Vacation rentals with a pool in Montgomery County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Montgomery County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

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.

Vacation home in Montgomery

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, 195 reviews

Top guest favorite

Home in Montgomery

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!

4.83 out of 5 average rating, 247 reviews

Top guest favorite

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!!!

4.94 out of 5 average rating, 124 reviews

Top guest favorite

A serene outdoor space is highlighted by a heated pool with fountain features, surrounded by lush greenery and colorful flowers. A stylish gazebo provides shaded seating, with comfortable lounge chairs positioned nearby. The natural landscape is enhanced by tall trees, creating a private and tranquil ambiance.

Home in Conroe

Country Sanctuary-5*Lux King Bed-2,400+ Sq Ft

This beautiful, custom-built 2,400+ sq ft home, that sits on 1 acre, is surrounded by the woods and the many deer, giving you all of the privacy you will need for a relaxing retreat. If you want to feel peace and tranquillity while listening to the birds chirping, you want to stay here. Please make the Country Sanctuary a favorite in your search by clicking on the RED HEART in the upper right hand corner, this will help you find it again and share with others. Christmas Tree for the Holidays

4.99 out of 5 average rating, 204 reviews

Top guest favorite

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

4.96 out of 5 average rating, 104 reviews

Guest favorite

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

4.88 out of 5 average rating, 158 reviews

Top guest favorite

Condo in Montgomery

Serene Lakeside 2BR • Sunset Views, Pool & 75" TV

Wake up to calm lakeside views in this comfortable 2BR/2BA waterfront condo overlooking the marina. Sip morning coffee on your private balcony as ducks glide by and squirrels play, then relax by the fire pit as sunset glows across the water. Enjoy community pools, gym, tennis/pickleball courts, and scenic walking/biking trails. Fast Wi‑Fi, dedicated workspace, nearby playground, dog park, and lakeside dining make it perfect for families, couples, and small groups seeking peaceful lake life.

4.97 out of 5 average rating, 103 reviews

Guest favorite

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.

Home in Montgomery

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 ; )

4.98 out of 5 average rating, 129 reviews

Guest favorite

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!

4.95 out of 5 average rating, 122 reviews

Guest favorite

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!

4.91 out of 5 average rating, 183 reviews

Guest favorite

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.

Home in Montgomery

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!

4.91 out of 5 average rating, 231 reviews

Top guest favorite

A serene pool area is surrounded by lush greenery and vibrant flowers. Natural stone steps lead down to the water, and tropical plants frame the scene. A stone waterfall cascades into the pool, creating a tranquil atmosphere in the outdoor space.

Guesthouse in Conroe

Fun, Relaxing Escape with Pool

Your family will be close to everything in The Woodlands when you stay at our centrally-located property. You will also be able to get away when you come back to relax on 5 acres. It is within walking distance to Jones State Forest. Within 5-15 minutes drive to The Woodlands Pavillon, mall, events, and restaurants. We live on the property in the house and will be there to assist you with whatever you may need while staying in our 1900 square foot bardominium.

4.98 out of 5 average rating, 133 reviews