Family-friendly holiday rentals in Lake Wales

4.98 out of 5 average rating, 169 reviews

An inviting living area features a comfortable tufted chaise lounge and a cozy recliner. A flat-screen TV is mounted above a classic fireplace, surrounded by soft curtains that frame bright windows. The floor showcases warm wooden tones, contributing to a homely ambiance.

Cottage in Lake Wales

Charming, renovated 1917 Cottage

Charming, renovated 1917 cottage in beautiful neighborhood. One block from large lake with walking/running trail, 3.5 miles to Bok Tower, 12 miles to Legoland, 38 miles to Disney World, 47 miles to Universal Studios, and 63 miles to Busch Gardens. Pet friendly! King size bed in bedroom, double sofa bed in living area. Newly renovated kitchen has full size refrigerator, sink, microwave, stove top and large toaster oven. Big backyard with beautiful landscaping. Separate driveway. Lots of privacy!

KitchenFamilyTV

4.86 out of 5 average rating, 100 reviews

Lake Retreat w/Pool & Hot Tub near Bok tower

Pool & Hot Tub in screened Lanai. Large 4 Bedroom home with Living & Family rooms, 3 dining areas (screened porch that sits 12+). Wood burning fireplace in family room & electric fireplace in primary bedroom. Primary bedroom: en suite bathroom, makeup counter, attached office and 2nd floor balcony with lake views. Stocked kitchen with pots/pans, silverware, cups and plates. Drip & K Cup for coffee, Bonus: french press & moka pot. Bathrooms: plenty of towels, shampoo, conditioner & body wash.

KitchenFamilyBackyard

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.

4.93 out of 5 average rating, 104 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.

FamilyKitchenLong stay

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

KitchenFamilyParks

4.93 out of 5 average rating, 136 reviews

Sunshine on the Lake | Boat Slip+Lakefront Fishing

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

Indoor spacesFamilyValue

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.

4.93 out of 5 average rating, 203 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.

FamilyIndoor spacesAmenities

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!

Indoor spacesFamilyNearby

4.91 out of 5 average rating, 137 reviews

A cozy living area features two leather sofas positioned around a wooden coffee table with a glass top. In the background, a well-equipped kitchen with wooden cabinetry is visible. Natural light fills the space, enhancing the warm tones of the decor.

Cottage in Lake Wales

The "Little ‘Toa" Ideal for short & long stays!

Welcome to the Little TOA, Central Florida's fishing, hunting and winter get away. The house sits just off the Kissimmee River which is part of the Kissimmee chain of lakes, connecting Lake Hatchineha and Kissimmee. This will be a great spot for you and your buddies or family for a short weekend trip or an extended stay. Come see old Florida, the area holds many things to occupy your vacation time. *Your pet is welcome, please let me know ahead of time. There is a one time fee for pets.

Indoor spacesKitchenOutdoor spaces

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, 102 reviews

"Cutty Shack" Waterfront Kissimmee River House 3/3

"Cutty Shack" is the perfect fishing retreat. It is a 3 bedroom, 3 bath home built by our family in 1969. The Cutty Shack will sleep 6-7. This large stilt home (all living area is upstairs) is situated directly over Kissimmee River and right next door to Camp Mack River Resort. You and your group can enjoy peaceful evenings in the house, or walk next door to grab a drink and watch a "weigh-in". Our family has enjoyed this retreat for five generations and we hope you will too!

FamilyKitchenHiking

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.

4.98 out of 5 average rating, 205 reviews

Linda Casita de Lake Wales

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.

FamilyIndoor spacesWi-Fi

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, 223 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.

Indoor spacesKitchenBarbecue

4.95 out of 5 average rating, 101 reviews

Cozy House near to Legoland FL

Comfortable and clean 3-bedroom, 2-bath home in a quiet Lake Wales neighborhood. Features a fully equipped kitchen, a King bed in the master bedroom, two Queen bedrooms, washer and dryer, dishwasher, A/C, Smart TVs, and ample parking. Just 14 miles from LEGOLAND® and 49 miles from Disney, SeaWorld, and Universal. Shared driveway with another home. Located in a peaceful rural setting where you can enjoy nature and may occasionally encounter local wildlife.

KitchenIndoor spacesAmenities

Popular amenities for Lake Wales family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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, 137 reviews

Legoland Splash Escape (pool and hotub)

FamilyKitchenComfort

4.89 out of 5 average rating, 133 reviews

Breathtaking Home

FamilyIndoor spacesCheckout

A screened-in pool area features a clear, inviting swimming pool surrounded by comfortable lounge chairs. A basketball hoop is positioned at one end of the pool, with a scenic view of the lake and trees visible through the enclosure.

4.96 out of 5 average rating, 104 reviews

Southern Dunes Lakeview Poolhome

KitchenIndoor spacesAir conditioning

4.98 out of 5 average rating, 134 reviews

Adult-Only Retreat w/ Pool & Spa | 18+, Private

Indoor spacesFamilyQuiet

4.97 out of 5 average rating, 145 reviews

Home in Davenport

Magical 2 pool-Spa & Game Room Villa near “Disney”

Indoor spacesKitchenCondition

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, 177 reviews

Luxury Home 4/3 near Disney, 2 Masters

KitchenFamilyAccess

4.96 out of 5 average rating, 116 reviews

A unique sleeping area features a round bed designed to resemble a giant clam shell. Vibrant murals depicting underwater scenes adorn the walls, complementing the ocean-themed decor. Soft curtains in shades of green flow down from the ceiling, adding color to the tranquil space.

Home in Davenport

Royal Retreat Disney Themed Pool Home, Arcade, Theater

Indoor spacesKitchenDecor

4.95 out of 5 average rating, 171 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

Indoor spacesKitchenPets

Family- and pet-friendly home rentals

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.

4.95 out of 5 average rating, 314 reviews

Horse Farm on a Beautiful Lake

Indoor spacesFamilyWi-Fi

Superhost

A wooden barrel sauna is situated in a serene garden space surrounded by bamboo. The sauna features two benches and a wooden door, with soft lighting highlighting its natural texture and the tranquil atmosphere of the area.

Campervan/RV in Lake Wales

4.81 out of 5 average rating, 156 reviews

Bamboo Bus -Sauna/Pool/Fire pit/Grill

KitchenFamilyValue

A modern living area features a sectional sofa adorned with blue and white decorative pillows. A round coffee table with a marble top sits on a textured area rug. Natural light fills the space through sheer curtains, complemented by a stylish console table and a round mirror.

4.99 out of 5 average rating, 118 reviews

Cozy 3 bedrooms 2 bathrooms

KitchenFamilyWalkability

An aerial view captures the serene waterfront landscape, showcasing a canal bordered by lush trees. The expansive body of water reflects the sky, with residential homes dotting the shoreline. The image highlights the peacefulness of the surroundings, inviting outdoor activities and relaxation.

4.98 out of 5 average rating, 122 reviews

Crooked Lake House With Dock

KitchenIndoor spacesCheck-in

Cottage in Cypress Gardens

The exterior of the home features a well-maintained facade with light blue siding and white trim. A spacious front porch is accessible by wooden steps, surrounded by landscaping with shrubs and small plants. Trees provide shade in the front yard.

4.91 out of 5 average rating, 169 reviews

3 - Lake Life House 1 bed/1bath - Unit 15

FamilyIndoor spacesTV

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.

4.97 out of 5 average rating, 150 reviews

The Dalt Retreat

Indoor spacesKitchenAir conditioning

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.

4.79 out of 5 average rating, 352 reviews

Florida Oasis w/ Pool near LEGOLAND

KitchenIndoor spacesParks

A large outdoor space features a private pool surrounded by loungers in blue and a shaded dining area. A patio table with chairs is placed in the foreground, while a safety fence encloses the pool area, providing a secure environment.

4.98 out of 5 average rating, 123 reviews

Kid-friendly Home w/ Pool & BBQ

KitchenIndoor spacesPets

Family-friendly home rentals with a pool

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, 107 reviews

4/2 House near Legoland w Optional Heated Pool

KitchenFamilyGetting around

4.85 out of 5 average rating, 183 reviews

A well-maintained villa is showcased, featuring a welcoming entrance with a single-car garage. Lush greenery and colorful shrubs line the brick pathway, while tall palm trees and vibrant landscaping enhance the cheerful exterior. Bright clouds are visible in a clear blue sky.

Villa in Haines City

Sandy's Southern Dunes Villa

Indoor spacesFamilyPool

A two-story, tropical style home is showcased, featuring a vibrant exterior in warm shades. A Tesla is parked prominently in the driveway, with lush palm trees and greenery flanking the entrance. The garage is accessible, contributing to the property's inviting curb appeal.

4.92 out of 5 average rating, 111 reviews

Luxury Tropical Themed Villa With Lake View!

KitchenIndoor spacesDecor

4.96 out of 5 average rating, 109 reviews

Harry Potter's 6bd 6.5ba Hogwarts Experience

FamilyKitchenLocation

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.

4.91 out of 5 average rating, 203 reviews

Southern Dunes Villa - Pool - Golf - near Disney

FamilyIndoor spacesWalkability

Apartment in Winter Haven

A themed room features a ceiling adorned with illuminated stars and spacecraft. Neon lights accentuate Star Wars decor, including wall murals and figures. A television is mounted on the wall above two comfortable seating areas, creating an immersive atmosphere for fans.

4.99 out of 5 average rating, 165 reviews

STAR WARS Galaxy WORLD near LEGO land/Disney World

FamilyKitchenLocation

4.76 out of 5 average rating, 58 reviews

Hotel room in Lake Wales

Hotel-Style Heated Pool Suite•Spa Shower•86” TV

Indoor spacesFamilyHospitality

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.