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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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Guest favourite
The outdoor salt-water pool and hot tub are illuminated in shades of blue, creating a serene nighttime ambiance. Soft lights outline the area, accentuating the smooth, curved edges and peaceful surroundings, inviting relaxation and tranquility.
Home in Conroe
4.89 out of 5 average rating, 112 reviews

ALOHA! Hawaii in The Woodlands 5BD/3BA Sleeps 10

Aloha and Welcome! Our home invites you to rest, relax, and recharge. Located on a quiet, tree lined cul-de-sac, our two-story, 5bd/2.5 ba salt water pool home offers: *A fully stocked kitchen with all kitchenware and cooking essentials *Dedicated work or entertainment space *Salt water pool & hot tub *Covered patio with outdoor tv (swivels to watch from the pool) & volcano rock fire pit *Outdoor kitchen with gas BBQ grill & fridge Your oasis awaits. Welcome home, Ohana! You belong here <3

Top guest favourite
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.
Holiday home in Montgomery
4.95 out of 5 average rating, 188 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.

Guest favourite
A spacious living area features plush gray sofas with tufted upholstery, complemented by black accent chairs. A neutral area rug covers the floor, while a round coffee table sits at the center. Natural light pours through large windows, enhancing the room's inviting atmosphere.
Home in Spring
4.93 out of 5 average rating, 116 reviews

Amazing getaway in the Woodlands with Private Pool

Located in The Woodlands, Texas. Enjoy the best of resort life when you stay at this vacation rental home with OUR PRIVATE HEATED POOL WITH JACUZZI and a beautiful backyard, that includes a Summer Kitchen with a Grill and a Mini Fridge. Located in the quiet community of Sterling Ridge, yet only a mile away from grocery stores, Starbucks and more. Only 15 min away from the Mall, Market St, The Waterway and less than 5 miles away from entertainment, fine dining and shopping. READY TO BE BOOKED!!

Guest favourite
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, 265 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
An inviting pool area is highlighted by a sparkling blue pool and a spa, both surrounded by lush greenery. Soft lighting is provided by string lights overhead, creating a serene evening atmosphere amidst the trees.
Home in Cochran's Crossing
4.91 out of 5 average rating, 152 reviews

Private house-The Woodlands w/pool and generator.

Entire house with a pool/spa and backup generator in The Woodlands, TX - 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 two adults; children under 13yrs no extra charge. Prefer self-sufficient guests.

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, 185 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

Top guest favourite
A large inground pool is surrounded by a spacious wooden deck, featuring lounge chairs and umbrellas for shade. The home, visible in the background, showcases large windows and a welcoming exterior, integrated seamlessly with the lush greenery of the surrounding area.
Home in Spring
4.96 out of 5 average rating, 167 reviews

Poolside Summer Large Family Home Gather Here

This spacious home offers a serene escape. With soaring ceilings, abundant natural light, huge deck featuring a sparkling pool, it's the perfect retreat for families and friends. Enjoy a master suite complete with a jacuzzi and loft, or unwind in the inviting living room, complete with wet-bar and stunning pool views. The well-equipped kitchen and dining areas make entertaining a breeze, while nearby amenities of The Woodlands provide endless opportunities for shopping, dining, and recreation.

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
4.9 out of 5 average rating, 189 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
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
4.91 out of 5 average rating, 148 reviews

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

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, 122 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 spacious living and dining area features a large wooden dining table with black chairs, complemented by a patterned table runner. A cozy seating arrangement is visible, with a fireplace adorned by decorative items. Natural light illuminates the open space, enhancing its welcoming ambiance.
Home in Shenandoah
4.99 out of 5 average rating, 160 reviews

EV-Charger-Clean- The Woodlands

Amazing LOCATION! About one mile to The Woodlands Mall, Waterway, Market Street, Cynthia Woods Pavilion and more. Family friendly neighborhood with multiple parks, near walking and bike paths. Home has everything you need to feel right at home. Indoor laundry room, coffee/tea bar, smart T.V.'s in each room with streaming programs included. Access to the home is gained by keyless entry. Long term renters are welcome (with prior approval needed). We are just a phone call away!

Superhost
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
4.88 out of 5 average rating, 295 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

Popular amenities for The Woodlands rentals with a pool

When is the best time to visit The Woodlands?

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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 £22 per night before taxes and fees

  • Verified guest reviews

    Over 5,810 verified reviews to help you choose

  • Family-friendly holiday rentals

    130 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 110 rentals that welcome pets

  • Rentals with dedicated workspaces

    140 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

  • 4.7 Average rating

    The Woodlands stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

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

Destinations to explore