Holiday rentals with a pool in The Woodlands

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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 The Woodlands
4.9 out of 5 average rating, 109 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

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 The Woodlands
4.93 out of 5 average rating, 115 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, 253 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, 177 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 The Woodlands
4.9 out of 5 average rating, 182 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, 144 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, 117 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.

Guest favourite
The living area features a comfortable sofa adorned with decorative pillows, alongside a standing lamp. A coffee table sits in front, and a media console holds a television. Floor-to-ceiling curtains frame sliding glass doors that open to a balcony, allowing natural light to enter.
Condo in Willis
4.86 out of 5 average rating, 167 reviews

The Lakeside Retreat Condo: On the Lake!

Quietly tucked away in the Seven Coves community, yet conveniently close to amenities. Spacious lake front condo with a full bath/kitchen. Complete with marble tile flooring and stainless steel appliances. BRAND NEW RENOVATED BATHROOM. Condo includes a WATER FRONT BALCONY off of the living room space & bedroom. See the light house during the day or lit up at night from the balcony and bedroom windows! Enjoy your stay right on Lake Conroe! Second floor entry by stairs or elevator.

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.
Guesthouse in The Woodlands
4.89 out of 5 average rating, 284 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
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
4.98 out of 5 average rating, 126 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.

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 Shenandoah
4.95 out of 5 average rating, 184 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, 133 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$243 AUD$239 AUD$284 AUD$296 AUD$297 AUD$282 AUD$300 AUD$277 AUD$269 AUD$269 AUD$277 AUD$276 AUD
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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 $42 AUD 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 and kid-friendly amenities

  • Pet-friendly accommodation

    Find 120 rentals that welcome pets

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

  • Wi-Fi availability

    220 of The Woodlands holiday rentals include Wi-Fi 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