Holiday rentals with a pool in The Woodlands

4.9 out of 5 average rating, 109 reviews

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 Harper's Landing

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

Holiday 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, 186 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 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, 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!!

4.88 out of 5 average rating, 255 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.

Home in Cochran's Crossing

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.

4.91 out of 5 average rating, 151 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 10yrs no extra charge. Prefer self-sufficient guests.

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, 179 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 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, 185 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.

4.76 out of 5 average rating, 106 reviews

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

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.

4.93 out of 5 average rating, 117 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 Harper's Landing

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 house 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, 285 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

4.98 out of 5 average rating, 127 reviews

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.

Guest house in Conroe

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.

4.95 out of 5 average rating, 186 reviews

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

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.

Popular amenities for The Woodlands rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 11 reviews

The Woodlands R&R

4.9 out of 5 average rating, 107 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

Paradise Garden Resort And Spa

4.92 out of 5 average rating, 12 reviews

A spacious backyard is shown, featuring a well-maintained lawn and a heated pool. The home's exterior is composed of natural stone and features large windows. A surrounding fence provides privacy, while nearby homes can be seen in the background under a clear blue sky.

Home in The Woodlands

Lakefront Luxury with Pool & Spa

4.91 out of 5 average rating, 219 reviews

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 April Sound

Serenity on the Lake

Home in Cochran's Crossing

An inviting outdoor space features a private pool surrounded by a curved patio. A spa sits adjacent to the pool, while comfortable seating areas are arranged under a shaded porch. Lush trees and a wooden fence provide privacy in the tranquil backyard.

4.95 out of 5 average rating, 20 reviews

Relaxing 4BR Home with Pool & Spa in The Woodlands

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.

4.92 out of 5 average rating, 86 reviews

Ultimate Escape Near Lake Conroe | 4BD | Pool Spa

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.

5 out of 5 average rating, 73 reviews

Lakehouse with Heated Pool & Infinity SPA*

5 out of 5 average rating, 13 reviews

A comfortable outdoor seating area features cushioned furniture arranged around a small table. An umbrella provides shade beside a newly installed private pool, which is surrounded by lush greenery and a wooden fence. A colorful float can be seen in the water.

Home in Indian Springs

NEW! Woodlands 4BR Retreat - Pool, Spa & Trails

Apartment rentals with a pool

A serene view is captured from the patio, featuring a calm lake surrounded by lush greenery and boats docked in the distance. Two chairs are positioned on the patio, offering a peaceful spot to enjoy the water and picturesque scenery.

4.97 out of 5 average rating, 229 reviews

Amazing Waterfront Renovated Condo on Lake Conroe

4.78 out of 5 average rating, 294 reviews

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.

Apartment in Willis

Gorgeous Lake Views- One Bedroom-142

4.95 out of 5 average rating, 115 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.

Apartment in April Sound

Sleeps 6 - Comfortable condo with great views!

A serene view of a calm cove is presented, featuring a small fishing boat on the water. Two colorful Adirondack chairs are positioned on the patio, overlooking the lush green lawn and flowering plants near the water's edge. The backdrop includes tranquil residential buildings.

4.94 out of 5 average rating, 128 reviews

✪ PARADISE COVE ⛱ Margarita-Time ⛱ Lakefront Oasis

A glass door opens to reveal a scenic water view, framed by a cozy seating area with woven chairs. A small circular table sits on the patio, complemented by a decorative plant nearby. The expansive outdoor space invites relaxation.

4.86 out of 5 average rating, 137 reviews

Stunning Waterfront Lake Conroe - Ground Floor

4.87 out of 5 average rating, 150 reviews

A calm waterfront scene is depicted, featuring a sprawling view of the lake under a gently colored sky. Ducks are seen floating on the water, while a boat dock with several slips is visible in the background, set against a lush green lawn.

Apartment in Willis

Lakeview and Casa Couture

A cozy living room features a leather sofa paired with a comfortable armchair. A coffee table is adorned with vibrant decor, while a patterned area rug adds warmth. Soft lighting is provided by blue lamps on side tables, and a colorful artwork of trees decorates the wall.

4.97 out of 5 average rating, 149 reviews

Rental Retreat TX-Come Relax on Lake Conroe!

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.

4.95 out of 5 average rating, 141 reviews

Lakefront | Pet Friendly | Paddleboard Incl | Pool

Other holiday rentals with a pool

A spacious exterior view of a well-appointed house is presented, surrounded by lush greenery in a tranquil, wooded area. The structure features a combination of stone and wood materials, with a large driveway leading to the entrance. A clear blue sky is visible overhead.

4.84 out of 5 average rating, 82 reviews

Modern Cabin in the Woods

5 out of 5 average rating, 11 reviews

Flat in Magnolia

Comfortable 2BR Getaway Close to The Woodlands

An outdoor seating area is displayed, featuring four blue chairs arranged around a small black table. A vibrant blue umbrella provides shade. In the background, a private in-ground pool is visible, surrounded by lush greenery and tall trees, creating a serene atmosphere.

4.96 out of 5 average rating, 28 reviews

Beach House in the Woods with a Private Pool

5 out of 5 average rating, 24 reviews

Ultra-Modern Condo *Lake Conroe*

The front view of a two-story house is surrounded by tall trees, providing a natural setting. A spacious driveway leads to the garage on the right. The house features a welcoming entrance with a decorative wreath, and a balcony extends over the entrance, framed by white railings.

4.98 out of 5 average rating, 87 reviews

Woodlands Oasis | 3 BR/2.5 BA | Heated Pool & Spa

5 out of 5 average rating, 3 reviews

A well-appointed living area features a white sectional sofa with a decorative throw, paired with a coffee table on a light-colored rug. Natural light pours in through the large window, illuminating minimalist décor and a dedicated workspace with a wooden chair. Wall art adds a touch of sophistication.

Flat in The Woodlands

2 Bedroom-Mid‑Century GEM | Music Space | King Bed

4.95 out of 5 average rating, 42 reviews

The resort-style pool area is framed by stylish lounge chairs and shade umbrellas. The clubhouse buildings provide a modern architectural backdrop, while large windows allow natural light to fill the space. A clear blue sky adds a bright atmosphere to the inviting outdoor setting.

Home in Magnolia

Modern Magnolia Cottage | Pool & Gym Access

A modern kitchen features white cabinetry and a large island with a granite countertop. Stainless steel appliances, including an oven and dishwasher, are visible. Natural light filters through multiple windows, creating a bright and functional cooking space.