Holiday rentals with lake access in Winter Haven

4.98 out of 5 average rating, 205 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, 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!

Cottage in Downtown Winter Haven

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.

4.81 out of 5 average rating, 226 reviews

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.

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, 146 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 one bedroom 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.

4.99 out of 5 average rating, 293 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!

4.89 out of 5 average rating, 124 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 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.

4.95 out of 5 average rating, 102 reviews

3/2 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, 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, 103 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.

Popular amenities for Winter Haven lake access rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Lake access house rentals

4.95 out of 5 average rating, 165 reviews

A spacious lawn is framed by large oak trees draped with Spanish moss. Comfortable lounge chairs are positioned facing the tranquil water, creating a serene outdoor space. The lake is visible in the background, enhancing the natural beauty of the setting.

Home in Auburndale

Lake Whistler Beach House with lakefront pool

A spacious screened-in patio features a refreshing swimming pool surrounded by a concrete deck. Two lounge chairs and a dining area are visible, along with a propane grill set against the wall. Clear blue skies and soft clouds complete the serene atmosphere.

4.92 out of 5 average rating, 39 reviews

Disney Castle Cove (Pool & Community Boat Ramp)

4.95 out of 5 average rating, 151 reviews

The exterior of the single-family home features a manicured lawn with lush greenery and vibrant plants. A spacious driveway leads to a garage, while decorative landscaping enhances the inviting atmosphere of the front yard.

Home in Lakeshore

Clean Lakeland Home w/ Water Views & RV Parking!!!

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.

4.89 out of 5 average rating, 45 reviews

Cozy Lakefront Home w/ Pool -7 mins from Legoland

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

5 out of 5 average rating, 12 reviews

4 bedrooms 3 full bathroom gorgeous home.

5 out of 5 average rating, 5 reviews

Lakefront home w/heated pool minutes from Legoland

Lake access apartment rentals

4.89 out of 5 average rating, 388 reviews

A vibrant living area features a comfortable sofa and dining table, with decorative blue walls enhancing the modern aesthetic. A well-equipped kitchenette is visible, and a spacious bedroom is partially seen through an open doorway, providing a glimpse of the inviting sleeping space.

Apartment in Kissimmee

King Bed Family Condo Orlando Disney Universal

A modern kitchen is highlighted with sleek, white cabinetry and stainless steel appliances. A marble countertop extends into a bar area with three cushioned stools. Glassware sits ready on the counter, complemented by a colorful towel and a decor piece.

4.87 out of 5 average rating, 147 reviews

Just Renovated 2/2 Resort Home

A canopy-covered terrace is accented by a comfortable seating area featuring plush blue cushions. Sun loungers are arranged alongside a dining table with umbrella, offering views of the surrounding landscape and sky.

4.92 out of 5 average rating, 102 reviews

Penthouse With EPIC Views

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.

4.85 out of 5 average rating, 167 reviews

BEST Views~2B2B~Universal~Disney

4.89 out of 5 average rating, 108 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, 201 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

4.95 out of 5 average rating, 148 reviews

The living area features a light-colored sofa adorned with decorative pillows, positioned in front of a wooden coffee table. A large television mounted on the wall displays a tropical beach scene. A blue sideboard complements the coastal-themed wallpaper in shades of blue and white.

Apartment in Kissimmee

Oceanic Oasis Near Disney

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.

4.97 out of 5 average rating, 102 reviews

2-Bedroom Renovated Lakeside Condo Near Disney

Lake access cottage rentals

4.95 out of 5 average rating, 19 reviews

Cottage in Auburndale

Lakefront Boho Cottage w/ Fire Pit | Still Waters

4.81 out of 5 average rating, 165 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, 239 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!

4.66 out of 5 average rating, 190 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