Vacation rentals with lake access in Winter Haven

Guest suite in Winter Haven

Three thoroughbred horses graze peacefully on a lush green pasture. The area is surrounded by tall trees, providing shade and a natural backdrop. A glimpse of a trailer can be seen in the background, indicating the farm's working environment.

4.96 out of 5 average rating, 303 reviews

Horse Farm on a Beautiful Lake

Small Thoroughbred Race Horse Farm on a beautiful lake. The dock has plenty of benches for fishing, picnicking, or just dreaming. There is a Swimming pool right out your door. Please note there is no barrier around pool and all children (anyone under age of 18)must be supervised at all times. Guests must swim at their own risk. You may see horses in the paddocks. The pool deck overlooks the lake for hanging out or quiet time. Please note price is for studio (sleeps 3 or more with sofa beds)

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, 131 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, 100 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!

4.81 out of 5 average rating, 227 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 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.

4.96 out of 5 average rating, 257 reviews

A wooden deck overlooks the calm waters of Lake Ariana, framed by greenery. A small table with two chairs is positioned to enjoy the view, while a potted plant adds a touch of nature to the space. Spanish moss drapes gracefully from nearby branches.

Apartment in Auburndale

Ariana Place - Tree House Like Lakefront Views

An Upstairs Sumptuous Tree house (like) Apt on Lake Ariana Waterfront. Upper Outside Deck with chairs & table. Quiet and tranquil with Hi-Speed Wifi for Business Travelers, Smart Antenna TV and Incredible Views for Romantic Get-Aways. Located near Disney, Legoland & Busch Gardens in Central Florida. Luxurious Bedding, Full Kitchen with Coffee & Wine Bar. One Complimentary Bottle of Cabernet per Stay. Sorry, No Pets. No Smoking inside Apt but allowed on property. Save 5% monthly

4.99 out of 5 average rating, 294 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!

4.88 out of 5 average rating, 125 reviews

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.

Home in Haines City

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, arcade and gym (extra fee), soccer & football field, & event center for parties & weddings. (Pet free home) 12 mi Legoland/19 mi Disney/26 mi SeaWorld & International Drive/29 mi Universal Studios.

Guesthouse in Winter Haven

A serene lakefront scene captures a sparkling pool surrounded by palm trees at sunset. The sky features vibrant hues of orange and purple, reflecting in the calm water. Two lounge chairs are positioned beside the pool, creating a peaceful retreat.

4.87 out of 5 average rating, 281 reviews

The Russell Lake House

This is a Cabana. It has 2 sets of bunk beds (4 total beds). Approx 400 sq. Ft. . Includes a bathroom with sink, toilet, and walk-in shower. AC and heat are available. The property has a pool that can be used while onsite. The entire property's back yard is on a lake (lakefront) with a dock. Ample off street parking, quiet neighborhood with a private entrance for guests. **** we are in the process of rebuilding the dock so it will be unavailable until further notice ****

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, 206 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.

Guesthouse in Winter Haven

A wooden dock extends over the calm waters of Lake Howard, bordered by lush grass on either side. A sign indicating 'Private Property' stands at the dock's entrance, while the clear blue sky is dotted with fluffy white clouds in the background.

5 out of 5 average rating, 106 reviews

Charming Lakeside Cottage

Escape to our cozy lakeside cottage, featuring a dock that’s perfect for watching sunrises, fishing, and launching your kayak. The property is on Lake Howard, which is part of the Winter Haven Chain of Lakes. Inside, you’ll find a fully equipped kitchen and comfortable living space for unwinding. Located just a short drive from the excitement of Legoland and Disney World, you can easily explore the area’s attractions while having a peaceful haven to return to.

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, 115 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 lake access rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Lake access house rentals

5 out of 5 average rating, 36 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, 38 reviews

An aerial view showcases a spacious yard bordering a peaceful canal, leading to a large lake. The well-maintained property features lush greenery and a swimming pool, inviting relaxation. The surrounding homes reflect a tranquil community atmosphere, enhancing the serene waterfront setting.

Home in Auburndale

Little Castle on the canal on lake Arietta

4.81 out of 5 average rating, 214 reviews

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.

Home in Lake Wales

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

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, 80 reviews

Stylish Lakehome w.HUGE Pool/Arcade/Theater

5 out of 5 average rating, 13 reviews

4 bedrooms 3 full bathroom gorgeous home.

5 out of 5 average rating, 6 reviews

Lakefront home w/heated pool minutes from Legoland

4.96 out of 5 average rating, 164 reviews

Home in Lakeland

Cute, Historic District Home - GREAT LOCATION

4.79 out of 5 average rating, 34 reviews

Historic Manor near Parks | venues | Lake access

Lake access apartment rentals

Apartment in Winter Haven

4.93 out of 5 average rating, 15 reviews

Serene, family Lakefront home with Jacuzzi

4.89 out of 5 average rating, 109 reviews

A light-filled living area features a neutral-toned couch adorned with decorative pillows. A natural fiber rug lies beneath, while a dining space with white chairs is seen in the background. Coastal artwork adds a subtle nautical touch to the decor.

Apartment in Kissimmee

Beach Heaven minutes from Disney

4.96 out of 5 average rating, 204 reviews

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.

Apartment in Lakeland

cozy guest house 2 miles from I4 long term welcome

4.97 out of 5 average rating, 103 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.

Apartment in Orlando

2-Bedroom Renovated Lakeside Condo Near Disney

4.99 out of 5 average rating, 103 reviews

A cozy balcony is furnished with a comfortable seating area, featuring a blue sofa and a light-colored table. Palm trees are visible in the foreground, along with a serene waterfront view that stretches into the distance under a clear blue sky.

Apartment in Orlando

Lake View Penthouse

4.92 out of 5 average rating, 159 reviews

A spacious living area features large windows offering expansive lake views. Comfortable seating is arranged around a coffee table, and a dining table accommodates four. A flat-screen TV is mounted on the wall, enhancing the inviting space. The decor includes light-colored walls and a decorative area rug.

Apartment in Orlando

2B Condo Amazing Disney+Lake View from 2 Balconies

4.89 out of 5 average rating, 74 reviews

The entrance to Bella Piazza features a stone façade complemented by lush greenery and palm trees. The sign is prominently displayed in the foreground, and the building showcases a blend of architectural styles with arched windows and a terracotta roof.

Apartment in Davenport

Apartamento 313 Club House -Davenport/Orlando- FL

4.93 out of 5 average rating, 101 reviews

A circular pool is surrounded by lush palm trees and tropical plants. Sun loungers are arranged along the water's edge. The clear blue sky enhances the inviting atmosphere, while a splash pad with a red slide is visible in the background.

Apartment in Kissimmee

Sunny Day At Runaway Beach Club

Lake access cottage rentals

4.95 out of 5 average rating, 20 reviews

Cottage in Auburndale

Lakefront Boho Cottage w/ Fire Pit | Still Waters

4.81 out of 5 average rating, 166 reviews

A modern vacation rental home is highlighted, featuring a charming exterior with a covered porch and white railings. Lush greenery surrounds the property, and two palm trees are visible, providing a tropical touch. A gravel pathway leads towards the entrance, creating an inviting approach.

Cottage in Winter Haven

6 - Just Beachin' Cabin 2bed/2bath - Unit 10

A well-lit living area features a modern television mounted on a textured wall. A comfortable sofa and sleek coffee table invite relaxation. Natural light enters through a window with light-filtering shades. Decorative elements such as a small plant and art pieces enhance the space.

Cottage in Kissimmee

4.83 out of 5 average rating, 286 reviews

15min away from Disney- Family home and pool

4.85 out of 5 average rating, 243 reviews

A cozy living area is highlighted by a deep blue sofa positioned against a light-colored wall. Colorful artwork adorns the walls, with a vibrant floral piece and a nature scene featuring birds. Natural light filters in through the window, creating a warm ambiance.

Cottage in Clermont

Charming Lakefront Cottage Near Disney

4.85 out of 5 average rating, 241 reviews

A charming cottage exterior is showcased, featuring a combination of white siding and brick accents. Lush greenery surrounds the entrance, while a stone wall and gate provide access. Large front windows invite natural light, offering a welcoming view of the home.

Cottage in Polk City

Cozy Historical Cottage

4.92 out of 5 average rating, 107 reviews

A serene outdoor area features a stone patio with a green metal table and matching chairs, surrounded by lush foliage. The screen-enclosed pool area is visible behind the home, providing a view of the tranquil setting and inviting swimming space.

Cottage in Lake Wales

Cottage w/ Private Pool - Walk to Lake Wales!

4.64 out of 5 average rating, 191 reviews

A spacious deck is furnished with comfortable seating, including two armchairs and a glass-top table. The serene view overlooks a tranquil body of water surrounded by lush greenery and trees, creating a peaceful outdoor gathering space.

Cottage in Kissimmee

Sunset Lake House