House vacation rentals in Cypress Gardens

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.

4.89 out of 5 average rating, 291 reviews

The Old Haven - An Enduring Piece of Nostalgia

This charming home was built in 1908 and is located 45 minutes from Tampa/Orlando. Fully furnished, this space is perfect for families and friends providing plenty of space to sleep 8 people comfortably. With games, puzzles and Dvds, backyard fun for kids while the parents watch from the porch. Enjoy downtown entertainment within walking distance! Home is centrally located to dining, shopping, and small town fare. 4 bar restaurants walking distance on the lake. Live music from Lake sometimes.

The two-story home is illuminated under a night sky, featuring clear glass windows that reflect soft light. Landscaped greenery surrounds the property, with a stone driveway leading to a garage. A large patio area is visible on the right side.

4.9 out of 5 average rating, 118 reviews

Breathtaking Home

New two story home with private pool, patio, barbecue area & game room. Surrounded by parks, gardens, tranquil lakes & walkways with breathtaking views. Resort amenities located right across the street with an amazing clubhouse (private owned), Bar & Grill restaurant, water park (extra fee), arcade, gym, volleyball court, soccer & football fields, & event center for parties & weddings. (Pet free home) 12 mi Legoland/19 mi Disney/26 mi SeaWorld & International Drive/29 mi Universal Studios.

The exterior of the home features a light-colored facade with a welcoming entrance. A neatly landscaped yard includes vibrant green shrubs and a palm tree. The driveway leads to a single-car garage with a white door, set against a backdrop of clear blue skies.

4.9 out of 5 average rating, 181 reviews

Southern Dunes Villa - Pool - Golf - near Disney

Stunning executive home with a south facing screened in-ground pool overlooking the 2nd hole of the Southern Dunes Golf Course. Only 13 miles from LEGOLAND and 22 miles from WALT DISNEY WORLD, this is the perfect place to relax after a busy day at the parks. Impeccably maintained, our villa features upgraded furniture, electronics, mattresses and flooring. Southern Dunes is a gated golf community that prides itself on the quality of its golf course and the security and beauty of its homes.

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.

4.94 out of 5 average rating, 152 reviews

*This must be THE PLACE FL*

Your place away from home! Have fun with the whole family at this unique and stylish place. You'll have everything you need to relax and recharge. It is located less than 10 mins away from Legoland, restaurants and convenience stores. This house offer 3 BR and 2 full BA as well as a fully-equipped kitchen. All bedrooms include TV, dresser, closet and memory foam mattress. The Master bedroom has a queen bed, and the other two bedrooms have full size beds. There is wifi and parking available.

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, 101 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. 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. (Additional guests must be pre-approved). Free boat parking and boat rental available. House is connected to the main home with a private keyless touchpad for contactless entry. Pet friendly with prior approval and pet deposit.

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, 140 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 two bedrooms, 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.

4.77 out of 5 average rating, 324 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.

The house exterior displays a blend of white wooden siding and warm wooden accents. Two white, vintage-style chairs are positioned on the porch, leading to a central door with decorative glass. A small set of stairs provides access to the entrance.

4.96 out of 5 average rating, 133 reviews

Freshly Renovated Home

Cute older house with modern amenities. Located right downtown within a block from the playpark, Lake Wailes lake, walking path, and the historic downtown shopping area. All of the appliances in the home are brand new, as well as the washer and dryer. There is a large TV in the living room, as well as one in each bedroom - each with Roku and Netflix. Each bedroom also has a mini split A/C unit to sleep as cold, or hot, as you like. Parking is in the rear covered carport.

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.

4.95 out of 5 average rating, 331 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!

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, 188 reviews

Legoland Lakehouse w/Pool &New AC

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.

4.97 out of 5 average rating, 103 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!

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, 117 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 Cypress Gardens house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.83 out of 5 average rating, 175 reviews

A private pool area is set within a spacious backyard, featuring a clear blue pool surrounded by stone tiles. Comfortable seating is arranged nearby, offering views of the yard. A floating lounge is visible in the water, adding an element of relaxation.

Home in Dixieland

Hollingsworth Pool Home

4.9 out of 5 average rating, 148 reviews

A bright and open living area features modern furnishings, including a sectional sofa and stylish yellow accent chairs. A large flat-screen TV is mounted on the wall, while decorative elements and a vibrant area rug contribute to the space's contemporary aesthetic.

Home in Davenport

Awesome Vacation Home w/ Private Heated Pool/Spa

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.

4.92 out of 5 average rating, 38 reviews

Cozy Lakefront Home w/ Pool -7 mins from Legoland

A large screened patio houses a swimming pool, the water reflecting shades of blue under natural light. Surrounding the pool are sun loungers and a metal chair, with a grassy area visible beyond the enclosed space.

4.85 out of 5 average rating, 48 reviews

John Shirley’s Retreat

4.97 out of 5 average rating, 113 reviews

A living area features a modern television displaying a virtual fireplace, paired with elegant wall art and a decorative plant. Below, a pool area is illuminated with soft purple lighting against a backdrop of warm string lights, creating a relaxed atmosphere.

Home in Kissimmee

Modern House with Private Pool Getaway Kissimmee

4.85 out of 5 average rating, 109 reviews

An outdoor space features a swimming pool with a spacious deck. A pergola provides shade over a dining area with four chairs and a table. Lounge chairs are positioned nearby, surrounded by greenery and a wooden fence marking the perimeter.

Home in Lakeland

Spacious Private Family Home with Pool

An aerial view showcases a single-story home surrounded by well-maintained landscaping, featuring palm trees and manicured grass. The house is positioned near a golf course, with views of the green in the background, presenting a tranquil setting within a gated community.

4.76 out of 5 average rating, 106 reviews

Lifes A Beach at Southern Dunes

A spacious living area features comfortable seating arranged around a central coffee table. A modern fireplace, framed by a white stone mantel, adds a focal point. Natural light fills the room through large windows, with views of the outdoor patio and pool area.

4.92 out of 5 average rating, 38 reviews

Legoland Poolside Paradise

Weekly house rentals

4.89 out of 5 average rating, 65 reviews

Modern 3br home

A bright living area showcases a light grey couch adorned with various patterned cushions, complemented by a matching armchair. A round wooden coffee table rests in the center, surrounded by natural light filtering through the open space. The kitchen area features stainless steel appliances and is visible in the background.

5 out of 5 average rating, 9 reviews

Bright Home Near Legoland & Lake

4.9 out of 5 average rating, 20 reviews

A comfortable living area is displayed, featuring a light gray sofa accented with colorful cushions. Glass side tables are positioned beside the sofa, and a large mirror enhances the space. A cozy throw blanket is draped over an ottoman, with a coffee table showcasing books and decorative items.

Home in Lake Alfred

Central Florida Bungalow! 2 Bedroom 1 Bath

5 out of 5 average rating, 18 reviews

A two-story ranch style home features a light exterior with contrasting dark trim. The entrance is highlighted by a decorative door, flanked by landscaped greenery. A manicured lawn extends around the house, with palm trees and other foliage providing a natural backdrop under a partly cloudy sky.

Home in Davenport

Private Ranch Style Home on Lake

A cozy loft bedroom features a spacious bed with soft linens and decorative pillows. A Roku screen projector casts images onto the slanted ceiling. Light from recessed fixtures brightens the room, while minimalist decor includes two small plants and a white dresser against the wall.

4.95 out of 5 average rating, 44 reviews

Lake House by Legoland + Loft & Private Dock

A modern living space is highlighted by a plush sectional sofa and a round coffee table atop a textured area rug. Two abstract wall art pieces bring color to the walls, while a sleek entertainment unit features an image of a serene beach. Natural light filters in through the windows.

4.95 out of 5 average rating, 76 reviews

Overlook Joy

A swinging hammock chair is suspended from a large oak tree, providing a cozy spot for relaxation. The inviting green house with a red door is visible in the background, surrounded by landscaped greenery and fallen leaves, which enhances the peaceful outdoor setting.

5 out of 5 average rating, 32 reviews

Perfect retreat for the family near Legoland!

4.78 out of 5 average rating, 64 reviews

House near Legoland Lake Eva Park Bok Tower Garden

Private house rentals

4.9 out of 5 average rating, 10 reviews

A serene waterfront view captures a vibrant sunset reflected on the lake's surface. Silhouetted palm fronds frame the scene, while a wooden dock extends into the water, creating a peaceful atmosphere for relaxation and contemplation.

Home in Eagle Lake

30 minutes to Disney and Universal Studios

The two-story lakehouse features light-colored exterior walls with blue shutters and a welcoming front door. Lush greenery surrounds the entrance, complemented by flower beds. The driveway leads to a spacious front yard, creating an inviting atmosphere in a tranquil neighborhood.

4.92 out of 5 average rating, 24 reviews

1937 family lakehouse kids and pet friendly

4.93 out of 5 average rating, 91 reviews

A screened-in pool area features a sparkling blue pool surrounded by light-colored concrete. Two lounge chairs with striped cushions are positioned adjacent to the water. A covered seating area with a table is visible in the background, providing shade.

Home in Davenport

Sweet vacation home.

4.94 out of 5 average rating, 65 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

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, 86 reviews

Kid-friendly Home w/ Pool & BBQ

The exterior of the luxury home presents a modern two-story design with a neutral color palette. A manicured lawn and colorful landscaping enhance the curb appeal. The driveway leads to a two-car garage, and large windows provide a view of the inviting interior.

4.79 out of 5 average rating, 62 reviews

Stunning 4BR home w/Pool

A hot tub is illuminated by soft lighting, surrounded by a wooden fence and lush greenery. Adjacent lounge chairs positioned under an umbrella provide additional seating. The artificial grass adds a vibrant touch to the tranquil outdoor setting, enhancing the relaxing atmosphere.

4.83 out of 5 average rating, 180 reviews

Hidden Gem - Hot Tub/ Fire pit/Hammock/Grill Area