Family-friendly holiday rentals in The Woodlands

The exterior of a charming one-story home is showcased, featuring a stone facade and a welcoming entrance. Lush greenery, including palm trees and well-maintained landscaping, complements the property's curb appeal. A paved driveway leads to an attached garage, all set against a backdrop of tall trees.

4.96 out of 5 average rating, 157 reviews

Luxury Woodlands home minutes from Houston!

Well appointed one-story home, fully furnished home nestled in a tree lined cul de sac. A huge backyard for the children to play in. Private study room. Only a 10 minute drive to Woodlands destinations, including: The Woodlands Mall, renowned Woodlands Golf Course, Market Street, Cynthia Woods Pavillion, Town Center and Hughes Landing. The Woodlands is Houston's vibrant community located only 30 minutes north of the downtown area, providing comfortable access to Houston's top attractions!

4.97 out of 5 average rating, 136 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 #1" - 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.

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.

4.99 out of 5 average rating, 189 reviews

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

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.

4.9 out of 5 average rating, 192 reviews

Lovely Woodlands home w/heated pool and spa!

Relax with the whole family at this peaceful Woodlands home. This house has free parking space and a heated pool to enjoy it during winter (spa's included but there is an additional charge for heated pool due to energy costs) 100% equipped and ready to become your home away from home. You’ll have this entire Woodlands home to yourself. Whether you are here for shopping, tourism or to visit one of the hospitals nearby, you’ll fall in love with this incredible house and the amenities provided.

4.93 out of 5 average rating, 122 reviews

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.

Townhouse in Spring

Escape to Luxury in The Woodlands & Enjoy

Remodeled, lots of windows. Beautyrest mattresses, primary TEMPUR-PEDIC topper, 2bed, 2 1/2 bath, a study, and laundry facilities on site. No carpet. Quartz countertops. Balcony off master. High-speed WiFi. TVs with Roku (login to your Netflix, Prime Video). 3 minutes to highway I-45, ideal for commuters to IAH airport, downtown Houston, and more. In the heart of The Woodlands, near Cynthia Woods Pavilion, Market Street, and plentiful night life opportunities. We look forward to hosting you!

The living area presents a blend of mid-century modern design with high ceilings and wooden accents. A large flat-screen TV is mounted on the wall, while comfortable seating is arranged around a wooden coffee table. Natural light emanates through large windows, enhancing the space.

4.98 out of 5 average rating, 121 reviews

MCManor Retreat home in golf course

Welcome to the MCManor Retreat House in Panorama Village, a golf club city in the north end of Conroe, Texas! Especially furnished and decorated to make this escape intriguing and yet warm so you feel at home in your own sanctuary. Staying here feels like a vacation, largely due to the friendly neighbors. We hope you really enjoy your time at the home and build enjoyable memories with your friends and family. Be sure to check out our GUIDEBOOK for ideas of places to go and things to do.

Guest house in Shenandoah

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.

5 out of 5 average rating, 176 reviews

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, 128 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

1 mile from everything!• Dining • Family Friendly

-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!

4.93 out of 5 average rating, 147 reviews

A spacious living area is centered around a plush brown sofa, complimented by light grey armchairs. A decorative rug lies underneath a round coffee table. A flat-screen TV is mounted on the wall, while a dining space with a circular table is visible in the background.

Townhouse in Spring

Treehouse Retreat | EV Charger | Low Cleaning Fees

Escape to a serene retreat in The Woodlands where modern comfort meets nature’s embrace. Nestled in a wooded neighborhood, our 2 bed 2 bath getaway exudes a captivating treehouse vibe. Close proximity to a variety of dining options, supermarkets, The Woodlands Mall and the scenic Lake Woodlands, making it ideal for both relaxation and exploration. Whether you’re seeking a peaceful sanctuary or an adventure-filled getaway, our charming treehouse style retreat offers the ultimate escape.

4.94 out of 5 average rating, 124 reviews

The exterior of a single-story home is showcased, featuring a manicured lawn and lush landscaping. A light-colored garage door is visible, complemented by a brick façade. Large windows allow natural light to illuminate the front interior, framed by greenery from nearby trees.

Home in The Woodlands

Woodlands Retreat 3bdrm 2bath

Long term stays welcomed ! One story home perfect for families. This home is located in a quaint cul-de-sac half a mile to i45. You are only minutes away from all the hospitals and shopping centers. Whether you are in town visiting family, here for an event, or seeking treatment this house is perfect for you and your family, this includes your four legged family as well. All mattresses are 12” memory foam for your comfort. Lots of near by amenities like a pool, tennis and playground.

A modern entrance is framed by sleek black stone features and minimalistic lighting. A pathway leads to a glass door, flanked by two tall plants, while grass borders the walkway, providing a clear view of the home's contemporary design.

4.99 out of 5 average rating, 144 reviews

IvoryEdition NEW Luxury Estate Mins From Woodlands

This unique place has a style all its own. Modern, Open-Concept Luxury Estate. Entire Home top to bottom Glass Sliders. Minutes away from all of The Woodlands Texas beautiful attractions. The perfect place to come and enjoy a luxurious stay by yourself or with friends, there is plenty of bedrooms with their own bathroom! Work from home in our dedicated built in workspace with beautiful woodland views. Create your own mood with the entire home being powered by Philips HUE Lights.

4.96 out of 5 average rating, 106 reviews

A spacious living area features large windows that allow natural light to fill the room, showcasing views of surrounding greenery. Comfortable green armchairs flank a modern sofa adorned with decorative pillows. A coffee table sits on a patterned area rug, enhancing the inviting ambiance.

Flat in The Woodlands

Private 1BR Apt in The Woodlands | Great Location

Private, spacious 1BR retreat in the heart of The Woodlands, tucked into a peaceful setting surrounded by greenery. Guests love the comfortable feel, great location, and that the space feels bigger than expected. Enjoy a detached apartment with a full kitchen, fast Wi-Fi, Washer/Dryer, dedicated workspace, and easy access to Hughes Landing, Market Street, the Pavilion, shopping, parks, and trails. Perfect for family visits, weekend stays, business travel, and longer bookings.

Popular amenities for The Woodlands family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

An inviting pool area is highlighted by a sparkling blue pool and a spa, both surrounded by lush greenery. Soft lighting is provided by string lights overhead, creating a serene evening atmosphere amidst the trees.

4.92 out of 5 average rating, 155 reviews

Private house-The Woodlands w/pool and generator.

A clear swimming pool is viewed from the water's edge, with glistening blue tiles reflecting the sunlight. In the background, a well-maintained two-story home is visible, featuring shaded windows and an awning. Surrounding greenery enhances the tranquil atmosphere.

4.86 out of 5 average rating, 107 reviews

Pool + Hot Tub | 5BR Retreat | Near The Woodlands

4.96 out of 5 average rating, 277 reviews

Tiny home in Spring

*HOT TUB! | Private+Spacious+Cozy+One-of-a-kind

A private backyard features a sparkling pool with a gentle waterfall, illuminated by soft outdoor lighting. Lounge chairs are positioned beside the pool, with a shaded seating area in the background providing a relaxing outdoor space.

4.93 out of 5 average rating, 144 reviews

Destination Pine Walk ·Pool+Spa Near The Woodlands

4.91 out of 5 average rating, 117 reviews

A spacious backyard features a vibrant pool area, beautifully illuminated by colorful night lights. Lush greenery surrounds the setting, complemented by a well-maintained lawn. A stone patio leads to the pool, which is adorned with a diving board and lounge chairs for relaxation.

Home in Houston

Paradise Garden Resort And Spa

Holiday home in Montgomery

A private pool is visible with a gently sloping lounge chair floating on the water's surface. Surrounding palm trees and natural stone formations create a serene ambiance under bright blue skies.

4.95 out of 5 average rating, 188 reviews

Prancing Horse Estates:10 acre resort w/pool, spa

4.79 out of 5 average rating, 132 reviews

A spacious living area features a light-filled layout with a comfortable sectional sofa and a modern coffee table. A dining table with grey chairs complements a neutral color scheme. A fireplace adds warmth, while a mounted TV and a decorative wall highlight the inviting atmosphere.

Home in Magnolia

Lovely & Comfortable Home in a Great Location

4.89 out of 5 average rating, 160 reviews

The outdoor area showcases a private pool with crystal-clear water, surrounded by lounge chairs. A hot tub is visible nearby, while a patio with dining and seating arrangements invites relaxation under shaded umbrellas. The home features a two-story design in the background.

Home in Cypress

4BR 30 mi to NRG Stadium, 2026 World Cup

Family- and pet-friendly home rentals

4.92 out of 5 average rating, 158 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!

5 out of 5 average rating, 47 reviews

A spacious living area is showcased, featuring a large sectional sofa and a cozy armchair. A flat-screen television is mounted above a fireplace, while natural light fills the room from arched windows. Decorative plants and a stylish chandelier enhance the comfortable ambiance.

Villa in Spring

Stylish 4BR Retreat w/ Coffee Bar & Backyard Oasis

4.9 out of 5 average rating, 208 reviews

Home in Shenandoah

Woodlands Oasis with Heated Pool

4.93 out of 5 average rating, 117 reviews

A well-lit open space features a cozy bed with yellow patterned bedding and a kitchen area equipped with modern appliances. A dining table with two chairs and a large wall-mounted television enhance the functional layout. Soft blue walls provide a calming backdrop.

Guest house in Spring

Cozy guesthouse for you!

4.92 out of 5 average rating, 111 reviews

A bright living area features a ceiling fan and large windows allowing natural light. A decorative rug adds warmth to the wooden floor. A wall-mounted TV stands opposite a cozy fireplace, while a breakfast bar with stools is positioned near the open layout.

Home in The Woodlands

Spacious & Cozy 4BR Home in The Woodlands

4.94 out of 5 average rating, 115 reviews

Retreat @ The One | Movie Theater | Coffee Bar

5 out of 5 average rating, 44 reviews

Hope House

An outdoor raised deck features a black metal dining table surrounded by multiple chairs with cushions. Decorative pillows add color to the seating. Soft lighting is provided by lamps, illuminating the space amidst the natural greenery of the surrounding trees.

4.77 out of 5 average rating, 146 reviews

Country Retreat 3B spacious, rustic, woodsy 1 acre

Family-friendly home rentals with a pool

5 out of 5 average rating, 9 reviews

Home in Tomball

The Redwood House

An open-concept living area features large windows allowing natural light to fill the space. A spacious, L-shaped sofa complements two blue armchairs around a wooden coffee table, with a light-colored area rug beneath. A staircase leads to a second level, enhancing the room's height and openness.

4.97 out of 5 average rating, 32 reviews

Luxury Woodlands Home - 4 BR, Pool, Private!

5 out of 5 average rating, 19 reviews

Chic TX House w/ Pool and Relaxing Atmosphere

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.

4.78 out of 5 average rating, 36 reviews

Luxury Loft Style House w Pool | The Woodlands

4.95 out of 5 average rating, 56 reviews

A spacious living area features a large flat-screen television mounted on a wooden console. Comfortable seating is provided by a brown leather sectional sofa, complemented by a round coffee table. Natural light fills the room through multiple windows, enhancing the contemporary decor.

Home in Shenandoah

Deck, Private Gym & Comm Pools near Woodlands Mall

5 out of 5 average rating, 27 reviews

New 4BR Retreat + Pool Near The Woodlands

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.

4.94 out of 5 average rating, 47 reviews

Unique Mid Century Modern Home in The Woodlands

Luxe