Holiday rentals with outdoor seating in Winter Haven

4.98 out of 5 average rating, 131 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)

The exterior of the home features a sleek black façade with large windows allowing natural light in. A neatly landscaped yard includes tropical plants and colorful foliage, enhancing the inviting entrance. The driveway leads to a single-car garage, with ample space to welcome guests.

4.99 out of 5 average rating, 143 reviews

Cheerful 4 Bed, 3 Bath Home with Screened Pool

Just 6 miles to Legoland! This stylish home is perfect for vacation. 2 ensuite bedrooms, 2 additional rooms and 2 additional semi private sleeping areas there is room for everyone. Every space is newly furnished with stylish pieces and comfortable beds. The pool area is fully screened so you can enjoy the Florida weather without the bugs. The open concept space is perfect for large groups and families and the kitchen is ready for you to make a meal. A laundry room houses a washer and dryer.

The exterior of a spacious home is presented, featuring a blue façade and a welcoming entrance. Lush tropical foliage surrounds the property, which is highlighted by palm trees and manicured lawns. A vibrant sunset casts colorful hues in the sky, enhancing the serene atmosphere.

4.98 out of 5 average rating, 137 reviews

Spectacular Waterfront Home in Winter Haven

Enjoy a wonderful family get away at this premier waterfront home on the famous Chain of (19) Lakes! Separate yourself from the crowd at this beautiful Cypress Gardens home set on an acre with lush tropical foliage and surrounded by 3 sides of water. Featuring a chef's kitchen, 2 private docks, the "New Florida Pool," 2 hot tubs, fire pit and many more amenities. Enjoy relaxed luxury at its finest. We are just a few minutes to Legoland, restaurants and shopping, but miles from ordinary!

An aerial view of a single-story home is presented, showcasing a well-maintained lawn and driveway. The surrounding neighborhood features a mix of greenery and residential structures, contributing to a welcoming suburban atmosphere.

4.95 out of 5 average rating, 101 reviews

Extra large home! Bring Your Boat & all the Toys!

Bring your boat, skis, fishin’ pole, or any other water toys! We supply ping pong, corn hole, bicycles and other toys! Directly across from Lake Howard boat ramp and 10 minutes from LegoLand! Enjoy this spacious, well-equipped 2300 sf home that has everything you need to enjoy your stay in Winter Haven, aka Chain of Lakes City, a quaint downtown with free parking-- and just a skip away from Disney and Universal. This getaway is an above-average accommodation both in style and comfort!

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.

4.88 out of 5 average rating, 114 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.

4.97 out of 5 average rating, 119 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.

4.96 out of 5 average rating, 115 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, 306 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!

Guest house in Winter Haven

A spacious room features a queen size bed with a neatly arranged white blanket. Light tiles enhance the bright atmosphere, while a barn-style door leads to a private bathroom. A small kitchenette area with dark cabinetry and a modern sink is visible in the background.

4.82 out of 5 average rating, 288 reviews

Adorable 1 bedroom Guesthouse near Lego Land

This is a beautiful and private place offers a queen size bed, newly renovated with private access and parking. It’s a great place to get away and relax with a large and beautiful backyard! We are located less than 8.6 miles from Legoland & under 6.2 miles from the Lake Myrtle Sports complex. Winter Haven is halfway between Orlando and Tampa. Around 29 miles to Disney World, Universal and Sea World. Around 38 miles to Bush Gardens, Dali museum, Aquarium and much more!

An inviting swimming pool is surrounded by a spacious patio area, featuring lounge chairs and a shaded table with an umbrella. The serene view of Little Lake Otis and lush greenery is visible in the background under a partly cloudy sky.

4.92 out of 5 average rating, 219 reviews

Legoland Lakehouse Canoe & Kayak Retreat

Relax in style in this 100 year old custom built home.Tall ceilings,large rooms and wood floors throughout.With an extra large swimming pool overlooking Little Lake Otis this outdoor area is second to none.Less than 2 miles from Legoland,Chain of Lakes Fieldhouse,and Downtown Winter Haven. It is possible that days may be available and not listed on the calendar. This is to give ample time for cleaning. Feel free to ask for additional availability and shorter stays.

A charming lake home is showcased with a light-coloured façade and blue shutters. A welcoming entrance is flanked by decorative chairs, with well-maintained landscaping featuring green grass and flower beds enhancing the outdoor appeal.

4.98 out of 5 average rating, 123 reviews

Lake View, Game Room, 10 min Legoland

Welcome to The Elby, a fully renovated 1940's lake home with spacious rooms, modern amenities, and indoor and outdoor games designed w/ family fun in mind! Only 3 min to charming downtown Winter Haven shopping & restaurants, 10 min to Legoland, 30 min to historic downtown Lakeland, & conveniently located between Tampa & Orlando (45 min to Disney & just 60 min to Tampa). We can't wait for you to enjoy the beautiful lakes of Winter Haven at The Elby!

Cottage in Cypress Gardens

The exterior of a charming single-story home features a welcoming front porch with wooden steps. Large windows allow natural light to fill the interior. Surrounding greenery includes shrubs and small plants, contributing to a pleasant outdoor space under a partly cloudy sky.

4.87 out of 5 average rating, 177 reviews

2 - Ships Ahoy Bungalow 2 bed/2 bath - Unit 17

Florida’s lakes and biggest attractions are calling you and your family to stay at this vacation rental in Winter Haven! From Legoland and Disney World to the famous Chain of Lakes and golf courses galore, this charming home in Cypress Inlet is minutes from it all. Take your boat out on Lake Eloise, through a private canal right outside the home, or take the kiddos to SeaWorld, a short drive away, before returning to this 2-bedroom 2-bath home.

Popular amenities for outdoor seating rentals in Winter Haven

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.95 out of 5 average rating, 171 reviews

A spacious lawn is framed by large oak trees draped with Spanish moss. Comfortable lounge chairs are positioned facing the tranquil water, creating a serene outdoor space. The lake is visible in the background, enhancing the natural beauty of the setting.

Home in Auburndale

Lake Whistler Beach House with lakefront pool

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.

4.76 out of 5 average rating, 176 reviews

The Blue Ranch

4.93 out of 5 average rating, 185 reviews

The image captures a serene lake view from a grassy area, with a wooden deck overlooking calm waters. Lush trees frame the scene, providing shade and a natural ambiance. Water lilies are visible on the surface, enhancing the tranquil lakeside setting.

Home in Crystal Lake

Charming Lakefront Cottage with Stunning Views

A spacious living area features a striking mural of a serene lake scene, complemented by a cozy seating arrangement. Tropical-themed decor and unique ceiling fixtures add to the ambiance. Natural light filters in, highlighting the stone floor and creating a welcoming environment.

4.99 out of 5 average rating, 151 reviews

Beautiful Lake House Boating Fishing near Legoland

The exterior of the home features a welcoming porch with seating, surrounded by lush greenery and colorful plants. A patio area with a black metal table and chairs invites outdoor gatherings, while the pathway is lined with decorative stones, enhancing the rustic charm of the property.

4.9 out of 5 average rating, 307 reviews

The Old Haven - An Enduring Piece of Nostalgia

A private backyard features a clean in-ground pool surrounded by a paved patio. Two lounge chairs are positioned beside the pool, and a dining set with four chairs sits nearby. Lush greenery and a white privacy fence enhance the serene outdoor setting.

4.97 out of 5 average rating, 146 reviews

The Dalt Retreat

A serene backyard features a clear swimming pool surrounded by a tiled deck. Sun loungers are positioned around the pool, with a shaded dining area beneath a striped umbrella. Lush greenery and tall trees provide a natural backdrop, enhancing the outdoor space.

4.78 out of 5 average rating, 347 reviews

Florida Oasis w/ Pool near LEGOLAND

4.89 out of 5 average rating, 133 reviews

Home in Haines City

Breathtaking Home

Apartment rentals with outdoor seating

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.

4.96 out of 5 average rating, 169 reviews

Hidden Ruby Apartment

4.99 out of 5 average rating, 128 reviews

Matty’s Citrus Connection

4.91 out of 5 average rating, 145 reviews

A welcoming living area features a dark brown sofa adorned with decorative pillows in warm tones. Greenery decorates the wall behind the sofa, complemented by a modern lamp. A nearby circular table and chair set add to the inviting space, with natural light filtering through a window.

Flat in Kissimmee

Lush Green Retreat 10 Min to Parks Pets Allowed

4.93 out of 5 average rating, 120 reviews

A canopy-covered terrace is accented by a comfortable seating area featuring plush blue cushions. Sun loungers are arranged alongside a dining table with umbrella, offering views of the surrounding landscape and sky.

Flat in Orlando

Penthouse With Epic Views

A comfortable living area features a light gray sofa with decorative pillows, complemented by a dark coffee table placed on a colorful area rug. Natural light fills the space through large windows with sheer curtains, and a potted plant adds a touch of greenery.

4.89 out of 5 average rating, 424 reviews

Cozy Hideaway W/ Big Yard and Wildflower Garden.

The studio features a colorful bedspread covering a spacious bed, surrounded by a vibrant accent wall. A ceiling fan is present, and a dresser stands nearby. Decor elements include shelves with plants and artwork, while a bright red curtain adds a pop of color.

4.95 out of 5 average rating, 217 reviews

cozy house close to I4 monthly rental also

4.94 out of 5 average rating, 112 reviews

A modern dining area features a spacious marble table surrounded by beige upholstered chairs. A Mickey Mouse artwork adorns the wall, complementing the nearby TV area with a cozy blue chair. The kitchen with wooden cabinetry is visible in the background.

Flat in Davenport

Disney 3/Bd Sleep 8~Pool~No Clean or Resort FEES!

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.

4.97 out of 5 average rating, 198 reviews

Your Charming Place in Central Florida

Apartment rentals with outdoor seating

Apartment in Four Corners

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.

4.88 out of 5 average rating, 146 reviews

Waterpark View, MickeyTheme 3BR Near Disney 1039

4.88 out of 5 average rating, 112 reviews

Apartment in Davenport

Luxurious living just 15 min/Disney

4.97 out of 5 average rating, 444 reviews

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.

Apartment in Orlando

Waterfront Condo minutes to Disney & Universal

4.91 out of 5 average rating, 179 reviews

Apartment in Kissimmee

Chic Disney Resort Condo • Pool Access Near Parks

4.95 out of 5 average rating, 137 reviews

Apartment in Orlando

Modern Lake view Condo 1 mile from Disney

4.85 out of 5 average rating, 179 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.

Apartment in Davenport

Orlando Spacious 2 Suites & Resort-Style Pool

4.94 out of 5 average rating, 203 reviews

A spacious living area features large glass doors that open to a scenic balcony overlooking the Arnold Palmer PGA golf course. Soft furnishings are complemented by a stylish coffee table and decorative accents. Nearby, a vibrant Star Wars-themed bedroom displays unique decor and multipurpose seating.

Apartment in Kissimmee

*Sunset Golf Views, Reunion Resort, Pools, Disney