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Vacation 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.

Guest favorite
Farm stay in Conroe
Country Retreat 5 Minutes from The Woodlands
Stay in the center of the action in this one-of-a-kind place next to the Jones State Forest near miles of trails for walking, biking, or horseback riding. 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 minutes from The Woodlands Mall where you can shop till you drop!
Aug 8 – 15
$88 per night
4.88 out of 5 average rating, 138 reviews
Guest favorite
Guesthouse in Anderson
Ponderita farms - peaceful getaway in Anderson, TX
Our 3-room private suite and pool in Anderson, TX is the perfect place for a quick country getaway. Our place features wide open views away from the city crush. The living room, dining room, and kitchenette are included in one open area. The bedroom is separate and includes a queen-size bed. There is a hallway leading from the living area to the full bath which includes a small closet for clothing. Here you will also find extra blankets, pillows, and linens for the queen air mattress.
Mar 7 – 14
$59 per night
4.96 out of 5 average rating, 188 reviews
Guest favorite
Home in The Woodlands
Charming Home with Pool & Spa in Alden Bridge
Central to everything in The Woodlands. Beautiful, spacious home in the village of Alden Bridge. Everything you need for a wonderful Texas vacation. Views of the tree canopy throughout, front porch and tranquil backyard with pool makes this property special. Playground, park, trailhead just one block away. The pool is heated in the winter months and there is a spa attached. The heating feature for the pool and spa are a complimentary feature subject to maintenance availability.
May 25 – Jun 1
$223 per night
4.93 out of 5 average rating, 186 reviews

Popular amenities for The Woodlands rentals with a pool

House rentals with a pool

Guest favorite
Home in Montgomery
Serenity on the Lake
May 21 – 28
$169 per night
4.95 out of 5 average rating, 124 reviews
Guest favorite
Home in Spring
Spacious Home for Gathering
Dec 10 – 17
$323 per night
4.95 out of 5 average rating, 141 reviews
Guest favorite
Home in Spring
Private house in the Woodlands w/pool and spa.
May 12 – 19
$278 per night
4.9 out of 5 average rating, 111 reviews
Guest favorite
Home in Shenandoah
Cozy home! Convenient 4 work/medical/sports/shop.
Apr 17 – 24
$384 per night
4.91 out of 5 average rating, 187 reviews
Guest favorite
Home in Cypress
🌟Houston Staycation☀️🔥Heated Pool🔥🎥Theater🎞 Family❤️
Dec 22 – 29
$365 per night
4.92 out of 5 average rating, 196 reviews
Guest favorite
Home in Montgomery
Water's Edge, Simply Picture Perfect.
Dec 13 – 20
$303 per night
4.95 out of 5 average rating, 134 reviews
Guest favorite
Home in Conroe
Country Sanctuary-5*Lux King Bed-2,400+ Sq Ft
Aug 12 – 19
$252 per night
5.0 out of 5 average rating, 77 reviews
Guest favorite
Home in Spring
Lovely Woodlands home w/heated pool and spa!
Dec 15 – 22
$252 per night
4.93 out of 5 average rating, 87 reviews
Guest favorite
Home in Magnolia
Apartment in Magnolia
Apr 5 – 12
$99 per night
4.95 out of 5 average rating, 21 reviews
Guest favorite
Home in Spring
Luxury Mansion Dream Home - 6 Bed, Pool, Grill
Mar 16 – 23
$381 per night
4.94 out of 5 average rating, 16 reviews
Guest favorite
Home in Tomball
A Peaceful Haven in The Woodlands
Aug 23 – 30
$190 per night
4.86 out of 5 average rating, 21 reviews
Guest favorite
Home in Conroe
Beautiful Cozy 4-Bedroom Home in a Gated Community
Aug 27 – Sep 3
$194 per night
5.0 out of 5 average rating, 59 reviews

Condo rentals with a pool

Superhost
Condo in Willis
Lakeside Condominium
Mar 13 – 20
$81 per night
4.87 out of 5 average rating, 125 reviews
Guest favorite
Condo in Willis
Beautiful Waterfront Condo on Lake Conroe
Apr 10 – 17
$146 per night
4.99 out of 5 average rating, 100 reviews
Guest favorite
Condo in Montgomery
Awesome 1 Bedroom Condo with many features!
Jun 21 – 28
$78 per night
4.88 out of 5 average rating, 113 reviews
Guest favorite
Condo in Willis
Lakefront Bliss
Mar 31 – Apr 7
$110 per night
4.87 out of 5 average rating, 209 reviews
Guest favorite
Condo in Montgomery
Amazing Waterfront Renovated Condo on Lake Conroe
Sep 22 – 29
$134 per night
4.96 out of 5 average rating, 183 reviews
Guest favorite
Condo in Montgomery
Rental Retreat TX-Come Relax on Lake Conroe!
Aug 11 – 18
$83 per night
4.96 out of 5 average rating, 109 reviews
Superhost
Condo in Willis
Gorgeous Lake Views- One Bedroom-142
Jun 13 – 20
$121 per night
4.78 out of 5 average rating, 230 reviews
Guest favorite
Condo in Montgomery
Lakefront Condo Retreat - sleeps 14
Aug 24 – 31
$199 per night
4.93 out of 5 average rating, 140 reviews
Guest favorite
Condo in Montgomery
Stunning Waterfront Lake Conroe - Ground Floor
Nov 30 – Dec 7
$156 per night
4.85 out of 5 average rating, 113 reviews
Superhost
Condo in Willis
1213 The Lakeside Getaway Condo: Studio Room
Mar 2 – 9
$52 per night
4.79 out of 5 average rating, 72 reviews
Guest favorite
Condo in Montgomery
Golfside Lux: Artistic Getaway on Lake Conroe
Sep 10 – 17
$108 per night
4.96 out of 5 average rating, 27 reviews
Guest favorite
Condo in Montgomery
Walden Condo w/ king bed, lake view, dock & pool.
Jul 14 – 21
$89 per night
5.0 out of 5 average rating, 21 reviews

Quick stats about vacation rentals with a pool in The Woodlands

Total rentals

240 properties

Rentals with dedicated workspaces

160 properties have a dedicated workspace

Pet-friendly rentals

90 properties allow pets

Family-friendly rentals

140 properties are a good fit for families

Total number of reviews

4.4K reviews

Nightly prices starting at

$20 before taxes and fees

Destinations to explore