House vacation rentals in Winter Haven

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, 121 reviews

Heated pool/hot tub, near Legoland, Disney,

Relax in the heated pool and hot tub after enjoying theme parks such as Busch Gardens, Disney world, and Universal Studios! LegoLand is 1 mile away! Lego bedroom for kids. Centrally Located in the middle of Florida allows beach trips to both east & west coast. air conditioned garage has been turned into a game room pool table, air hockey and a miss pac-man arcade game! Private boat & RV parking with RV outlet thru gate in backyard. Pool can be heated to 85 degrees for a small fee if $10/ day

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, 184 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.

4.98 out of 5 average rating, 106 reviews

Home in Lake Wales

Fishing Lakefront Paradise w/ Boat Slip & Parking!

Welcome to Florida Lakefront Paradise! ⭐️ Breathtaking Sunsets ⭐️ Bass Fishing ⭐️ Reserved Boat Slip ⭐️ Fish Cleaning Station ⭐️ Boat Wash Station ⭐️ Marina with Ice/Gas ⭐️ Large Fire Pit Area ⭐️ Located on Kissimmee Chain of Lakes ⭐️ Smart TV's ⭐️ Screened Lakefront Back Patio ⭐️ High Speed Internet ⭐️ Spacious ⭐️ Balcony Facing the Lake ⭐️ 30 minutes to Lego Land ⭐️ 20 minutes to Bok Tower Gardens ⭐️ 1 hour to Disney World ⭐️ 18 minutes to Spook Hill ⭐️ 18 minutes to Kissimmee State Park

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, 127 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!

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, 141 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 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, 118 reviews

Fantastic Water Front Home on the Chain of Lakes

We are sharing our dream home with you! This home offers one of the best open layouts in Winter Haven. Great open kitchen with granite counter tops, stainless steel appliances, and numerous appliances. The large TV room features a Samsung smart 65" TV that connects to the Lanai/Pool area. A must see to believe! Numerous pictures provided to allow your mind to wonder. My interaction with you will be based on you. We have keypad entry for your convenience. I am here for you though!

Superhost

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, 329 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.

4.96 out of 5 average rating, 142 reviews

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.

Home in Lake Wales

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, 337 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.

4.92 out of 5 average rating, 193 reviews

Legoland Lakeside Splash 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.

4.97 out of 5 average rating, 106 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!

Popular amenities for Winter Haven house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

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, 39 reviews

Cozy Lakefront Home w/ Pool -7 mins from Legoland

4.89 out of 5 average rating, 9 reviews

Spacious Winter Haven Retreat w/Pool&Pet Friendly!

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, 120 reviews

Breathtaking Home

A spacious backyard is enclosed by a white picket fence, featuring a large pool with a deck area. Sun loungers are positioned beside the pool, while a covered section of the pool retains the solar cover, ensuring it is ready for use. The modern home is visible in the background.

4.97 out of 5 average rating, 39 reviews

4/2 New Spacious Pool Home

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.

4.83 out of 5 average rating, 53 reviews

John Shirley’s Retreat

Superhost

The exterior features a light blue structure complemented by a covered carport. A well-maintained lawn with decorative stones and shrubs adds to the inviting atmosphere. Large windows provide natural light into the living spaces.

Home in Kissimmee

4.93 out of 5 average rating, 138 reviews

Winter Villa in Florida by the Lakes

An inviting outdoor space features a private swimming pool surrounded by a sun deck with lounge chairs. A glass-top dining table is set for four beside a BBQ grill, with green views beyond the screened enclosure.

4.84 out of 5 average rating, 129 reviews

Southern Dunes Golf Vacation Villa

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

A spacious bedroom features a ceiling fan with light fixtures and a comfortable bed adorned with a patterned bedspread. A dresser with a mirror is positioned next to a small table holding a television. A window with a blinds offers natural light.

5 out of 5 average rating, 13 reviews

Cozy2BR/2BR Near Legoland & Winter Haven Hospital

5 out of 5 average rating, 13 reviews

Legoland Pool House with Suite 4br/2bth

4.94 out of 5 average rating, 67 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 spacious living area is highlighted by large windows allowing natural light to fill the space. A dark sectional sofa is positioned centrally, complemented by decorative cushions. Light wood flooring extends throughout, and a ceiling fan adds functionality. The adjoining room features a cozy seating arrangement.

4.95 out of 5 average rating, 76 reviews

Holiday Specials! Legoland, Pet Friendly, 7 Beds!

4.91 out of 5 average rating, 23 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, 22 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

5 out of 5 average rating, 23 reviews

Home in Edgewood

Karen’s Happy House

4.86 out of 5 average rating, 37 reviews

A spacious living area with a light-colored sofa and a glass coffee table is featured. A modern kitchen with wooden cabinetry is visible in the background. A large wall-mounted TV displays a tropical scene, while a vintage-style chair adds character to the space.

Home in Davenport

Tranquil Haven, Near Disney

Private house rentals

5 out of 5 average rating, 11 reviews

Family Vacation Home - 8 Minutes from Legoland

A serene lakeside view is captured at sunset, with the sun reflecting on the water. Silhouettes of buildings are visible across the lake. A lush green tree and grass line the foreground, framing the scene. Utility poles and wires are present in the background.

4.88 out of 5 average rating, 51 reviews

Lakeside Bungalow - Winter Haven Chain-of- Lakes

5 out of 5 average rating, 43 reviews

5bd Villa Eman Private Pool/Hot Tub close2Legoland

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, 79 reviews

Overlook Joy

4.93 out of 5 average rating, 60 reviews

Arcade+Pingpong + 10 guests + 11 mil to Lego Land!

4.92 out of 5 average rating, 37 reviews

A cozy living area features a light grey sectional sofa facing a large wall-mounted TV. Soft lighting is provided by a ceiling fan and lamps. A decorative black cabinet adds contrast, while a round table is set in the dining area, visible through an adjacent doorway.

Home in Lakeland

Blue Cottage On Parker [Downtown Lakeland]

5 out of 5 average rating, 14 reviews

A modern kitchen space is presented with white cabinetry and a marble-topped island featuring three brown leather stools. Open shelving holds kitchen essentials, with a gas stove and stainless-steel appliances visible. Natural light filters in through a nearby window, enhancing the inviting atmosphere.

Home in Lakeland

Luxury Modern Home In S Lakeland