Condo vacation rentals in Winter Haven

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Top-rated condo rentals in Winter Haven

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Guest favorite
A spacious living area features large windows framed by bright curtains, providing natural light. A cozy bed is adorned with themed decor, and a comfortable sofa complements the surrounding furnishings. An aerial view showcases the resort's heated pool, surrounded by lush landscaping.
Condo in Kissimmee
4.9 out of 5 average rating, 251 reviews

Disney Oasis by the lake

Discover our charming condo near Disney, nestled in a resort-style community. Enjoy complimentary parking and No resort fees!The beautiful clubhouse offers a game room, gathering areas, and a fitness center. Unwind by the serene heated pool or take advantage of the second pool. Engage in activities at the golf cage, tennis, basketball, and volleyball courts, or let kids play at the playground. Stroll along scenic walking trails that wind through landscaped areas and ponds for a tranquil retreat.

Guest favorite
The living room features a comfortable sofa and two accent chairs, complemented by a wooden coffee table. A flat-screen TV is mounted on the wall, and natural light fills the space from sliding glass doors that lead to a private outdoor area.
Condo in Davenport
4.9 out of 5 average rating, 329 reviews

Amazing 2 Bed, 2 Bath condo only 10 min to Disney

Tuscana Resort Orlando is a Mediterranean-style villa resort minutes from DisneyWorld. Universal, Sea World ,LEGOLAND are close as well. A family friendly villa resort the amenities are top notch with a beautiful swimming complex that includes pool, hot tub, cabanas, kiddie pool, fitness centre. The very spacious 2-bed/2-bath condo is 1200sqft! Recently painted with fully equipped kitchen and washer and dryer! The unit has 1 King size bed in Master room and two twin beds in the spare bedroom.

Top guest favorite
An open living space features large French doors leading to a balcony, allowing natural light to brighten the area. Stylish seating is arranged around a coffee table, while artwork resembling a Marvel theme decorates a wall in the adjacent bedroom. Views of palm trees and a nearby pool can also be seen.
Condo in Kissimmee
4.97 out of 5 average rating, 128 reviews

Golf Front Luxury Penthouse: Views, Marvel, 2Pools

This modern 3-bedroom TOP FLOOR (with an ELEVATOR right to the door) luxury condo has one of the most PICTURESQUE VIEWS in the Reunion Resort of the Arnold Palmer PGA golf course. Combining STYLISH DESIGN and LUXURIOUS COMFORT, there are 2 KING bedrooms and a playful MARVEL themed bedroom with a classic Arcade machine & PlayStation. 4 TVs with DirecTV, free high-speed wifi, your own washer & dryer, access to 6 resort pools, 2 of which are only a 3 minute walk away, only a short drive to Disney.

Guest favorite
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
4.83 out of 5 average rating, 151 reviews

Orlando Spacious 2-Suites & Resort-Style Pool

BEAUTIFULLY RENOVATED 2BD/2BA condo next to ChampionsGate golf, 19 min from Disney, and 30 min from Epic Universe & Universal Parks. Enjoy Tuscana Resort’s top amenities—no extra fees! They include a large heated pool with a preservation view and relaxing hot tub. The resort holds TripAdvisor’s Certificate of Excellence. It is near Publix, Walgreens, Panera, Miller’s Ale House, and several cafes and restaurants, making it a perfect choice for exploring Orlando and Central Florida attractions.

Guest favorite
An open-concept living area features a spacious gray sofa with decorative pillows, a coffee table, and a dining set for six. Natural light fills the room through a large window, while a modern ceiling fan provides comfort. The kitchen area, visible in the background, showcases dark cabinetry and pendant lighting.
Condo in Reunion
4.92 out of 5 average rating, 238 reviews

NEW 3 Bedroom Resort Condo - Disney - Universal

Step into a luxurious three-bedroom condo in the desirable golf-community of Champions Gate Resort. Grab your clubs and take advantage of two award winning PGA golf courses. Also located 8 miles from Walt Disney World and 11 miles from Universal Studios, you will be perfectly situated to all the best Orlando has to offer. This getaway offers stunning nature and water views, an open-floor plan layout with fully equipped kitchen, breakfast bar, and spacious bedrooms that sleep up to 10 guests.

Top guest favorite
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, 420 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.

Top guest favorite
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
4.9 out of 5 average rating, 117 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)

Guest favorite
A serene pool area is surrounded by lush palm trees, with the ocean visible in the background. Comfortable lounge chairs are arranged around the pool, along with umbrellas offering shade. A 'No Diving' sign is posted, ensuring safety for all guests.
Condo in Davenport
4.85 out of 5 average rating, 112 reviews

peaceful resort condo. 601

Platform fee 18.5% is paid by host. Spacious two-bedroom unit offers approx. 1,400 sft of comfort in community with 24-hour security. Guests enjoy access to pools, a clubhouse, tennis and sand volleyball courts, a scenic nature trail, and an on-site restaurant. Conveniently located just 8 mi from Walt Disney World. A comfortable stay at great value. not perfection or hotel service. **Primary guest registration with ID required through guest portal.

Top guest favorite
The image showcases a resort pool surrounded by lounge chairs with palm trees in the background. A comfortable living area features a sectional couch and large windows allowing natural light. A themed bedroom displays a bed with a Mickey Mouse design. A backdrop of Cinderella Castle and Disney characters concludes the collage.
Condo in Kissimmee
4.94 out of 5 average rating, 104 reviews

Fireworks Nightly Penthouse, Two Exits From Disney

Welcome to our quietly gated condo at Tuscana Resort, which has a large resort style pool, bar and restaurant located in Champions Gate, it is one of the nicest communities near Disney World with dozens of restaurants and amenities. You'll be staying in a themed three bedroom unit only a few miles from Disney World and other theme parks! With a King Bed, Queen Bed and bunk beds, there is comfortable space for the entire family!

Guest favorite
The open living area features a round dining table with four chairs, a wall-mounted TV, and a comfortable sofa. Natural light enters through sliding glass doors leading to a scenic outdoor view. A rustic wood accent wall adds texture to the space.
Condo in Four Corners
4.88 out of 5 average rating, 171 reviews

"Ocean's Gate" - 2BD/2BA condo near Disney

Welcome to our beautiful ground-level condo! With the prime location at ChampionsGate Resort near Disney World and major parks, this 2BD/2BA condo unit is designed for your best accommodation. Spread out in 1,558 Sq. Ft., the unit offers a fully equipped kitchen, a cozy living room, a working station, and comfortable bedrooms. With access to the Clubhouse and resort amenities, you’ll spend amazing days in our home!

Top guest favorite
A Star Wars themed bedroom features two twin beds with themed bedding. A decorative quilt with a pattern of star fighters is placed over one bed, while the other is dressed in a space-themed cover. A bedside table holds a lamp shaped like a lightsaber, with blue walls adorned with framed artwork.
Condo in Kissimmee
4.91 out of 5 average rating, 187 reviews

Themed Resort Condo | Pool | Spa | Mins to Disney

The Magic Galaxy – an affordable 3 bedroom, 2 bath condo in the gated Windsor Palms resort, known for its cleanliness and thematic charm. The retreat features themes from Star Wars, Mickey Mouse, Jurassic World, and Harry Potter. Enjoy resort amenities like a pool, spa, splash pad, courts for basketball, tennis, and volleyball, a movie theater, game room, gym, Tiki bar and grill, and a sundry shop.

Top guest favorite
A cozy living area is furnished with a turquoise sofa and matching loveseat. A wooden coffee table is topped with decorative items. A television is positioned against the wall, displaying a vibrant image, while a lamp adds warm lighting beside it. An open layout reveals the kitchen area in the background.
Condo in Davenport
4.95 out of 5 average rating, 137 reviews

Lovely family-friendly condominium close to parks

Lovely accommodation for the whole family to create unforgettable memories. Close distance to the parks plus all Bahama Bay Resort amenities to your disposition. Disney parks 15 minutes. Universal Studios and Sea World 25-30 minutes. Relax in a cozy condominium or play and enjoy of a whole community designed for great vacation experience.

Popular amenities for Winter Haven condo rentals

Quick stats about condo rentals in Winter Haven

  • Nightly prices starting at

    Winter Haven vacation rentals start at ﺩ.ﺇ257 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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