Vacation rentals with lake access in Winter Haven

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.

4.9 out of 5 average rating, 312 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.

4.98 out of 5 average rating, 210 reviews

The living area features a modern sectional sofa with colorful throw pillows in vibrant red and yellow. A matching ottoman sits in front, accompanied by stylish side tables with lamps. Bright blue walls create a lively backdrop, enhanced by a large abstract painting and adjacent dining space.

Villa in Lake Wales

Lakefront, Dock, 2 Kayaks, near Bok & Legoland

** New Construction ** Breathtaking view of lake, private dock (2 kayaks for guests included), beach/swim area, outdoor shower, large private balcony w/gas grill and gorgeous sunsets! 2 Bedrooms each w/walk in closet, two full baths, full kitchen w/all amenities. All new furnishings, (3) 4K Smart TV's, FAST free wifi. Gorgeous location, quiet street, private free parking, 2 private entrances. Villa is detached from main house. Near Disney, LegoLand, Bok Tower. WEEKLY & MONTLY DISCOUNTS

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, 138 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!

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.

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)

4.95 out of 5 average rating, 314 reviews

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, 101 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!

4.96 out of 5 average rating, 116 reviews

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.

Home in Cypress Gardens

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.

4.99 out of 5 average rating, 310 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!

4.95 out of 5 average rating, 107 reviews

An outdoor dining area is shown under a shaded pergola, featuring a large table surrounded by comfortable chairs. The spacious pool is visible in the background, with a patio area adorned with colorful tiles. Lush greenery frames the scene, adding a tranquil vibe.

Home in Cypress Gardens

4/2 House near Legoland w Optional Heated Pool

Relax with the whole family at this peaceful home in Winter Haven 5mins to Legoland and the new Peppa Pig theme park, perfect for your next family vacation! Right across the street from lake Ned park with lake View from the front porch and office, bring your small water toys as there is a public boat ramp across the street. There are many restaurants as well as a Publix grocery store all within 2 miles from the home! Downtown winter haven is a short 10 minute commute.

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, 222 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.

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.

4.98 out of 5 average rating, 126 reviews

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.

4.98 out of 5 average rating, 124 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 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, 151 reviews

Beautiful Lake House Boating Fishing near Legoland

Welcome to The Executive Lake House 15 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 2 bedrooms and a kids loft. A full kitchen and laundry and one full bathroom The backyard has a playground and pool area that is on the property in backyard and is shared with other guests who may be staying here.

Popular amenities for Winter Haven lake access rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Lake access house rentals

4.92 out of 5 average rating, 106 reviews

A comfortable living area features a spacious sectional sofa adorned with neutral-toned cushions. A patterned area rug lies beneath, and a wall-mounted television is positioned above a wooden shelf. Natural light enters through the large window covered with light curtains.

Home in Wahneta

Hidden 💎 Minimalist Design | Lego+Disney

4.89 out of 5 average rating, 133 reviews

Home in Haines City

Breathtaking Home

4.93 out of 5 average rating, 188 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 Crystal Lake

Lakefront 3BR/2BA near downtown Lakeland

4.96 out of 5 average rating, 102 reviews

The living room features a vintage vinyl record wall that adds character. A spacious white sofa and a brown leather couch are positioned for relaxation. Natural light filters through shuttered windows, illuminating the hardwood floor and a round area rug with a geometric pattern.

Home in Lakeland

LKLD Legacy near Downtown Lakeland

4.86 out of 5 average rating, 100 reviews

Home in Lake Wales

Lake Retreat w/Pool & Hot Tub near Bok tower

4.93 out of 5 average rating, 136 reviews

Home in Lake Wales

Sunshine on the Lake | Boat Slip+Lakefront Fishing

4.94 out of 5 average rating, 190 reviews

Home in Lakeland

Cute, Historic District Home - GREAT LOCATION

5.0 out of 5 average rating, 42 reviews

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.

Home in Cypress Gardens

Winter Haven Waterfront Retreat

Lake access apartment rentals

4.96 out of 5 average rating, 266 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

5.0 out of 5 average rating, 154 reviews

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.

Apartment in Lakeland

Romantic Lakefront – Feed Swans – Walkable Dining

4.95 out of 5 average rating, 219 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 house close to I4 monthly rental also

A dining table is set for six, adorned with teal plates and drinking glasses. The living area features a comfortable gray sofa and a TV mounted on the wall, with natural light filtering in from the balcony doors, which lead to a green outdoor seating area.

4.94 out of 5 average rating, 424 reviews

Great Full Apartment. Just 5' from Disney Orlando

The living area features a modern sectional sofa with light-colored upholstery, complemented by bright throw pillows. A wall-mounted TV is positioned above a low media console, and large sliding doors open onto a patio overlooking the lake, creating an airy and spacious feel.

4.89 out of 5 average rating, 102 reviews

3141-103 Resort Lake View Disney Universal Orlando

Superhost

A private terrace is presented with ample lounge chairs facing a scenic waterfront view. Lush greenery surrounds the area, and a bright blue sky is visible above, enhancing the open atmosphere. The cityscape with buildings is visible in the distance.

Apartment in Orlando

BEST Views~2B2B~Universal~Disney

4.84 out of 5 average rating, 180 reviews

Superhost

A spacious balcony is equipped with woven seating and a glass-top table. Views of a tranquil waterway and lush greenery are visible, framed by modern railings. Soft clouds drift across the sky, enhancing the overall serene atmosphere of the outdoor space.

4.76 out of 5 average rating, 133 reviews

★BRAND NEW APT with LAKEVIEW - Close to Disney★

4.79 out of 5 average rating, 158 reviews

Cozy Vacation Condo next to Disney Universal

Lake access cottage rentals

4.86 out of 5 average rating, 250 reviews

Cottage in Polk City

Cozy Historical Cottage

4.99 out of 5 average rating, 202 reviews

A themed kitchenette features a bamboo bar with high seating and colorful pendant lighting. The walls are adorned with tribal art and shelves hold various artifacts. Kitchen appliances, including a refrigerator and counter space, reflect a blend of modern convenience and cultural decor.

Cottage in Kissimmee

Tahiti Gil’s Mananui: Disney Poly & Tiki Inspired!

4.84 out of 5 average rating, 259 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

Superhost

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

15min away from Disney- Family home and pool

4.82 out of 5 average rating, 299 reviews

4.85 out of 5 average rating, 138 reviews

Cottage in Kissimmee

Chic Cottage near Disney - Lots of Amenities!

4.94 out of 5 average rating, 32 reviews

Cottage in Auburndale

Lakefront Cottage • Kayaks • 10 Min Lake Myrtle

4.92 out of 5 average rating, 111 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!