Vacation rentals in Pleasanton

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Top-rated vacation rentals in Pleasanton

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Guest favourite
A spacious outdoor area reveals a shimmering pool surrounded by comfortable lounge chairs. The landscape features rolling hills and greenery under a bright blue sky with fluffy clouds. A stylish circular table is placed near the pool, enhancing the relaxation space.
Guest suite in Helotes
4.94 out of 5 average rating, 877 reviews

Luxurious Retreat Between Six Flags and SeaWorld.

Hill Country retreat overlooking the city. Private quarters with separate entrance, spacious living room, full kitchen, bedroom w/closet, bathroom w/shower, and a covered sitting area overlooking city. 15 minutes from Fiesta Texas and Sea World, 25 minutes from downtown, and one mile away from Old Town Helotes. Pool & hot tub are available for additional fee of $50 per pool use in the morning 9:00 - 4:00, or in the evening 4:00 -10:00. Pool is not heated during colder months, only hot tub is.

Guest favourite
Home in Jourdanton
4.93 out of 5 average rating, 15 reviews

NEW•Jtown Junction•Luxe•FastWifi•Patio•PrivateYard

Skip the hotel. Stay in a full 3 BR home minutes from Pleasanton. J-town Junction is a fully furnished 3BR/2BA 1,523 sq. ft. home built for comfort, space & downtime. Ideal for energy sector professionals, families, hunters & small groups. It features comfy beds, Smart TVs, fast Wi-Fi, an equipped kitchen, full laundry & granite throughout. Whether you're working nearby or enjoying a weekend away, this quiet, updated home makes it easy to settle in & stay a while. Discounts for longer stays!

Top guest favourite
Industrial-style metal pipes are prominently featured, creating a unique steampunk aesthetic. An antique gauge with a circular face and clear numeric indicators is visible, contributing to the immersive atmosphere of the space.
Home in San Antonio
5 out of 5 average rating, 319 reviews

The Sherlock Home a House of Conundrums!

The Sherlock Home is an immersive overnight experience. Please note- due to its unique escape-like intricate game there is an extra guest fee of $40 per guest over the initial two guests. Become Sherlock Holmes surrounded by a Victorian/steampunk setting filled with puzzles and conundrums to solve while you stay. The Sherlock home is like no other Airbnb. If you are looking for a one-of-a-kind adventure, come stay and play at The Sherlock Home. Deduce, decode, decipher -The game is afoot!

Guest favourite
Home in Von Ormy
4.93 out of 5 average rating, 84 reviews

Peaceful 4-Bedroom Escape sitting on 40 acres

Welcome to your serene 4-bedroom escape nestled on 30 acres of natural beauty. The house is located on a ranch (The ranch by GMV) a wedding venue is located in front of the property; the house is located at the back of the road. This spacious house offers an idyllic getaway in a gated site, complete rustic comforts and outdoor delights. Enjoy a view at the pond, you can feed the ducks and immerse yourself in the tranquil surroundings, create cherished memories. Your perfect retreat awaits.

Guest favourite
An open-concept living space features a modern dining area with a circular table and white chairs. A kitchen bar with sleek wooden countertops is complemented by black bar stools. The ceiling showcases wooden beams, while light floods through large windows, creating an airy atmosphere.
Home in Von Ormy
4.94 out of 5 average rating, 51 reviews

The black stone luxury retreat

Discover a perfect blend of city convenience and serene and unique retreat just outside San Antonio! Located on 40 acres of peaceful land that was once a golf course, this luxury modern getaway offers the best of both worlds—just a short drive from downtown attractions like the River Walk, Alamo, and SeaWorld, but far enough from city. Our spacious, modern retreat is ideal for families, couples, or contractors in the area, it’s perfect for those who want to relax and reconnect with nature.

Guest favourite
A spacious living area features a spiral staircase leading to an upper level. Soft lighting is provided by two table lamps beside comfortable seating. A stone fireplace is centered against the wall, and a flat-screen television is mounted above it, enhancing the cozy ambiance.
Farm stay in Castroville
4.84 out of 5 average rating, 217 reviews

Hill Country Hideaway minutes from City !!

Hill Country Ranch Hideaway minutes from San Antonio ! This open spacious beautiful custom finished 2 bedroom 2 bath Southwest Hill Country designed home with wrap around porches sits on a 122 acre working farm with spectacular nature views just 2 miles north of Castroville Alasation community nestled in the Texas Hill Country but minutes from popular San Antonio attractions like Downtown, Sea World, Lackland AFB, Fiesta Texas, or just venture out to Medina Lake or a Wine country tour !

Guest favourite
A spacious bedroom is adorned with a large area rug and decorative wall art featuring intricate patterns. A comfortable bed is positioned in the center, flanked by two windows that allow natural light. A desk and chair are placed in one corner, enhancing the room's functionality.
Home in Pleasanton
5 out of 5 average rating, 17 reviews

Un Lugar De Paz, a Place of Peace to Unwind

Wide open spaces to accommodate you and your family or friends. A place to unwind, and/or to host a large gathering. 20 minutes South of San Antonio, it puts you close enough for an easy commute but far enough to escape into the peaceful country. Home can sleep up to 8 guests comfortably and host parties up to 50 guests comfortably. Large parking space available. Guesthouse off the main house has additional sleeping accommodations & rents separately through my other listing.

Top guest favourite
The interior space features wooden beams and rustic red wall paneling. A chandelier hangs from the ceiling, providing soft lighting. Two elegant sconces flank a trio of artwork depicting a Highland cattle, enhancing the warm ambiance of the room.
Apartment in Jourdanton
5 out of 5 average rating, 12 reviews

Rockin’ N- Jourdanton, TX

This reclaimed 19th century buggy barn tells a unique story featuring heirloom furniture and nostalgic touches branded with my husband’s cattle brand! The ROCKIN’ N is a one-of-a-kind space in the heart of Jourdanton, Tx. Being centrally located to all the essentials, the Rockin’ N is great for special occasions, getaways (30 minutes from San Antonio) and work (especially extended stays)! Whether coming to play, work or relax, you will relive the romance of a simpler life.

Top guest favourite
A stylish home features a stone facade framed by a tiled roof. The entrance, highlighted by tall red doors, is surrounded by lush greenery and well-trimmed bushes. Large arched windows permit ample natural light, enhancing the inviting exterior.
Home in San Antonio
4.94 out of 5 average rating, 205 reviews

5-Star Private Luxurious Golf Villa

Come stay at this beautifully appointed 3 bedroom, 3-1/2 bath home at The Villas at Briggs Ranch located inside the prestigious community of Briggs Ranch. This home has a state-of-the-art kitchen, high ceilings and spacious rooms. This is perfect home for relaxing away from the stresses of day to day living! Only 20 minutes from downtown San Antonio and 10 minutes from Lackland! We are surrounded by 2 golf courses! Briggs Villa offers serene seclusion and security.

Guest favourite
The image showcases a wooden deck railing overlooking an expansive field, with vibrant green grass stretching towards the horizon under a clear blue sky. The serene landscape is dotted with a few trees, enhancing the sense of open space.
Farm stay in Adkins
4.87 out of 5 average rating, 120 reviews

Private 3-Acre Ranch | Horses · Near SA

Set over 3 sprawling acres right outside of San Antonio. Enjoy waking up in nature while hearing the birds chirp and the roosters crow to a fresh brewed coffee. The beautiful scenery and nature filled noises will have you wanting to stay longer. Just 20 minutes away from Downtown San Antonio. Whether you are looking to unplug from the city vibes for a couple days or looking for a long term stay, this home is built for all your booking needs!

Superhost
A charming tiny home features a welcoming front porch with railings and two planters containing vibrant plants. A bright yellow door serves as a focal point, while large windows allow natural light to brighten the entryway. The surrounding area is open, with a view of the countryside.
Tiny homes in San Antonio
4.85 out of 5 average rating, 115 reviews

Lovely Cottage by TX A&M & Palo Alto College

This memorable place is anything but ordinary. It’s fully equipped to be very comfortable and cozy. You will be able to feel right at home but with a touch of the country with cows and nature on sight. This tiny home is located 15 min from downtown, less than 10 minutes from Texas A&M University and Palo Alto College. 281 Country Club is located 2 min away for off-roading and ATV park.

Top guest favourite
The exterior of the casita is highlighted by a wraparound deck, with a spacious patio area featuring comfortable seating. The structure is framed by a grassy lawn and trees, with a colorful sunset in the background, enhancing the tranquil setting.
Tiny homes in Devine
5 out of 5 average rating, 157 reviews

Relax, Recharge at our Romantic Casita in Devine

Welcome to our Simpli Devine Casita, a beautiful, peaceful, private 400 sq ft living space with stylish décor, indoor fireplace & 12-foot ceilings. If you’re looking to unwind and get away from the everyday city life our Casita is the perfect little getaway. Relax with a good book or a glass of wine on the wraparound deck and enjoy the calm peaceful natural setting.

Popular amenities for Pleasanton vacation rentals

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