Family-friendly vacation rentals in Montgomery County

Vacation 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, 132 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.

4.9 out of 5 average rating, 150 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, 122 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 ; )

An aerial view reveals a large, private property surrounded by lush greenery on Lake Conroe. The well-maintained lawn showcases vibrant landscaping, and a spacious dock extends into the water, providing direct access for activities. The main house and additional structures are set amidst the wooded backdrop.

4.96 out of 5 average rating, 118 reviews

Lake Conroe Resort Style Vacation House

NO PETS PERMITTED. Situated on 4 private, wooded acres on Lake Conroe with a huge picture window and a stunning view of the lake & the National Forest - no other houses or a bridge. Smartly decorated and fully furnished over 3500 square feet. Direct waterfront to a 1600 sqft Trex dock with great swimming, lounging and fishing. Dock space is available to moor your boat or jet ski. Large driveway to park six to eight vehicles. Totally separate house allowing full privacy. Nothing else like it.

4.9 out of 5 average rating, 115 reviews

Home in Conroe

Your peaceable kingdom on the lake in Conroe Texas

Lake living at its best. Freshly aired and professionally cleaned between guests. Fully equipped kitchen. Well stocked office away from home. Accessible entryway and shower for easy mobility. 15 minutes away from The Woodlands, shopping, malls, movie theaters, great restaurants, Panorama Village golf course, water sports and everything Conroe has to offer. Enjoy walking trails around the beautiful lake with ducks, grey herons and other wildlife. No small dogs in backyard. No cats please.

4.93 out of 5 average rating, 120 reviews

A charming tiny home is depicted, set against a backdrop of lush greenery. Purple flowers are visible in the foreground, with the home featuring large windows and a welcoming porch. The surrounding area is enhanced by tall trees and a well-maintained lawn.

Tiny home in Willis

The Lantana ~ Intimate Cottage~ Hottub/Doggy Yard

A Hot Tub, The Big Texas Sky, And a Doggy Play Yard for Your Best Friend. Make memories that last & enjoy the relaxation of our premium 600 Sq Ft tiny home. This little home sleeps 5 with a King bed in the main bedroom. A luxury pullout Queen in the living room & a Twin pull-out for extra room. The fully equipped kitchen is perfect to whip up your gourmet meals. It also has a private hot tub tucked on the back of this quiet retreat. Perfectly located next to our glistening stocked pond.

4.83 out of 5 average rating, 214 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!

4.98 out of 5 average rating, 113 reviews

A fire pit area is surrounded by log seating, inviting relaxation under string lights. The tiny cabin is visible nearby, nestled among tall trees. This setting provides a serene atmosphere, perfect for gatherings or enjoying evenings by the fire.

Cabin in Montgomery

Lake Cabin in the Forest - Houston National Forest

This is a great place to relax and unwind while enjoying the beautiful sunset and sunrise at the lake in Sam Houston National Forest with the geese, the ducks, and the birds, and keeping an eye out for the deer enjoying the lake. There's plenty of yard for your furbabies to enjoy. There's lots of scenery on the drive to the cottage (forests, wildlife, lakes, countryside, wineries, farms, wedding venues, etc.); you never know what you can capture, so bring your camera.

4.97 out of 5 average rating, 150 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, 516 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.