Family-friendly holiday rentals in The Woodlands

A spacious pool area features a rock formation waterfall and a curved deck surrounding the water. Cabanas and sun loungers provide relaxation spots, while colorful umbrellas offer shade. Lush greenery and trees frame the backdrop, enhancing the outdoor space.

4.92 out of 5 average rating, 104 reviews

Resort Backyard Escape | Pool Spa + Outdoor Cinema

Escape to your private resort style oasis near Lake Conroe, where comfort meets unforgettable fun. This modern, fully electric home features 4 spacious bedrooms with 6 beds and 3.5 baths, perfect for groups and families. Enjoy movie nights under the stars, air hockey in the living room, a built in BBQ island, and life size games in the expansive backyard. Lounge on the stylish patio, relax poolside with sun loungers and cabanas, and make memories that last a lifetime in your ultimate getaway!!!

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!

4.85 out of 5 average rating, 157 reviews

A single-story brick house is featured surrounded by a well-maintained lawn. The front porch, framed by symmetrical green shutters, offers two seating areas. A clear path leads to the entrance, bordered by neatly trimmed shrubs, creating a welcoming appearance.

Home in Shenandoah

Spacious 4BR near Woodlands - Perfect for Groups!

You’ll love this centrally-located house close to the Woodlands in a safe, quiet neighborhood with easy access to I-45. Relax in the jacuzzi tub and enjoy the covered backyard patio w/ pet-ready fenced yard & fun play set for kids. 3 minute drive - Memorial Hermann, St.Luke’s, Texas Children’s Hospital & Portofino to shop and dine. 5 minute drive - The Woodlands Mall, Market Street, Waterway Square, The Pavilion, Hughes Landing, Restaurant Row and various wedding venues & sports complexes.

4.93 out of 5 average rating, 103 reviews

A cozy living area is presented with a warm brown sofa, a coffee table, and two chairs. Light wood flooring complements the space, which features a fireplace and a wall-mounted television. Natural light enters through the windows, enhancing the neutral color palette.

Home in Tomball

Home In Tomball/The Woodlands

Discover our charming Scandinavian home, located just 45 min from Houston and a quick 3 minutes from the Woodlands. This cozy retreat offers your own office and a delightful lighted patio with swings, perfect for enjoying a glass of wine. You can also indulge in shopping at nearby malls and savor delicious meals at a variety of restaurants. Take peaceful morning walks in the neighborhood park. Complete with a fully equipped kitchen and outdoor grill. No smoking, dogs, or parties allowed.

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, 175 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!

4.94 out of 5 average rating, 146 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.

Guest house 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.

4.88 out of 5 average rating, 303 reviews

Lakefront Guesthouse: Pool, BBQ, Bike, Paddle Boat

Welcome to your lakefront escape - a spacious (~900 sq ft) private guesthouse suite with gorgeous Lake Paloma views, infinity pool access, and all the comfort you need for an easy, memorable stay. Perfect for families or small groups - up to 4 adults (or 5 guests including kids). NOTE: The guesthouse is attached to our home, where we live. Guests have a private entrance and private guesthouse space (not shared). The only shared areas are the driveway and backyard

4.94 out of 5 average rating, 131 reviews

Woodlands 4BR | 11 Guests Near Pavilion & Waterway

🏡 Your Woodlands home base! Spacious 4BR sleeps 11, minutes from Cynthia Woods Mitchell Pavilion (Top 5 amphitheater worldwide!), The Woodlands Waterway, Market Street luxury shopping. ☕ Fast WiFi • Full Kitchen • Free Parking • Self Check-In 🎵 Pavilion — same zip! | 🏬 Mall — 10 min | ✈️ IAH — 22 min | 🏙️ Downtown Houston — 29 min Perfect for: concert-goers, business travelers, medical travelers, families, large groups, extended stays!

4.9 out of 5 average rating, 207 reviews

Home in Shenandoah

Woodlands Oasis with Heated Pool

Experience comfort and convenience in this welcoming 4‑bedroom home with a private pool in Shenandoah/The Woodlands. Perfect for vacations, business travel, medical visits, relocations, or during home renovations. Minutes to ExxonMobil, top hospitals, Market Street, and The Woodlands Mall. Family‑ and pet‑friendly with easy access to I‑45, Hardy Toll Rd & 99. Long‑term stays welcome! (Local 7% lodging tax collected at check‑in.)

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

4.95 out of 5 average rating, 103 reviews

A spacious backyard is highlighted by a well-maintained lawn, featuring seating areas and a jacuzzi under a covered patio. The two-story home with large windows can be seen in the background, reflecting the warm colors of a sunset.

Home in Tomball

Spacious Modern Retreat + Spa

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

4.98 out of 5 average rating, 129 reviews

A serene pool area is surrounded by lush greenery and vibrant flowers. Natural stone steps lead down to the water, and tropical plants frame the scene. A stone waterfall cascades into the pool, creating a tranquil atmosphere in the outdoor space.

Guest house in Conroe

Fun, Relaxing Escape with Pool

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, 143 reviews

Destination Pine Walk ·Pool+Spa Near The Woodlands

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

4.89 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

4.82 out of 5 average rating, 115 reviews

A spacious outdoor area is featured, surrounded by greenery and landscaped with gravel pathways. The mobile home, with a light exterior, is complemented by a shaded seating area under an umbrella. Two hammocks are visible, offering relaxation options under the trees.

Tiny home in New Caney

Sweet little casita Two-bedroom home in New Caney

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!

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

4.96 out of 5 average rating, 140 reviews

A brown horse grazes peacefully in a grassy area near a tiny house. The tiny house features a wooden exterior, with a porch that has a chair visible. Trees surround the property, offering a sense of tranquility and connection to nature.

Farm stay in Katy

Tiny House on the Prarie

4.93 out of 5 average rating, 356 reviews

A cozy sleeping area features a spacious bed with a textured white blanket and a decorative headboard. Two matching bedside tables hold green lamps. Wall art with soothing designs complements natural wood paneling, contributing to a serene atmosphere.

Cottage in Tomball

Main Street Loft

4.94 out of 5 average rating, 525 reviews

A serene scene features a wooden dock extending over calm lake waters, with a dog standing nearby. The sunrise casts a warm glow over the landscape, while mist rises gently from the surface of the lake, creating a peaceful atmosphere.

Home in Montgomery

The Quick Getaway: Entire house on private lake!

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.

4.95 out of 5 average rating, 149 reviews

Contemporary 3 Bedroom-Rooftop- Home

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!

4.98 out of 5 average rating, 124 reviews

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.

Home in Montgomery

New Lake House by Golf course + Kayaks & Game Room

Family-friendly home rentals with a pool

4.82 out of 5 average rating, 624 reviews

A cozy bedroom features a beige tufted headboard with decorative pillows in yellow and gray colors. Two bedside lamps provide soft lighting beside wooden nightstands. Artwork depicting sea life adorns the walls, and neatly arranged towels sit on a tray at the foot of the spacious bed.

Apartment in Willis

The Lakeside Hideaway - Fish from the balcony!

4.85 out of 5 average rating, 158 reviews

A calm waterfront scene is depicted, featuring a sprawling view of the lake under a gently colored sky. Ducks are seen floating on the water, while a boat dock with several slips is visible in the background, set against a lush green lawn.

Apartment in Willis

Lakeview at Casa Couture

5 out of 5 average rating, 47 reviews

A brightly colored bedroom features a full-size bed with a striped duvet cover. Above it, a twin bunk bed provides additional sleeping space. A red sofa is positioned near the foot of the bed, complementing the room's modern, geometric design.

Villa in Spring

Near Woodlands | King Bed | Coffee Bar | Fire Pit

Luxe

4.96 out of 5 average rating, 53 reviews

The Black Oak: Forest & Chill

5 out of 5 average rating, 19 reviews

Chic TX House w/ Pool and Relaxing Atmosphere

5 out of 5 average rating, 18 reviews

Contemporary Woodlands Getaway with Private Pool

5 out of 5 average rating, 5 reviews

Home in Tomball

The Maple House

An inviting outdoor space features a private pool surrounded by a curved patio. A spa sits adjacent to the pool, while comfortable seating areas are arranged under a shaded porch. Lush trees and a wooden fence provide privacy in the tranquil backyard.