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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

Hot tubOutdoor spacesKitchen

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 tubGrill

4.99 out of 5 average rating, 114 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!

Hot tubBathroomValue

4.96 out of 5 average rating, 144 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.

Outdoor spacesHot tubParking

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.

BathroomOutdoor spacesWifi

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 spacesBathroomComfort

4.92 out of 5 average rating, 138 reviews
Guest favorite
Guesthouse in Winter Park

Cozy RV Stay|Hot Tub•Pool• FirePit •Private Patio

Escape to a cozy Winter Park glamping retreat beneath beautiful oak trees. Enjoy your own private patio plus access to our backyard oasis with a pool, hot tub, fire pit, outdoor TV & peaceful water feature. When you’re ready to explore, discover Winter Park’s charming boutiques, cafés, art galleries, museums, scenic boat tours, wine experiences & historic areas perfect for date nights or days out exploring. Then come home, unwind under the string lights & enjoy the best of both worlds. ✨

BathroomOutdoor spacesCondition

4.94 out of 5 average rating, 100 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!

Hot tubBathroomCondition

4.85 out of 5 average rating, 167 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 tubOutdoor spacesNearby

4.99 out of 5 average rating, 210 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.

Hot tubBathroomAmenities

4.93 out of 5 average rating, 200 reviews
Guest favorite
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.
Home in Orlando

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.

Hot tubBathroomGrill

4.92 out of 5 average rating, 181 reviews
Superhost
A stylish seating area features a plush red couch adorned with decorative pillows, complemented by a neon 'SPEAKEASY' sign. In a second section, paddleboards and kayaks are neatly arranged near a wooden dock overlooking the lake, while a vibrant outdoor space is illuminated at night with garden lights.
Home in Azalea Park

Retreat | Lake Hot Tub Paddle Boards Speakeasy

Modern, spacious, and perfect for families! Enjoy private lake access with paddle boards, great fishing, yard games, and a tropical backyard with VIP cabanas. Kids play, parents relax — or sneak off to the hidden speakeasy in a converted shed. Unwind in the hot tub, stream with full WiFi, and sleep soundly in ultra-comfy beds. Tons of parking, great vibes, and fun for all ages. Your family getaway starts here!

Hot tubOutdoor spacesWifi

4.88 out of 5 average rating, 189 reviews

Popular amenities for Winter Park hot tub rentals

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a hot tub

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

Outdoor spacesBathroomWifi

4.97 out of 5 average rating, 133 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

Hot tubOutdoor spacesLayout

4.94 out of 5 average rating, 186 reviews
Top guest favorite
The pool area is enclosed with a protective screen, featuring a spacious heated pool surrounded by a wooden deck. A green umbrella provides shade over a small table and chairs, while a bright yellow building is visible in the background.
Home in Altamonte Springs

Tropical Pool/Spa Home-Disney-Theme Parks-Beaches

BathroomOutdoor spacesLong stay

4.98 out of 5 average rating, 120 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

BathroomOutdoor spacesSleep quality

4.89 out of 5 average rating, 231 reviews
Guest favorite
Home in Orlando

Key West Themed Lakefront Oasis with Sailboat

BathroomOutdoor spacesDecor

4.89 out of 5 average rating, 106 reviews
Superhost
A cozy living area features a plush gray sofa adorned with decorative pillows and a glass coffee table atop a colorful area rug. Two accent chairs in yellow and red provide additional seating. An archway leads to a modern kitchen with sleek bar stools.
Home in Union Park

Stylish Orlando Retreat

BathroomOutdoor spacesWifi

4.89 out of 5 average rating, 303 reviews
Guest favorite
An open living space features a dining area with a modern table set for four. Industrial-style stools provide seating. The background reveals a connected kitchen with stainless steel appliances. Natural light fills the room through large windows, creating a bright and inviting atmosphere.
Home in Orlando

Cozy 3-bedroom home 4-min from Universal Studios

Outdoor spacesHot tubWalkability

4.94 out of 5 average rating, 197 reviews
Guest favorite
Two red kayaks are positioned on a tree trunk beside a peaceful lake, reflecting blue skies and lush greenery. A covered patio area is visible, alongside a hot tub, creating an inviting space for relaxation by the water.
Home in Lake Mary

Independent Unique Lake guest house/kayaks/jacuzzy

Hot tubOutdoor spacesCheckout

4.85 out of 5 average rating, 376 reviews

Villa rentals with a hot tub

Top guest favorite
Villa in Kissimmee

Luxury Villa! /Game Room/ Pool Heater

Hot tubBathroomIndoor spaces

4.93 out of 5 average rating, 121 reviews
Top guest favorite
The exterior of a single-story home is presented, featuring a paved driveway leading to a two-car garage. Lush green grass surrounds the house, and palm trees are positioned near the entrance. A colorful sunset sky provides a picturesque backdrop.
Villa in Kissimmee

Pet-Friendly Disney Theme 4BR•Heated Pool•Game Rm

BathroomHot tubIndoor spaces

4.99 out of 5 average rating, 161 reviews
Guest favorite
A private theater is presented with six reclining seats, arranged in rows facing a large 155-inch screen. The room is accented by dark walls and illuminated with blue lighting, enhancing the cinematic atmosphere. Movie posters adorn the walls, contributing to the entertainment theme.
Villa in Kissimmee

Disney Fun Time 8BD 4K Movie Theater Jacuzzi Pool

Hot tubOutdoor spacesCheckout

4.91 out of 5 average rating, 106 reviews
Superhost
The image captures a view from the pool, showcasing the villa's large glass windows and covered outdoor seating area. Loungers are positioned around the pool, offering ample space for relaxation. The sparkling water reflects the modern architecture above, framed by a screened enclosure.
Villa in Kissimmee

Private Pool & Free Heat - Close to Disney!

Hot tubOutdoor spacesFamily

4.91 out of 5 average rating, 142 reviews
Guest favorite
Villa in Kissimmee

Storey Lake 10BR Villa Near Disney, Pool Waterpark

Hot tubBathroomLaundry

4.95 out of 5 average rating, 136 reviews
Guest favorite
A private pool is framed by a stone patio, with lounge chairs positioned nearby for relaxation. Lush greenery and palm trees surround the area, creating a serene outdoor environment. A spa is positioned next to the pool, providing an inviting space for relaxation.
Villa in Four Corners

The Golden Bear Villa | Private Pool & Theater

Outdoor spacesBathroomTV

4.97 out of 5 average rating, 124 reviews
Top guest favorite
A screened-in pool area features inviting turquoise water, complemented by a sunken hot tub. Outdoor furniture, including a dining set and lounge chairs, is arranged beneath soft, ambient lighting. A basketball hoop is positioned near the pool, with lush greenery visible beyond the enclosure.
Villa in Kissimmee

Villa Sol Peaceful Pool/Hot Tub Home

Outdoor spacesBathroomQuiet

5.0 out of 5 average rating, 142 reviews
Guest favorite
A spacious living room features a large sectional sofa arranged around a wall-mounted television. Natural light enters through large windows, enhancing the airy atmosphere. A game room showcases a pool table and arcade games, while the private pool area is enclosed with a netted structure, ensuring safety and comfort.
Villa in Kissimmee

Unique 6BR Home • Private Pool & Full Game Room +

BathroomOutdoor spacesAccuracy

4.87 out of 5 average rating, 150 reviews

Cabin rentals with a hot tub

Top guest favorite
A simple cabin rests on a lush green lawn, surrounded by tall trees. A small porch extends from the front of the cabin, and the serene setting is complemented by a calm waterway in the foreground, with scattered lily pads visible.
Cabin in St. Cloud

“Tailypo” - Charming Newly Remodeled Studio Cabin

Outdoor spacesBathroomAccuracy

4.96 out of 5 average rating, 121 reviews
Guest favorite
A hammock is gently suspended between trees in a wooded area, inviting relaxation. The log cabin is visible in the background, with vibrant green chairs arranged nearby. Sunlight filters through the trees, enhancing the serene outdoor setting.
Cabin in Geneva

Relaxing Summer Retreat | Near Disney & Beaches

Hot tubOutdoor spacesAmenities

5.0 out of 5 average rating, 38 reviews
Top guest favorite
Cabin in Kissimmee

Authentic Disney Fort Wilderness Cabin near WDW-2

BathroomIndoor spacesDecor

5.0 out of 5 average rating, 36 reviews
Guest favorite
A cozy cabin exterior features natural wood siding, complemented by vibrant green doors. A spacious front deck with a railing offers seating, while a picnic table sits on the grassy area nearby, surrounded by lush trees and foliage.
Cabin in Kissimmee

Mouse House Cabin/ Legacy Disney Fort Wilderness

Outdoor spacesTVFamily

4.98 out of 5 average rating, 48 reviews
Guest favorite
Cabin in Kissimmee

Winnie the Pooh Themed Tiny Home • Near Disney•

BathroomSleep qualityCleanliness

4.95 out of 5 average rating, 20 reviews
Guest favorite
Cabin in Kissimmee

The porch

Hot tubLocationAccuracy

4.89 out of 5 average rating, 19 reviews
Cabin in Kissimmee

Lichita's House

Parks

New place to stayAn outdoor seating area is displayed, featuring a square table surrounded by four light-colored chairs. The setting is complemented by a pathway of large stone pavers and nearby greenery, with a yellow exterior wall and glass doors providing a welcoming entrance.
Cabin in Kissimmee

Happy Margaritaville Cottage w Amenity Access

Hot tubCheck-inCleanliness

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