Family-friendly holiday rentals in The Woodlands

4.97 out of 5 average rating, 106 reviews

A cozy sleeping area features a spacious bed adorned with a light blanket and a vibrant yellow throw. A large window allows natural light to fill the room, providing a view of the surrounding trees and greenery. Shelving units and a wall-mounted TV are also present.

Tiny home in Magnolia

"Smouse" - A Romantic Escapade !

From the founders of SerendipTINY & Bonnie Lou Tiny home as featured on the popular TV show, Tiny House Nations on Netflix! WELCOME to "Smouse" - A Romantic Escapade in Magnolia Tiny Home Village. 250+ sqft indoor and abundance of outdoor patio and lounge space w/ hammock, fire pit & more. 1 queen in loft and 1 queen sofa bed w/ full kitchen. PRO-decor and furnished. Insta-gram READY! Experience the world of GLAMPING. Romance and Fun for ALL!Reconnect with nature at this unforgettable escape.

4.88 out of 5 average rating, 238 reviews

A spacious living area is highlighted by a high open ceiling and large windows allowing for natural light. A dark leather sofa and two accent chairs are positioned around a decorative rug. A media console holds a flat-screen TV, creating a comfortable lounge environment.

Farm stay in Conroe

Country Retreat close to The Woodlands w/Pool

Stay 5 Min from The Woodlands in this one-of-a-kind retreat next to the Jones State Forest. 1/2 mile to walking, biking, or horseback riding on forest trails. At night you’ll gaze at twinkling constellations poolside or relax in our massage chair or jetted garden tub. Attend an outdoor concert at the nearby Cynthia Woods Mitchell Pavilion, one of the top amphitheaters in America. We are 5 min from The Woodlands Medical Center, and 10 min from The Woodlands Mall where you can shop till you drop.

4.99 out of 5 average rating, 169 reviews

A serene outdoor space is highlighted by a heated pool with fountain features, surrounded by lush greenery and colorful flowers. A stylish gazebo provides shaded seating, with comfortable lounge chairs positioned nearby. The natural landscape is enhanced by tall trees, creating a private and tranquil ambiance.

Home in Conroe

Country Sanctuary-5*Lux King Bed-2,400+ Sq Ft

This beautiful, custom-built 2,400+ sq ft home, that sits on 1 acre, is surrounded by the woods and the many deer, giving you all of the privacy you will need for a relaxing retreat. If you want to feel peace and tranquillity while listening to the birds chirping, you want to stay here. Please make the Country Sanctuary a favorite in your search by clicking on the RED HEART in the upper right hand corner, this will help you find it again and share with others. Christmas Tree for the Holidays

4.9 out of 5 average rating, 432 reviews

A tranquil evening view of a gently flowing waterway is highlighted by vibrant pink lights reflecting off the surface. Modern buildings and illuminated archways frame the scene, while a clear moon hangs in the sky, casting a soft glow over the surroundings.

Home in Conroe

WOW!❤️Hidden Gem in Woodlands!💎Boat/RV allowed⭐️

Come home to this enchanting retreat in The Woodlands and near Houston! Only minutes to great shopping, dining, and entertainment, yet tucked in a relaxing natural garden oasis! Boats and RV's are welcome! Chic spacious bedrooms all furnished with Memory Foam beds and new 50" 4K TV's in each! Less than 30min to IAH and Lake Conroe, and less than 1hr from Houston! Minutes to Waterway, Hughes Landing! Walk to beautiful nearby hike/bike trails through wildflower gardens and bird sanctuaries!

5 out of 5 average rating, 152 reviews

A kitchenette is displayed, featuring a sleek countertop with a stainless steel sink. An electric countertop oven sits alongside a coffee maker, complimented by a shelf holding dishware and decorative items. A roll of paper towels and dish soap are positioned for easy access.

Guesthouse in Shenandoah

The Woodlands/Shenadoah Casita

Right in the heart of all of the action, you will find this super cute, well appointed Casita with queen bed. You will have your own space and everything you need for your getaway. We provide off street parking, outside patio, hot tub and access to the grill. This casita is located across the patio from our primary residence. While you do have your own space you may bump into us outside feeding the chickens or letting our little Yorkie out to potty. You’ll access through the side gate.

4.99 out of 5 average rating, 109 reviews

The exterior of a modern home is shown, featuring a stone-accented facade. A neatly landscaped lawn is visible, complemented by a curved driveway leading to two wooden garage doors. Lush greenery lines the path to the entrance, creating a welcoming approach.

Home in The Woodlands

Best location in Woodlands! 1 mile from everything

-Best location in The Woodlands! 3 bedroom peaceful home, walking distance from Hughes Landing. 1 mile from Woodlands Mall, Market St, Waterway, hospitals, & Whole Foods. -Access to tree lined walking/biking trails next to house. -3 bedrooms, 2.5 bathrooms, 2 living rooms. Small private backyard w/patio furniture. -Family friendly home; I provide pack n play, highchair, toys, dishes, & some baby proofing. -Desk & remote working area -coffee/tea bar & ample kitchen supplies provided!

4.96 out of 5 average rating, 228 reviews

An outdoor patio space is presented, featuring two black chairs beside a table. A hot tub is situated to the left, while glass doors lead into a cozy interior that includes a comfortable living area with soft seating and a dining space lined with modern amenities.

Tiny home in Spring

*HOT TUB* | Spacious 400 Sqf Tiny Home Experience!

Welcome to The Garage-- A one of a kind, super private, super spacious barn-style tiny home! At 400 Sf, you'll get the same comfort & amenities you would from a big home while being able to tell your friends you stayed in a tiny one! Here for work? Only 3 blocks from I-45 & HYPER fast wifi gives you access to the interwebs or the interstate so you can work efficiently. Here to AVOID work? Me too! Enjoy a romantic sunset from our cozy patio or a nice beverage in our bubbling hot tub!

Guest suite in The Woodlands

A two-story lakefront guesthouse is featured, showcasing expansive windows and a tiled roof. Lush greenery surrounds the property, and a patio area with outdoor seating is visible along the water's edge. The tranquil setting offers a serene view of the lake.

4.89 out of 5 average rating, 275 reviews

Lakefront Guesthouse: Pool, BBQ, Bike

Lakefront Guesthouse with private access to the Lake. Spacious 1-Bed Suite (900sft) for peaceful and comfortable stay for your family (1 King Bed and 1 Queen Bed). Can accommodate up to 4 adults or 5 people including kids Enjoy the Lakeview, Pool, Sunrise/Sunset, Grill and Patio. Please note, the Guesthouse is attached to the main house where we live. All the interior pictures are from the Guesthouse. Guests don’t share any space with us except the driveway and backyard.

4.94 out of 5 average rating, 241 reviews

The exterior of the hobbit house features a charming round door surrounded by natural wood siding and decorative circular windows. A wooden pathway leads to the entrance, bordered by neatly arranged flower beds, enhancing the whimsical character of the retreat.

Tiny home in Houston

Houston Hobbit House

This hobbit house, belonging to a little hairy footed fellow, has a life long journey of accumulating artifacts of the wonderous eras of ancient. You will find a vast collection of books both rare and of great value to feast your imagination and curiosity. This cozy haven, though adorned with swords and weapons of the great heroes of old, serves as a reminder that it is the little things that keep the darkness at bay, “small acts of kindness and love”.

4.94 out of 5 average rating, 128 reviews

A cozy sleeping area showcases a queen-sized bed draped with a soft throw, accented by a patterned coverlet. Nearby, a warm-toned wooden dresser is positioned beside the bed. Red and black curtains frame the window, enhancing the rustic interior highlighted by wooden beams.

Barn in Montgomery

Valhalla!

This memorable place is anything but ordinary. A Viking-inspired getaway complete with porch, shower, bathroom, kitchen and a full-functioning sauna! This mini-apartment is in the top section of a barn and you may have to duck your head. There is a queen-sized bed and an additional mattress for someone else if needed. Take a stroll in the woods or take a quick 5 minute drive to the lake! Now with upgraded Air Conditioning! Pets welcome, $$Fee.

4.91 out of 5 average rating, 163 reviews

The living room features a comfortable sectional sofa and a flat-screen television, with natural light flowing through large windows. A coffee table is centered on a patterned rug, complemented by two modern armchairs. Potted plants are placed throughout, adding a touch of greenery.

Townhouse in Conroe

★Amazing house in Woodlands fully equipped for 6

Amazing Woodlands townhouse with ample parking space, 100% equipped and ready to become your home away from home. You’ll have the entire place to yourself so you can enjoy the comfort of a cozy atmosphere especially designed to receive guests. Whether you are here for shopping, tourism or to visit one of the many hospitals around the area, you’ll fall in love with this incredible house and the amenities provided.

4.9 out of 5 average rating, 138 reviews

A cozy sleeping area features a spacious bed, dressed with soft neutral bedding and decorative pillows. Natural light enters through multiple windows, with light curtains framing the view. The wooden accents and flooring add warmth to the overall atmosphere of the space.

Campervan/RV in Conroe

The Hangout Spot

Recharge your soul in our cozy renovated Airstream! Whether you are traveling for work, visiting friends or trying to take a break from the chaos of life this is the perfect glamping experience. Enjoy a spacious layout that includes a queen sized bed, kitchenette with all the basics should you decide to cook a meal, nice dining area that could also double as a workspace, and comfortable shower.

Popular amenities for The Woodlands family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A spacious outdoor area features a patio with two black wicker chairs and a round table, set against a backdrop of lush greenery. A pool glistens nearby, surrounded by neatly landscaped borders, while large windows illuminate the inviting interior of the home.

4.89 out of 5 average rating, 176 reviews

Lovely Woodlands home w/heated pool and spa!

A serene waterfront view showcases the sun setting over Lake Conroe, its reflection shimmering on the water. A deck is visible with white railings, offering an inviting space to enjoy the peaceful surroundings. Lush greenery outlines the horizon, enhancing the natural beauty.

4.95 out of 5 average rating, 120 reviews

Found! Lakefront-Family Retreat w/Panoramic Views

4.84 out of 5 average rating, 106 reviews

A circular fire pit surrounded by several wooden chairs invites conversation. The area is bordered by manicured grass, and lounge chairs with red umbrellas are visible in the background. Clear blue skies create a bright atmosphere, enhancing the space's warmth.

Home in Willis

Lakefront Resort Tiny Living by RelaxSTR

4.95 out of 5 average rating, 366 reviews

A cozy sleeping area features a low platform bed with soft bedding, enhanced by modern furnishings. A wall-mounted television and a desk provide functional workspace, while a window allows natural light to brighten the space. Decorative art and plants add a touch of warmth.

Tiny home in Houston

Wabi Sabi | Japanese Experience

4.83 out of 5 average rating, 230 reviews

A spacious guest room features a comfortable bed with crisp linens and decorative pillows. A swing chair is positioned nearby, while a wall-mounted television is visible. Natural light enters through a dark window treatment, and a mirror is mounted on the wall opposite the bed.

Guesthouse in Houston

Delightful Private Suite Escape

An open-concept living area showcases a spacious lounge with three large sofas facing a central coffee table. Natural light fills the room from large windows, and a modern kitchen is visible in the background, accented by industrial-style lighting and greenery.

4.98 out of 5 average rating, 115 reviews

Stylish Home with Hot Tub & Gaming Garage

A spacious living area features plush gray sofas with tufted upholstery, complemented by black accent chairs. A neutral area rug covers the floor, while a round coffee table sits at the center. Natural light pours through large windows, enhancing the room's inviting atmosphere.

4.93 out of 5 average rating, 112 reviews

Amazing getaway in the Woodlands with Private Pool

4.91 out of 5 average rating, 128 reviews

The living area features comfortable leather recliners facing a wall-mounted television and an electric fireplace. A dining table is visible in the background, with a ladder leading to a loft area above. Natural light streams through multiple windows adorned with blinds.

Tiny home in Willis

Luxury Tiny House in Lake Resort

Family- and pet-friendly home rentals

A serene outdoor area features wooden decking adjacent to a calm lake, shrouded in morning mist. Potted flowers and lush greenery are present, along with rustic seating options. Soft lighting from overhead fixtures enhances the peaceful atmosphere of this lakeside retreat.

4.96 out of 5 average rating, 363 reviews

A Close Getaway - Entire house on a private lake

Townhouse in Cochran's Crossing

A cozy living area is presented with light-colored furniture arranged around a dark coffee table. Natural light enters through large windows, revealing a view of greenery outside. A television is positioned on a media console, and a stylish lamp adds soft illumination to the space.

4.93 out of 5 average rating, 113 reviews

Escape to Luxury in The Woodlands & Enjoy

4.95 out of 5 average rating, 128 reviews

A rooftop space showcases a 75-inch television mounted on a gray wall. Two modern wicker chairs with blue cushions flank a circular wooden coffee table, which is adorned with a variety of magazines. Green foliage is present, adding a refreshing touch to the area.

Home in Conroe

Contemporary 3 Bedroom-Rooftop- Home

4.85 out of 5 average rating, 20 reviews

The exterior of a modern two-story structure is showcased, featuring a distinctive octagonal shape with a metal roof. Large glass windows allow for ample light and provide views of the landscaped backyard, which is bordered by trees and decorative stones.

Guesthouse in Spring

Retreat w Pool in The Woodlands

4.94 out of 5 average rating, 126 reviews

A spacious home is surrounded by a wooded area, featuring a driveway leading up to the entrance. The structure showcases a combination of grey and stone exteriors. The view captures the picturesque setting near a lake, adorned with autumn foliage.

Guest suite in Conroe

Nature's Nook Studio

Home in Cochran's Crossing

A serene outdoor space is featured, showcasing a sparkling pool illuminated by soft lighting. Surrounding greenery adds a natural touch, while a stone landscape provides texture. Comfortable lounge seating is positioned nearby, inviting relaxation. Bright windows of the home offer a view of the interior.

4.92 out of 5 average rating, 36 reviews

Unique Mid Century Modern in The Woodlands

4.92 out of 5 average rating, 282 reviews

A charming cabin surrounded by lush greenery features a welcoming front porch with a wooden railing. Rocking chairs offer a comfortable spot for relaxation. The entrance is highlighted by warm tones and natural textures, creating a cozy and inviting appearance.

Cabin in Magnolia

Cloud's Cabin-Cozy Cabin Combo in the Piney Woods

5 out of 5 average rating, 19 reviews

A private outdoor space features a wooden dining table with four chairs, surrounded by lush greenery. A shaded seating area contains a lounge suite, with an umbrella overhead. The area is well-lit by string lights, creating a relaxing atmosphere in the inviting backyard.

Home in The Woodlands

The DOVI Collection | Gated Luxury Retreat & Pool

Family-friendly home rentals with a pool

4.78 out of 5 average rating, 285 reviews

A serene view from a balcony overlooking Lake Conroe at dawn. The calm water reflects soft hues of orange and pink from the sunrise, while the silhouette of trees lines the far shore. The railing, delicate and elegant, frames the tranquil scene.

Condo in Willis

Gorgeous Lake Views- One Bedroom-142

4.95 out of 5 average rating, 110 reviews

The kitchen area features modern cabinetry and a spacious countertop. A dining table set for four is visible, paired with comfortable chairs. A spiral staircase leads to the upper level, while large windows allow natural light to fill the space, showcasing views outside.

Condo in Montgomery

Sleeps 6 - Comfortable condo with great views!

4.99 out of 5 average rating, 169 reviews

A cozy armchair with a tufted design features soft blankets and decorative pillows. Large glass doors provide a view of the serene lake, allowing natural light to fill the space. A balcony with seating is visible beyond, enhancing the waterfront atmosphere.

Condo in Willis

Beautiful Waterfront Condo on Lake Conroe

5 out of 5 average rating, 37 reviews

A welcoming living area is arranged with a mix of seating, including two armchairs and a sofa. A coffee table sits in the center, and a mantel with a fireplace provides a focal point. A flat-screen TV is mounted above, and light floods the space through French doors.

Townhouse in Montgomery

The Pink Magnolia-walk to lake/playground/dog park

4.84 out of 5 average rating, 139 reviews

A spacious king bed is dressed in a checkered duvet and accent pillows. Two cozy chairs are positioned near the bed. The bathroom entrance is visible in the background, showcasing a tiled shower curtain and light-colored walls.

Condo in Willis

The Lakeside Getaway Condo: Studio Room

A fire pit area is surrounded by a circular seating arrangement featuring five black Adirondack chairs. The space is illuminated by overhead string lights, casting a warm glow over the grassy lawn and gravel pathway leading to the firepit.

4.99 out of 5 average rating, 108 reviews

New Lake House by Golf course + Kayaks & Game Room

5 out of 5 average rating, 3 reviews

Contemporary Woodlands Getaway with Private Pool

The image collage showcases various aspects of The Carlton Family Lake House, including a cozy bedroom with stylish decor and a serene view of the lake from the living area. Natural light floods the space, enhancing the calm atmosphere, while outdoor scenes capture the tranquility of the lakeside setting.