Condo holiday rentals in Winter Haven

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Top-rated condo rentals in Winter Haven

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Guest favourite
A spacious bedroom is adorned with a blue accent wall featuring a starry pattern. A large, plush bed covered in a soft blue throw and white linens is centrally placed. A framed picture is mounted above the bed, and a small plant adds a touch of greenery.
Condo in Kissimmee
4.9 out of 5 average rating, 249 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 favourite
The master bedroom features a spacious bed with a tufted headboard, complemented by a decorative mirror and framed artwork. Natural light streams in through a large window, revealing views of greenery. A warm color palette and wood accents create a relaxing atmosphere.
Condo in Kissimmee
4.94 out of 5 average rating, 132 reviews

*NEW* Adventureland Stay / Sleeps 6 / Near Disney

Welcome to the Adventureland bungalow! This 2 bd/ 2 ba stay features a Tiki room living room with a sofa bed. The upgraded kitchen and bamboo bar are perfect to kick back and relax, or enjoy the screened in patio with tiki torches and seating area. The Jungle Cruise master bedroom features a king size bed and lovely waterfront views with lush greenery. The Pirate bedroom is fit for a captain (or two!) and has two twin xl beds. Air conditioning throughout. Located on the third floor/stair access.

Guest favourite
The living room features a grey sofa adorned with decorative pillows, paired with a glass coffee table and a vibrant area rug. The open space leads to a dining area and modern kitchen, highlighted by yellow bar stools at the countertop under soft lighting.
Condo in Orlando
4.86 out of 5 average rating, 331 reviews

BreathtakingView-1BR/2BA-1 Mile to Disney-Sleeps 5

Located 1 mile to Disney Springs in a Gated-Community A NEWLY REFURBISHED Spacious 1-bedroom, 2-bath Condo in Lakefront luxury @ Blue Heron Beach Resort nestled on shores of 400+ acre Lake Bryan, 2 blocks off I4 @ Lake Buena Vista exit. This luxurious condo overlooks the Pool & Lake Bryan. Sleeps 4 It’s all here! The ultimate Walt Disney World vacation right here at your fingertips! From the best of Disney or Work Travel this property offers the perfect environment to spend a lifelong memory

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
4.82 out of 5 average rating, 146 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 favourite
A Pirates of the Caribbean themed bedroom is presented with two twin beds, featuring bedding adorned with nautical maps. The wall is decorated with a large mural of a pirate skull, and a bedside lamp provides soft lighting. Dark curtains frame a window.
Condo in Davenport
4.95 out of 5 average rating, 110 reviews

Themed Resort Condo-Pool | Spa | Beach | 1st Floor

The Magic Treasure – an affordably luxurious 3-bedroom, 2-bath first-floor condo in the family-friendly Bahama Bay resort, known for its cleanliness and thematic allure. A short drive from Disney parks, the master suite features a king bed and en-suite bathroom. Guests can enjoy the Pirates of the Caribbean themed bedroom or the Finding Nemo themed bedroom. Resort amenities include multiple pools, hot tubs, a sandy beach, splash pad, game room, day spa, tiki bar, restaurant, and sundry shop.

Top Guest favourite
The exterior of a modern two-story building is shown, featuring a combination of light grey and white siding. Lush palm trees frame the front, with a paved driveway visible. A parked vehicle is positioned in front of the entrance, and a sunny blue sky is above.
Condo in Champions Gate
4.95 out of 5 average rating, 147 reviews

Spacious Condo for 8 Golf Waterpark 15 min Disney

Welcome to your Orlando family getaway! This 3-BR condo at Champions Gate offers a direct Golf Course view and sleeps up to 4 adults and four kids. Two rooms feature King beds, and one has two Full beds. Just 15 mins from Disney Parks! Enjoy complimentary access to the fabulous Oasis Club (3 pools, gym, Tiki Bar) and the Retreat Club. Full kitchen access saves you money. Champions Gate also boasts a 36-hole Greg Norman championship golf course! Location & luxury for all ages.

Guest favourite
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, 161 reviews

Premium Tuscana Resort Condo - 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
An aerial view captures the sandy beach area lined with palm trees and shaded cabanas. Lounge chairs are arranged neatly in front of the beach, while a pool area with vibrant blue water is visible in the background surrounded by lush landscaping.
Condo in Davenport
4.85 out of 5 average rating, 188 reviews

Full-Service Gated Resort, Disney, Universal, MCO!

Minutes to Theme Parks, Full-Service Resort, Space for the Whole Family, Pools, Splash Pad & Much More! This 3-bedroom villa at Bahama Bay Resort & Spa is ideal for family or group vacations. Comfortable queen beds are standard in the main bedroom and first guest bedroom, while the second guest bedroom features two twin beds. The villa features two full bathrooms. All resort amenities are free and available to guests. 24/7 guard gate and front desk service.

Top Guest favourite
An aerial view of the resort's expansive pool area features multiple pools, including a lazy river and heated pools, surrounded by lush palm trees. Lounge chairs are arranged neatly along the deck, with red umbrellas providing shade throughout the space.
Condo in Davenport
4.89 out of 5 average rating, 159 reviews

Resort fee paid, 3bd/3ba townhome, lazy river, 323

Platform fee 18.5% is paid by host. Host paid resort fee for guest stay, added value at $22/day plus tax. A comfortable stay at great value. not perfection or hotel service. The resort includes Heated pools, lazy river, fitness center, barbecue stations, two bars including poolside Tiki bar, arcade, Cenot Spa, Restaurant & Pub, less than 1 mile from Publix store & golf course. **Primary guest registration with ID required through guest portal.

Superhost
A spacious dining area features a modern table set for six, complemented by a chandelier above. A living space is visible in the background, with a comfortable couch and large windows allowing natural light. Decorative elements include a floral arrangement on the table.
Condo in Davenport
4.81 out of 5 average rating, 178 reviews

3BR/2BA Mediterranean Style Condo Near Disney

Newly renovated and refreshed. 10 mins from Disney, this Mediterranean-inspired condo is located at the World Famous Champions Gate Golf Course! Amenities include swimming pool, hot tub, cinema, fitness center, bbq area, tavern bar, spa services, restaurants etc. Tuscana Resorts has received the Certificate of Excellence from TripAdvisor for 5 years running!

Top Guest favourite
A balcony view captures a vibrant sunset over Lake Bryan, with hues of pink and orange reflected on the water. Outdoor seating includes two chairs and a small round table, inviting relaxation while enjoying the scenic surroundings.
Condo in Orlando
4.98 out of 5 average rating, 221 reviews

Lakefront Resort Condo near Disney and Universal

Your magical getaway starts here—just minutes from Disney & Universal Parks ! Relax on your balcony overlooking stunning Lake Bryan, splash in the heated pool, sip at the Tiki bar, and stream your favorite shows with HBO & Netflix. Concierge for park tickets, free parking, 24-hr security. No deposit, no extra fees—just fun, sun, and memories waiting!

Top Guest favourite
Condo in Kissimmee
4.97 out of 5 average rating, 131 reviews

Sol y Mar Resort Style Condo - NO RESORT FEES

This 3 bedroom, 2 bath condo has everything you could possibly need for the perfect vacation away from home. This is a gated community with 24 hour security. Located just a few miles from Walt Disney World and the Magic Kingdom, Margaritaville Resort, Epcot, Animal Kingdom, and Hollywood Studios theme parks.

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 $121 NZD per night before taxes and fees

  • Verified guest reviews

    Over 50 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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