Vacation rentals with a hot tub in Winter Park

Find and book unique hot tub rentals on Airbnb

Quick stats about vacation rentals with a hot tub in Winter Park

Total vacation rentals
Explore 10 vacation rentals in Winter Park
Nightly prices starting at
Winter Park vacation rentals start at G$6,276 GYD per night before taxes and fees
Verified guest reviews
Over 1,080 verified reviews to help you choose
Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 10 rentals that welcome pets
Vacation rentals with a pool
10 properties feature pools
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
10 of Winter Park vacation rentals include wi-fi access
Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winter Park rentals
4.9 Average rating
Winter Park stays are highly rated by guests—averaging 4.9 out of 5!
Nearby attractions
Winter Park's top spots, include Orlando Science Center, Harry P. Leu Gardens, and Orlando Museum of Art

Top-rated hot tub rentals in Winter Park

Guests agree: these hot tub rentals are highly rated for location, cleanliness, and more.

1 of 1 pages1 / 1

Top guest favorite

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.

Home in Orlando

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

Outdoor spacesHot tubWalkability

4.96 out of 5 average rating, 172 reviews

Top guest favorite

A bright living space features a comfortable sectional sofa adorned with decorative pillows, paired with a light-colored armchair. A wooden coffee table sits on a textured area rug, while a ceiling fan and pendant lighting add modern touches. The kitchen bar is equipped with high stools, enhancing the open layout.

Guesthouse in Orlando

Livingston Hideaway • Walk To Lake Eola • Hot Tub

Welcome to Livingston Hideaway, a charming historic duplex in downtown Orlando, just two blocks from Lake Eola. This private space offers a quiet, residential feel while being steps from dining, nightlife, and events. Perfect for couples or business travelers, it features a private entrance, fenced outdoor area with hot tub and putting green, free parking, and fast Wi-Fi. Thoughtfully updated with modern comforts, Livingston Hideaway blends historic character with walkable downtown convenience.

Outdoor spacesHot tubCondition

4.99 out of 5 average rating, 113 reviews

Guest favorite

The living space features a large window allowing natural light to fill the room, showcasing a comfortable bed with an elegant coverlet. A game table and a full-sized pool table with cues are visible, alongside a modern kitchen area equipped with appliances.

Home in Oviedo

Chill 4/2, Lakefront, Game Room, Fishing & Hot Tub

The view of the lake from the patio is worth the price of admission! Tastefully decorated home & comfortable beds makes this a can't miss, home away from home! *Centrally Located (Walmart/Publix ~1 mi) *Close to Parks: Universal, Disney (30 min/40 min) *Short Drive to Beaches (1 hr) *UCF/Winter Park very close (5 min/15 min) *Bunk/Game Room w/pool table, Xbox & Full sized Pac-Man Arcade *Hot tub, Fishing, Games, Grill, Comfort *Close enough to do it all, far enough away for peace & quiet

Hot tubOutdoor spacesNearby

4.94 out of 5 average rating, 182 reviews

Top guest favorite

A serene pool area is surrounded by lush tropical greenery, including palm trees and bamboo. A spa is integrated into the pool with a stone wall feature. Chaises with striped cushions are positioned beside the water, and a spacious patio includes various stone pavers.

Guesthouse in Orlando

1924 Spanish Carriage House Lower

Enjoy a shared but private compound resort in the heart of downtown Orlando! Centrally located and within walking distance to major events at the Kia Center, Dr. Phillips Performing Arts Center, restaurants, and downtown nightlife. Park on site, relax and enjoy all that this historic home has to share! Besides a fresh and clean private lodging, you'll enjoy use of the tropical pool, hot tub, gas grill, covered seating and dining area. A washer and dryer are just steps away for your use.

BathroomOutdoor spacesCheckout

4.98 out of 5 average rating, 151 reviews

Guest favorite

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

BathroomOutdoor spacesAir conditioning

4.93 out of 5 average rating, 137 reviews

Top guest favorite

Guest suite in Orlando

Lakefront Hot Tub Retreat | Sunset View | Near UCF

Guest suite on private property overlooking beautiful Lake. just 10 min from UCF and 15 minutes to downtown Orlando. Disney is 34 miles while Universal is only 15 miles from the house. This cozy guest suite includes, a private parking spot, luxury rainfall shower, Comfortable Queen size bed, Smart TV, full size refrigerator, Keurig coffee maker, and washer and dryer. The back patio overlooking the lake makes it the perfect spot to watch the sunset while sitting in your private hot tub.

Hot tubOutdoor spacesCheck-in

4.99 out of 5 average rating, 200 reviews

Guest favorite

Home in Orlando

Key West Themed Lakefront Oasis with Sailboat

Please read the entire description before booking (including "policies and rules"). This is the lower half of a large lakehouse. Enjoy a resort-like experience with a private pool, heated spa, and stunning sunsets. With a fun Key West theme, it comfortably sleeps your group and features a separate entrance for complete privacy. Enjoy an outdoor kitchen, fire pit, and even a sailboat for a unique stay. Perfect for families seeking a memorable getaway. Kayaks are included for you to explore.

BathroomOutdoor spacesComfort

4.89 out of 5 average rating, 106 reviews

Top guest favorite

A screened-in pool area features a clear blue pool surrounded by landscaped greenery. A stone waterfall adds a natural touch, complemented by decorative plants and a Zen-inspired statue. Sunlight filters through the trees, enhancing the tranquil ambiance.

Home in Longwood

Relaxing 3-Bedroom Pool Getaway

This is a 3-bedroom 2-bath home, bathroom in the main bedroom connects directly to the pool. Accommodates comfortably up to 6 people. We have a wide range of amenities including wifi, TV, covered pool, fully equipped kitchen, and more! This is located in a quiet neighborhood located 30 minutes from Universal Studios, Sea World, and Disney World. The home comes with pool toys, board games, a space for an outdoor bar! The outdoor space is enclosed to keep out mosquitos and other pests.

Hot tubOutdoor spacesValue

4.97 out of 5 average rating, 132 reviews

Guest favorite

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!

BathroomOutdoor spacesBackyard

4.85 out of 5 average rating, 167 reviews

Top guest favorite

A private outdoor area is showcased, featuring a sparkling pool accompanied by a hot tub. Lush greenery and colorful plants surround the space, while comfortable seating options, including bright blue chairs, invite relaxation. A pergola provides shade, enhancing the tranquil atmosphere.

Guest suite in Orlando

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

Outdoor spacesHot tubShared spaces

4.93 out of 5 average rating, 417 reviews

Top guest favorite

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.

Hot tubBathroomComfort

4.99 out of 5 average rating, 209 reviews

Guest favorite

A scenic hot tub is surrounded by a stone patio and lush greenery, providing a serene outdoor space. Features include decorative tile accents and a gentle water feature, contributing to a calming atmosphere. Comfortable seating is positioned nearby for relaxation.

Home in Azalea Park

Hot Tub, Fire Pit, Private Backyard, King Bed

Welcome to our home centrally located between Downtown Orlando, UCF, Orlando Airport, and near to the parks. Our 2 bed 1.5 bath home with an additional sleeper sofa is a great vacation spot for your next visit to Central Florida. Beaches, Disney, the Amway Center, Dr. Phillips Center, UCF and so much more. Our home is a quiet place to rest your head at night or enjoy a relaxing beverage in our custom hot tub after a long day enjoying all Orlando has to offer.

BathroomOutdoor spacesLaundry

4.89 out of 5 average rating, 230 reviews