Condo vacation rentals in Winter Haven

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.

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.

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.

4.82 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.

A modern living area features a white sectional sofa and a stylish coffee table with gold accents. A flat-screen television is mounted on the wall, complemented by minimalist shelving. Large windows dressed with sheer curtains allow natural light to fill the space, creating a bright and welcoming environment.

4.94 out of 5 average rating, 101 reviews

Resort Style Sunshine Oasis near Theme Parks

Discover Orlando's charm at our resort-style oasis in a gated community with lots of amenities! Nestled near Disney, this modern haven features 2 stunning pools for ultimate relaxation. Delight in nearby restaurants, perfect for foodies. Families will love the kid-friendly atmosphere, and fitness enthusiasts can stay active in the on-site gym. Our clean, contemporary design ensures a comfortable stay, making it an ideal choice for your Orlando getaway. Conveniently located on the first floor.

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.

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.

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, 413 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.

4.95 out of 5 average rating, 147 reviews

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

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.

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, 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!

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.

4.88 out of 5 average rating, 138 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.

4.87 out of 5 average rating, 167 reviews

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

"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!

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.

4.93 out of 5 average rating, 117 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.

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.

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!

4.97 out of 5 average rating, 131 reviews

Sol and 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

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

5 out of 5 average rating, 66 reviews

The exterior features a single-car garage with a white door and steps leading to a private entrance. The adjacent yard is bordered by a fence, providing a sense of privacy. Inside, a modern kitchen is visible, showcasing sleek cabinetry, a spacious island, and ample natural light from large windows.

Condo in Auburndale

Costa 1BRD LakeFront Condo | Peaceful | Paradise

A cozy bedroom is featured, showcasing a spacious bed with a beige and white coverlet. Two bedside tables with lamps are placed on either side. Framed artwork adorns the walls, and a wooden dresser adds warm tones to the room.

4.92 out of 5 average rating, 85 reviews

Spacious 2BDR Disney Villa – Pool & Hot Tub

An aerial view captures a resort-style pool surrounded by lush greenery. The pool features multiple sections and shaded seating areas. Sun loungers and umbrellas are arranged around the water, with palm trees adding a tropical touch. Nearby, a winding road leads through the community.

4.79 out of 5 average rating, 82 reviews

Lovely 1 Bedroom Apartment with Pool and Jacuzzi!

5 out of 5 average rating, 5 reviews

Disney Area! Modern Luxe King Villa! Resort Pool!

4.82 out of 5 average rating, 90 reviews

Newly Remodeled 2-bedroom 15 minutes to the parks

4.75 out of 5 average rating, 4 reviews

The spacious living area features a sofa and two accent chairs arranged around a coffee table, creating a welcoming setting. A dining table for four is visible nearby, and the kitchen area can be seen in the background. Natural light brightens the neutral-toned decor.

Condo in Winter Haven

Cozy 2BR Lake Condo w/ Pool Access

4.98 out of 5 average rating, 51 reviews

The living area features a brown leather sofa, two green accent chairs, and a wooden coffee table atop a grey rug. A dining area with metal chairs is visible in the background, along with kitchen cabinetry and pendant lighting that provides a modern touch.

Condo in Four Corners

Condo Near Theme Parks!

5 out of 5 average rating, 10 reviews

Cozy condo in waterpark resorts and golf course

Pet-friendly condo rentals

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.

4.92 out of 5 average rating, 121 reviews

Pet friendly Orlando area near ESPN Center

The living room features large sliding glass doors that open to the balcony, providing a view of the lake. A contemporary electric fireplace sits beneath a 65-inch smart TV. Comfortable seating includes a sofa, an armchair, and a coffee table, with warm curtains adding a touch of color.

4.96 out of 5 average rating, 102 reviews

Penthouse Lakeview Minutes to Disney/ Universal

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, 247 reviews

Brand New AwardWinning Renovated Condo Near Disney

A spacious living area features large windows allowing natural light and views of green trees outside. A sectional sofa in a neutral tone is complemented by decorative blue cushions. A glass coffee table rests on a textured area rug, and a television is positioned on a low media console.

4.9 out of 5 average rating, 119 reviews

Home away from home for the Parks!

A clear view of a pool surrounded by lounge chairs and palm trees, reflecting the sunlight. Umbrellas provide shade, and green lawns are visible in the background. The calm water enhances the serene environment, creating a relaxing outdoor space.

4.82 out of 5 average rating, 232 reviews

Family Friendly I Mins from Disney I Resort Pool

4.78 out of 5 average rating, 194 reviews

Amazing Pet-Friendly 3BR condo near Epic Universe!

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.

4.85 out of 5 average rating, 119 reviews

Westgate Vacation Villas - 1 Bedroom

A stylish living room features a large gray sectional sofa complemented by bright orange cushions. A black coffee table stands in the center, while two lamps provide soft lighting. Wall decor includes mirrors and artwork, enhancing the airy ambiance created by the large windows.

4.8 out of 5 average rating, 140 reviews

Newly Renovated Premium Condo, Vista Cay - 2002

Condo rentals with a pool

The living room and dining area feature a spacious layout with two brown leather couches, a beige armchair, and a wooden dining table seating four. A large flat-screen TV is mounted on the wall, and natural light enters through the large windows dressed with dark curtains.

4.98 out of 5 average rating, 42 reviews

South Orlando Family Condo near Disney

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, 83 reviews

Gated resort minutes from all major attractions

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, 68 reviews

Aqua Dream > Tropical Bahama Bay Condo Near Disney

An airy dining area features a round table with five elegant chairs, complemented by a modern chandelier. A backdrop of mirrors adds depth, while the kitchen with stainless appliances is visible in the background, enhancing the open layout of the space.

4.91 out of 5 average rating, 45 reviews

Beautiful NEWLY remodeled 2BD CONDO close toDISNEY

A large zero-entry pool is illuminated with soft lighting, surrounded by palm trees and sun loungers. The resort's main building, featuring a tile roof and stone accents, is visible in the background, providing a welcoming atmosphere for guests.

4.88 out of 5 average rating, 69 reviews

Ohana Oasis • Family-Friendly Disney Resort w/Pool

The exterior of Wyndham Bonnet Creek Resort is framed by palm trees, showcasing a large building with multiple stories and a welcoming entrance. A landscaped area with pools and seating is visible in the foreground. Mickey Mouse is illustrated in the corner, enhancing the family-friendly atmosphere.

4.98 out of 5 average rating, 64 reviews

Wyndham Bonnet Creek ツ 1 Bedroom Deluxe!

A modern living room is featured with a plush gray sectional sofa and an accent chair. A sleek coffee table sits in the center, surrounded by a soft area rug. A large television displays a serene beach scene, while a dining area can be seen in the background, illuminated by a contemporary light fixture.

4.86 out of 5 average rating, 71 reviews

Cozy escape 3BD/Sleeps8/Disney/Pool/Spa/Restaurant

A cozy living area features a grey sofa with decorative cushions, complemented by two accent tables with lamps. A wooden coffee table rests in front, while a round dining table is visible nearby. Warm lighting from the wall and natural light enhance the welcoming atmosphere.