House vacation rentals in Lake Wales

A spacious living area features a light-colored sofa and a round coffee table at the center, surrounded by distinctive tile flooring. Large windows invite natural light, while plants and a ceiling fan add to the relaxed ambiance. The circular design enhances the open feel of the space.

4.91 out of 5 average rating, 82 reviews

La Casita Redonda (The little round house)

Enjoy a memorable visit when you stay in this unique and historical place in Lake Wales, FL. Constructed in 1936 this home is nestled within a quiet and friendly neighborhood just minutes from the downtown area and just a short walk to Lake Wailes itself. Although the current owner updated the home with practical renovations, the peculiar house still has the character and features from the time it was built, features that once granted it a place among the pages of Ripley’s Believe it or Not.

4.9 out of 5 average rating, 185 reviews

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.

Home in Haines City

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

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 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.

4.94 out of 5 average rating, 155 reviews

*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.

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.

Two blue kayaks are positioned on a sandy shore, facing a calm lake. Lush greenery is visible in the background, contrasting with a clear blue sky dotted with white clouds. A paddle rests beside one of the kayaks.

5 out of 5 average rating, 49 reviews

Lake Front! Spacious Home w/heated pool & kayaks

Escape to our charming lakefront home with 4 BR/3BA, including 2 BR & 1 BA w/ direct pool access. Enjoy stunning sunsets by the lake. Rest by the large fireplace in the family room. Dine in one of three dining areas, including outdoors with a BBQ grill. Explore walking and biking trails around the lake leading to downtown Lake Wales. Just 1 mile from Bok Tower Gardens. Fully stocked kitchen with drip, K-Cup coffee, and French press. Perfect for family getaways or weddings nearby.

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.

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.

4.96 out of 5 average rating, 142 reviews

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, 107 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 Lake Wales house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 123 reviews

The Dalt Retreat

4.98 out of 5 average rating, 64 reviews

3 Bed 2 Bath Home • Pool • 3 minutes from Legoland

4.99 out of 5 average rating, 151 reviews

An expansive outdoor pool deck is featured, surrounded by lounge seating and shaded areas. A giant outdoor chess set stands nearby, along with a view of the scenic forest and pond. A brightly decorated game area showcases themed decor and entertainment options.

Home in Four Corners

*Luxurious Paradise Mansion: Pool, Spa & Cinema

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, 28 reviews

Winter Haven Waterfront Retreat

4.9 out of 5 average rating, 120 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

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,

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.

4.8 out of 5 average rating, 54 reviews

John Shirley’s Retreat

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.

4.84 out of 5 average rating, 31 reviews

Escape Comfort Property

Weekly house rentals

A cozy loft bedroom features a spacious bed with soft linens and decorative pillows. A Roku screen projector casts images onto the slanted ceiling. Light from recessed fixtures brightens the room, while minimalist decor includes two small plants and a white dresser against the wall.

4.91 out of 5 average rating, 46 reviews

Lake House by Legoland + Loft & Private Dock

4.89 out of 5 average rating, 28 reviews

A spacious game room is featured, highlighted by a red pool table situated beneath ceiling fans. Large, open windows provide views of the outdoor area, creating a seamless connection to the surrounding nature. Nearby, a hot tub and comfortable seating areas invite relaxation.

Home in Eagle Lake

Sunset Lakefront Home | Hot Tub, Private Dock

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

4.94 out of 5 average rating, 52 reviews

A spacious living area features a comfortable sofa complemented by decorative cushions. A large flat-screen TV is mounted on the wall, displaying a tropical beach scene. Natural light fills the space through sliding glass doors that lead to a patio, framed by light, airy curtains.

Home in Lakeshore

Secluded villa/pool/hot tub/ washer/dryer

A wooden dock extends over the calm water of Walk In Water Lake. Two folding chairs are placed beside a bench, providing seating to enjoy serene views. The tranquil setting is complemented by a ceiling fan and string lights suspended from the overhead structure.

5 out of 5 average rating, 10 reviews

Month Stays Ok | Lakefront Fishing w/ Dock & Canoe

A large stilt house is portrayed above the serene waters of Kissimmee River, surrounded by lush greenery and lily pads. The structure features a wide porch and multiple windows, reflecting a rustic charm with the sky scattered with clouds in the background.

4.91 out of 5 average rating, 96 reviews

"Cutty Shack" Waterfront Kissimmee River House 3/3

A private outdoor area features a serene pool surrounded by lush greenery and palm trees. A paved patio includes a table with chairs and a lounge chair, inviting relaxation. The clear blue sky complements the tranquil ambiance of the space.

4.97 out of 5 average rating, 38 reviews

Live your best Florida life!

4.82 out of 5 average rating, 28 reviews

Fresh & Modern Home

Private house rentals

5 out of 5 average rating, 10 reviews

Home in Davenport

Family-Friendly Disney Retreat

The inviting exterior of a lakefront hideaway is highlighted by its bright yellow façade. The home features a symmetrical design with a circular stone staircase leading to an arched front door. Surrounding shrubbery and clear blue skies contribute to a friendly atmosphere.

4.71 out of 5 average rating, 17 reviews

Vibrant 1936 Lakefront Hideaway

5 out of 5 average rating, 69 reviews

Home in Lake Alfred

Majors House #5 - 1BR / 1.5BA

4.94 out of 5 average rating, 68 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

5 out of 5 average rating, 43 reviews

Home in Haines City

5bd Villa Eman Private Pool/Hot Tub close2Legoland

A cozy outdoor seating area features four adirondack chairs arranged around a fire pit, surrounded by a landscaped yard. The exterior of a spacious building is visible in the background, with large windows allowing natural light to enter.

5 out of 5 average rating, 15 reviews

Reel Simple

4.88 out of 5 average rating, 33 reviews

The exterior entrance of the vacation home is framed by two white columns and a decorative wreath on the front door. Brick walls and large windows complement the inviting porch, which is surrounded by landscaped shrubs and a concrete pathway leading up to the entrance.

Home in Frostproof

Lake Reedy Resort

A charming single-story home is set in a spacious outdoor area, featuring a wide driveway leading to a covered porch. The front yard is framed by lush greenery, with a large tree providing shade to the house and the surrounding landscape.