Vacation rentals with a washer and dryer in Winter Haven

Home in Downtown Winter Haven

A well-lit living room features a comfortable gray sofa and a light pink chair. A round coffee table is centered on a soft rug, while a contemporary TV stand holds a flat-screen television. Large windows provide natural light, and a door leads outside.

4.9 out of 5 average rating, 161 reviews

3/2 Great Family Home Near Legoland

Enjoy easy access to Legoland (4 mi) & charming Downtown (1 mi) from this centrally-located home. Designed to make you feel right at home during your family getaway, the whole home is private to you. We are pet friendly! Featuring a kitchen ready to make a home meal, a fully fenced private back yard, keyless entry, & free, ample parking for multiple cars and a trailer. Street parking is also allowed. Locally owned & operated. We are excited to share our city and provide exceptional service

4.97 out of 5 average rating, 108 reviews

Adult-Only Getaway w/ Mermaid Pool | 18+, Private

🗝️ Adults only. Ready to turn your vacation into an experience? Explore your fantasies at our romantic getaway, featuring four themed bedroom options* designed to inspire you. Bring your fave toys, experiment with our spicy 🌶️ amenities, or peruse our shop to bring home a little extra to keep the fire going after you leave. You will love our mermaid pool 🧜🏿‍♀️, jetted spa, & stone meditation deck while you soak up the sun or stargaze. 🌟 Your next adventure awaits. (*1 per 2 guests)

Cottage in Downtown Winter Haven

An outdoor patio features a glass-top table surrounded by six black mesh chairs. A small wooden shed is visible in the background, while a stone pathway leads through the well-maintained yard, enclosed by a wooden fence and dotted with greenery.

4.8 out of 5 average rating, 223 reviews

Sweet Cottage- 5 mi to Legoland & 0.5 mi to dwntwn

This delightful lake-life inspired cottage includes 2 bedrooms and 1 ½ baths, a fooseball table, and easily sleeps 7 guests comfortably. Located just 15 minutes from Legoland and 45 minutes from Tampa & Orlando, this home is perfect for both families and those traveling for work. In fact, this Home is centrally located to dining, shopping, and small town fare. Come stay and enjoy downtown entertainment within walking distance (0.5 miles), or a quick car drive to Legoland (5.2 miles).

A charming single-story home is set in a spacious outdoor area, featuring a wide driveway leading to a covered porch. The front yard is framed by lush greenery, with a large tree providing shade to the house and the surrounding landscape.

4.89 out of 5 average rating, 102 reviews

Newly remodeled House 3BR/2BA

Centrally located in Winter Haven, FL and within minutes to Legoland. Only a 45-60 minute drive to local theme parks Disney and Busch Gardens. West/East Coast Florida Beaches are only a 90 minute drive. This newly remodeled 3/2 is a very spacious and accommodating home to any family wanting to get away on a peaceful vacation or weekend retreat. Quiet neighborhood with no HOA and within walking distance to several downtown restaurants, grocery stores, and shopping establishments.

A large outdoor space features a private pool surrounded by loungers in blue and a shaded dining area. A patio table with chairs is placed in the foreground, while a safety fence encloses the pool area, providing a secure environment.

4.98 out of 5 average rating, 100 reviews

Kid-friendly Home w/ Pool & BBQ

Enjoy a delightful stay in our Renovated 3BD house for your Winter Haven trip. The unit is equipped with dryer, washer, Wi-Fi, fully equipped kitchen, baby proofed, and BBQ to make your stay comfortable. Enjoy the private pool, free parking, and large patio. Our house is 20 mins away from LEGOLAND and 50 mins away from Disney Parks and attractions. Discover Winter Haven’s chain of lakes with all the water sports and its surroundings in the best way. We look forward to hosting you!

A serene lakeside view is observed, featuring gently swaying palm trees on the left and a wooden dock extending into the water. A boat is anchored at the dock, surrounded by lush greenery and a clear blue sky.

4.95 out of 5 average rating, 109 reviews

Lakefront Home on the Winter Haven Chain O’Lakes!

Completely renovated 2 Bedroom, 1.5 bath home location on beautiful Lake Roy on the Winter Haven Chain O’Lakes. This is a mother-in-law suite that is connected to the main home. One bedroom on the lower level with a queen bed. Second story with king bed and twin bed. Full bath located upstairs). Comfortably sleeps 5. Dog welcome with prior approval and pet fee. Boat parking at dock. Boat rental available at Central Florida Water Sports. Private entry with keyless touchpad.

4.99 out of 5 average rating, 289 reviews

A view of the blue lake house is presented with a well-manicured lawn leading up to it. The house is framed by mature trees, providing shade. A wooden walkway extends toward the entrance, while the serene lake is visible in the background.

Cottage in Eagle Lake

Roe Family Lake House (Lake Mcleod)

We can't wait for you to enjoy our fully renovated, family friendly lake house. It's a happy home that provides a wonderful backdrop to any vacation. Centrally located to many Florida destinations- Legoland is only 7 miles away, Disney World is 35 miles away, and you are less than 50 miles from Tampa. The house is located on over an acre of lakefront property. The lake has a public boat launch if your family enjoys water sports or fishing or use the kayaks we provide on site!

4.84 out of 5 average rating, 158 reviews

The entrance features wooden steps leading up to a covered porch, flanked by tropical foliage. Two chairs are positioned on the porch, offering a place to relax. The home’s exterior is painted in soft green, complemented by light-colored trim.

Cottage in Winter Haven

5 - Life's a Beach Retreat 1bed/1bath - Unit 13

The 1-bedroom, 1-bathroom home features a fully equipped kitchen and covered front porch, making it the perfect spot to reel in a relaxing getaway. A cozy one-bedroom unit on the property of Cypress Inlet. Less than 10 minutes from LegoLand and Peppa Pig theme park. The property is on a canal that leads to Lake Eloise and the WH Chain of Lakes, and has boat ramp access and docks available; this vacation rental is an angler's paradise!

4.81 out of 5 average rating, 148 reviews

An aerial view presents the stylish exterior of KokomoVilla, showcasing a well-maintained garden and driveway. The property is bordered by lush greenery and overlooks the golf course, with a sunset casting a warm glow across the sky, enhancing the serene atmosphere of the neighborhood.

Home in Haines City

KokomoVilla Pool Home at Southern Dunes

Welcome to KokomoVilla at Southern Dunes! Our 4-bedroom pool home offers a serene golf course view in the renowned Southern Dunes Golf & Country Club. Perfectly positioned between Disney and Legoland, this luxurious retreat is ideal for families and golf lovers. Enjoy a fully equipped home, private pool, and easy access to Central Florida’s attractions. KokomoVilla is not just a stay, but an unforgettable experience!

Guest suite in Winter Haven

Three thoroughbred horses graze peacefully on a lush green pasture. The area is surrounded by tall trees, providing shade and a natural backdrop. A glimpse of a trailer can be seen in the background, indicating the farm's working environment.

4.96 out of 5 average rating, 297 reviews

Horse Farm on a Beautiful Lake

Small Thoroughbred Race Horse Farm on a beautiful lake. Fishing available on site. New dock just finished with plenty of benches for fishing, picnicking, or just dreaming. There is a Swimming pool right out your door, horse paddocks and patio overlooking the lake for hanging out or quiet time. Please note price is for studio (sleeps 3 or more with sofa beds)

4.92 out of 5 average rating, 115 reviews

A modern kitchen area is visible, featuring a sleek countertop with place settings for four. Two pendant lights hang above the bar stools. In the background, a living area is seen, illuminated by natural light from glass doors leading to a balcony.

Apartment in Davenport

Cozy Modern 1 Bedroom Apartment

Warm welcome to our modern one bedroom apartment. We are happy to be your host for your stay. Located minutes away from attractions such as Walt Disney World and Universal Studios. During your stay you will find comfort with a brew of a delicious cup of coffee as the sun rises. Book your next stay with us. We would love to be your host!

A spacious living area is presented with a sectional sofa, a wooden coffee table, and a wall-mounted television. Large windows allow natural light and views of the outdoor patio. The room features light-colored walls and art pieces that add a modern touch.

4.95 out of 5 average rating, 152 reviews

Legoland Getaway 7 mins • Sleeps 7 • Elevator

Come relax with your family in this peaceful 2BR/2.5BA home, just 7 minutes from LEGOLAND®. Sleeps up to 7 guests, with pool access, board games, and arcade fun for all ages! Wheelchair accessible with elevator between floors. No parties, no smoking. Primary guest must be 25+ and present during stay; ID may be required.

Popular amenities for Winter Haven washer and dryer rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a washer and dryer

Apartment in Cleveland Heights

A spacious bedroom is highlighted by a wooden headboard above a queen-sized bed. The soft beige bedding complements the neutral wall color. A bedside lamp provides gentle light, while a partial view of an additional sleeping area can be seen through an open doorway.

4.95 out of 5 average rating, 154 reviews

Hidden Ruby Apartment

4.99 out of 5 average rating, 101 reviews

Apartment in Lakeland

Matty’s Citrus Connection

Apartment in Winter Haven

A balcony view overlooks a serene lake, framed by lush palm trees and vibrant green foliage. Bright blue skies and scattered clouds add to the tranquil setting, while glimpses of the driveway and nearby structures can be seen in the distance.

4.98 out of 5 average rating, 163 reviews

Florida Penthouse in luxurious mansion!

4.93 out of 5 average rating, 110 reviews

An open living area features a modern design with a spacious layout. A comfortable sofa with accent pillows and a coffee table is set in front of a large window. The adjacent kitchen is equipped with sleek cabinetry and modern appliances, complemented by a dining space visible in the background.

Apartment in Kissimmee

3180-207 Resort Pool View Disney Universal Orlando

4.96 out of 5 average rating, 254 reviews

A wooden deck overlooks the calm waters of Lake Ariana, framed by greenery. A small table with two chairs is positioned to enjoy the view, while a potted plant adds a touch of nature to the space. Spanish moss drapes gracefully from nearby branches.

Apartment in Auburndale

Ariana Place - Tree House Like Lakefront Views

4.81 out of 5 average rating, 303 reviews

The bedroom features a spacious bed adorned with soft pillows and a textured throw blanket. Flanking nightstands hold stylish lamps, providing gentle lighting. A framed landscape image above the bed complements the neutral color scheme, and doorways to additional spaces are visible in the background.

Apartment in Clermont

Charming Lakefront Apt. Near Disney

4.92 out of 5 average rating, 115 reviews

Apartment in Davenport

The Cozy Escape

4.97 out of 5 average rating, 189 reviews

A living area features comfortable leather seating with red accent pillows and a coffee table. A wall-mounted television is positioned across from the seating. Two framed art pieces and green plants add decor to the neutral-colored walls and tiled flooring.

Apartment in Lakeland

Your Charming Place in Central Florida

House rentals with a washer and dryer

4.9 out of 5 average rating, 73 reviews

Modern 3br home

4.92 out of 5 average rating, 193 reviews

A renovated house is framed by mature trees, displaying a fenced front yard that features a paved walkway leading to the entrance. The structure includes a simple facade with large windows, allowing natural light to enter the interior.

Home in Auburndale

three bedroom family house, near legoland

A single-story ranch home features a blue exterior with a stone accent wall. A well-kept lawn surrounds the house, which is bordered by neatly trimmed bushes. Two large windows and a centered front door are visible on the facade, contributing to a welcoming appearance.

4.75 out of 5 average rating, 170 reviews

The Blue Ranch

4.95 out of 5 average rating, 81 reviews

A spacious living area features a comfortable gray sofa and a wooden coffee table adorned with a floral arrangement. Natural light fills the space through large windows, while a dining area with a light-colored table and chairs is visible in the background.

Home in Auburndale

Encanto At Auburndale

4.93 out of 5 average rating, 44 reviews

An enclosed swimming pool area is surrounded by a spacious screen enclosure, providing a clear view of lush greenery and a privacy fence in the background. Sunlight streams in, creating a bright and inviting atmosphere, while potted plants add touches of color around the pool's edge.

Home in Auburndale

Florida Oasis

The outdoor pool area features a heated saltwater swimming pool with colorful floats, including a swan and a duck. The patio is paved with light-colored tiles and is surrounded by comfortable seating and decorative lighting, reflecting a welcoming space for relaxation and fun.

5 out of 5 average rating, 76 reviews

Waterfront Heated Pool Putting Green Dock Legoland

A screened-in pool area features a spacious pool with clear blue water, surrounded by a concrete deck. A hot tub is adjacent, and a view of the lake is visible beyond. Lush greenery and a few lounge chairs complement the outdoor ambiance.

4.93 out of 5 average rating, 121 reviews

Fantastic Water Front Home on the Chain of Lakes

4.92 out of 5 average rating, 172 reviews

A dining area is presented with a round wooden table surrounded by four green upholstered chairs. A decorative plant is centered on the table. The walls feature art and a glowing sign, while natural light enhances the inviting atmosphere.

Home in Lake Wales

*This must be THE PLACE FL*

Condo rentals with a washer and dryer

Condo in Highlands Reserve

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.

4.89 out of 5 average rating, 198 reviews

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

4.81 out of 5 average rating, 186 reviews

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

3BR/2BA Mediterranean Style Condo Near Disney

4.84 out of 5 average rating, 158 reviews

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

Orlando Spacious 2 Suites & Resort-Style Pool

4.84 out of 5 average rating, 103 reviews

An aerial view showcases a large pool area surrounded by lush landscaping and palm trees. The complex features a main pool, children's pool, and several cabanas. The orange-roofed building provides a welcoming focal point, while the well-kept grounds invite relaxation and fun.

Condo in Davenport

Spacious 2bd/2ba (No stairs) Disney/Championsgate

4.88 out of 5 average rating, 176 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

4.91 out of 5 average rating, 225 reviews

A spacious living area is highlighted by modern furnishings, including a gray sofa adorned with colorful cushions. A decorative coffee table sits centrally on a patterned rug. The dining area features a contemporary table set, and the kitchen is partially visible with stylish bar stools.

Condo in Orlando

Sensational Water View, Only 1 mile to Disney!

4.86 out of 5 average rating, 111 reviews

A dining area features a round table set with white plates and glasses, complemented by woven placemats. A cozy seating area with a brown leather couch and decorative pillows is visible, alongside a large window offering natural light and views of the outdoor space.

Condo in Celebration

Private balcony, Disney under 10 mins, Roku+Cable