Condo vacation rentals in Winter Haven

4.95 out of 5 average rating, 132 reviews

Modern Lake view Condo 1 mile from Disney

You will love our updated 1 bedroom, 2 bathrooms, spacious 798 sq ft condo so close to Disney at Blue Heron Beach Resort in wonderful Lake Buena Vista, home to lots of restaurants and shopping! Enjoy spectacular sunrise views from your private balcony overlooking the lake. Resort amenities include large swimming pool, kiddie pool, hot tub, tiki bar, fitness rooms & game room. Located on peaceful Lake Bryan, you have access to water sports like kayaking, boating, jet skis & fishing on the lake.

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.

4.88 out of 5 average rating, 126 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!

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.

4.85 out of 5 average rating, 170 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.

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.

4.87 out of 5 average rating, 141 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!

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.

4.97 out of 5 average rating, 437 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.

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.

4.83 out of 5 average rating, 337 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!

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.

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!

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.

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!

A vibrant living area features a Super Mario-themed mural depicting iconic characters against a blue backdrop. Plush seating surrounds a coffee table styled with bright colors, while a playful rug showcases a character from the Mario universe, creating a fun and inviting atmosphere for relaxation and gaming.

4.95 out of 5 average rating, 178 reviews

Super Mario's Sky Suite - Epic Universe 3 BD SUITE

Welcome to your ultimate Nintendo getaway where every room is artfully and thoughtfully designed with a unique Super Mario theme. From custom decor to playful details, every corner is a tribute to the beloved world of Mario and friends. With classic Nintendo consoles at your fingertips, you’ll have everything you need to relive your favorite gaming memories in style. Unwind, play, and immerse yourself in the colorful world of Nintendo - TRUE SUPER MARIO ENTHUSIASTS ONLY :)

4.88 out of 5 average rating, 106 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!

4.88 out of 5 average rating, 138 reviews

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

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

4.96 out of 5 average rating, 107 reviews

Home Suite Home #2

Our Vacation Condo has a homey atmosphere and is very bright. The property has a small Gym that all guests are welcome to use. We are located about 25 to 30 minutes from Disney, 45 minutes from Universal and 1 hour from Legoland. We are in the Champions Gate area, in a quiet and safe Gated Community. The Property surrounded by restaurants, an Aldi's supermarket & Publix only 5 minutes away. You're sure to make fantastic memories with a stay at our place.

Popular amenities for Winter Haven condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

4.94 out of 5 average rating, 48 reviews

Condo in Reunion

Outstanding condo with sensational views on golf r

Superhost

The exterior of the contemporary condo is shown, featuring a stone accent wall and a wide staircase leading to the entrance. Lush greenery and colorful plants frame the pathway, while the upper balconies provide access to the second-floor units.

Condo in Haines City

4.78 out of 5 average rating, 36 reviews

Peaceful modern retreat

A modern kitchen is featured with elegant cabinetry, stainless steel appliances, and granite countertops. A dining table is positioned to the left, surrounded by several chairs. Natural light enters through a nearby doorway, enhancing the sleek tile and hardwood flooring throughout the space.

4.92 out of 5 average rating, 96 reviews

Gated resort minutes from all major attractions

5 out of 5 average rating, 16 reviews

New! Seven Eagles Hideaway at Reunion Resort

4.93 out of 5 average rating, 41 reviews

The living area features a blue couch with decorative pillows, a wooden coffee table, and a small dining table with white chairs. Natural light fills the space from sliding glass doors that open to a view of the outdoors, where patio chairs are positioned.

Condo in Mulberry

Heron Haven Comfy 2BR condo w/pool Great Location

A spacious outdoor pool area is surrounded by lush palm trees and vibrant landscaping. Lounge chairs are arranged around the pool, which is accented by umbrellas. Cobblestone paving offers a sturdy surface, inviting relaxation in a sunlit setting.

4.87 out of 5 average rating, 92 reviews

Spacious & Peaceful Condo Near Champions Gate

4.87 out of 5 average rating, 86 reviews

Ohana Oasis • Family-Friendly Disney Resort w/Pool

4.94 out of 5 average rating, 93 reviews

A spacious living area features modern furnishings in a light color scheme. A large sectional sofa is complemented by a decorative throw. A wall-mounted television displays a colorful animation. Natural light fills the space, highlighting the wooden accent wall.

Condo in Four Corners

Orlando Family Retreat – 3BR Near Parks

Pet-friendly condo rentals

An aerial view of a resort pool area showcases a winding pool surrounded by lush palm trees and tropical landscaping. Lounge chairs are arranged along the poolside, with shaded cabanas nearby. The resort features a terracotta roof and is set against a backdrop of greenery.

4.85 out of 5 average rating, 295 reviews

Magical Champions Gate 3/2 Tuscan Penthouse

The open-plan living area features a spacious dining table surrounded by elegant chairs, complemented by designer lighting. A comfortable sectional sofa is positioned opposite a large TV, while large windows allow natural light to illuminate the room.

4.95 out of 5 average rating, 170 reviews

Vista Cay Luxury Vision, Next to EPIC and OCCC

The image captures a vibrant pool area surrounded by lush palm trees and comfortable lounge chairs. An inviting infinity pool is centrally located, accompanied by cabanas and umbrellas. Multiple water slides are visible in one corner, enhancing the family-friendly atmosphere of the space.

4.93 out of 5 average rating, 141 reviews

Pet friendly Orlando area near ESPN Center

The living room features a spacious sectional sofa and a flat-screen TV mounted on a wooden console. Large glass doors provide a view of the patio and golf course, while natural light fills the room through the sheer curtains. A potted plant adds a touch of greenery.

4.95 out of 5 average rating, 148 reviews

3 Bedroom w/large patio on Resort Golf Course

Superhost

A spacious bedroom features a plush, tufted headboard and a large window allowing natural light to fill the room. Two bedside lamps provide additional illumination, while modern furnishings add contemporary flair. A round mirror is mounted above the bed, reflecting the inviting ambiance.

4.79 out of 5 average rating, 263 reviews

Brand New AwardWinning Renovated Condo Near Disney

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.

4.92 out of 5 average rating, 156 reviews

*NEW* Adventureland Stay / Sleeps 6 / Near Disney

The exterior of the Westgate Vacation Villas showcases an elegantly designed building with multiple levels. Soft lighting from street lamps illuminates the entrance. Rows of golf carts are parked in front, surrounded by manicured landscaping and palm trees under a clear blue sky.

4.87 out of 5 average rating, 506 reviews

Westgate Vacation Villas - 1 Bedroom

A modern living area is showcased with a sectional sofa, lounge chairs, and a coffee table. Open shelving displays decorative items. The kitchen area is visible in the background, featuring pendant lighting and sleek appliances. Natural light enhances the neutral tones of the space.

4.93 out of 5 average rating, 163 reviews

Remodeled 2BR/2BA Near Disney, Pool +WiFi +Parking

Condo rentals with a pool

5 out of 5 average rating, 12 reviews

2 bedroom Balcony King Suite - Lake & Pool view

An inviting living space features a modern gray sofa centered around a round coffee table, set on a plush area rug adorned with a playful pattern. A wall-mounted fan circulates air beneath a vibrant Mickey Mouse artwork, while a dining table for four is positioned nearby.

4.93 out of 5 average rating, 194 reviews

🏖 Resort Condo | 🎢 2mi -> Disney | 💦 Waterpark Fun

A balcony view showcases a round table and two chairs facing the expansive lake. The serene water reflects the clear blue sky, while the railing provides safety and openness to the picturesque landscape.

4.98 out of 5 average rating, 131 reviews

Disney Area Updated Lakefront Resort Condo 2 POOLS

A cozy, screened patio features a comfortable seating area with soft pillows and a round chair. A small table is set with natural placemats, surrounded by greenery and a lantern, providing a serene view of the lawn and trees outside.

5 out of 5 average rating, 80 reviews

Aqua Dream • Tropical Bahama Bay Condo Near Disney

4.95 out of 5 average rating, 79 reviews

Elegant 3BR Condo Near Disney w/ Pool

An aerial view captures the resort's landscaped grounds featuring a large swimming pool surrounded by tropical plants and lounge chairs. Below, the intimate living area displays a light-colored couch and a coffee table, while the bedroom showcases a cozy bed, wood accents, and natural light from the window.

5 out of 5 average rating, 37 reviews

Resort poolside condo/near Disney *no resort fees*

4.93 out of 5 average rating, 27 reviews

Sea World Orlando Apts - Parks/Convention Centre

A spacious living area features a comfortable sectional sofa and a coffee table atop a textured rug. Light blue walls enhance the bright atmosphere, while artwork adorns the walls. The open kitchen includes wooden cabinetry and modern appliances, with seating available at the countertop.