Holiday rentals with a hot tub in Winter Haven

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Top-rated rentals with a hot tub in Winter Haven

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

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Top guest favourite
A single-story home features a light blue exterior with neatly trimmed hedges and palm trees in the front yard. The driveway leads to a two-car garage, and large windows reflect natural light, enhancing the welcoming ambiance of the property.
Home in Haines City
4.95 out of 5 average rating, 170 reviews

Luxury Home 4/3 near Disney, 2 Masters

Luxury 4 bedroom home located in a quiet, gated community about 15 miles from Disney World. The travel time to Disney will depend on the traffic but is usually between 30 and 40 minutes. Fully furnished with 2 master King bed suites, one queen bedroom and one bedroom with 2 twin beds. 3 full baths. 5 high definition televisions, high speed Wifi, free long distance phone calls to US, Canada and UK. Large pool and spa. Large game room with many games and activities for children of all ages.

Top guest favourite
The Tiny House is situated in a serene outdoor setting, featuring a light-blue exterior with a metal roof. A wooden porch with rocking chairs extends at the front, while the surrounding landscape includes lush green grass and landscaping along a gravel path.
Tiny home in Lakeland
4.99 out of 5 average rating, 141 reviews

Charming Tiny House on 5 acres with POOL/ HOT TUB

Escape to the heart of Lakeland where our charming Tiny House awaits. Nestled on 5 acres of tranquility, you'll experience the best of both worlds: a peaceful retreat and easy access to local shopping centers just a stone's throw away. The Tiny House is furnished with a queen size bed and a king sized bed in the upstairs loft, kitchen, full bath as well as a designated work area. Take a refreshing dip in the shared pool, unwind in the hot tub, or simply soak up some sun on the lounge chairs.

Top guest favourite
Home in Winter Haven
4.97 out of 5 average rating, 119 reviews

Adult-Only Getaway w/ Mermaid Pool | 18+, Private

🗝️ Adults only. Ready to turn your vacation into an experience? Explore your fantasies at our romantic getaway, featuring four themed bedroom options* designed to inspire you. Bring your fave toys, experiment with our spicy 🌶️ amenities, or peruse our shop to bring home a little extra to keep the fire going after you leave. You will love our mermaid pool 🧜🏿‍♀️, jetted spa, & stone meditation deck while you soak up the sun or stargaze. 🌟 Your next adventure awaits. (*1 per 2 guests)

Guest favourite
The exterior of a spacious home is presented, featuring a blue façade and a welcoming entrance. Lush tropical foliage surrounds the property, which is highlighted by palm trees and manicured lawns. A vibrant sunset casts colorful hues in the sky, enhancing the serene atmosphere.
Home in Winter Haven
4.98 out of 5 average rating, 132 reviews

Spectacular Waterfront Home in Winter Haven

Enjoy a wonderful family get away at this premier waterfront home on the famous Chain of (19) Lakes! Separate yourself from the crowd at this beautiful Cypress Gardens home set on an acre with lush tropical foliage and surrounded by 3 sides of water. Featuring a chef's kitchen, 2 private docks, the "New Florida Pool," 2 hot tubs, fire pit and many more amenities. Enjoy relaxed luxury at its finest. We are just a few minutes to Legoland, restaurants and shopping, but miles from ordinary!

Top guest favourite
Bungalow in Davenport
4.98 out of 5 average rating, 100 reviews

Spectacular sunset villa, stunning saltwater pool

Stunning sunset villa. Spectacular saltwater pool & spa. On the safe secure Highlands Reserve golf course . Beautiful conservation & golf course views. Luxury bespoke villa with 3 large bedrooms 2 bathrooms & occasional sofa bed in den. Fabulous deck ,private outlook . Walking distance Public,shops,restaurants or 5 min drive.15 mins Disney ,35 universal. Pool/Spa heat advised Oct/ April at an additional cost. There is a ring door bell at the property. NO EV charging allowed at the property

Guest favourite
A screened-in pool area features a spacious pool with clear blue water, surrounded by a concrete deck. A hot tub is adjacent, and a view of the lake is visible beyond. Lush greenery and a few lounge chairs complement the outdoor ambiance.
Home in Winter Haven
4.93 out of 5 average rating, 121 reviews

Fantastic Water Front Home on the Chain of Lakes

We are sharing our dream home with you! This home offers one of the best open layouts in Winter Haven. Great open kitchen with granite counter tops, stainless steel appliances, and numerous appliances. The large TV room features a Samsung smart 65" TV that connects to the Lanai/Pool area. A must see to believe! Numerous pictures provided to allow your mind to wonder. My interaction with you will be based on you. We have keypad entry for your convenience. I am here for you though!

Guest favourite
Home in Haines City
4.79 out of 5 average rating, 101 reviews

Entire Vacation Home- Legoland

Take a break in this oasis of peace where you can relax and have a cozy space to work from a mini office. This beautiful house with a strategic location near markets such as Walmart, Publix, Winn Dixie, as well as restaurants near the area, just minutes from the Disney attraction parks and approximately 30 minutes from Orlando International Airport. Feel calm in this community that offers 24 hour security and a gated community so that you can enjoy your family peacefully.

Guest favourite
Home in Davenport
4.96 out of 5 average rating, 128 reviews

Magical 2 pool-Spa & Game Room Villa near “Disney”

Looking for stay away from the crowd but yet close to Disney ? This private pool themed home is perfect to complete your Dream Disney family vacation you always wanted. 15 miles /Magic kingdom -13 miles from Disney springs -15 miles from Epcot center -25 miles / 30 Universal Studios Make your stay Magical with our custom made themed rooms Star Wars play area and kitchen Romantic master Arabian night Avatar pandora Moana bedroom Just less than 2 miles from I4 hw

Guest favourite
Apartment in Davenport
4.87 out of 5 average rating, 103 reviews

A luxurious living just 15 min/Disney!

Get ready for an exciting family adventure at our fabulous 2-bedroom condo in the breathtaking Tuscana Resort. Our unbeatable location places you at the center of all the action, whether you're eager to dive into the thrilling theme parks, tee off on a beautiful golf course, treat yourself to some fantastic shopping, or simply soak up the radiant Florida sun. This is the perfect spot for an unforgettable Orlando vacation—there's endless fun waiting for everyone!

Guest favourite
A private screened patio features a heated swimming pool and a Jacuzzi surrounded by a spacious deck. Outdoor seating is provided, with a dining table and lounge chairs positioned for relaxation. Sunlight glimmers on the water, creating a serene atmosphere.
Villa in Davenport
4.91 out of 5 average rating, 141 reviews

Cozy 3 bed, 2 bath home w/ pool and jacuzzi

Gorgeous 3 bedroom, 2-bathroom villa set on a 1/4 acre of land, with our own screened, private, heated swimming pool & Jacuzzi, and high speed internet. Situated in a quiet residential community on the sought after Sunridge Woods in Davenport, only 9 miles from Disney. Please note smoking or parties are NOT allowed in house premises. No pool heater available during May through October. **You also MUST be 21 or older to rent this property**

Guest favourite
Home in Davenport
4.89 out of 5 average rating, 108 reviews

PrivatePool•WaterPark•2 KingBeds•NearDisney•HotTub

🏝️ Welcome to Themed Retreat Villa – A Family-Focused Escape Near Orlando 🌴Pet Friendly Step into a one-of-a-kind family vacation experience at this 4- edroom, 3-bathroom themed villa—nestled in the same sought-after neighborhood as Blue Paradise Villa. Designed for fun, comfort, and unforgettable memories, this home offers a fully immersive stay with four uniquely themed bedrooms: 🎥 Avatar 🌿 Jungle Cruise 💚 Shrek 🌊 SpongeBob SquarePants

Guest favourite
The living area features a dark brown couch adorned with orange throw pillows, positioned near a small wooden table. A vibrant yellow door and light green cabinetry add a cheerful touch. A rug with floral patterns is laid on the floor, creating a cozy atmosphere.
Guest house in Winter Haven
4.8 out of 5 average rating, 121 reviews

Cozy guest house w/ fenced yard and hot tub

Whether you're looking for a base for your next adventure or a cozy home away from home, we've got you covered! Close to Legoland and less than an hour from both Disney World and Busch Gardens- located between Orlando and Tampa for the best of both worlds! Remodeled using reclaimed wood, this quaint home is minutes away from several lakes and nature trails and is a short walk away from Lake Cannon.

Popular amenities for rentals with a hot tub in Winter Haven

When is the best time to visit Winter Haven?

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Avg. price$247 SGD$264 SGD$273 SGD$249 SGD$212 SGD$223 SGD$214 SGD$206 SGD$241 SGD$240 SGD$203 SGD$254 SGD
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Quick stats about holiday rentals with a hot tub in Winter Haven

  • Total holiday rentals

    Explore 30 holiday rentals in Winter Haven

  • Nightly prices starting at

    Winter Haven holiday rentals start at $25 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,310 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Winter Haven holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winter Haven rentals

  • 4.8 Average rating

    Winter Haven stays are highly rated by guests – averaging 4.8 out of 5!

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