Condo holiday rentals in Winter Haven

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Quick stats about condo rentals in Winter Haven

Nightly prices starting at
Winter Haven holiday rentals start at $122 NZD per night before taxes and fees
Verified guest reviews
Over 70 verified reviews to help you choose
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winter Haven rentals
4.6 Average rating
Winter Haven stays receive an average rating of 4.6 out of 5 from guests

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

Two thatched-roof cabanas are set on a sandy area, providing shaded spots for relaxation. Lush greenery surrounds the space, and a hammock can be seen hanging nearby. The clear blue sky enhances the tranquil environment.

Condo in Davenport

4.88 out of 5 average rating, 128 reviews

Bahama Bay Hideaway - Condo by Orlando theme parks

Modern condo in beautiful Bahama Bay resort, in the heart of Orlando's theme park district. Perfect for families, couples or young groups, the condo is just 20 minutes from Disney, 35 from Universal, and a couple of hours from Florida's east or west coast. The spacious condo is on the second floor with two private balconies. The stunning resort includes walking/running routes around Lake Davenport, on-site dining and four luxurious pools with hot tubs. There's 24/7 security and free parking too!

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

4.85 out of 5 average rating, 173 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

4.87 out of 5 average rating, 143 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

4.88 out of 5 average rating, 136 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!

Guest favourite

The living area includes a sectional sofa and an armchair, accented by soft throw pillows. A wooden coffee table sits in the center, with a basket for convenience. Large sliding glass doors lead to a patio, framed by blue curtains, allowing natural light to fill the space.

Condo in Davenport

4.97 out of 5 average rating, 242 reviews

Disney Orlando Bahama Bay Resort, Pools & Games!

➤ Caribbean-Style 1st floor 3 Bed 2 Bath Condo with Pools & Hot Tubs • Near Walt Disney World, Universal Studios, Sea World Orlando & Restaurants ! ★ RESORT AMENTIES: •4 heated pools, 6 hot tubs, children's splash park •Sandy Beach on Lake Davenport · BBQ grills •Tennis, TT , basketball, volleyball, & a fishing dock •Closest unit to Gran Bahama Pool •The unit has everything you need including linens, towels •Fully equipped kitchen, Dining, Living Room ➤ Please add us to your WISHLIST !

Guest favourite

Condo in Davenport

4.85 out of 5 average rating, 111 reviews

Spacious 2bd/2ba 1st floor- No stairs Disney/golf

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, 123 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 favourite

A welcoming living area is highlighted with a comfortable, light-toned sofa adorned with patterned cushions. An open layout leads to a modern kitchen, visible in the background, while ambient lighting creates a cozy atmosphere. Entertainment options are displayed, including Smart TV access to various streaming services.

Condo in Davenport

4.82 out of 5 average rating, 342 reviews

3/2 Lake View King Bed Disney Family Condo Resort

✨ Second-Floor Condo (No Elevator) Completely remodeled 3-bedroom, 2-bath condo in a Caribbean-style resort 🏖️. Features include a Kids Splash Zone, spa, restaurants, lake with dock, and private beach. Smart TVs (Netflix & more). 🌸 Relax on the balcony with peaceful views. Conveniently located, just 15 minutes from Disney, perfect for an unforgettable getaway! 🚗NEED A CAR? Ask us about our 8-passenger minivan. You can plan your stay and car rental all in one go. Ask us for the link!

Top Guest favourite

A view of the pool area is visible from the second-floor balcony. The inviting pool features surrounding lounge chairs and well-maintained landscaping. The building's exterior is highlighted by stone accents, with a common area structure visible in the background, framed by greenery and pathways.

Condo in Davenport

4.97 out of 5 average rating, 105 reviews

No Cleaning fee - 3 bed 3 full bath near Disney

New Paint, New Carpets, New bedding, completely refurbished during lockdown and ready for guests. Mediterranean Style resort with 3 pools & Gym. 1,400+ sq. ft Condominium with 3 bedrooms and THREE BATHROOMS, everyone gets their own bathroom. Bella Piazza Resort is a short walk to Publix Supermarket, Irish Pub, English Pub, several other restaurants and take aways, don't want to drive you don't have to. Conveniently located for all the theme parks, especially Disney Parks. NO RESORT FEES!

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, 171 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

The exterior of Bella Piazza features a Mediterranean-style architecture with a stone facade and terracotta roof. Lush landscaping surrounds the building, including palm trees and manicured grass. A fountain stands in front of the entrance, enhancing the inviting ambiance of the property.

Condo in Davenport

4.9 out of 5 average rating, 207 reviews

3Bdr, 3BA, 8 mi to Disney. Close to restaurants

3 br, 3 bath Second floor condo in Elevator building. Ceiling fan in each room. Private balcony overlooking the pool area. The 3 BATHROOMS offer privacy! Quiet & relaxing vocation home for quiet groups. BBQ by pool. next to clubhouse and business center. Walk distance to restaurants and grocery. 1227 sqft comfortable stay at great value—ideal for guests seeking relaxation, not perfection or hotel-style service. **Primary guest registration with ID required through guest portal.

Guest favourite

Condo in Davenport

4.88 out of 5 average rating, 109 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!