House vacation rentals in Winter Haven

A single-story home features a light blue exterior with neatly trimmed hedges and palm trees in the front yard. The driveway leads to a two-car garage, and large windows reflect natural light, enhancing the welcoming ambiance of the property.

4.95 out of 5 average rating, 169 reviews

Luxury Home 4/3 near Disney, 2 Masters

Luxury 4 bedroom home located in a quiet, gated community about 15 miles from Disney World. The travel time to Disney will depend on the traffic but is usually between 30 and 40 minutes. Fully furnished with 2 master King bed suites, one queen bedroom and one bedroom with 2 twin beds. 3 full baths. 5 high definition televisions, high speed Wifi, free long distance phone calls to US, Canada and UK. Large pool and spa. Large game room with many games and activities for children of all ages.

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, 192 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. 13 miles from LEGOLAND, 22 miles from DISNEY, 29 miles from UNIVERSAL, 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 & the security & beauty of its homes.

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.

4.91 out of 5 average rating, 159 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

4.93 out of 5 average rating, 170 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*

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.

Home in Lake Hollingsworth

The open living area features a comfortable sofa set, a stylish area rug, and large windows allowing natural light to fill the space. An island kitchen with contemporary bar seating and modern appliances is visible, creating a seamless flow between dining and living spaces.

4.98 out of 5 average rating, 158 reviews

Gorgeous Gem in the Heart of Lakeland

LOCATION, LOCATION! This gorgeous, spacious, newly renovated home is located on one of the most desired and safest streets in all of Lakeland, and steps away from the beautiful Lake Hollingsworth and Trail. Close to the lake, and a short drive to downtown Lakeland, this gem is in the perfect location! This home features zero gravity beds, a gourmet kitchen, private laundry, smart TVs and WiFi, comfortable sofas with ample seating for entertainment, dining and more. You'll love this place!

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.

4.9 out of 5 average rating, 157 reviews

Awesome Vacation Home w/ Private Heated Pool/Spa

Sunshine living at its best! The Abbey at West Haven is an enclave of exclusive vacation homes. This gem has been totally redesigned and upgraded for your vacationing pleasure and is the IDEAL choice for your next family vacation or getaway in Central Florida. Stores, restaurants and golf courses are all within 5 mins and Disney just 15 mins away. After a long day at the Theme Parks or a round of golf, relax at the private, pool and spa or enjoy a BBQ on the enormous covered patio.

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, 106 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 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

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!

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, 336 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 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, 199 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 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, 126 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.

4.93 out of 5 average rating, 167 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

Welcome to our lake house retreat in Lakeland, Florida. You can enjoy a peaceful getaway with beautiful sunset views and tranquil waters during the evenings, and still visit major cities such as Orlando and Tampa during the day which are less than an hour away. Minutes from Southeastern University, Florida Southern, Lake Hollingsworth, and other attractions in the Lakeland area.

Popular amenities for Winter Haven house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.97 out of 5 average rating, 105 reviews

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

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, 128 reviews

Spectacular Waterfront Home in Winter Haven

A two-story, tropical style home is showcased, featuring a vibrant exterior in warm shades. A Tesla is parked prominently in the driveway, with lush palm trees and greenery flanking the entrance. The garage is accessible, contributing to the property's inviting curb appeal.

4.91 out of 5 average rating, 89 reviews

Luxury Tropical Themed Villa With Lake View!

A single-story home is showcased, featuring a light-colored exterior and a neatly landscaped front yard. Lush palm trees and shrubs enhance the lush green lawn. A driveway leads to a garage, while clouds drift in a clear blue sky overhead.

5 out of 5 average rating, 63 reviews

La Casita in Kokomo Bay

The image presents a collage featuring a private pool area with a screened enclosure under a blue sky, a cozy bedroom with green accents and a whimsical theme, and an elegant living space with modern furnishings. Natural light brightens each area, showcasing inviting design elements.

4.95 out of 5 average rating, 115 reviews

Great Location | Heated Pool | Awesome Design

The outdoor pool area features a screened enclosure with views of the golf course beyond. A circular table is set with blue napkins and dinnerware, surrounded by blue chairs. Six lounge chairs are positioned alongside the shimmering pool, providing a comfortable space to relax.

4.94 out of 5 average rating, 114 reviews

"Cozy Retreat with something for everyone"

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.

4.83 out of 5 average rating, 135 reviews

Southern Dunes Golf Vacation Villa

A heated pool and spa are enclosed within a screened patio, providing a sunny retreat. The clear blue water glimmers under the open sky, while lounge chairs are positioned nearby for relaxation. Lush greenery surrounds the area, offering a tranquil backdrop.

4.99 out of 5 average rating, 113 reviews

Sweet Sunshine. 4 king beds. Heated pool.

House rentals with a hot tub

4.9 out of 5 average rating, 71 reviews

Modern 3br home

The image captures a serene sunset viewed through a protective mesh enclosure, with silhouetted trees against a vibrant sky. In a second view, a two-story vacation home is presented, showcasing a well-maintained exterior surrounded by lush landscaping and palm trees.

4.93 out of 5 average rating, 121 reviews

Beautiful Pool Home With Rear Conservation Views

4.99 out of 5 average rating, 103 reviews

A spacious living area is furnished with a large sectional couch, accented by colorful throw pillows. A wall-mounted TV is positioned above a wooden console. Natural light filters through large windows, and the open layout connects to a dining area featuring a well-set table.

Home in Four Corners

Luxury Vacay Home w/ Pool 5Br/5Bath near Disney

An inviting outdoor space features a gently curving pool with a built-in hot tub, surrounded by a screened enclosure. Comfortable lounge chairs are arranged nearby, with two patterned hammocks and a dining area visible in the background. Soft evening colors fill the sky above.

4.79 out of 5 average rating, 121 reviews

There is no other place you want to be than here.

4.96 out of 5 average rating, 204 reviews

A private pool area featuring a clear blue pool with spa and surrounding palm trees. A giant outdoor chess set is visible nearby, along with a colorful tube slide leading to a vibrant bunk bed room. A game table with billiards is also showcased in the movie theater room.

Home in Four Corners

Luxurious Golf Front Oasis: Pool, Spa, View&Cinema

An aerial view of the resort reveals a sprawling water park, featuring winding lazy rivers and multiple pools surrounded by lush palm trees. Access to sports courts and landscaped areas can be seen, offering a vibrant atmosphere for leisure activities.

4.95 out of 5 average rating, 124 reviews

Lazy River, Pool, Slide, Cafe / 4 Bedroom Villa

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.

4.88 out of 5 average rating, 127 reviews

Heated pool/hot tub, near Legoland, Disney,

4.93 out of 5 average rating, 161 reviews

A private, screened-in pool area features a sparkling blue pool with a built-in hot tub on one side. Sunlight reflects off the water, creating a serene environment, while surrounding greenery provides a sense of privacy.

Home in Clermont

Stylish Villa Private Pool-SPA Near Parks Disney!

House rentals with free parking

A spacious living area features a grey sectional sofa and large windows that provide views of the golf course. Natural light fills the room, highlighting the open layout, which connects to the dining area and fully equipped kitchen with wood cabinetry and stainless steel appliances.

4.74 out of 5 average rating, 27 reviews

Elegant Golf Course Home in Southern Dunes

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, 20 reviews

Cozy2BR/2BR Near Legoland & Winter Haven Hospital

Home in Lake Hollingsworth

An open-concept living area showcases a cozy blue sofa and plush area rug. A large flat-screen television is mounted on the wall, while a light-filled space connects to the kitchen and dining area, defined by modern furnishings and an inviting color scheme.

4.97 out of 5 average rating, 86 reviews

3 Bedroom House | 2 Blocks from Lake Hollingsworth

4.9 out of 5 average rating, 31 reviews

Home in Lake Alfred

Pet friendly Central Florida Bungalow

A modern lakefront home is showcased with a clean, spacious facade. Well-maintained landscaping features palm and leafy plants, complementing the beige exterior. A curved driveway leads to a two-car garage, with panoramic views of the lake apparent beyond the property.

5 out of 5 average rating, 31 reviews

Winter Haven Waterfront Retreat

4.94 out of 5 average rating, 67 reviews

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

4.84 out of 5 average rating, 19 reviews

Home in Auburndale

Country Blue Getaway by the Ranch Fields

A spacious entryway features a decorative 'HOME' sign on the wall, with a neutral-coloured living area visible to the left. Light-toned wood flooring extends throughout, complemented by subtle wall art and a glimpse of additional rooms in the background.