Vacation rentals with a pool in Winter Park

Private pool home near Downtown

Thorton Park home embracing the "Florida lifestyle" with private backyard! This two bedroom and one bathroom home has a full kitchen and is best suited for up to five guests. Enjoy your large private pool surrounded by fenced in backyard and tropical plants. Just outside of your "new oasis", feel free to walk, bicycle or scooter to nearby eateries, Downtown Orlando and Lake Eola Park. Or take a short drive to The Kia Center, Dr. Philips Center, Camping World and Inter&Co Stadiums and much more!

Maitland-Orlando Area, FL. Pool House Bungalow

Large open space adjacent to a beautiful pool, waterfall, and fantastic lake view. 27 miles to Disney World, close to Park Avenue, local hospitals, Universities, and less than an hour to local beaches. Only 18 miles to MCO-Orlando International Airport. Great shopping within 3 miles. Location is secluded with large trees, lakeside, and adjacent to the commuter train track. The train runs by on regular basis. Please note in the pictures the pool creates the ambiance to make your stay complete.

Modern Tropical House Heated Salt Pool

☞Superhost 9 years ☞ Large Salt Pool (W/ heated option $ Oct-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 ☞65in Smart TV with Netflix in TV room ☞Dimmer mood lighting ☞Illuminated pool & landscape lighting ☞Pool Lounge Floats ☞Full Kitchen ☞Dining & Picnic table seats 6 to 8 guests ☞Hi speed 231mb internet ☞Uber Eats Food Delivery

St.John suite

Luxurious space with PRIVATE ENTRANCE, BATHROOM, and breakfast kitchenette. Located on a large lake front property with amenities that include private dock, pool, large manicured lawns and much more. Ideal for canoeing, watching the sun rise or doing nothing at all. Close to theme parks and beaches. Spring Valley is a peaceful community with age old oak tree lined streets, Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting.

"Winnie's Place" A Peaceful Guesthouse with Pool.

Share the backyard and NON Heated Pool with your hosts if we are home. Between Disney & the beaches. 12 years & older only. Sofa extends to a single bed. Minutes from I-4 makes commuting easy. NOT a heated pool. Wheelchairs are fine. Driveway Entry gate 39"- Breezeway to Ramp entrance 32"- Slider Entrance 33"-Bedroom door 35"-Shower (no step) 35"-Laundry 32"-Closet 35"-Queen bed 31". We are not Handicap Certified but most wheelchair guests do not have issues. Grab bars in the bathroom.

Bonheur Ala Maison

Bonheur A la Maison is the home that offers a beautiful, comfortable, spacious, convenient and all around happy feeling with the little extras and attention to detail to make you feel like you're basking in a lot of luxury for a simple price! Its everything you need from your blow dryer, to your plush robe and from your USB outlets at all bedsides to your built in wireless speakers for your music of choice. We tried to think of it all. Conveniently located near lots of shops and parks!

Luxe Guesthouse w/Pool/Hot tub-Near Rollins/UCF

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.

Apt F -Modern Elegance in the Heart of Winter Park

Great Location! If you haven't explored Winter Park's Park Avenue, then you must! Three blocks to Park Ave and two blocks to the Winter Park Village! Cozy and modern space. Pool, outdoor grill and bikes for your enjoyment. Enjoy the convenience and tranquility of one of Florida's greatest walking communities while residing in style and sophistication. The pool and grill stations are shared. Fast internet speed: 139MBPS download and 21.5 MBPS upload!

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.