Vacation rentals with a pool in The Woodlands

Vacation home in Montgomery

4.95 out of 5 average rating, 171 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.

4.91 out of 5 average rating, 143 reviews

Private house in the Woodlands w/pool and spa.

Entire house with a pool/spa in The Woodlands, TX, in a quiet cul de sac - 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 tow adults; children under 10yrs no extra charge. Prefer self-sufficient guests.

4.94 out of 5 average rating, 147 reviews

Spa & Pool Oasis: Prime Location in The Woodlands

Nestled in the heart of The Woodlands, & recently named the #1 place to live! Enjoy an incredible small-town with high-end activities. This home is perfect for friends & family! The home offers peaceful comfort with its private backyard pool & spa! Inside, guests enjoy reclining seats and entertainment area or warm up in the evenings by the cozy fireplace. Close to golf courses, trails, festivals, The Pavilion, festivals & Town Center (our Downtown). *Spa comes w/remote & instructions to heat.

4.91 out of 5 average rating, 211 reviews

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.

4.99 out of 5 average rating, 146 reviews

Home in Conroe

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

4.92 out of 5 average rating, 155 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.

4.82 out of 5 average rating, 44 reviews

Home in Magnolia

Cozy Apartment in Magnolia

Enjoy this luxury 1-King Bed charming, efficiency apartment located close to The Woodlands, Conroe and Spring, TX. Close to many restaurants, The Woodlands Mall, grocery and retail stores. Guest will have 1 personal assigned covered carport, pool, high speed Wi-Fi. Smart TVs in all rooms. Super stylish/modern lounge area. Eat-in kitchen island with motion led lights for extra lighting at night! Home is very nice and quiet. Due to allergies, we do not accept animals.

4.91 out of 5 average rating, 67 reviews

Apartment in Spring

Perfect Getaway w/ Pool | Gym | Lake Views

Relax in this luxury 1 bedroom apartment for up to 3 guests! The space is conveniently located minutes away from downtown Houston in the suburb of Spring, TX, and close to all major attractions. Featuring a pool, gym, beautiful lakefront view, a fully equipped kitchen, free WiFi, and free parking. This space is sparkling clean! With everything you need for a memorable stay, this space is perfect for city explorers, short stays, business travelers, or medical professionals!

4.91 out of 5 average rating, 116 reviews

Modern Farmhouse w/ private Heated Pool and Spa

Welcome to our newly remodeled modern farmhouse. Enjoy your getaway with family/friends at our warm and cozy home, complimented by a private pool and spa. The property has plenty of rooms and activities for everyone. Each room of the house has large windows which allows natural light through out the house. Located in Spring Texas, the property is just minutes away from The Woodlands, Conroe and Houston. Come and experience the "home away from home" feeling at our house.

4.97 out of 5 average rating, 113 reviews

Guesthouse 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.

4.98 out of 5 average rating, 53 reviews

Guesthouse in Spring

Private retreat in The Woodlands

Welcome to our fully renovated designer guesthouse nestled in the heart of The Woodlands. This private oasis offers easy access to major corporations like Exxon, Huntsman, and Chevron, as well as popular attractions such as Market Street and the Cynthia Woods Mitchell Pavilion. Houston Methodist, MD Anderson, Texas Children’s, and Memorial Hermann are just moments away. You will also be minutes from incredible golf, tennis, pickleball, and world class dining.

4.94 out of 5 average rating, 161 reviews

Tiny home in Conroe

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.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Popular amenities for The Woodlands rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.89 out of 5 average rating, 18 reviews

Home in Houston

Beautiful 5BR home w/ nice pool

CynthiaRating, 5 stars1 month ago

Beautiful home with brand new appliances and pristine kitchen with everything you will ever need!

4.97 out of 5 average rating, 77 reviews

Home in Cypress

Waterfront $ Heated Pool $ Theater | Smart Home

JacquelineRating, 5 stars3 weeks ago

James was a great host! Very friendly and helpful. He provided prompt access info and instructions. We all loved the relaxing pool, ping pong table in the game room, the space throughout the house, the sound system and grilling on the patio. The details were a wonderful bonus such as the throw blankets, kitchen utensils, and the beach towels and pool toys. Very family friendly home and a great place to retreat.

5 out of 5 average rating, 10 reviews

Home in Tomball

Villa for 50 ppl-Pool & Private Cinema

JackieRating, 5 stars2 weeks ago

Excellent service, communication, preparation, and preparation. We used this property as a sales team base in the area for a blitz and team building location. Worked out perfectly!

5 out of 5 average rating, 7 reviews

Home in The Woodlands

Berryline

GayleRating, 5 stars1 week ago

We really enjoyed our stay in the Woodlands. The house was very clean and comfortable with plenty of space for our whole family. We really enjoyed the pool and the bikes. I would definitely stay there again! Thank you!

5 out of 5 average rating, 15 reviews

Luxury Woodlands Home - 4 BR, Pool, Private!

ElizabethRating, 5 stars1 month ago

This was a great stay. The house was beautiful, pool was relaxing, and an amazing host. The kitchen had everything you could possibly need. Tons of space. We loved it!

4.84 out of 5 average rating, 56 reviews

Home in The Woodland

The Woodlands Luxury Private Estate pool &spa

BrandyRating, 5 stars1 month ago

Lori's place was great. Good location right on the running course of Ironman Texas. Quiet neighborhood. Close to trails and outdoor recreation. The pool was clean and inviting. Good communication from host. She responded quickly to our questions. We along with our kids give it 5 stars.

5 out of 5 average rating, 9 reviews

Relaxing 4BR Home with Pool & Spa in The Woodlands

MeganRating, 5 stars1 month ago

Our stay was perfect. Judy was very responsive when we needed to make adjustments to our reservation. The kids loved the pool and the layout was perfect for us. Highly recommend!

4.86 out of 5 average rating, 7 reviews

Home in Cypress

Lazy River Retreat

MicahRating, 5 stars1 month ago

Staying at the Lazy River retreat was a pleasure. The location, property, and space was perfect. The home was quite comfortable and stocked with everything we needed. Maelia was always available to answer our questions. It was perfect for our family event.

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Condo rentals with a pool

4.96 out of 5 average rating, 222 reviews

Condo in Montgomery

Amazing Waterfront Renovated Condo on Lake Conroe

TishaRating, 5 stars3 weeks ago

We had a fantastic stay at this condo! The entire space was very clean and well-maintained, making it easy to settle in and enjoy right away. The highlight for us was definitely the beautiful lake view—it was so peaceful to wake up to each morning. The easy access to the pool was also a huge plus, especially for relaxing afternoons in the sun. The comfort, location, and amenities were great and we’d absolutely stay here again and recommend it to anyone looking for a relaxing getaway with all the right touches.

4.94 out of 5 average rating, 352 reviews

Reel in Romance ~ Lake Conroe ~ fish on balcony

HollieRating, 5 stars3 weeks ago

My husband and I enjoyed our stay. Tiffany communciated with great detail and was very friendly. Great location, beautiful view, and comfortable, cute condo. Definitely worth it and would book again.

4.99 out of 5 average rating, 154 reviews

Beautiful Waterfront Condo on Lake Conroe

StephanieRating, 5 stars3 days ago

We had a wonderful stay at Bob & Jing’s condo. The view is breathtaking! The place was very clean and had updated features. We loved relaxing on the balcony, watching the sunrise, and catching a few fish. There is a restaurant in walking distance so we never had to leave. It’s the perfect relaxing getaway! Can’t wait to plan our next visit!

4.94 out of 5 average rating, 125 reviews

Condo in Montgomery

✪ PARADISE COVE ⛱ Margarita-Time ⛱ Lakefront Oasis

DavidRating, 5 stars1 week ago

Peaceful condo on Lake Conroe. As a country boy living in Houston, it’s nice to get away from the hustle and bustle of city life. This was the perfect place to enjoy some swimming and fishing. Quiet and peaceful. Highly recommended for a weekend getaway.

4.88 out of 5 average rating, 125 reviews

Lakeview at Casa Couture

ThoRating, 5 stars1 month ago

Beautiful house, definitely coming back

4.87 out of 5 average rating, 131 reviews

Condo in Montgomery

Stunning Waterfront Lake Conroe - Ground Floor

PhilipRating, 5 stars3 days ago

What a great waterfront find with comfortable amenities and friendly surroundings! Anna’s property is as advertised and has every comfort needed. The views are amazing, the community amenities are phenomenal, and the condo is a great place to enjoy it all!

4.83 out of 5 average rating, 121 reviews

The Lakeside Getaway Condo: Studio Room

HayleighRating, 5 stars2 weeks ago

This was a wonderful place to stay! Jessica was so responsive to messages, even when it was later during the night when we had questions. We would have stayed another day but it was already booked. Thank you Jessica for a wonderful place to stay!