
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.

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

Beautiful Waterfront Condo on Lake Conroe
Located in Seven Coves. Ideal getaway on Lake Conroe. Balcony is right over the water. Fishing from balcony is OK without fishing license! This is not a fish camp. Pls clean up all fish remains & gear. Main Bdrm: King Size bed w/ Tempur-Pedic mattress. The inside stairs leads to upstairs loft: 2 Queen beds and a full bathroom. Restaurant, swimming pool, tennis court, basketball court, marina, bike & boat rentals, playground & dinner cruise boat within walking distance. Combo washer/dryer unit.

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.

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

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.

Tranquil Studio, Pool, Downtown View, Work-Ready
Relax in this super vibey, plant-filled studio with a private downtown view balcony and access to a 24/7 rooftop pool. Guests rave about the calming energy, greenery, décor, and peaceful atmosphere, perfect for unwinding or working. Centrally located and safe, this dog-friendly quiet retreat also features high-speed Wi-Fi and is ideal for solo travelers, couples, or business. With a host who goes above and beyond, experience the peaceful energy that makes this space unforgettable. Book now!

Serenity on the Lake
Forget your worries at The Carlton Family Lake House. It’s truly serenity on the lake…the calmness and peaceful you’ll feel here. This property on Lake Conroe in April Sound gated community is dedicated to ensuring a peaceful, comfortable & rejuvenating experience. The spacious 1,824 sq ft condo is perfect for a group of friends & family of 6 comfortably. Located conveniently near wedding venues, breweries, Margaritaville & many restaurants. Come & relax on your lake front property.

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.

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

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.

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.

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
House rentals with a pool

Heated Pool Theater Luxury 4BR Retreat

Private house-The Woodlands w/pool and generator.

Town House in Montgomery texas

The Black Oak: Forest & Chill

Kid‑Friendly Woodlands Home with Pool and Space

Paradise Garden Resort And Spa

New Lake House by Golf course + Kayaks & Game Room

Sweet home with plenty space, great neighbors.
Apartment rentals with a pool

Amazing Waterfront Renovated Condo on Lake Conroe

Reel in Romance ~ Lake Conroe ~ fish on balcony

Gorgeous Lake Views- One Bedroom-142

Sleeps 6 - Comfortable condo with great views!

✪ PARADISE COVE ⛱ Margarita-Time ⛱ Lakefront Oasis

Stunning Waterfront Lake Conroe - Ground Floor

The Lakeside Getaway Condo: Studio Room

Ultra-Modern Condo *Lake Conroe*
Other holiday rentals with a pool

Luxe Lakefront, Fire Pit, Cowboy Pool, Kayak, Dock

Oasis on the green!

Teal Oasis - 1 Bedroom/1 Bathroom Condo

New 4BR Retreat + Pool Near The Woodlands

Lakehouse with Heated Pool & Infinity SPA*

Double C Ranch @ Lake Conroe

Waterfront Walden Lodge *Discounted Monthly Stays!

Unique Mid Century Modern Home in The Woodlands
When is the best time to visit The Woodlands?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £127 | £125 | £149 | £155 | £156 | £148 | £157 | £145 | £141 | £141 | £145 | £145 |
| Avg. temp | 12°C | 14°C | 18°C | 21°C | 25°C | 28°C | 30°C | 30°C | 27°C | 22°C | 17°C | 13°C |
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 5,530 verified reviews to help you choose

Family-friendly holiday rentals
140 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 120 rentals that welcome pets

Rentals with dedicated workspaces
130 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

4.8 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
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- Rentals with pools Montgomery County
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- NRG Stadium
- The Galleria
- George R. Brown Convention Center
- Houston Museum District
- Houston Zoo
- Toyota Center
- Minute Maid Park
- White Oak Music Hall
- Memorial Park
- The Cynthia Woods Mitchell Pavilion
- Rice University
- Downtown Aquarium
- Typhoon Texas Waterpark
- Space Center Houston
- Buffalo Bayou Park
- Highrise Houston
- Huntsville State Park
- The Menil Collection
- University of Houston
- Hurricane Harbor Splashtown
- Gerald D. Hines Waterwall Park
- Stephen F. Austin State Park
- Miller Outdoor Theatre
- Contemporary Arts Museum Houston




