Holiday rentals with outdoor seating in Cypress Gardens

4.97 out of 5 average rating, 117 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)

4.81 out of 5 average rating, 228 reviews

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.

Cottage in Winter Haven

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.

4.88 out of 5 average rating, 108 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, 110 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, 114 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.

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, 146 reviews

Beautiful Lake House Boating Fishing near Legoland

Welcome to The Executive Lake House ten minutes from Lego Land in beautiful Winterhaven, Florida. The brand new rental home sits on a lake and offers a dock, with boats, fishing gear and beautiful views of the lake. The home offers one bedroom a full kitchen and laundry and one full bathroom The backyard has a playground and pool area that is ( not) included at this price point. If wanting an additional charge of 20 dollars per night Will be charged. Let me know at booking.

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, 339 reviews

Florida Oasis w/ Pool near LEGOLAND

We have added a modern twist to the design of this 1950's home with all the modern appliances and finishes. This home is nestled in-between 2 lakes among the Winter Haven Chain of Lakes! The backyard is a Florida Oasis of a great pool and pool deck with plenty of fun available with games for you and the kids, or just enjoy laying peacefully in the sun! 2.5 mile drive from Legoland 3.5 mile drive from Downtown Winter Haven with great restaurants and small town unique shops.

An open-plan living area features a blue couch set against a light wall, complemented by a patterned area rug. A dining table and four chairs are situated nearby, with a glimpse of the kitchen visible in the background.

4.94 out of 5 average rating, 351 reviews

Spacious 3 Bed, 2 Bath Home Near Legoland

Enjoy family vacation in this fresh, clean 3-bedroom, 2-bathroom home. With keyless entry and a private fenced backyard, you'll have everything you need for a comfortable stay. 4 miles from Legoland 1 mile from downtown Locally owned & operated As residents of Winter Haven, we're passionate about sharing our community with you. We're always ready to assist you with any questions or requests during your stay. Book your stay today and discover the charm of Winter Haven!

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.

4.81 out of 5 average rating, 277 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.

4.91 out of 5 average rating, 207 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.

Guest suite in Winter Haven

A comfortable living space features a large sectional couch adorned with decorative pillows. A mirror and wall art enhance the ambiance. Natural light enters through the front door, and a dining table is situated nearby. A ceiling fan provides a refreshing atmosphere.

4.89 out of 5 average rating, 114 reviews

Cute & Cozy in Winter Haven, Florida

The guesthouse Cute & Cozy is private yet adjacent to the main house (owner lives) and has its own entrance. Located in central Florida, between Orlando and Tampa; 3 miles from Legoland, 5-10 minute walk from shopping and restaurants on Cypress Gardens Blvd. The Cute & Cozy is also in a great location from Florida's amazing beaches, just under 2 hours east or west. Maybe an hour drive to Disney, SeaWorld and Universal (depends traffic)

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.

4.98 out of 5 average rating, 132 reviews

The Dalt Retreat

The Dalt Retreat in Winter Haven (LEGOLAND) Fl is named after our 10 year old Grandson Dalton. It’s a great spot to relax by the in ground pool and fenced in back yard. Enjoy the outside with your family and cookout. We want you to love The Dalt as much as we do. Located in Winter Haven and Central FL area easy to enjoy the local lakes. Also not too far from other central Fl attractions and beaches from East or West coast.

Popular amenities for outdoor seating rentals in Cypress Gardens

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

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, 172 reviews

The Blue Ranch

4.94 out of 5 average rating, 170 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 Lakeland

Charming Lakefront Cottage with Stunning Views

4.89 out of 5 average rating, 9 reviews

Family Winter Haven Retreat w/ Pool & Game Room

4.92 out of 5 average rating, 38 reviews

Florida Dream Vacation House

A fire pit is centrally positioned on a stone surface, with flames dancing above decorative stones. Beyond the screen enclosure, lounge chairs are placed near a private pool, surrounded by lush greenery and a thatched-roof palapa, creating a relaxing outdoor setting.

4.89 out of 5 average rating, 46 reviews

Cozy Lakefront Home w/ Pool -7 mins from Legoland

A serene bedroom is showcased, featuring two unique boat-shaped beds with wooden accents. A large mural of a scenic lake and mountains enhances the space, while natural light filters in through the window, framed by white curtains. A ceiling fan adds a cool breeze.

4.91 out of 5 average rating, 81 reviews

Stylish Lakehome w.HUGE Pool/Arcade/Theater

A cozy living area features a light brown sectional sofa and a matching sofa adorned with patterned cushions. A modern coffee table sits in the center, with a remote control placed on top. A large artwork of a character hangs above, flanked by two lamps.

4.89 out of 5 average rating, 134 reviews

Family Fun Oasis near Legoland Pool and Hot Tub

5 out of 5 average rating, 6 reviews

Lakefront home w/heated pool minutes from Legoland

Apartment rentals with outdoor seating

Flat 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.

4.96 out of 5 average rating, 161 reviews

Hidden Ruby Apartment

4.99 out of 5 average rating, 109 reviews

Flat in Lakeland

Matty’s Citrus Connection

4.89 out of 5 average rating, 403 reviews

Flat in Dixieland

Cozy 2B/1 Hideaway, Wildflower Garden in bloom.

4.97 out of 5 average rating, 105 reviews

A private balcony is showcased with a round table and two woven chairs, providing a serene view of the lake and surrounding landscape. Soft morning light reflects on the water, while a small potted plant adds a touch of greenery to the setting.

Flat in Orlando

2-Bedroom Renovated Lakeside Condo Near Disney

4.82 out of 5 average rating, 221 reviews

An aerial view reveals a sprawling lagoon-style pool surrounded by lush green landscapes, highlighted by winding water features. A well-appointed bedroom presents a spacious bed framed by modern decor and natural light filtering through a window. The living area showcases an elegant dining setup alongside a stylish sofa, while a vibrant children's room features a bunk bed and playful accents.

Flat in Kissimmee

2Bedrooms/2 Bathrooms Storey Lake Resort 3150-404

4.97 out of 5 average rating, 194 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.

Flat in Lakeland

Your Charming Place in Central Florida

Flat in Lake Hollingsworth

An inviting living space is seen, featuring a green sofa and a patterned rug. A kitchenette with stainless steel appliances is visible. Natural light filters through sheer curtains, illuminating various furnishings, including a small table and a dresser, creating a functional and cozy environment.

4.97 out of 5 average rating, 106 reviews

Serenity Studio is steps from Lake Hollingsworth

Flat in South Lake Morton Historic District

A bright workspace is showcased with large windows offering views of the lake. Two yellow armchairs sit beside a glass-top table. A desk with a lamp is positioned against the wall, with a potted plant adding a touch of greenery.

5 out of 5 average rating, 130 reviews

Romantic Lakefront – Feed Swans – Walkable Dining

Apartment rentals with outdoor seating

4.87 out of 5 average rating, 102 reviews

Apartment in Davenport

A luxurious living just 15 min/Disney!

4.96 out of 5 average rating, 110 reviews

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.

Apartment in Orlando

Penthouse Lakeview Minutes to Disney/ Universal

4.97 out of 5 average rating, 131 reviews

An open living space features large French doors leading to a balcony, allowing natural light to brighten the area. Stylish seating is arranged around a coffee table, while artwork resembling a Marvel theme decorates a wall in the adjacent bedroom. Views of palm trees and a nearby pool can also be seen.

Apartment in Kissimmee

Golf Front Luxury Penthouse: Views, Marvel, 2Pools

4.95 out of 5 average rating, 129 reviews

Apartment in Orlando

Modern Lake view Condo 1 mile from Disney

5 out of 5 average rating, 105 reviews

Apartment in Kissimmee

Cozy Condo at Secret Lake near Disney

4.84 out of 5 average rating, 165 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

4.88 out of 5 average rating, 103 reviews

A living area is presented with a blue sofa and two matching side tables. A large mirror reflects light from an adjacent lamp. A wooden dining table with two chairs is positioned near the sliding glass door, which is dressed with vertical blinds.

Apartment in Mulberry

Tranquil Escape