Vacation rentals with a pool in The Woodlands

Vacation home in Montgomery

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.

4.95 out of 5 average rating, 194 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.

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.

4.93 out of 5 average rating, 115 reviews

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!!!

4.88 out of 5 average rating, 281 reviews

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

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.

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.

4.99 out of 5 average rating, 200 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

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.

4.96 out of 5 average rating, 172 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.

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.

4.9 out of 5 average rating, 199 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.

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.

4.96 out of 5 average rating, 102 reviews

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

An outdoor area features a serene blue pool surrounded by tropical landscaping. A red umbrella provides shade over lounge chairs. Stone borders the pool, while vibrant flowers are positioned in planters nearby. The modern architecture of the house is visible in the background under a partly cloudy sky.

4.8 out of 5 average rating, 160 reviews

Tropical Private Villa with Pool, Modern decor.

Bring the whole family to this great place 4,700 sqf. with lots of room for fun. Spacious 4 bedroom, 4.5 bathrooms, large game room, and huge home theater room, sleeps up to 8 people. Clean, bright, sunlit living space with brand new furnishings. 2 King beds, 3 queen beds. Tropical backyard, KitchenAid grill and outdoor lounge with newly renovated pool and spa (Remodeling was completed May 30th 2022). Entertainment has Neflix, Paramount, Disney Plus, and Amazon Prime. Happy stays.

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.

4.86 out of 5 average rating, 118 reviews

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

Aloha and Welcome! Whether you’re visiting Lake Conroe for the weekend, working in The Woodlands, attending a concert at Cynthia Woods Mitchell Pavilion, competing in the Iron Man, traveling as a medical professional, or bringing the family for a tournament, our home is designed to help you relax after a busy day. Enjoy spacious bedrooms, fast Wi-Fi, a fully stocked kitchen, and easy access to shopping, restaurants, and major employers. Your island oasis awaits. Welcome home, Ohana!

4.94 out of 5 average rating, 129 reviews

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

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.

4.99 out of 5 average rating, 167 reviews

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

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!

Guesthouse in The Woodlands

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.

4.88 out of 5 average rating, 314 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

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.93 out of 5 average rating, 118 reviews

Amazing getaway in the Woodlands with Private Pool

4.91 out of 5 average rating, 120 reviews

A spacious backyard features a vibrant pool area, beautifully illuminated by colorful night lights. Lush greenery surrounds the setting, complemented by a well-maintained lawn. A stone patio leads to the pool, which is adorned with a diving board and lounge chairs for relaxation.

Home in Houston

9ft Deep Pool & Spa • 1/4 acre yard •IAH 15 min

4.98 out of 5 average rating, 145 reviews

Stylish Home with Hot Tub & Gaming Garage

4.98 out of 5 average rating, 127 reviews

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

4.96 out of 5 average rating, 102 reviews

An elevated view of the outdoor area shows a private pool surrounded by loungers and colorful inflatable floats. A well-maintained basketball half-court and pickleball court occupy the space, with manicured grass and landscaped borders enhancing the recreation area.

Home in North Houston

Downtown, Pickleball, Pool, Karaoke, Golf, King bd

5.0 out of 5 average rating, 30 reviews

Chic TX House w/ Pool and Relaxing Atmosphere

Luxe

A modern home features large glass windows and a striking black exterior, framed by lush greenery. The driveway leads to a two-car garage, while a covered entryway invites guests to the front door. Soft evening light highlights the architectural details.

4.97 out of 5 average rating, 58 reviews

The Black Oak: Forest & Chill

5.0 out of 5 average rating, 23 reviews

Home in The Woodlands

Gated Luxury Haven w/ Pool | The Woodlands, TX

Condo rentals with a pool

A cozy armchair with a tufted design features soft blankets and decorative pillows. Large glass doors provide a view of the serene lake, allowing natural light to fill the space. A balcony with seating is visible beyond, enhancing the waterfront atmosphere.

4.98 out of 5 average rating, 183 reviews

Beautiful Waterfront Condo on Lake Conroe

A balcony area features a wicker sofa adorned with navy cushions. A decorative wooden table holds a simple arrangement of blue and white flowers. The railing offers an unobstructed view of the water, while homes line the distant shore.

4.92 out of 5 average rating, 164 reviews

Lakeview Condominium

A cozy bedroom features a beige tufted headboard with decorative pillows in yellow and gray colors. Two bedside lamps provide soft lighting beside wooden nightstands. Artwork depicting sea life adorns the walls, and neatly arranged towels sit on a tray at the foot of the spacious bed.

4.82 out of 5 average rating, 635 reviews

The Lakeside Hideaway - Fish from the balcony!

4.93 out of 5 average rating, 161 reviews

A shaded balcony offers a view of the waterfront, featuring a table and chairs arranged for outdoor relaxation. Lush trees provide natural greenery, while the lake stretches out beyond well-maintained lawns and adjacent patio areas.

Condo in Montgomery

Lakefront | Pet Friendly | Paddleboard Incl | Pool

A serene view from a balcony overlooking Lake Conroe at dawn. The calm water reflects soft hues of orange and pink from the sunrise, while the silhouette of trees lines the far shore. The railing, delicate and elegant, frames the tranquil scene.

4.79 out of 5 average rating, 310 reviews

Gorgeous Lake Views- One Bedroom-142

4.95 out of 5 average rating, 120 reviews

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!

A spacious king bed is dressed in a checkered duvet and accent pillows. Two cozy chairs are positioned near the bed. The bathroom entrance is visible in the background, showcasing a tiled shower curtain and light-colored walls.

4.8 out of 5 average rating, 158 reviews

The Lakeside Getaway Condo: Studio Room

A waterfront view is presented, showcasing a well-maintained grassy area leading to the water's edge. The spacious multi-story building is visible in the background, with a marina and a paddleboat docked nearby. The sky is clear, extending to the horizon.

4.86 out of 5 average rating, 263 reviews

Lakefront Bliss

Other vacation rentals with a pool

4.88 out of 5 average rating, 157 reviews

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

5.0 out of 5 average rating, 52 reviews

A spacious living area is showcased, featuring a large sectional sofa and a cozy armchair. A flat-screen television is mounted above a fireplace, while natural light fills the room from arched windows. Decorative plants and a stylish chandelier enhance the comfortable ambiance.

Villa in Spring

Stylish 4BR Retreat w/ Coffee Bar & Backyard Oasis

4.92 out of 5 average rating, 53 reviews

Tiny home in Montgomery

Pine Lake Escape: Lakefront Tiny House

4.95 out of 5 average rating, 98 reviews

A cozy guest room features a spacious king-size bed dressed in crisp white linens, complemented by decorative pillows. A vibrant blue couch offers seating, with a rustic table positioned nearby. Natural light streams through large glass doors, providing views of the serene outdoor greenery.

Guesthouse in Spring

Private retreat in The Woodlands

A serene outdoor space is featured, showcasing a sparkling pool illuminated by soft lighting. Surrounding greenery adds a natural touch, while a stone landscape provides texture. Comfortable lounge seating is positioned nearby, inviting relaxation. Bright windows of the home offer a view of the interior.

4.92 out of 5 average rating, 53 reviews

Unique Mid Century Modern Home in The Woodlands

5.0 out of 5 average rating, 18 reviews

Place to stay in Spring

“Garden Oasis” 1 of 4 Airbnb on 5 1/2 acre resort

A heated pool and spa are visible, surrounded by a stone patio. Lounge chairs are positioned nearby, overlooking a man-made lake. Lush trees frame the scene, while a covered space can be seen on the right, providing shade and relaxation options.

4.99 out of 5 average rating, 97 reviews

Lakehouse with Heated Pool & Infinity SPA*