Vacation rentals with a pool in Winter Park

This spacious backyard features a uniquely-shaped pool surrounded by loungers and umbrellas, perfect for soaking up the sun. Lush greenery and palm trees provide a tropical retreat, while soft evening lighting adds to the serene atmosphere, making it an inviting spot for relaxation.

4.95 out of 5 average rating, 101 reviews

Private Pool Oasis w/Xbox, Fireplace, Projector

Discover Orlando from this beautifully remodeled home, perfectly located near Disney, Universal Studios, downtown, and prime shopping. Enjoy the serene private pool with stunning day and night lighting. The home features three stylish bedrooms with private TVs, two modern bathrooms, and a cozy fireplace with a dedicated seating area. Offering a blend of comfort and convenience, this home is your ideal base for an unforgettable Orlando experience. Book your stay to create unforgettable memories!

A heated pool surrounded by lush greenery features a stone ledge and a small waterfall. Hammocks are placed for relaxation. The screened patio allows for unobstructed views of the sunset, creating a tranquil setting. Warm lighting highlights the natural textures of the landscape.

4.96 out of 5 average rating, 166 reviews

Spacious Home with Pool & Hot Tub near Downtown

Nestled in one of the most coveted neighborhoods near Downtown Orlando (Ivanhoe Village), you'll be within a 5-min walk to tons of restaurants, bars, breweries, and boutique shops. Boasting a heated pool, hot tub, tiki bar, patio area w/seating & two living areas -you'll have ample room to play, entertain or relax in your Tropical Oasis! ☀ Harry P. Leu Gardens – 4 mins ☀ Orlando Museum of Art – 4 mins ☀ Universal Studios – 19 mins ☀ Walt Disney World – 24 mins ☀ The Mall at Millenia – 16 mins

4.86 out of 5 average rating, 125 reviews

An outdoor space features a large pool surrounded by a patio area. Comfortable seating and an umbrella are positioned under a shaded area. Lush greenery lines the back and sides, providing privacy, while the main house showcases a welcoming design with large doors leading out to the pool.

Home in Winter Park

Charming Retreat In Winter Park

“Welcome to our renovated Winter Park home! This modern one-story property features 3 bedrooms plus a loft, comfortably sleeping 6 guests. Enjoy the large backyard with an extra-large pool and outdoor shower. Conveniently located near Orlando’s attractions, including Disney And Universal Studios as well as Rollins Collage and the Kia Center. Indulge in over 60 restaurants with in 10 min. Winter Park Village and Park Ave. Shopping. Experience comfort and style in this charming Florida retreat!”

A tranquil backyard features a sparkling pool surrounded by lush greenery and palm trees. Sunlight reflects off the water, creating a serene atmosphere. A covered seating area adds to the comfort, enhancing the outdoor space that overlooks a picturesque view of Lake Gandy.

4.87 out of 5 average rating, 102 reviews

Recharging Lakeview Oasis w/Pool centrally located

Fall in love w/ our peaceful home w/ incredible backyard & pool overlooking Lake Gandy! Experience the tranquility of this safe, residential area. New furnishings for your comfort, cozy living room w/ an 85" Smart TV, comfortable bedrooms, laundry room & fully-equipped kitchen for a nice meal. Have fun at our spacious backyard, great for entertainment, bbq's & fire pit s’mores nights! Enjoy delicious organic fruit in the yard! Only 25min away from amusement parks & MCO! Superb for long stays!

4.93 out of 5 average rating, 136 reviews

A refreshing pool is captured, with sunlight sparkling on the water's surface. The stone-accented summer kitchen with a wooden pergola is visible in the background, along with plants and seating, creating a relaxed outdoor setting.

Home in Casselberry

Villa with Guest House & Pool-Patio

Welcome to this Amazing House Pool-Patio with 4 Bedrooms + 2 Bathrooms and optional guest house to complete the 10 guests. True gem with covered summer kitchen, covered pergola, garage for two cars and a large driveway. 30 Minutes distance to Universal, Sea World, Volcano Bay and others. UCF in 15 minutes and Daytona beach/Cape Canaveral in 50’. Great restaurants and shops. The house is conveniently located for all attractions in Central Orlando. Airport is 25 minutes. SAFE NEIGHBORHOOD

4.85 out of 5 average rating, 162 reviews

A spacious living area features a modern sectional sofa arranged facing a stone fireplace. Large glass doors provide natural light and views of the outdoor space. Decorative plants and a wall-mounted mirror add elegance to the cozy atmosphere.

Home in Maitland

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!

4.95 out of 5 average rating, 187 reviews

A private pool area is surrounded by lush tropical landscaping, featuring tall palm trees and vibrant greenery. The sparkling blue water of the pool reflects the sky, while a paved pathway leads to the entrance. A serene atmosphere is created by the nearby plants and outdoor decor.

Home in Maitland

Orlando area pool home in Maitland

Everyone finds our home fun & relaxing. We are close to tons of restaurants & shopping. Only 1 mile from the intersection of I-4 & 414 (Maitland Blvd). Home, it is fully stocked. Plus a gas grill. Towels & linens provided. Games and toys for all ages. Pets are welcome with pet fee. Guests have private use of property, 2 bedrooms & 2 full baths and all living areas, back yard and porch with pool . There is an optional third bedroom available for an additional $35 a night fee.

4.98 out of 5 average rating, 127 reviews

The screened-in pool area features a tranquil pool with a soft blue hue, surrounded by white decking. A small table holds a lit lantern beside two lounge chairs, providing a serene space for relaxation under the evening sky.

Home in Maitland

Florida Poolside Paradise a Great Place to Unwind!

Welcome to our exquisite 4-bedroom vacation rental in the heart of Maitland, Florida – a true gem where luxury meets convenience. This upscale home boasts fine furnishings and a private pool, making it the ideal retreat for families or groups seeking both comfort and style during their Sunshine State getaway. The house is located in a residential neighborhood with plenty of restaurants and shopping within a 5 minute drive. Convenient location off Rt 436. and half hour to the airport.

A serene pool area is featured, reflecting the clear blue sky and surrounding greenery. The pool is bordered by a tiled edge, with colorful plant life adding vibrancy. A covered patio with a picnic table sits in the background, offering a shaded relaxation area.

4.91 out of 5 average rating, 173 reviews

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

4.99 out of 5 average rating, 200 reviews

A spacious living area is highlighted by a sleek, modern design featuring polished floors. A green couch and two accent chairs are arranged around a wooden coffee table. A dining table with ample seating is situated nearby, complemented by decorative wall art and soft lighting.

Guesthouse in Orlando

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.

4.83 out of 5 average rating, 127 reviews

A modern kitchen is seen, featuring white cabinetry and a speckled granite countertop. Stainless steel appliances, including a microwave and toaster, are positioned conveniently. A small potted plant adds a touch of greenery, while natural light filters in through the window above the sink.

Condo in Winter Park

Lovely Winter Park Home close to Hospitals !

Lovely Condo close to Full Sail, Rollins College, Valencia College, UCF and Advent Health Winter Park Hospital. Close to Park Avenue - Winter Park’s shopping, dining and cultural gem – boasts more than 140 boutiques, sidewalk cafes, and museums, all in the shadow of oak-canopied Central Park. In addition to the shops, dining and cultural offerings, you can plan a trip around special events that include seasonal art shows, concerts and fashion events.

An outdoor space features a heated pool and a hot tub, surrounded by stone masonry. A custom bar, crafted from wood, is visible alongside tropical plants. Two built-in TVs are fitted above the bar area, enhancing the outdoor living experience.