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Condo holiday rentals in Winter Haven

Find and book unique condos on Airbnb

Top-rated condo rentals in Winter Haven

Guests agree: These condos are highly rated for location, cleanliness and more.

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Guest favourite
A resort-style pool area is surrounded by palm trees and lush landscaping, with inviting lounge chairs arranged nearby. The clear water reflects a bright sky, and a separate lounge area with a decorative façade is partially visible in the background.
Condo in Davenport
4.84 out of 5 average rating, 162 reviews

Orlando Spacious 2 Suites & Resort-Style Pool

Freshly renovated condo featuring TWO SPACIOUS PRIVATE SUITES, each with its own full bathroom — ideal for families, couples, and business stays. Located in ChampionsGate, 19 minutes from Disney and 30 minutes from Epic Universe and Universal Parks. Only 4 minutes from the Omni Orlando Resort at ChampionsGate, popular for golf, conferences, and special events. Enjoy full access to Tuscana Resort amenities at no extra cost, including a heated pool with conservation views and a relaxing hot tub.

Guest favourite
A bright living space is showcased, featuring a circular dining table set with four plates. A comfortable teal seating area is arranged against the wall, complemented by a nature-inspired wall art piece and greenery. Large glass doors provide a view of the outdoors and invite natural light.
Condo in Kissimmee
4.86 out of 5 average rating, 136 reviews

Stylish Condo 20 mins to Disney/King Bed

Escape to our lovely vacation villa, nestled in the vibrant heart of Orlando's premier golfing destination. Just a 7-mile drive from Disney attractions and 30 minutes from Orlando International Airport. Discover the awe-inspiring Reunion Resort, offering an array of delights. Indulge in delectable dining experiences, take a dip in sparkling pools, savor refreshing drinks at poolside bars and grill. Embark on an extraordinary getaway that exceeds all expectations. Book your stay with us today!

Guest favourite
A spacious living room is highlighted by a large television displaying a castle scene. A cozy sectional sofa in grey is complemented by vibrant green accent chairs. A contemporary coffee table sits in front, and the kitchen area features modern appliances visible in the background.
Condo in Four Corners
4.86 out of 5 average rating, 124 reviews

Magic Gate: Amazing Condo Near Disney Delights

Nestled in the prime locale of ChampionsGate Resort, just moments away from Disney and other major attractions, this 3BD/2BA unit awaits to make your vacation dreams come true. Spanning 1,558 Sq. Ft. has a fully equipped kitchen for culinary adventures, a cozy living room for family gatherings, a dedicated working station with desk and chair, a delightfully themed bedroom for the young, and a private game room ensuring endless family fun. Your ultimate retreat for cherished moments together!

Top Guest favourite
The living area is brightened by large windows offering views over the lake. A comfortable sofa and seating area complement a dining table set for six. A television is positioned adjacent to a ceiling fan, creating a welcoming space for relaxation and dining.
Condo in Orlando
4.95 out of 5 average rating, 224 reviews

Bird’s-Eye View! 2bd/2 King/2Bath Disney Area

2 KING/ 2 BATH/ 2 BALCONY condo for an ideal getaway. Condo located within 10 min. from Disney, 15 min. for Universal, 25 min. to Downtown Orlando, and 1 hr to the beach. From the 12th floor unit, you can enjoy the sunrise over Lake Bryan in the morning and sunset - book the extra day, you’re gonna wish you did. Yep, that's right - your view is SKY HIGH, the best in Central Florida. Unit is fully equipped and very luxurious. Parking included in price and there are NO ADDITIONAL RESORT FEES.

Top Guest favourite
A private balcony offers serene views of Lake Bryan and a swimming pool area. A small round table with two chairs invites relaxation, while warm colors from the sunset enhance the tranquil setting. Lush trees frame the scene, creating a peaceful atmosphere.
Condo in Orlando
4.97 out of 5 average rating, 429 reviews

Waterfront Condo minutes to Disney & Universal

Just minutes from Disney World and Universal Studios, this condo places you in the heart of Orlando’s top attractions, including Disney Springs, Islands of Adventure, SeaWorld, Magic Kingdom, Epcot, two outlet malls, and more. Relax on your private balcony with breathtaking views of Lake Bryan, or enjoy the resort-style pool with a full Tiki bar and dining menu. Additional perks include free parking, 24-hour security, and complimentary HBO & Netflix. No deposit required and no extra fees.

Guest favourite
An aerial view showcases a large pool area surrounded by lush landscaping and palm trees. The complex features a main pool, children's pool, and several cabanas. The orange-roofed building provides a welcoming focal point, while the well-kept grounds invite relaxation and fun.
Condo in Davenport
4.85 out of 5 average rating, 105 reviews

Spacious 2bd/2ba (No stairs) Disney/Championsgate

Tuscan style, *Newly Updated* clean & spacious 2 bd/ 2 ba FIRST FLOOR condo (no steps) located at the beautiful Tuscana Resort in Championsgate. Location is ideal for an Orlando vacation whether you're going to the parks, playing golf, shopping or just want to relax in the Florida sun. Facilities include free WiFi, large pool, jacuzzi, kids pool, free cabanas, gym, playground, grills, restaurant/bar onsite and NO RESORT FEES! We have no doubt that guests of all ages will enjoy their stay.

Guest favourite
An aerial view showcases a large pool surrounded by lounge chairs and palm trees. The pool area is defined by well-maintained landscaping, with a hot tub and a nearby shaded structure visible in the background, creating an inviting atmosphere.
Condo in Osceola County
4.89 out of 5 average rating, 120 reviews

Stunning Orlando Condo 3 BR/2 bath, pets OK

This resort community is amazing to drive around in, let alone stay in. Just 20 to 25 minutes away from Disney World and Universal Studios and everything Orlando has to offer. Convenience stores (7-11), Dunkin' Donuts, CVS pharmacy, restaurants and grocery stores within walking distance. Three gorgeous pools and hot tub Jacuzzis, and world-class gym in the resort in this gated community with security. 5 minute drive to Champions Gate and I-4 highway. Up to 2 dogs/cats ($25/day/animal)

Superhost
A living area features a gray sofa adorned with colorful pillows, a striped area rug, and two green armchairs. A wooden entertainment unit holds a large TV, while natural light filters through large windows dressed in sheer curtains, providing a connection to the outdoors.
Condo in Davenport
4.89 out of 5 average rating, 166 reviews

ChampionsGate Tuscana Resort - Minutes to Disney!

* 10 MINUTES to WALT DISNEY WORLD and other Orlando attractions! * Free access to HEATED RESORT POOL! * Located close to the POOL! * Over 1100 sq. ft of living space! * FULLY EQUIPPED kitchen! * Private SCREENED BALCONY! * WASHER & DRYER in the unit! * LINENS & BEACH TOWELS provided! * Starter supply of toiletries! * PACK 'N PLAY and HIGH CHAIR provided! * ELEVATOR! * FREE PARKING in front of the building! * Walking distance from local RESTAURANTS and GROCERY STORES! * GATED entrance!

Guest favourite
A large community pool reflects bright blue skies, framed by a spacious clubhouse featuring a yellow exterior. Sun loungers line the pool area, while palm trees add a touch of greenery. The clubhouse provides a welcoming space for relaxation and socializing by the pool.
Condo in Davenport
4.89 out of 5 average rating, 144 reviews

tranquil resort, near Disney, no extra fee.208

Platform fee 18.5% is paid by host. Gated community second floor 2 bedroom, 2 bath end unit, Large screened balcony. Guests have access to 4 community pools, a clubhouse, a tennis court, sand volleyball courts, scenic nature walk and an on-site restaurant/pool bar. Less than 10 miles from Walt Disney World. 1176 sqft of comfort and value—Comfortable stay at great value, not hotel-style luxury or perfection. **Primary guest registration with ID required through guest portal.

Guest favourite
Condo in Davenport
4.89 out of 5 average rating, 99 reviews

The thrill of 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
The living area features a light-filled open layout with two comfortable sofas facing a wooden coffee table. Colorful artwork adorns the walls, and a ceiling fan provides airflow. The modern kitchen is visible in the background, complemented by a dining area with stylish lighting.
Condo in Four Corners
4.88 out of 5 average rating, 129 reviews

Waterpark View, MickeyTheme 3BR Near Disney 1039

Welcome to Our Stunning 3-Bedroom condo– Perfect for Families & Groups! Experience luxury, comfort, and top-tier hospitality in our brand-new 3-bedroom, 2-bathroom home, designed to accommodate up to 8 guests. Whether you're planning a family vacation or a getaway with friends, our spacious retreat has everything you need for an unforgettable stay. Prime Location at Champions Gate Resort, just a few miles from the Disney area. Free Resort-Style Amenities

Top Guest favourite
A serene sunset over Old Lake Davenport is captured, with vibrant hues of orange and purple reflecting on the calm water. Silhouettes of trees line the horizon, creating a peaceful atmosphere as day transitions to night.
Condo in Davenport
4.93 out of 5 average rating, 119 reviews

Fabulous condo-Bahama Bay Resort, Close to Disney

Bahama Bay is a gated resort Bahama Bay Resort with a'colonial island vibe' on Old Lake Davenport. Disney parks are approximately a 20-minute drive away. Close to all resort amenities which include free use of charcoal and gas grills, pools, hot tubs, sauna, fitness center, dock, nature trails, children’s play area, pickle ball, tennis, basketball and more. Complimentary Wi-Fi is resort wide.

Popular amenities for Winter Haven condo rentals

Quick stats about condo rentals in Winter Haven

  • Nightly prices starting at

    Winter Haven holiday rentals start at $102 AUD per night before taxes and fees

  • Verified guest reviews

    Over 60 verified reviews to help you choose

  • 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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