Holiday rentals in The Woodlands Waterway

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Top-rated holiday rentals in The Woodlands Waterway

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Home in The Woodlands
4.95 out of 5 average rating, 60 reviews

The Woodlands Retreat Getaway & Theater Luxury

Welcome Home, The Woodlands Retreat Getaway! Enjoy your private Theater, 3 Luxury Suites and only minutes from The Woodlands’ top venues, parks, and medical centers. Open concept living space with quartzite countertops, a waterfall island, and stainless steel appliances. Close to The Cynthia Woods Mitchell Pavilion, Market Street, and scenic spots like Lake Woodlands and George Mitchell Nature Preserve, our home offers the convenience and tranquility in a family-friendly, nature-filled setting.

Superhost
The exterior of a modern two-story structure is showcased, featuring a distinctive octagonal shape with a metal roof. Large glass windows allow for ample light and provide views of the landscaped backyard, which is bordered by trees and decorative stones.
Home in Spring
4.78 out of 5 average rating, 37 reviews

Luxury Loft Style House w Pool | The Woodlands

Escape to a peaceful loft-style retreat in Grogan’s Mill with a spacious layout, full kitchen, modern comforts, private parking, and relaxing poolside setting. Perfect for couples, solo travelers, business guests, concert weekends, golf trips, medical stays, or extended visits. The Woodlands favorites: TW Trails 1 min Cynthia Woods 3 min Tournament Course 3 min Market Street 5 min The Woodlands Mall 5 min Waterway Square 7 min Hughes Landing 8 min Memorial Herman Hospital 10 min IAH 21 min

Top guest favourite
Home in The Woodlands
5 out of 5 average rating, 18 reviews

Gated Luxury Haven w/ Pool | The Woodlands, TX

✨ A Woodland Haven of Luxury ✨ Experience luxury living in The Woodlands, TX in this gated 3-bedroom home perfect for families, groups, or pet-friendly getaways. Enjoy private community access, a refreshing pool, free parking, and easy drives to The Woodlands Mall, Waterway, Market Street and local nature trails. What You’ll Love: 🏡Private, Gated Community 🌲Walking Trails & Nature Nearby 💦Community Pool Access 🛍️ Minutes to The Woodlands’ Top Spots 🚗 Easy Access for Seamless Travel

Top guest favourite
A kitchenette is displayed, featuring a sleek countertop with a stainless steel sink. An electric countertop oven sits alongside a coffee maker, complimented by a shelf holding dishware and decorative items. A roll of paper towels and dish soap are positioned for easy access.
Guest house in Shenandoah
5 out of 5 average rating, 177 reviews

The Woodlands/Shenadoah Casita

Right in the heart of all of the action, you will find this super cute, well appointed Casita with QUEEN bed. You will have your own space and everything you need for your getaway. We provide off street parking, outside patio, hot tub and access to the grill. This casita is located across the patio from our primary residence. While you do have your own space you may bump into us outside feeding the chickens or letting our little Yorkie out to potty. You’ll access through the side gate.

Top guest favourite
The exterior of a modern home is shown, featuring a stone-accented facade. A neatly landscaped lawn is visible, complemented by a curved driveway leading to two wooden garage doors. Lush greenery lines the path to the entrance, creating a welcoming approach.
Home in The Woodlands
4.99 out of 5 average rating, 129 reviews

1 mile from everything!• Dining • Family Friendly

-Best location in The Woodlands! 3 bedroom peaceful home, walking distance from Hughes Landing. 1 mile from Woodlands Mall, Market St, Waterway, hospitals, & Whole Foods. -Access to tree lined walking/biking trails next to house. -3 bedrooms, 2.5 bathrooms, 2 living rooms. Small private backyard w/patio furniture. -Family friendly home; I provide pack n play, highchair, toys, dishes, & some baby proofing. -Desk & remote working area -coffee/tea bar & ample kitchen supplies provided!

Top guest favourite
A modern entrance is framed by sleek black stone features and minimalistic lighting. A pathway leads to a glass door, flanked by two tall plants, while grass borders the walkway, providing a clear view of the home's contemporary design.
Home in Conroe
4.99 out of 5 average rating, 145 reviews

IvoryEdition NEW Luxury Estate Mins From Woodlands

This unique place has a style all its own. Modern, Open-Concept Luxury Estate. Entire Home top to bottom Glass Sliders. Minutes away from all of The Woodlands Texas beautiful attractions. The perfect place to come and enjoy a luxurious stay by yourself or with friends, there is plenty of bedrooms with their own bathroom! Work from home in our dedicated built in workspace with beautiful woodland views. Create your own mood with the entire home being powered by Philips HUE Lights.

Top guest favourite
Home in Spring
4.99 out of 5 average rating, 141 reviews

Modern Woodlands Getaway Near Waterway & Pavilion

Enjoy a relaxing stay in the heart of The Woodlands 🌳 explore The Waterway, Market Street, Hughes Landing, and The Pavilion, then return to a bright, welcoming home designed for gathering and unwinding. 🏡 ⭐️Featuring vaulted ceilings, natural light, an open-concept layout, fire pit, hammock, covered patio, and large backyard, this peaceful retreat is perfect for weekend getaways, concert trips, work travel, wedding guests, and extended stays. ⚽️ Shuttle nearby to the World Cup!

Top guest favourite
A spacious living area features large windows that allow natural light to fill the room, showcasing views of surrounding greenery. Comfortable green armchairs flank a modern sofa adorned with decorative pillows. A coffee table sits on a patterned area rug, enhancing the inviting ambiance.
Flat in The Woodlands
4.96 out of 5 average rating, 107 reviews

Private 1BR Apt in The Woodlands | Great Location

Private, spacious 1BR retreat in the heart of The Woodlands, tucked into a peaceful setting surrounded by greenery. Guests love the comfortable feel, great location, and that the space feels bigger than expected. Enjoy a detached apartment with a full kitchen, fast Wi-Fi, Washer/Dryer, dedicated workspace, and easy access to Hughes Landing, Market Street, the Pavilion, shopping, parks, and trails. Perfect for family visits, weekend stays, business travel, and longer bookings.

Luxe
Home in Conroe
4.96 out of 5 average rating, 53 reviews

The Black Oak: Forest & Chill

Discover The Black Oak: Forest & Chill—a brand new home nestled among the trees. Meticulously designed by The Build Co., this brand-new haven showcases abundant natural light, a Tulum-inspired outdoor shower, and spacious bedrooms with private patio access. Outside, relax with the family in the Japanese-inspired area under a covered porch. Perfectly located, you’re just moments from The Woodlands' upscale dining, shopping, and all the area’s best attractions.

Top guest favourite
The living room showcases a spacious sectional sofa, complemented by two upholstered chairs. A round wooden coffee table sits in the center, surrounded by a soft area rug. Natural light enters through the window, illuminating the neutral-toned walls and decorative elements.
Townhouse in The Woodlands
4.96 out of 5 average rating, 217 reviews

Beautiful 3-Bedroom Townhome!!!

Beautiful 3-Bedroom town-house in a quiet neighborhood in The Woodlands Texas!! 4min drive to local grocery store and restaurants. Features 3 bedrooms, 2.5 bathrooms, 2 stories, sleeps 8 in beds with Backyard. 1 King, 1 Queen, 1 full and 2 twins, 1 sofa baby playpen available. amenities include hi-speed internet, washer/dryer, TV in livingroom. NO EVENTS ALLOWED. Max 8 people, parking around the property. No Pets

Guest favourite
Home in Shenandoah
4.91 out of 5 average rating, 11 reviews

Spacious Home Near The Woodlands & Hospitals

Step into a peaceful Shenandoah retreat designed for families, medical visitors, and long‑stay guests. With a full kitchen, fast Wi‑Fi, work desk, and laundry, it’s built for comfort and routine. Tucked in a quiet neighborhood just minutes from The Woodlands Mall, dining, and top hospitals—arrive settled, stay productive, and leave refreshed.

Guest favourite
Home in Spring
4.94 out of 5 average rating, 31 reviews

House in The Woodlands

Your family will be close to everything when you stay at this centrally-located place. So quiet, spacious, and peaceful. Nestled next to everything you could ever ask for. Just a few minutes from the 45 freeway, Cynthia Woods, Mitchell pavilion, H-E-B, the waterway, Hughes Landing, 200+ miles of hiking trails, and numerous restaurants.

Popular amenities for The Woodlands Waterway holiday rentals