Holiday rentals with a pool in Round Top

Cottage w/ Pool in Historic Downtown

Smithville is a quaint, thriving city with a very relaxing feel. It has numerous outdoor activities within 30 minutes if you enjoy hiking, canoe/kayaking, biking, fishing, etc. The cottage is within walking distance to downtown restaurants and shops. The town offers many great boutiques and antique stores. The cottage is a block from famous homes featured in the movies, Hope Floats and The Tree of Life. You can see the Hope Floats house from the porch! Come unwind and enjoy the small-town life!

Retro Ranch- Bastrop Historic District

Step inside a beautiful Mid Century Modern Ranch, set on a large lot in Bastrop’s Historic District. Come relax in this spacious backyard, equipped with a fire pit, covered porch, and Cowboy Pool! Walking distance to the best bars and restaurants Bastrop has to offer. Even today the lovely Texas town of Bastrop retains its historic charm: brick storefronts line the streets, artisans and artists display their handcrafted wares, and local chefs crisp chicken-fried-steak and catfish to perfection.

Texas Swiss Alp Chalet w/ Pool!

Swiss Alp Chalet is an updated 1956 mid century modern home with views of the rolling hills of the Swiss Alp community. Easy access to US Hwy 77 to get you where you need to go to explore the area. Located 6 miles north of Schulenburg and 10 miles south of La Grange. Three bedrooms, 2.5 baths, kitchen, with living areas, our guests have plenty of room to gather with up to 10 people comfortably. During the warmer months guests can make a splash in the screened in back yard pool. Self check in.

The Ella Norah, A Bespoke Luxury Retreat, Pool Spa

Welcome to The Ella Norah. A 1910 Cyprus Greek Revival that has been fully restored to modern day luxurious glory while still retaining its historic charm. Relaxing & gorgeous haven surrounded by large Magnolia & Oak trees. A bird lover's paradise.This unique place has a style all its own & is in the central historic district of quaint charming, Smithville, Texas. A fabulous place to gather with family & celebrate special occasions, all within steps of Main Street shopping & restaurants.

Sleeps 17 • 2 Homes • Pool • Petting Zoo

This private property hosts a swimming pool, petting zoo, fire pits, and 17-person capacity. Across two private residences, we have two full kitchens and laundry rooms, 6 bedrooms, and 3 bathrooms and provide ample space. A short distance to wineries, breweries, and renowned antique fairs. Come explore nearby attractions and unwind in our serene property. It's the perfect retreat to escape the hustle and bustle of everyday life and immerse yourself in a tranquil environment. Dog Friendly.

Pool, HotTub- Cardinal Cottage, RoundTop/Brenham

-Private home & large lap pool for your use during your stay. No other renters on the property. -Wide open outdoor spaces to get away. A breath of fresh air. See the stars at night! -GREAT WiFi signal. - 1600 sq ft home on 11 acres. Common areas downstairs, bedrooms upstairs. -Lap Pool (not heated) and spa hot tub (heated year round). Pool towels provided. -Firepit area. I provide firewood, fire starters, & lighter. -Brenham 10 minute drive. Round Top 20 minute drive. Sorry, no pets.

Emma’s-Where The World Slows Down

Emma’s at The Patch in Paige is more than a place to stay—it’s a peaceful Texas retreat where guests come to slow down, soak in the Cowboy Pool, breathe a little deeper, and reconnect with what matters. Surrounded by 28 acres of family land, ponds, trails, wildlife, and wide open skies, Emma’s offers the quiet many guests say they didn’t realize they needed. Inside you’ll find a comfortable home with thoughtful touches, fully stocked kitchen, and everything needed to settle in quickly.

Hilltop getaway w/sweeping views & pool/hot tub

Escape the city and relax at this peaceful getaway. Just over an hour from Houston and Austin. This 3 bedroom, 2.5 bath home is perfect for 2 families. Pool (pool not heated, hot tub heating fee $50/day), patio, grill and firepit to enjoy the sweeping views and constant breeze on the 6 acre property. Open family room tied to the kitchen to enjoy meals. Large master w/ a sitting area when the adults need time apart. Dogs welcome ($50 deposit/dog). Just 15 minutes from Brenham.

Paradise Pines

Private. Peaceful. Hugged by the forest. A romantic getaway or refuge from the city. Whether you are interested in soul searching, bird watching, skinny dipping, or exploring the many offerings of the local area, you will discover why it’s aptly named Paradise Pines. A well equipped kitchen and an outdoor grill will meet your needs. Swim in the heated pool underneath a canopy of pine trees and keep cool for an outdoor dining experience behind mosquito curtains.

Round Top Ranch Retreat-Pickleball Court!

Come enjoy the solitude of a rustic country escape with beautiful sunrises and sunsets. The 19 acre property includes a pool, pickleball + basketball court, and full kitchen. But, we are not a fancy ranch, we are a rural country escape! We do our best with regular pest control, but you may encounter unwanted country intruders like scorpions, spiders, or even an occasional mouse. Please book elsewhere if that’s outside your comfort zone!

La Grange Guesthouse with Pool

Lovely, comfortable guest house in a fabulous location near Round Top, Warrenton, Fayetteville, Smithville, Schulenburg and Flatonia. Ample parking, privacy and a pool to enjoy after a long day of shopping, cycling or hiking. Also includes access to a refrigerator and outdoor kitchen. You will have all of the necessities, plus little extras like Amazon Echo, smart TV and charging side tables.

Colorado River Escape

Experience the ultimate Colorado River lifestyle in beautiful Smithville, Texas, just 30 minutes east of the Austin airport. In the heart of town, this property has direct frontage on the river, with panoramic views and direct access to the water. Main Street and all its shopping and dining are just one block away! "Small town, big heart" is our motto in this gem we call Smithville!