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Family-friendly vacation rentals in Madisonville

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Madisonville

  • Total vacation rentals

    Explore 30 vacation rentals in Madisonville

  • Nightly prices starting at

    Madisonville vacation rentals start at G$12,552 GYD per night before taxes and fees

  • Verified guest reviews

    Over 720 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Madisonville vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Madisonville rentals

  • 4.8 Average rating

    Madisonville stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated family-friendly rentals in Madisonville

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
Home in Madisonville

Peaceful Retreat

Close to downtown Madisonville, Kentucky Sports Factory/Sports Plex and one mile from Mahr park (walking trails, picnic pavilions, kayak launch,etc). Private backyard with patio, table/chairs and BBQ grill. Home has Smart TV w/ streaming channels, DVD player, WiFi, Keurig and drip coffee, toaster, pots, pans, cookie sheet, mixing bowls, etc. One queen bed, one king, single over full bunk and single day bed. Full size inflatable mattress upon request. Bedrooms are upstairs. No smoking. No pets.

FamilyIndoor spacesQuiet

5.0 out of 5 average rating, 17 reviews
Top guest favorite
A cozy living area is presented with a comfortable seating arrangement, featuring a light grey armchair and a patterned upholstered sofa. A flat-screen TV is positioned on a stylish console, and large windows allow natural light to illuminate the space, offering views of the outdoor setting.
Home in Madisonville

Whippoorwill Farmhouse

Relax with the whole family at this peaceful place to stay. Located just two miles from the city, this fourth generation 1933 farmhouse has been recently remodeled inside and out. Enjoy relaxing in the enclosed front porch or the wrap around deck with views of the 180-acre working crop farm. Guests can enjoy a nice stroll around the farm, drop a line in the stocked pond, and spend time around the fire talking and roasting smore's. Ask your host about group events and hayrides around the farm.

Indoor spacesKitchenCheckout

4.99 out of 5 average rating, 107 reviews
Guest favorite
A cabin with a rustic wooden exterior features a welcoming wrap-around porch supported by sturdy posts. Large windows invite natural light, and a balcony extends from the upper level. Surrounding greenery offers a peaceful setting, enhancing the cabin’s connection to nature.
Cabin in Lewisburg

White Bluff Cabin with Hot tub on lake Malone

White Bluff Cabin sits in a quiet,friendly neighborhood overlooking Lake Malone. It is privately owned and offers all the accommodations to make your stay a relaxing one. It is fully furnished. FREE WIFI and parking. There is also a RV hookup available to cabin guests only for an additional fee. Just a short hike down to the boat dock and you will see the white bluff to your left which the cabin sets on. Or simply rock away on the spacious wrap-around porch, sipping coffee or iced sweet tea!

KitchenFamilyDecor

4.96 out of 5 average rating, 202 reviews
Top guest favorite
The exterior of a rustic cabin features a combination of log siding and a green metal roof. A spacious covered porch welcomes guests, with large columns supporting the overhang. Surrounding trees provide shade and natural beauty, enhancing the serene rural setting.
Cabin in Russellville

Cozy Cabin with Private Walking Trail

Relax and retreat to this peaceful rural cabin with modern amenities and charming outdoor spaces situated on a working farm. Enjoy the walking trail through 10 acres of woods or swing while enjoying beautiful country views. Experience the best of both worlds in the historic 19th century cabin with a modern addition. A short drive to quaint downtown Russellville, Auburn, or Franklin KY each with plenty of shopping. The nearby Red River provides opportunities for kayaking, tubing or fishing.

Indoor spacesFamilyNearby

4.94 out of 5 average rating, 215 reviews
Top guest favorite
Cabin in Dixon

Crouse’s North Ninety Lake House

If you want a place where you can be socially distanced, this is the place! (discounts for weekly or monthly stays.) The cabin is set in a 90 acre area surrounded by woods with two small lakes (fishing, walking trails and paddle boating available at no extra charge). There is only one other cabin on the 90 acres. Nearest town, Dixon (3 miles), Madisonville (20 miles, Henderson 21 miles), Evansville, IN (has a regional airport about 35 miles). Truly a relaxing getaway place.

Indoor spacesKitchenPets

4.96 out of 5 average rating, 346 reviews
Guest favorite
The treehouse is illuminated by soft outdoor lights, highlighting its wooden structure and welcoming design. A gently curving walkway leads to the entrance, surrounded by tall trees and a glimpse of Lake Malone visible in the background.
Treehouse in Lewisburg

Treehouse with HOT TUB!(Lake Malone)

Prepare to be taken to new heights as you enjoy this beautiful, private treehouse located on Lake Malone. It features an absolutely stunning view of the lake through an 8x14 glass door that opens up to allow the cool lake breezes to waft your cares away as you relax in the recliner. It also features a hot tub, large deck, full kitchen, Jacuzzi tub, rainfall shower, beautiful woodwork, two complimentary kayaks, and many other unique features that will make your stay unforgettable.

KitchenFamilyParking

4.95 out of 5 average rating, 169 reviews
Top guest favorite
Farm stay in Princeton

LUX Secret House & RED ROOM

IF THIS LISTING IS BOOKED… find our Lux Secret Room #2 Grooms Suite! Luxury Guest House & Historical Gypsy horse farm and wedding venue with an adult theme room just a short drive from Nashville TN. Kentucky's finest example of a working horse farm woven into a magically designed wedding venue. Our herd of Gypsy horses is sure to capture your heart!!! Just 4 miles from I-24 and close to dining and fun Patti’s 1880 Settlement! Perfect couple getaway for adults.

FamilyKitchenCondition

5.0 out of 5 average rating, 122 reviews
Top guest favorite
A modern duplex with a crisp white exterior is presented, featuring a dark roof and large windows. Two front doors, one for each unit, are framed by charming landscaping. Surrounding trees display vibrant autumn foliage, enhancing the inviting outdoor space.
Apartment in Madisonville

Modern, Quiet, Hidden Gem: Manna House (5)

Kick back and relax in this peaceful, brand new, stylish space. Located close to town yet feels like a hidden country paradise. This unit is one of two units available at a duplex situated on 5 acres. With 10 foot ceilings this one bedroom feels so much bigger! It offers a walk in tile shower, King bed and Queen sleeper sofa, full kitchen with Quartz countertops, KitchenAid appliances, and includes full size stacked washer/dryer. We think you will love it here!

FamilyIndoor spacesLayout

5.0 out of 5 average rating, 101 reviews
Top guest favorite
The entrance to the cabin is framed by wooden siding, featuring a central door adorned with a seasonal wreath. Natural elements, including pumpkins, are arranged on a small porch flanked by rustic decorations and a wooden fence made of branches.
Cabin in Dixon

Handcrafted Cabin in Woodsy Heaven

PLEASE read listing before booking. Custom built wood cabin nestled in the rolling hills of western Kentucky. Cozy decor with vintage theme, handcrafted wood floors, and outdoor space overlooking wooded property. Rustic studio space full of modern amenities. Close proximity to 5450 acre Wildlife Management Area with hiking, horseback riding, fishing, hunting, and swimming. Perfect location to get back to nature. Great peaceful weekend or overnight getaway.

Indoor spacesKitchenPets

4.91 out of 5 average rating, 556 reviews
Superhost
A well-lit studio space featuring large windows with sleek blinds. The area includes a spacious bed with a textured cover, a mounted flat-screen TV, and a small seating area with a table and chairs, perfect for relaxation or work.
Apartment in Hopkinsville

Spacious studio apartment blocks from downtown

Welcome to your private apartment in an old Victorian Era home, located right on the edge of downtown Hopkinsville. This space blends unique historic character with the comforts of a modern, private retreat. It also holds a special piece of local history—this home once belonged to and built by Lucian M. Cayce, a former Hopkinsville mayor and uncle of the world-famous mystic Edgar Cayce. Book your stay and experience a unique piece of Hopkinsville history!

KitchenIndoor spacesQuiet

4.77 out of 5 average rating, 107 reviews
Guest favorite
A charming three-bedroom house features a welcoming front porch with white railings. Dark shutters frame the windows, and the landscaping includes well-maintained grass and decorative stone elements. The inviting entrance is flanked by small bushes, enhancing the home's curb appeal.
Home in Madisonville

Loop Haven

Welcome to our delightful three-bedroom house, nestled in the heart of a quaint small town. Perfect for a relaxing getaway, this home offers all the comforts you need for a peaceful and enjoyable stay. The interior is warm and inviting, featuring a comfortable living room where you can unwind after a day of exploring. Local shops, cafes, and parks are just a short drive away, offering plenty of opportunities to explore and enjoy the area.

FamilyIndoor spacesCleanliness

4.9 out of 5 average rating, 30 reviews
Top guest favorite
The kitchen features a U-shaped countertop with wooden cabinetry and a deep sink, complemented by a tile backsplash. A dining area with a round table and chairs is visible in the background, along with a decorative wall piece and clock adding subtle detail to the space.
Farm stay in Hopkinsville

Quiet country setting.

Hello! Thank you for considering staying with us during your stay in or around Hopkinsville, Ky. Whether you’re coming for work, pleasure or, to visit family, we think you’ll love staying here. It’s a warm and inviting home, with all the amenities you need for the perfect stay. We live on the farm, and will be around if you require anything during your stay. Please email if you have any questions. We look forward to hearing from you.

KitchenIndoor spacesView

4.86 out of 5 average rating, 150 reviews

Popular amenities for Madisonville family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favorite
The cabin features a welcoming front porch with wooden railings and steps leading up to a central door with a rustic design. Natural wood elements complement the structure, blending with the surrounding greenery for an inviting appearance.
Cabin in Hopkinsville

1 Bedroom, 1 Bathroom Cozy Cabin with Hot Tub.

KitchenIndoor spacesOutdoor spaces

4.95 out of 5 average rating, 331 reviews
Top guest favorite
Two painted horses trot across a grassy field as the sun sets in the background, casting warm hues of orange and pink in the sky. Lush trees border the scene, enhancing a sense of tranquility in the natural landscape.
Cabin in Russellville

Keehn Hideaway-Hot tub/King bed/Horses/Secluded!

Indoor spacesFamilyOutdoor spaces

4.99 out of 5 average rating, 227 reviews
Superhost
The exterior of the house features a multi-level structure with wooden decks surrounded by green foliage. Steps lead up to the main entry, where lighting fixtures illuminate the space. A screened-in porch is visible on the upper level, providing access to outdoor relaxation.
Home in Lewisburg

Laid Back Lake House w/ hot tub and private dock❗️

KitchenIndoor spacesLaundry

4.91 out of 5 average rating, 171 reviews
Guest favorite
A spacious living area is furnished with a large sectional sofa, complemented by decorative pillows. A ceiling fan provides airflow, while natural light filters through the window blinds. A guitar hangs on the wall, and a wall-mounted artwork adds a pop of color.
Home in Owensboro

The Bluegrass House

Indoor spacesKitchenRiver

4.9 out of 5 average rating, 136 reviews
Guest favorite
Vacation home in Cadiz

Spacious Lakehouse w/ Hot Tub, Firepit & Game Room

Indoor spacesFamilyQuiet

4.9 out of 5 average rating, 136 reviews
Guest favorite
A serene outdoor space features a grassy area leading to a calm lake. Multiple red Adirondack chairs are arranged around a fire pit, nestled among trees. A wooden dock extends into the water, complementing the peaceful natural surroundings.
Home in Cadiz

Beautiful Waterfront, w/ Dock, Firepit, Hot tub

KitchenIndoor spacesPets

4.95 out of 5 average rating, 128 reviews
Superhost
An aerial view captures the serene landscape of Lake Barkley, showcasing a collection of residential homes along the shoreline. Lush green trees and open spaces surround the area, with the tranquil water reflecting the sky. The horizon features rolling hills extending into the distance.
Cottage in Eddyville

"My Happy Place"- Hot Tub & Lake Views

FamilyIndoor spacesLocation

4.79 out of 5 average rating, 101 reviews
Guest favorite
A spacious sleeping area features a large bed adorned with decorative pillows. The headboard is complemented by a green floral wall, while warm lamp lighting creates a calming ambiance. A cozy seating area and an intricately designed cabinet are also visible, adding a touch of charm.
Barn in Clarksville

Tiny Barn on a Farm Hot Tub 45 min to Nashville

Indoor spacesKitchenCheck-in

4.9 out of 5 average rating, 455 reviews

Family- and pet-friendly home rentals

Guest favorite
The interior showcases a warm, wooden design with vaulted ceilings and exposed beams. A modern television is mounted on the wall above a stone fireplace, while a cozy seating area is arranged with a dark sofa and wooden coffee table. The space is well-lit and inviting.
Cabin in Corydon

The Geneva Cabin

Indoor spacesFamilyComfort

4.93 out of 5 average rating, 136 reviews
Top guest favorite
The charming front porch is visible, featuring two red rocking chairs and a welcoming American flag. Lush green bushes frame the path leading up to the entrance, while a well-maintained yard provides a spacious outdoor feel. A bright blue sky complements the inviting atmosphere.
Home in Beaver Dam

Country Charm

KitchenFamilyBathroom

4.95 out of 5 average rating, 374 reviews
Top guest favorite
An open living area features large windows that allow natural light to fill the space. A comfortable sofa and patterned chair are arranged around a central area rug. A wooden table and chairs are positioned nearby, offering additional seating options.
Loft in Henderson

The Lifeboat Loft - in the Heart of Henderson

Indoor spacesFamilyTV

4.99 out of 5 average rating, 107 reviews
Top guest favorite
A cozy living area features large windows that overlook a serene lake at sunset, creating a vibrant display of colors in the sky. Comfortable seating is provided by a dark sofa and armchairs, accompanied by small tables for convenience.
Home in Cadiz

Entire Waterfront Home - 6 Bed/4.5 Baths

FamilyKitchenCheck-in

4.9 out of 5 average rating, 121 reviews
Top guest favorite
A modern kitchen showcases sleek black cabinetry and a light wooden countertop. The black hexagonal tile floor enhances the contemporary design. A dining area is visible in the background, featuring a black table surrounded by chairs, with natural light entering through the windows.
Home in Oak Grove

Welcome to The Honeycomb.

FamilyIndoor spacesAccess

4.9 out of 5 average rating, 196 reviews
Top guest favorite
A scenic view of Lake Malone at sunset is captured, displaying a vibrant pink and purple sky reflecting on the water's surface. Silhouetted trees frame the scene, adding depth to the tranquil atmosphere. A drinking vessel is positioned in the foreground, suggesting a moment of relaxation.
Home in Lewisburg

Water’s Edge (No cleaning/Pet Fees)

KitchenFamilySleep quality

4.94 out of 5 average rating, 102 reviews
Guest favorite
The tranquil lake scene is framed by lush greenery and tall trees. A wooden dock extends into the water, with a blue floating platform nearby. Boats are gently moored, reflecting the serene surroundings under a bright sky.
Home in Lewisburg

⭐️The Maya II on Lake Malone⭐️

FamilyKitchenPets

4.85 out of 5 average rating, 135 reviews
Superhost
A spacious kitchen features wooden cabinets and a granite countertop island. Four wooden dining chairs surround a rectangular table. A door leads outside, and natural light enters through two windows dressed with light curtains.
Vacation home in Owensboro

The little big cozy house

KitchenFamilyAccuracy

4.88 out of 5 average rating, 163 reviews

Family-friendly home rentals with a pool

Guest favorite
The cottage features a welcoming front porch adorned with red shutters and a bright red door. Two large, round rocking chairs are positioned on the porch, surrounded by greenery and a blue planter. The pathway leads to the spacious entrance.
Cottage in Maceo

Hattie's Hill Cottage

KitchenIndoor spacesView

4.96 out of 5 average rating, 189 reviews
Guest favorite
A modern kitchen features dark cabinetry complemented by light granite countertops. Stainless steel appliances, including a refrigerator and microwave, are visible. Two pendant lights hang above the kitchen island, and a sink is positioned between the counter space. A decorative sign is displayed on the backsplash.
Home in Clarksville

Beautiful Townhome with Pool

Indoor spacesKitchenAmenities

4.9 out of 5 average rating, 128 reviews
Guest favorite
Home in Trigg County

New Dock, Pool, Hot Tub, Games, Sleeps 18

KitchenFamilyOutdoor spaces

4.97 out of 5 average rating, 33 reviews
Top guest favorite
A spacious swimming pool is surrounded by a wooden deck, featuring colorful floats and a beach ball. Sun loungers are positioned near the pool, offering views of the waterfront and trees in the background.
Home in Murray

Lakefront Getaway | Pool, Pickleball, Dock

Indoor spacesKitchenCheck-in

4.98 out of 5 average rating, 65 reviews
Top guest favorite
The image displays various areas of a spacious vacation home. A bright kitchen is seen with modern appliances and ample counter space. A cozy dining area accommodates multiple guests. Outside, a hot tub offers relaxation, and an outdoor patio with seating is visible, surrounded by greenery.
Home in Owensboro

Hot Tub on Hill Sleeps 12 | POOL|Hot Tub & Firepit

KitchenIndoor spacesBackyard

5.0 out of 5 average rating, 51 reviews
Guest favorite
Place to stay in Owensboro

Woodsy Waterfront Cabin with Loft

Indoor spacesKitchenAmenities

4.91 out of 5 average rating, 58 reviews
Guest favorite
A spacious living area is highlighted by a decorative fireplace with a round mirror above it. A modern ceiling fan hangs overhead, while a glass coffee table sits on an area rug. A compact desk and television unit are also visible, contributing to a warm atmosphere.
Home in Owensboro

Bluegrass Getaway • Swim, Relax & Unwind

Indoor spacesFamilyQuiet

4.84 out of 5 average rating, 57 reviews
Guest favorite
Cabin in Eddyville

Lakeview Log Cabin

ComfortCleanlinessHospitality

5.0 out of 5 average rating, 5 reviews

When is the best time to visit Madisonville?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$26,987 GYDG$28,033 GYDG$28,033 GYDG$28,033 GYDG$28,243 GYDG$28,243 GYDG$28,243 GYDG$28,243 GYDG$25,732 GYDG$26,987 GYDG$28,243 GYDG$26,150 GYD
Avg. temp3°C5°C9°C15°C20°C24°C26°C25°C21°C15°C9°C4°C