Vacation rentals with a pool in The Woodlands

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in The Woodlands

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

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Guest favorite

Home in Spring

4.94 out of 5 average rating, 123 reviews

Spa & Pool Paradise- Pavilion/Waterway/Town Center

Nestled in the heart of The Woodlands, & recently named the #1 place to live! Enjoy an incredible small-town with high-end activities. This home is perfect for friends & family! The home offers peaceful comfort with its private backyard pool & spa! Inside, guests enjoy reclining seats and entertainment area or warm up in the evenings by the cozy fireplace. Close to golf courses, trails, festivals, The Pavilion, festivals & Town Center (our Downtown). *Spa comes w/remote & instructions to heat.

Guest favorite

Home in Conroe

5 out of 5 average rating, 114 reviews

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

Guest favorite

Tiny home in Conroe

4.94 out of 5 average rating, 135 reviews

Cozy tiny house on small lake "The Maryhannah"

Relax and enjoy the calm serene of a country vibe feel in the middle of the city! This cozy tiny house feels like a gentle hug. Float around the seasonal saltwater splash pool, soak in the hot tub, enjoy a small container fire, or sit by the lake and watch the fish. Bring your fishing pole for catch and release stocked pond in this small vintage fishing community. Unit is on the back of the main house - yard is split for privacy. Main house has area on the other side that you can’t see.

Guest favorite

Home in Spring

4.91 out of 5 average rating, 128 reviews

Lovely Woodlands home w/heated pool and spa!

Relax with the whole family at this peaceful Woodlands home. This house has free parking space and a heated pool to enjoy it during winter (spa's included but there is an additional charge for heated pool due to energy costs) 100% equipped and ready to become your home away from home. You’ll have this entire Woodlands home to yourself. Whether you are here for shopping, tourism or to visit one of the hospitals nearby, you’ll fall in love with this incredible house and the amenities provided.

Guest favorite

Farm stay in Conroe

4.91 out of 5 average rating, 180 reviews

Country Retreat 5 Minutes from The Woodlands

Stay in the center of the action in this one-of-a-kind place next to the Jones State Forest near miles of trails for walking, biking, or horseback riding. At night you will gaze at twinkling constellations poolside or relax in our massage chair or jetted garden tub. Attend an outdoor concert at the nearby Cynthia Woods Mitchell Pavilion, one of the top amphitheaters in America. We are 5 min from The Woodlands Medical Center, and 10 min from The Woodlands Mall where you can shop till you drop!

Guest favorite

Home in Montgomery

4.96 out of 5 average rating, 161 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.

Guest favorite

Home in Montgomery

4.9 out of 5 average rating, 101 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.

Guest favorite

Home in Spring

4.91 out of 5 average rating, 135 reviews

Private house in the Woodlands w/pool and spa.

Entire house with a pool/spa in The Woodlands, TX, in a quiet cul de sac - Ideal for a family holiday or weekend getaway. Minutes to Cynthia Woods Pavilion; Market St./Waterway; 160+ miles of pathways and trails serving as a safe venue to enjoy the outdoors; a 20-minute drive to Lake Conroe and Renaissance Festival NOTE: No parties. Limit 2 cars on the driveway. House fits 6 people but $25/person/night after 1st tow adults; children under 10yrs no extra charge.

Guest favorite

Guesthouse in Conroe

4.97 out of 5 average rating, 105 reviews

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.

Guest favorite

Home in Montgomery

4.81 out of 5 average rating, 105 reviews

Country Home in Montgomery TX

20 MINUTES FROM RENFEST. Book early. 10 minutes from Lake Conroe 15 minutes from Sam Houston National Forest. Relax with the whole family at this peaceful country getaway. Enjoy our colorful sunsets from the pool, the gazebo, or from the dining room table. Located just minutes from Lake Conroe, boat rentals, wineries, live music, and a variety of restaurants. We're near several wedding venues. We love to host the families and friends attending weddings.

Guest favorite

Home in Spring

4.92 out of 5 average rating, 176 reviews

🏝 Vacation home on a golf course. POOL and SPA 🏝

Have fun with the whole family at this stylish vacation home. Enjoy the outdoor living space, complete with outdoor kitchen, outdoor TV and surround sound, fire pit, heated pool, and spa. Six bedrooms (1 king bed, 4 queen beds, 1 bunkbed with 2 full size mattresses. Two sectionals, air hockey table, refrigerated wine cellar, and so much more. Bring your family and friends and stay under one roof.

Guest favorite

Condo in Montgomery

4.97 out of 5 average rating, 281 reviews

Waterfront Gem on Lake Conroe near Margaritaville

Relax on your own patio overlooking the calm waters of Lake Conroe while wildlife such as fish, ducks, squirrels, and turtles can be spotted frequently. Our place is on the 2nd (top) floor, stair access only, in a secluded community. Complex pool, and close to golfing attractions. Centrally located to popular wedding venues and a quick drive to many stores/ restaurants. 45 min. from IAH airport.