Holiday 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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Superhost
A spacious living area is highlighted by a high open ceiling and large windows allowing for natural light. A dark leather sofa and two accent chairs are positioned around a decorative rug. A media console holds a flat-screen TV, creating a comfortable lounge environment.
Farm stay in Conroe
4.88 out of 5 average rating, 245 reviews

Country Retreat close to The Woodlands w/Pool

Stay 5 Min from The Woodlands in this one-of-a-kind retreat next to the Jones State Forest. 1/2 mile to walking, biking, or horseback riding on forest trails. At night you’ll 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.

Top guest favourite
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
4.99 out of 5 average rating, 176 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 favourite
A spacious outdoor area features a patio with two black wicker chairs and a round table, set against a backdrop of lush greenery. A pool glistens nearby, surrounded by neatly landscaped borders, while large windows illuminate the inviting interior of the home.
Home in Spring
4.89 out of 5 average rating, 179 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 favourite
The tranquil pool area is illuminated with vibrant purple and green lighting, highlighting the lush tropical flora surrounding it. A waterfall feature is visible, and the serene water reflects the ambient lighting, creating a peaceful nighttime atmosphere.
Villa in Conroe
4.8 out of 5 average rating, 100 reviews

Huge Private Pool + Slide on Golf Course

Charming Poolside Retreat Minutes from The Woodlands Mall Escape to your serene oasis, just ten minutes from The Woodlands Mall. Our villa features a spa for 8 adults, a cozy living room with a fireplace and egg chairs, and a private pool with optional heating. Enjoy arcade machines, skeeball, and three large TVs. Nearby attractions: The Woodlands Waterway for a romantic stroll, golf course, The Woodlands Shopping Center, tranquil forest walks, concerts, and Lake Conroe for an adventure.

Top guest favourite
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
4.94 out of 5 average rating, 211 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.

Top guest favourite
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
4.93 out of 5 average rating, 113 reviews

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.

Top guest favourite
A stock tank pool is situated beside a compact mobile home, surrounded by a wooden deck and outdoor shower. Bright sunlight filters through the trees, casting gentle shadows on the serene space. A shaded area offers a relaxing comfort for outdoor enjoyment.
Tiny home in Houston
4.91 out of 5 average rating, 163 reviews

The Fifth Wheel | Camp Fire | Stock Tank Pool

Are you a lone traveler and wonder what is it like to live in a true tiny house on wheels, or a couple looking to experience tiny living, but with all the amenities? Welcome to the Fifth Wheel! We are inspired with utilizing small space and turn them into amazing living experience. the home equipped with everything you need when traveling. The home is pack with efficient design, front porch with cover, stock tank pool, outdoor shower, Wifi, comfy bed and pillow & free parking

Superhost
Home in Shenandoah
4.9 out of 5 average rating, 200 reviews

Best location-Woodlands! 4BDR, Pet Yes! Fast WIFI!

Tailored for your vacations, business trips, medical stays, or while your home is under renovation! Conveniently located in Shenandoah/The Woodlands with easy access to I-45, Hardy Toll Road, and Grand Parkway. Minutes from ExxonMobil, hospitals, Market Street, and The Woodlands Mall. Features a private (unheated) pool. Great for families, wedding guests, travel nurses, and more. Ask about long-term stays! Note: 7% local lodging tax applies and will be collected at check-in.

Guest favourite
A spacious bedroom features a wooden accent wall and vaulted ceilings, complemented by large windows allowing natural light. A comfortable bed is positioned in the center with a cozy chair nearby. A flat-screen TV is mounted on the wall, providing entertainment options.
Tiny home in Houston
4.91 out of 5 average rating, 243 reviews

The Rustic Casita - Tiny Home, Cozy Patio, Jacuzzi

Escape to our charming Rustic Casita, a private studio apartment nestled in the back of our home, perfect for a romantic Couples Retreat or a relaxing getaway. Our secluded espace offers; •Keyless Gated Entrance EV ⚡️CHARGING ( Bring your own Cable) Dining table under a covered porch •Private jacuzzi spa for ultimate relaxation Located near Heights and Garden Oaks, just 12 minutes from downtown Houston and 20 minutes from IAH airport ✈️ Long Term Stays Welcome 🙏

Guest favourite
A two-story lakefront guesthouse is featured, showcasing expansive windows and a tiled roof. Lush greenery surrounds the property, and a patio area with outdoor seating is visible along the water's edge. The tranquil setting offers a serene view of the lake.
Guest house in The Woodlands
4.89 out of 5 average rating, 277 reviews

Lakefront Guesthouse: Pool, BBQ, Bike, Paddle Boat

Welcome to your lakefront escape - a spacious (~900 sq ft) private guesthouse suite with gorgeous Lake Paloma views, infinity pool access, and all the comfort you need for an easy, memorable stay. Perfect for families or small groups - up to 4 adults (or 5 guests including kids). NOTE: The guesthouse is attached to our home, where we live. Guests have a private entrance and private guesthouse space (not shared). The only shared areas are the driveway and backyard

Top guest favourite
An open living space combines a cozy sleeping area with a spacious bed covered in light bedding. A colorful light fixture hangs from the ceiling, illuminating decorative accents along the walls. A dining area and kitchenette are visible in the background, complemented by a small seating area.
Tiny home in Conroe
4.95 out of 5 average rating, 180 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 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. Main house has area on the other side that you can’t see.

Top guest favourite
The exterior of a well-maintained home is presented, featuring a mix of brick and stone facades. A double garage is visible, with stylish light fixtures on either side of the entrance. Landscaping includes low shrubs and a manicured lawn, framed by a paved driveway.
Home in Conroe
5 out of 5 average rating, 129 reviews

Beautiful Cozy 4-Bedroom Home in a Gated Community

This is a gorgeous, home with high ceilings, hardwood floors, and a walk-in closet in a gated community and gated driveway for additional security. The home is furnished with stainless steel appliances including fridge, granite countertops in the kitchen and a large island, coffee maker, air fryer, multi-purpose pressure cooker and other cooking utensils. The house has cameras mounted both in front and at the back of the house for additional safety

Popular amenities for The Woodlands rentals with a pool

When is the best time to visit The Woodlands?

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Avg. price$221 SGD$217 SGD$259 SGD$269 SGD$270 SGD$256 SGD$273 SGD$252 SGD$244 SGD$254 SGD$260 SGD$252 SGD
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Quick stats about holiday rentals with a pool in The Woodlands

  • Total holiday rentals

    Explore 230 holiday rentals in The Woodlands

  • Nightly prices starting at

    The Woodlands holiday rentals start at $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 5,530 verified reviews to help you choose

  • Family-friendly holiday rentals

    140 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 120 rentals that welcome pets

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

  • Wifi availability

    220 of The Woodlands holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across The Woodlands rentals

  • 4.8 Average rating

    The Woodlands stays are highly rated by guests – averaging 4.8 out of 5!

  • Nearby attractions

    The Woodlands’s top spots include The Cynthia Woods Mitchell Pavilion, Market Street and AMC Metropark 10

Destinations to explore