home rentals

Photo|Casiola Vacation Homes| Provided by BOOKING.COM

Casiola Vacation Homes offers a variety of rental properties with private pools, as well as gourmet timber-finished kitchens, contemporary in-home entertainment, multiple bedrooms and private balconies or patios. The resort also features communal leisure facilities, including outdoor pools, a hot tub and a game room. You can shoot hoops on the basketball court, work in the internet cafe or watch movies in the cinema.

Enjoy a convenient location about 20 minutes’ drive from Orlando International Airport and Walt Disney World. Positioned near Lake Cay, the resort is also a great spot to enjoy some lakeside jogging or picnics. 

Why You Should Stay Here

  • Large private homes with individual pools and balconies.
  • Resort-style facilities, including a basketball court and game room.
  • A short drive from the airport and theme parks.

Star Rating: 3*
Price: USD 246 – USD 369
Guest Rating: No Rating
Address: Various Addresses, International Drive, Orlando, United States

Encore Resort 4201 6 Bedroom Water Park

Encore Resort 4201 6 Bedroom Water Park, Orlando home rentals

Photo|Encore Resort 4201 6 Bedroom Water Park| Provided by BOOKING.COM

Perfect for families or large groups, Encore Resort 4201 6 Bedroom Water Park is a two-storey home with six bedrooms and bathrooms, a flat-screen TV in every bedroom and a large kitchen. It also comes with a private patio, eight-seater dining table, a washer/dryer and two-car garage. Guests staying three nights or more also have access to the home’s sun-drenched pool, hot tub and sun loungers.

Part of Encore Resort, this holiday home also grants access to a range of family-friendly facilities, including the sprawling AquaPark with four slides, private cabanas and a pool. Along with fitness classes and tennis and basketball courts, the resort has video game nights, pool parties and scavenger hunts. It also offers on-site dining at The Shark Lounge, The Bis Grill and Finns Restaurant. 

Why You Should Stay Here 

  • Poolside hamburgers, smoothies and glasses of wine at The Bis Grill.
  • A large private pool with a barbecue grill and sun loungers.
  • On-site activities, including wine tastings and trivia.

Star Rating: No Rating
Price: USD 1,331 – USD 1,741
Guest Rating: No Rating
Address: 7393 Marker Avenue, Orlando, Florida, United States

Venetian Bay Resort

Located in Kissimmee, Venetian Bay Resort is a short drive east of Orlando’s biggest theme parks, including Walt Disney World and Gatorland. The street is surrounded by scenic ponds, while the property features comfortable vacation homes within a gated community. These homes come with Smart TVs, full kitchens, multiple bedrooms and separate dining and living areas, along with private pools in some.

Venetian Bay Resort offers numerous leisure facilities, such as a playground, tennis courts and a sprawling swimming pool with umbrellas and sun loungers. Along with being excellent value for your money, this property is just a short drive from the shops and restaurants along U.S. Highway 192, including the Medieval Times Dinner & Tournament theatre. 

Why You Should Stay Here 

  • Excellent value-for-money vacation homes for families.
  • Resort-style on-site facilities, including a pool and tennis courts.
  • Positioned in a quiet neighbourhood with nearby shops and restaurants.

Star Rating: 4*
Price: USD 129 – USD 885
Guest Rating: 8
Address: Venetian Bay Drive, Kissimmee, Orlando, United States

Hotel Location

Planning to visit Las Vegas? Top 12 Las Vegas Hotels with Private Pools

Live Like an A-List Celebrity at These Orlando Vacation Homes

Orlando’s luxurious vacation homes treat you like a celebrity with their ample space, exclusivity and generous on-site perks. Along with providing their own comfortable havens with flat-screen TVs, private pools, patios and chef-worthy kitchens, these holiday homes typically offer resort-style facilities, including game rooms, gyms and tennis courts.

Which one is your favourite Orlando vacation home with a private pool? Let us know in the comments.

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