Vacation rentals with a pool 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.

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.

4.95 out of 5 average rating, 197 reviews

4.84 out of 5 average rating, 250 reviews

Quiet Cozy Retreat 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!

4.94 out of 5 average rating, 126 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!!!

4.98 out of 5 average rating, 187 reviews

A cozy armchair with a tufted design features soft blankets and decorative pillows. Large glass doors provide a view of the serene lake, allowing natural light to fill the space. A balcony with seating is visible beyond, enhancing the waterfront atmosphere.

Condo in Willis

Beautiful Waterfront Condo on Lake Conroe

Located in Seven Coves. Ideal getaway on Lake Conroe. Balcony is right over the water. Fishing from balcony is OK without fishing license! This is not a fish camp. Pls clean up all fish remains & gear. Main Bdrm: King Size bed w/ Tempur-Pedic mattress. The inside stairs leads to upstairs loft: 2 Queen beds and a full bathroom. Restaurant, swimming pool, tennis court, basketball court, marina, bike & boat rentals, playground & dinner cruise boat within walking distance. Combo washer/dryer unit.

4.96 out of 5 average rating, 105 reviews

A bright living area features a comfortable sofa and two armchairs positioned around a coffee table. A smart TV is mounted on the wall, while sliding glass doors lead to a scenic outdoor balcony. Natural light floods the space, enhancing the calming ambiance.

Condo in Willis

Cozy&Stylish lake condo:balcony fishing.

Welcome to our lakeside retreat! King Size Bed 2 queen size beds Cotton towels Makeup towels Body wash, shampoo &conditioner Fishing rods, bait, tackle box Tennis rackets & balls 5G complimentary WiFi 50 inch smart TV with Roku Netflix downstairs 46 inch TV upstairs with Roku Netflix DVD player and DVDs Board/card games Fully stocked kitchen Toddler friendly utensils, plates & cups Pots/pans/bakeware Keurig &complimentary regular/decaf/tea Ninja blender Stainless steel knives Clean bedding

4.88 out of 5 average rating, 159 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, 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 ; )

4.95 out of 5 average rating, 124 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!

4.93 out of 5 average rating, 134 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.

A spacious, two-story waterfront home is presented, featuring a covered deck with ample seating options. Lush green lawn surrounds the space, complemented by a wooden walkway leading to the entrance. The upper balcony showcases additional seating, enhancing outdoor relaxation opportunities.

4.88 out of 5 average rating, 104 reviews

Gorgeous Waterfront Lake Conroe Home Sleeps 10

This waterfront home offers all of the comforts of home perfectly situated on the water in a beautiful country club neighborhood. You will have access as our guests to the pool, gym, restaurant for a fee per Club Corp. Offering three large, spacious bedrooms each with full bathrooms and walk in closets. A fully equipped kitchen opens up to a family dining room overlooking the water. Guests may use our covered boathouse; this is a single slip with a lift and a 5,000 lb max.

4.93 out of 5 average rating, 165 reviews

A shaded balcony offers a view of the waterfront, featuring a table and chairs arranged for outdoor relaxation. Lush trees provide natural greenery, while the lake stretches out beyond well-maintained lawns and adjacent patio areas.

Condo in Montgomery

Lakefront | Pet Friendly | Paddleboard Incl | Pool

Welcome to Alluring Lakefront Condo — a stylishly furnished 2-bedroom, 2-bath retreat with direct lake views and a relaxing, resort-style feel. Whether you’re here for a weekend getaway, fishing trip, wedding, or extended escape, you’ll find everything you need for a comfortable and memorable stay — including a Complimentary Self-INFLATABLE PADDLEBOARD for you to enjoy on the lake. Just steps from the water and minutes from dining, shopping, and outdoor adventure.