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, 195 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.

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4.83 out of 5 average rating, 247 reviews

Quiet Country Home w/Fire-pit and Pool

5-20 min from popular Wedding Venues! 20 min FROM TX. REN- FESTIVAL. Book early. 10 min from LAKE CONROE, boat rentals, wineries, live music, and a variety of restaurants. 15 min from SAM HOUSTON NATIONAL FOREST (Dirt bike trails anyone? Call park to check schedule ). Relax at our peaceful country getaway. We are a family/friends retreat and not a party venue. Enjoy our colorful sunsets from the pool, gazebo, or dining room table. We love to host your family/friends attending weddings!

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4.94 out of 5 average rating, 124 reviews

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.

Home in Conroe

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!!!

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4.96 out of 5 average rating, 164 reviews

Townhouse in Montgomery

Lakefront Retreat | Swim, Park Boat & Paddleboard

🚤Escape to EverGreen Cove, a pet-friendly, 4BR/3BA lakeside townhouse on Lake Conroe. 🐟 Wake up to calm cove views, spend the day paddle boarding and swimming off the bulkhead, then grill dinner while the sun sets over the lake. ☀️Paddle boards included 🏊🏼Swim directly from the property 🎣Fish from the bulkhead 🚤Bring your boat and tie up on our bulkhead 🤿Pool access 🍔Grill and outdoor dining (bring your own charcoal) 🌅Sunset on the deck ⚓️Nearby boat rentals and lakeside restaurants

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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, 129 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 ; )

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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.

4.94 out of 5 average rating, 126 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.

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4.91 out of 5 average rating, 183 reviews

Villa in Montgomery

The Waterfront Villa

Plan your lake escape to this contemporary lakeside villa. This modern luxury getaway is located directly on Lake Conroe! Whether you're here for boating, fishing or lounging poolside, this is the perfect spot. This luxurious 5-bedroom, 3.5-bathroom home features a fully equipped gourmet kitchen, 3 master suites, as well as two bunk rooms equipped to sleep up to 16 guests comfortably. Enjoy the gorgeous deck, extended balcony, fire pit, and numerous spots for lounging with your friends!

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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, 152 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.

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4.96 out of 5 average rating, 103 reviews

A functional garage with a white door is complemented by a covered gazebo, creating a shaded outdoor area. The structure is surrounded by lush green trees and a well-maintained yard, offering a peaceful setting for relaxation.

Cottage in Montgomery

The Dairy Barn & Parlor

Set on 12 acres this secluded little house is the perfect get-a-way place to enjoy some down time. Close to fishing at Lake Conroe this cottage serves also as a central point to enjoy some of the local wineries, visit historic downtown Montgomery, explore the Sam Houston National Forest or spend time at the Texas Renaissance Festival which is only 20 minutes away. The physical address and entrance road name has changed several times in the past few years so the GPS address may not work.

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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, 543 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.

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4.99 out of 5 average rating, 236 reviews

A spacious green lawn is surrounded by tall trees, with dappled sunlight filtering through the leaves. The cabin's front porch features wooden railings and is set against the backdrop of a natural landscape, inviting relaxation in a serene environment.

Cabin in Magnolia

Woodlands Retreat - Looks Rustic, Feels New

This freshly renovated retreat in Magnolia is the perfect relaxing getaway. Enjoy the peace and quiet of a 5-acre natural wonderland. Minutes away from world-class shopping, dining, and recreation in The Woodlands, TX. The home features 4 furnished bedrooms, a fully furnished kitchen and dining area, a spacious living room with pull-out sofa, 2 full baths, high-end linens, a stocked laundry room, and plenty of outdoor space to enjoy. We hope to see you soon!

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