Holiday rentals with a pool 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, 186 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.

4.91 out of 5 average rating, 146 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

4.95 out of 5 average rating, 117 reviews

The kitchen area features modern cabinetry and a spacious countertop. A dining table set for four is visible, paired with comfortable chairs. A spiral staircase leads to the upper level, while large windows allow natural light to fill the space, showcasing views outside.

Condo in Montgomery

Sleeps 6 - Comfortable condo with great views!

Whether coming for business or fun, Lake Conroe has it all! This 2 br, 2 ba 1226 sq ft condo is located in the gated community of April Sound on Lake Conroe. It is centrally located off Hwy 105, with everything you need near by. You will find multiple bed sizes and a fully equipped kitchen along with an AMAZING open water view, thanks to it's location on the second floor. High speed fiber optic internet is included with stay, along with every basic necessity you need for a comfortable stay!

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, 119 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 ; )

4.92 out of 5 average rating, 166 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!

Superhost

The image collage showcases various aspects of The Carlton Family Lake House, including a cozy bedroom with stylish decor and a serene view of the lake from the living area. Natural light floods the space, enhancing the calm atmosphere, while outdoor scenes capture the tranquility of the lakeside setting.

4.91 out of 5 average rating, 220 reviews

Serenity on the Lake

Forget your worries at The Carlton Family Lake House. It’s truly serenity on the lake…the calmness and peaceful you’ll feel here. This property on Lake Conroe in April Sound gated community is dedicated to ensuring a peaceful, comfortable & rejuvenating experience. The spacious 1,824 sq ft condo is perfect for a group of friends & family of 6 comfortably. Located conveniently near wedding venues, breweries, Margaritaville & many restaurants. Come & relax on your lake front property.

4.95 out of 5 average rating, 131 reviews

Tiny home in Willis

Tiny Blue Lake House

Welcome to our Little Blue Lake House in the Thousand Trails Resort on Lake Conroe. Do you want to get away? Do you enjoy glamping? Whether you want to relax and unwind, or partake in the many amenities, there is something for everyone! Little Blue is the place for you! We are 45 minutes North of Downtown Houston, in Willis, Texas. Our Tiny Home is located on a Large End Lot in the Hidden Cove neighborhood of the Resort. Gated Resort offers Lake Access with Beach, Boat Ramp and Pool.

4.97 out of 5 average rating, 149 reviews

A cozy living room features a leather sofa paired with a comfortable armchair. A coffee table is adorned with vibrant decor, while a patterned area rug adds warmth. Soft lighting is provided by blue lamps on side tables, and a colorful artwork of trees decorates the wall.

Condo in Montgomery

Rental Retreat TX-Come Relax on Lake Conroe!

Experience beautiful sunsets on the lake!! 1st floor w/all amenities, 1 bedroom (queen), & living room w/sleeper sofa (queen). Quick access to pool & lake. Kitchen cooking utensils, dishes, range, refrigerator, microwave & dishwasher. Shower & tub, washer & dryer. Access to fitness & racquet club, yacht club & grill, and private boat launch. Parking close to the door. Fishing, golfing, boating, tennis, swimming, walking trails and close proximity to Sam Houston National Forest.

4.85 out of 5 average rating, 171 reviews

The living area features a comfortable sofa adorned with decorative pillows, alongside a standing lamp. A coffee table sits in front, and a media console holds a television. Floor-to-ceiling curtains frame sliding glass doors that open to a balcony, allowing natural light to enter.

Condo in Willis

The Lakeside Retreat Condo: On the Lake!

Quietly tucked away in the Seven Coves community, yet conveniently close to amenities. Spacious lake front condo with a full bath/kitchen. Complete with marble tile flooring and stainless steel appliances. BRAND NEW RENOVATED BATHROOM. Condo includes a WATER FRONT BALCONY off of the living room space & bedroom. See the light house during the day or lit up at night from the balcony and bedroom windows! Enjoy your stay right on Lake Conroe! Second floor entry by stairs or elevator.

The exterior of a two-story house is shown with a metal roof and large glass doors facing a private pool. A fountain splashes in the foreground, while a shaded seating area with a parasol is visible on the patio. Lush trees frame the scene.

4.91 out of 5 average rating, 111 reviews

Stonehouse Estate 5 acre Private Retreat!

Texas hill country stone meets modern French farmhouse at this private luxury retreat on 5 wooded acres in Montgomery, Texas. This hidden gem has plenty of room for your group and is close to Lake Conroe! A warm, inviting fireplace in the living room opens up to a beautiful kitchen and dining area, overlooking a private pool with a lush grove of trees for a backdrop. The perfect space for your vacation or small event. Located near everything including Magnolia and The Woodlands.

4.82 out of 5 average rating, 202 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!