House holiday rentals in Lake Wales

A bright and airy living space features a comfortable sofa and a coffee table atop a decorative rug. A ceiling fan and large glass doors lead to an outdoor area, while a sleek television adorns the wall opposite. Natural light enhances the neutral color palette.

5 out of 5 average rating, 16 reviews

Premium Lake Wales Getaway!

Beautiful townhouse, conveniently located in growing Lake Wales! Hotel-like feel with home-like comfort. Whether you're visiting for one night or planning an extended stay, this updated and stylish space lacks for nothing. We have you covered! Conveniently located near the infamous Bok Tower Gardens, Legoland, Peppa Pig Theme Park, with Disney World and world-famous, FL beaches within a couple hours away your options are endless. We hope you choose to stay with us for your special getaway!

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, 80 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.

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, 184 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. 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, 104 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

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 swinging hammock chair is suspended from a large oak tree, providing a cozy spot for relaxation. The inviting green house with a red door is visible in the background, surrounded by landscaped greenery and fallen leaves, which enhances the peaceful outdoor setting.

5 out of 5 average rating, 34 reviews

Perfect retreat for the family near Legoland!

Relax with the whole family at this peaceful place to stay. Quiet privacy on a dead-end street with few neighbors. The feel of the country yet close to large attractions like Bok Tower and LEGOLAND. Have a bite to eat and enjoy live music and wild alligators at Cherry Pocket Restaurant 1 mile away. Enjoy your mornings and evenings on the large shaded front porch under the live oak trees. Space for kids to play. Bring your boat, trailer, or RV; plenty of parking. Boat ramp close by.

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, 101 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. 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. (Additional guests must be pre-approved). Free boat parking and boat rental available. House is connected to the main home with a private keyless touchpad for contactless entry. Pet friendly with prior approval and pet deposit.

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.

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, 140 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 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, 191 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, 105 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

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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

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, 151 reviews

Awesome Vacation Home w/ Private Heated Pool/Spa

4.89 out of 5 average rating, 9 reviews

Spacious Winter Haven Retreat w/Pool&Pet Friendly!

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, 118 reviews

Fantastic Water Front Home on the Chain of Lakes

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.

4.83 out of 5 average rating, 30 reviews

Escape Comfort Property

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.

4.94 out of 5 average rating, 109 reviews

Great Location | Heated Pool | Awesome Design

4.86 out of 5 average rating, 112 reviews

An outdoor space features a swimming pool with a spacious deck. A pergola provides shade over a dining area with four chairs and a table. Lounge chairs are positioned nearby, surrounded by greenery and a wooden fence marking the perimeter.

Home in Lakeland

Spacious Private Family Home with Pool

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, 165 reviews

Luxury Home 4/3 near Disney, 2 Masters

Weekly house rentals

4.82 out of 5 average rating, 33 reviews

A cozy bedroom features a spacious bed dressed in a light blue quilt. Natural light enters through a window covered by dark curtains. A standing lamp and a bedside table accent the room, while decorative wall art adds a touch of style.

Home in Kissimmee

Lux Vacation Villa w/ Free Prkg | Pool | Sleeps 6

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.

5 out of 5 average rating, 21 reviews

Private Ranch Style Home on Lake

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.

4.96 out of 5 average rating, 45 reviews

Lake House by Legoland + Loft & Private Dock

A sprawling water park is displayed with multiple pools and slides. Lush palm trees provide shade, while guests enjoy leisurely floats in a lazy river. An array of colorful water slides adds vibrancy, surrounded by modern resort buildings, creating an inviting and fun atmosphere.

4.94 out of 5 average rating, 77 reviews

Spectacular Condo 2Bed/2Bath Close to Disney

The kitchen area features modern appliances including a refrigerator, oven, and microwave. A dining table for six is positioned in front of a large window. Natural light fills the space, highlighting the sleek cabinetry and warm hardwood flooring.

4.98 out of 5 average rating, 62 reviews

Modern 3 Bed 2 Bath Home • 3 minutes from Legoland

A fenced heated pool area is visible, surrounded by lush greenery and palm trees. The villa entrance features a welcoming façade and a spacious driveway. Inside, a games room showcases vibrant Nemo-themed murals, along with seating and game tables for recreational enjoyment.

5 out of 5 average rating, 19 reviews

Adult Luxury - Magic for Families!

5 out of 5 average rating, 4 reviews

ChampionsGate Pool Townhouse • Resort Luxury

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

Private house rentals

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

A modern kitchen is characterized by sleek white cabinetry and a large island with a marble finish. Full-size appliances are positioned against the wall, while a contemporary hood vent is mounted above the cooking area. Bright lighting enhances the spacious feel of the room, complemented by glossy tile flooring.

4.89 out of 5 average rating, 71 reviews

Gorgeous Newly Renovated Home

A heated swimming pool is framed by a screened enclosure, reflecting the tranquil sunset over the water. An outdoor kitchen area is visible in the background, surrounded by potted flowers and shaded by large trees, enhancing the relaxing atmosphere.

5 out of 5 average rating, 19 reviews

Lake Home w/Heated Pool, Dock, Kayaks & EV Charger

4.91 out of 5 average rating, 22 reviews

A comfortable living area is displayed, featuring a light gray sofa accented with colorful cushions. Glass side tables are positioned beside the sofa, and a large mirror enhances the space. A cozy throw blanket is draped over an ottoman, with a coffee table showcasing books and decorative items.

Home in Lake Alfred

Central Florida Bungalow! 2 Bedroom 1 Bath

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, 14 reviews

Reel Simple

4.93 out of 5 average rating, 42 reviews

A well-appointed bedroom features a spacious bed flanked by two bedside lamps on matching nightstands. Light streams through two windows with blinds, and a seating bench adds convenience at the foot of the bed. Subtle wall decor complements the neutral color scheme.

Home in Dundee

Charming Home in Dundee

A screened-in pool area features a vibrant pool surrounded by greenery. A comfortable seating arrangement is offered, alongside a grill for outdoor cooking. The pool floats in a sunny yellow design while golf course views are visible in the background.