Holiday rentals with a pool in Orlando

Unique Spacious Home w/ Pool near Downtown Orlando

Nestled on a quiet street, 15 mins from Downtown Orlando. This home has a massive pool, hot tub, water fountain, real outdoor and indoor fire place, outdoor patio area w/seating. The Kitchen is equipped with everything you need to make delicious meals, and there are two living areas to provide ample space for relaxation. There is also a designated office area to take work calls. ☀ College Park – 10 mins ☀ Downtown Orlando – 15 mins ☀ Universal Studios – 28 mins ☀ Walt Disney World – 34 mins

InternationalDr. Private Theater. Salt Pool. Sauna

This special place is close to everything, making it easy to plan your visit. • Community: Paradiso Grande • 6 Bedrooms/6 Baths/Sleeps 16 • Disney - 10 miles • SeaWorld - 1.5 miles • ICON PARK - 4 miles • Convention Center - 3 miles • Universal - 7 miles • Exercise Equipment • Private SALT WATER Pool (new!) • Game Room with Arcade with 7500 Games, Pinball, Air Hockey • Private $35,000 Home Theater with 133" Screen and shakers on seats • Business Grade Internet • Sauna • EV CHARGER

Chic Vibes Comfy King Bed Next to Parks/Food/shops

Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!

Modern Tropical House Heated Salt Pool

☞Superhost 9 years ☞ Large Salt Pool (W/ heated option $ Sept-April) ☞3 Bedroom 3 Full Bath W/extra 4th queen daybed ☞ Easy access to the 417 East West express way (toll rd.) to get around Orlando ☞Easy smart lock self Check-in ☞ Driveway Parking ☞ Luxury bedding ☞Smart TV's with Netflix in each room ☞Dimmer mood lighting ☞Illuminated pool & landscape lighting ☞Full Kitchen ☞Dining & Picnic table seats 6 to 8 guests ☞Hi speed 231mb internet ☞Uber Eats Food Delivery

Downtown Orlando Garden Retreat

This space is a mother-in-law suite, completely private from the main house, accessible through a private entrance outside and entering through the garage. THIS IS NOT THE ENTIRE HOUSE! There is a queen size bed... perfect for a couples getaway! It is conveniently located about 15 min. from OIA and 5 min. from downtown Orlando. There is a beautiful pool and hot tub with stunning sunset views of across the lake... so peaceful and you feel like you are in a resort

Luxe Guest House| Pool, HotTub| UCF, Rollins

This luxury guesthouse (on the same property as our main house but they are completely separate) is a hidden oasis conveniently located in the middle of downtown Winter Park (Rollins College/Full Sail) and UCF. It's roughly 10 minutes to each. Close to 417 expressway (toll road) so you can easily get around to the other areas of Orlando. Note: The guesthouse is 35 minutes to Disney, 25 minutes to Universal Studios and 20 minutes to Orlando International Airport.

Royal Retreat Disney Themed Pool Home, Arcade, Theater

Welcome to The Royal Retreat. Located just 10 miles away from the entrance of WDW, our rental is the perfect place to stay for your Disney vacation. Our 5 star home features 8 themed bedrooms and 5 bathrooms, a fully-equipped kitchen, private heated pool, private arcade, home theater & BBQ! Free Pool heat & the 1st tank of propane for the BBQ are included. Booking with us includes full access to the Champions Gate Clubhouse, Oasis Resort and Retreat Club!

Waterfront Wizarding Near Universal's Harry Potter

This spellbound stay, situated in the prestigious Lake Berkley Resort, boasts lake views & private pool. With 6 bedrooms, 3 bathrooms, well equipped kitchen & comfy living spaces, this thematic home is ideal for families & friends seeking an immersive vacation. A 10min drive to Disney, 15min to Sea World & 20min to Universal's Wizarding World of Harry Potter, this magical manor provides a convenient home base for exploring Orlando's famous attractions.

Stunning Orlando Getaway w/Spa & Heated Pool

The whole group will enjoy easy access to everything from this centrally located Orlando location. This 1950s beautifully designed space has all modern amenities with an amazing outdoor living space. Located in College Park situated close to many amenities Orlando has to offer. Only 9 Minutes to downtown Orlando or 15 Minutes to Universal. The Acre & The Cottage Wedding venues are both within Walking Distance. Dubsdread is only 4 Minutes Away.

*Luxurious Paradise Mansion: Pool, Spa & Cinema

The perfect balance of STYLISH DESIGN, LUXURIOUS COMFORT, & ENDLESS ENTERTAINMENT in the stunning 3.5 square mile Reunion Resort. You will have your own private pool, spa, movie theater - game room, 3 master suites, 3 incredible themed bedrooms (MARVEL, FROZEN II, NASA) for kids or adults, the latest Xbox Series X game station, a 2500 ft2 pool deck overlooking a beautiful forest and pond, fire pit, & billiards table, minutes to Disney.

Private Country House | 16 Guests | Gatherings

Bring the whole family to this private 5-acre retreat, situated in one of the few hilly regions of Florida. Enjoy privacy, nature, spectacular sunsets, and starry nights—perfect for relaxing or enjoying outdoor activities. ⚠️ Gatherings require prior approval—please contact us before booking. Note: There is another house on the property that may be rented by other guests. Both are completely private, with no shared areas or parking.

7851 Luxury 5BR Home w/ Private Pool Near Disney

Create unforgettable memories in this modern 5-bedroom, 5-bathroom home in Reunion Village, near Disney. Enjoy a private screened-in pool, game room, second-floor loft, open-concept living and dining area, modern kitchen, multiple king-sized bedrooms, themed bedrooms, high-speed Wi-Fi, TVs, washer/dryer, free parking, self check-in, and access to eligible Encore Club amenities. Ideal for families and groups.