Family-friendly holiday rentals in Montgomery County

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

Welcome to Prancing Horse Estates! This is a private gated 10 acre estate with private pool, spa and waterfall + 4 bedroom home. You’ll love it if you like upscale indoor style combined with beautiful outdoor space. 10 acres- 4 meadow and 6 densely wooded with 2 paths along the creek, with lovely poolside space with seating for 16+. Well stocked library, children’s room, indoor/outdoor games. Certified Wildlife Habitat® site with the National Wildlife Federation and Texas Conservation Alliance.

4.97 out of 5 average rating, 129 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.

4.95 out of 5 average rating, 144 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

Kick back and relax in this new construction, modern, stylish home. Located in the heart of downtown Conroe. Extremely close to great dining, entertainment, and the Conroe convention center. About 15 minutes from Lake Conroe, this vacation will be one to remember! Enjoy a movie on the rooftop under the stars or make memories around the outdoor fire pit in the backyard. Get cozy in front of the 75” television. With televisions in every room, enjoy a peaceful night’s rest on comfortable beds.

4.91 out of 5 average rating, 148 reviews

A front deck offers a view of a serene private lake, bordered by tall trees. A path leads down to the water, while a grassy area and seating can be seen nearby, providing a peaceful outdoor space.

Cottage in Montgomery

The Cottage at Pine Lake

Take a break & unwind at this peaceful oasis. Kayak, catch a fish, take a swim in the pool across the street or just relax on the front deck and watch the birds. Great location on private lake with pier. Close to local Montgomery wedding venues( Lumineer 2 min, Pine Lake Ranch 5min) Short drive to Margaritaville resort. Spend the day on beautiful Lake Conroe, bring your boat/ jet ski and launch down the road at the marina. Short drive to Sam Houston national forest to enjoy nature and hiking

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.

4.98 out of 5 average rating, 121 reviews

New Lake House by Golf course + Kayaks & Game Room

Welcome to THE LAKE HOUSE - our spacious and welcoming getaway. Here you'll enjoy all the luxuries with an added plus of fun and activities. Whether your looking for some fun in the sun or a stay-cation at the Lake, you will find this to be your perfect destination. We have immediate access to the lake, Walden Golf course, and driving range. Looking to work from home? We got you covered. Looking for a fun-filled night in? Our game room has you covered - no cheating or whining allowed ; )

A single-story home is framed by lush green grass and mature trees. The smooth exterior features arched windows and a welcoming entrance. A driveway leads to a two-car garage, providing ample space for vehicles. The surrounding yard offers plenty of open space for outdoor activities.

4.97 out of 5 average rating, 146 reviews

Paradise Lakeside Retreat 6 Rooms 8 Beds sleeps 16

Great location. This property offers a nature and peaceful setting with easy access to Lake Conroe, Marina, The Luminaire Venue, Pine Lake Ranch Venue, other venues in the area and restaurants. Property has all the essentials for cooking, baking and grilling to accommodate a large group. Property is perfect for families, couples, large groups or girls getaway. Perfect place to relax, hike, bike, ride golf cart or visit the lake. Property’s location is very convenient to many dining options.

4.97 out of 5 average rating, 119 reviews

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.

Home in Conroe

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.

4.99 out of 5 average rating, 167 reviews

A serene outdoor deck is furnished with vibrant chairs, overlooking a peaceful lake surrounded by trees. The interior features a modern bathroom with a freestanding tub and chic fixtures, while a stylish exterior of the treehouse is lit by ambient lighting, complemented by kayaks on the water.

Treehouse in Montgomery

Lux Treehouse: Lake, Views, Gameroom, Kayaks, Fun

Escape w/ the family to "Iron Pine Treehouse" next to Lake Conroe on a small private lake. Enjoy lake views from nearly every room w/ luxury finishes. Trees intersect the deck--a canopy of leaves overhead for a treehouse effect! 13 beds, sleeps 17 comfortably: 1 King, 2 Queens, 9 Twin bunks, 1 queen sofa bed Kayaks/Paddleboards and a game-room. There's even a connected studio with a full kitchen! Fish off the private dock | Only 3 minutes to Lake Conroe public boat ramp or boat rentals!

4.82 out of 5 average rating, 207 reviews

Quiet Montgomery Home w/ firepit and pool

5-20 Minutes from popular Wedding Venues! 20 MINUTES FROM TX. REN- FESTIVAL. Book early. 10 minutes from LAKE CONROE, boat rentals, wineries, live music, and a variety of restaurants. 15 minutes from SAM HOUSTON NATIONAL FOREST (Dirt bike trails anyone? Call park to check schedule ). Relax with whole family at this peaceful country getaway. Enjoy our colorful sunsets from the pool, gazebo, or dining room table. We love to host your family/friends attending weddings!

4.97 out of 5 average rating, 147 reviews

A modern cabin is set within a forested area, featuring a welcoming front porch with steps leading up and outdoor seating. Large windows are present, allowing natural light to fill the interior. A well-maintained grassy yard surrounds the cabin, enhancing the serene environment.

Cabin in Montgomery

Cabin In The Forest - Houston National Forest

Kick back and relax in this calm, stylish cabin in the forest. It's only walking distance to the beautiful Lone Star Trail in Sam Houston National Forest. This forest cabin has access to a fishing pier that is fully stocked with native fish (no license required); please follow lake rules. Bring your kayaks and paddleboards to enjoy the lake. There's lots of scenery (forests, wildlife, lakes, countryside, etc.); you never know what you can capture, so bring your camera!

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.

4.94 out of 5 average rating, 511 reviews

The Quick Getaway: Entire house on private lake!

Need to escape? We've done the work! INCLUDED: Breakfast - eggs, bagels, coffee, filtered water, creamers, sugar & a selection of teas. Location is secluded, not remote! Got a boat? Bring it! Boat access inc. @ neighborhood ramp. 1100 SF lakefront house in Montgomery, TX. Max 4 PPL - 2 Bdrms: 2 queen beds, 2 bathrooms, 2 porches, charcoal grill & paddle boat! * FIDO friendly <30lbs, $25 fee - per pet ESA pets the same. We love all pets, got a big dog? Ask us.