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$6,277 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.

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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

BathroomHot tubTV

4.96 out of 5 average rating, 173 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 tubLong stay

4.99 out of 5 average rating, 114 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

Outdoor spacesBathroomCondition

4.94 out of 5 average rating, 186 reviews

Top guest favorite

The exterior of the house showcases a striking blend of wood and stone finishes, featuring large windows that illuminate the interior. An expansive, clear blue pool reflects the sky, with a bridge extending over the water leading to the main entrance.

Villa in Orlando

The Lakeview Oasis - XL Pool & Jacuzzi - Orlando

Welcome to our stunning lakefront resort, where luxury meets tranquility! Dive into our expansive 100,000-gallon pool, enjoying a refreshing swim surrounded by breathtaking views. Inside, our tastefully designed space features midcentury modern amenities ensuring you have everything for a perfect getaway. Each bedroom offers serene views and plush bedding for a restful night’s sleep. Whether you seek adventure or relaxation, this is your ideal getaway. Book now for unforgettable memories!

Outdoor spacesBathroomQuiet

4.96 out of 5 average rating, 143 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 spacesTV

4.98 out of 5 average rating, 155 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 spacesHospitality

4.99 out of 5 average rating, 206 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

Outdoor spacesBathroomIndoor spaces

4.93 out of 5 average rating, 137 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!

Outdoor spacesBathroomTV

4.85 out of 5 average rating, 167 reviews

Guest favorite

Guesthouse in Winter Park

Cozy RV Glamping Backyard Oasis

Ever wanted to go glamping without owning an RV or booking a campsite? Nook Haven makes it easy. Enjoy a cozy backyard glamping retreat beneath beautiful oak trees with your very own private patio and a oasis featuring a pool, hot tub, fire pit, outdoor TV, and peaceful water features. Wake up to birds singing and unwind surrounded by nature. A perfect central location away from the tourist crowds, yet minutes from shopping, dining, and Orlando’s top attractions. ✨

Outdoor spacesBathroomKitchen

4.94 out of 5 average rating, 100 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 tubBathroomKitchen

4.99 out of 5 average rating, 210 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 spacesAir conditioning

4.89 out of 5 average rating, 231 reviews

Guest favorite

The exterior of a modern shipping container suite is displayed, featuring large windows that allow natural light to flood the interior. The surrounding landscape includes gravel and low-maintenance foliage, with a small deck leading to the entrance, emphasizing the blend of nature and contemporary design.

Tiny home in College Park

Luxury Shipping Container-HotTub- 30 min to Disney

Step into this unique experience: a shipping container transformed into a luxury 1 bedroom 1 bathroom suite. The space is perfect for couples, business travelers, tourists, and families. After a busy day in the parks or shopping, come back to a cozy outdoor paradise with lights strung up under a covered pergola. Lounge on the couch and enjoy a gas fireplace table, grill a meal on the Weber Spirit 2 gas grill, and soak your tired feet in the hot tub.

Outdoor spacesBathroomGetting around

4.93 out of 5 average rating, 200 reviews