Family-friendly holiday rentals in Cypress

4.95 out of 5 average rating, 122 reviews

A brown horse grazes peacefully in a grassy area near a tiny house. The tiny house features a wooden exterior, with a porch that has a chair visible. Trees surround the property, offering a sense of tranquility and connection to nature.

Farm stay in Bridgeland

Tiny House on the Prarie

Tiny House on the Prairie is waiting to include you and your guest in this picturesque escape from the city. Snuggle up like a bug in a rug in the King size bed nestled in the loft. Wake up to a view of the grazing horses and cows. Watch the sunrise from the porch. This Tiny House is located on a 205 acre working ranch and riding stables. Enjoy living amongst the herd or venture out to old town Katy about 20 minutes south. There are cute antique shops and some mom-and-pop restaurants. Pets Yes

4.98 out of 5 average rating, 126 reviews

A cozy sleeping area features a spacious bed adorned with a light blanket and a vibrant yellow throw. A large window allows natural light to fill the room, providing a view of the surrounding trees and greenery. Shelving units and a wall-mounted TV are also present.

Tiny home in Magnolia

"Smouse" - A Romantic Escapade !

From the founders of SerendipTINY & Bonnie Lou Tiny home as featured on the popular TV show, Tiny House Nations on Netflix! WELCOME to "Smouse" - A Romantic Escapade in Magnolia Tiny Home Village. 250+ sqft indoor and abundance of outdoor patio and lounge space w/ hammock, fire pit & more. 1 queen in loft and 1 queen sofa bed w/ full kitchen. PRO-decor and furnished. Insta-gram READY! Experience the world of GLAMPING. Romance and Fun for ALL!Reconnect with nature at this unforgettable escape.

4.97 out of 5 average rating, 458 reviews

A charming log cabin features a spacious porch with wooden railings and steps leading to the front entrance. A grassy area surrounds the cabin, and a fire pit made of stone can be seen nearby, with logs positioned for seating.

Cabin in Hockley

The Texian Cabin

Enjoy a unique 1700 sqft Texas themed log cabin in the woods! This 1.5 story home, located on a small family farm, has three bed rooms and two bathrooms with an open living room, dining area and kitchen. Toast marshmallows under the stars, grill burgers on the fire pit, play horseshoes or corn hole, lead your own yoga with our goats, collect eggs from the chickens, relax in a hammock, play tetherball, wander the woods, or head inside and dance to classic Texas country on the record player.

4.96 out of 5 average rating, 330 reviews

A modern kitchen and living area are featured, with a grey sofa accented by blue cushions. A dining table with high stools stands near the kitchen, which includes stainless steel appliances and ample cabinetry. Natural light is provided by two windows, enhancing the inviting atmosphere.

Guest suite in Cypress

Cozy and Private Guest Apartment with King Bed!

Enjoy privacy and comfort in this lovely guest apartment in Cypress, TX. Enjoy a king bed, screaming fast Internet, washer/dryer, water filter/softener, TV with Hulu, sofa bed, with queen memory foam mattress. Located between Cypress Outlets, Katy MIlls, hospitals, and approx. 30 miles to downtown. Enjoy some time by the lake, the Boardwalk is only about 3 miles away; or take in a movie down the street. If you want an adventure or a place to relax, this guest apt is right for you

An open floor plan living area features a stylish sofa, a dining table with light-colored chairs, and a fully equipped kitchen. Ample natural light filters through multiple windows, enhancing the fresh finishes and neutral decor throughout the space.

4.9 out of 5 average rating, 184 reviews

🏡 FAMILY MUTUAL FUN | Beautiful new home in Katy

• Book & Enjoy this one story house (built 2022) furnished with new furniture, beautifully decorated, high speed internet , 65"TV with Netflix in the quiet neighborhood and the great community. • Perfect for family or business stay in Katy. This cozy and spacious house has 3 bedroom, 2 bath, home conveniently minutes away from major highways 99 & 529, shopping, eateries, parks and entertainment centers. • Have fun and relax with the whole family at this stylish and peaceful place.

The outdoor area showcases a private pool with crystal-clear water, surrounded by lounge chairs. A hot tub is visible nearby, while a patio with dining and seating arrangements invites relaxation under shaded umbrellas. The home features a two-story design in the background.

4.88 out of 5 average rating, 154 reviews

Upscale Cypress Stay Pool, Hot Tub, EV, Sleeps 20

Welcome to the Boutique Bunkhouse—your spacious Cypress getaway just 5 minutes from Houston Premium Outlets. This 3,600+ sq ft home features 4 bedrooms, 3.5 baths, a private pool, freestanding hot tub, billiards room, theater with Xbox, and full kitchen. Sleeps up to 20 with 2 king beds, 1 queen-over-queen bunk, and 3 full-over-full bunks. Perfect for professionals, families, and group travel. EV charger, Smart TVs, and pet-friendly. Quiet hours 8 PM–8 AM. No events or parties allowed.

4.91 out of 5 average rating, 173 reviews

A stock tank pool is situated beside a compact mobile home, surrounded by a wooden deck and outdoor shower. Bright sunlight filters through the trees, casting gentle shadows on the serene space. A shaded area offers a relaxing comfort for outdoor enjoyment.

Tiny home in Houston

The Fifth Wheel | Camp Fire | Stock Tank Pool

Are you a lone traveler and wonder what is it like to live in a true tiny house on wheels, or a couple looking to experience tiny living, but with all the amenities? Welcome to the Fifth Wheel! We are inspired with utilizing small space and turn them into amazing living experience. the home equipped with everything you need when traveling. The home is pack with efficient design, front porch with cover, stock tank pool, outdoor shower, Wifi, comfy bed and pillow & free parking

4.99 out of 5 average rating, 225 reviews

A spacious green lawn is surrounded by tall trees, with dappled sunlight filtering through the leaves. The cabin's front porch features wooden railings and is set against the backdrop of a natural landscape, inviting relaxation in a serene environment.

Cabin in Magnolia

Woodlands Retreat - Looks Rustic, Feels New

This freshly renovated retreat in Magnolia is the perfect relaxing getaway. Enjoy the peace and quiet of a 5-acre natural wonderland. Minutes away from world-class shopping, dining, and recreation in The Woodlands, TX. The home features 4 furnished bedrooms, a fully furnished kitchen and dining area, a spacious living room with pull-out sofa, 2 full baths, high-end linens, a stocked laundry room, and plenty of outdoor space to enjoy. We hope to see you soon!

4.97 out of 5 average rating, 109 reviews

Cottage in Tomball

Cozy Cottage on Farm Away from City

Whether looking to get away from the City & recharge or looking for a unique stay during your travels, The Cottage is sure to please. Lovingly remodeled & outfitted with vintage details, you'll feel right at home & ready to relax. You'll enjoy the picturesque 10 acres that surround you. Close enough to get to the City if you need, but feels like you're world's away! Explore idyllic Downtown Tomball, or sit in our rockers, sip some lemonade, and relax!

An indoor putting green is featured prominently, surrounded by vibrant seating and decor. A wooden bar provides a gathering spot while a colorful game board and a surfboard add playful elements to the room. Light enters through the windows, highlighting the cozy atmosphere.

5 out of 5 average rating, 183 reviews

Not So Basic N' Cypress, TX!

Welcome to Not So Basic! Located in the heart of Cypress, TX, offering over 3,350 sq. ft. of living space. This property is ideal for both a quick weekend getaway or an extended relaxing stay. Home has a hockey table, pool table, giant connect 4, as well as an indoor putting green. Accommodations include three spacious king-sized beds and two queen-sized beds, ensuring comfort for all guests. Check out our other Airbnb! airbnb.com/h/thezenfulretreat

A private pool is highlighted beneath a spacious covered patio. Comfortable lounge seating surrounds the pool area, while a basketball hoop is visible at one end. Warm sunlight reflects off the water, creating a serene and inviting outdoor space.

4.89 out of 5 average rating, 266 reviews

Heated Pool Theater Luxury 4BR Retreat

Welcome to your luxury 4-bedroom retreat! Enjoy a heated pool, private home theater and spacious living area perfect for families or groups. 4 plush bedrooms & 3.5 baths Fully equipped chef’s kitchen Fast Wi-Fi & dedicated workspace Backyard seating and grill Minutes to dining, shopping and major highways—yet tucked in a quiet neighborhood for restful nights. Book now to secure your dates and start planning an unforgettable stay!

The kitchen features warm wood cabinetry and a combination of stainless steel and black appliances. A large center island with seating is complemented by a round dining table. Soft overhead lighting adds to the bright atmosphere of the space.

4.89 out of 5 average rating, 177 reviews

Quiet Elegance

My home is inviting because it provides peaceful, tranquil and a relaxing space for you to come when traveling. We are located near the Cypress Outlet, the newest restaurants and easy access to major freeways. People from all backgrounds are welcome in my home. Designed for family or couple get-aways. It's not suitable for big parties... Yet! Enjoy

Popular amenities for Cypress family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.9 out of 5 average rating, 186 reviews

A spacious outdoor area features a patio with two black wicker chairs and a round table, set against a backdrop of lush greenery. A pool glistens nearby, surrounded by neatly landscaped borders, while large windows illuminate the inviting interior of the home.

Home in The Woodlands

Lovely Woodlands home w/heated pool and spa!

4.95 out of 5 average rating, 188 reviews

An open living space combines a cozy sleeping area with a spacious bed covered in light bedding. A colorful light fixture hangs from the ceiling, illuminating decorative accents along the walls. A dining area and kitchenette are visible in the background, complemented by a small seating area.

Tiny home in Shenandoah

Cozy tiny house on small lake "The Maryhannah"

4.96 out of 5 average rating, 263 reviews

Tiny home in Spring

*HOT TUB! | Private+Spacious+Cozy+One-of-a-kind

4.9 out of 5 average rating, 111 reviews

The outdoor salt-water pool and hot tub are illuminated in shades of blue, creating a serene nighttime ambiance. Soft lights outline the area, accentuating the smooth, curved edges and peaceful surroundings, inviting relaxation and tranquility.

Home in The Woodlands

ALOHA! Hawaii in The Woodlands 5BD/3BA Sleeps 10

4.94 out of 5 average rating, 135 reviews

A tranquil pool area is highlighted, featuring clear blue water reflecting the evening sky. A pink inflatable float rests gently on the surface. The backdrop consists of a cozy brick home with outdoor seating arrangements beneath a shaded gazebo.

Home in Westbury

HTX Hideaway Houston Rodeo Ready Pool / Big Yard

A spacious backyard features a vibrant pool area, beautifully illuminated by colorful night lights. Lush greenery surrounds the setting, complemented by a well-maintained lawn. A stone patio leads to the pool, which is adorned with a diving board and lounge chairs for relaxation.

4.9 out of 5 average rating, 109 reviews

Paradise Garden Resort And Spa

Holiday home in Montgomery

A private pool is visible with a gently sloping lounge chair floating on the water's surface. Surrounding palm trees and natural stone formations create a serene ambiance under bright blue skies.

4.95 out of 5 average rating, 187 reviews

Prancing Horse Estates:10 acre resort w/pool, spa

4.76 out of 5 average rating, 110 reviews

The tranquil pool area is illuminated with vibrant purple and green lighting, highlighting the lush tropical flora surrounding it. A waterfall feature is visible, and the serene water reflects the ambient lighting, creating a peaceful nighttime atmosphere.

Villa in Conroe

Huge Private Pool + Slide on Golf Course

Family- and pet-friendly home rentals

An outdoor space features a cozy fire pit surrounded by stonework, with a pool visible nearby. The home's two-story facade showcases large windows and a balcony overlooking the backyard, while a bar area with seating is positioned adjacent to the pool.

4.88 out of 5 average rating, 43 reviews

Unwind in Cypress Golf Course Serenity & Pool Fun

4.92 out of 5 average rating, 196 reviews

The exterior of the vacation home features a welcoming front porch with two sets of white columns. A neat pathway leads to a red door, while lush green grass surrounds the property. Nearby trees and a fenced yard enhance the outdoor space.

Home in Tomball

Red Door Retreat- Stroll to Main St. X & festivals

A spacious living room features a comfortable brown leather sofa and two armchairs, positioned to face a 55-inch Smart TV displaying Netflix. A light fixture hangs from the ceiling, and large curtains frame the window. A decorative fireplace adds a cozy touch to the setting.

4.97 out of 5 average rating, 37 reviews

Cypress Gem | Cozy, Central & Pet-Friendly Retreat

5 out of 5 average rating, 225 reviews

A well-maintained outdoor area features a grassy lawn surrounded by a wooden fence. Comfortable lounge chairs are arranged around a fire pit, with a shaded seating structure overhead. Lush greenery and ornamental plants enhance the space, creating a serene environment.

Guest house in Houston

Centrally-Located Studio Apartment on Spacious Lot

5 out of 5 average rating, 4 reviews

Home in Harris County

Spacious Retreat

A spacious backyard showcases an inviting heated pool adorned with inflatable flamingos. A covered gazebo is positioned nearby, complemented by lounge chairs and a vibrant umbrella providing shade. The area is enclosed by a fence, enhancing the privacy of this relaxing outdoor retreat.

4.89 out of 5 average rating, 117 reviews

Flamingo Pool Oasis |45 min WC Stadium |Sleeps 12

An indoor heated pool is featured, surrounded by light-colored tiles and accented by a stone waterfall. Lush greenery and potted plants are included, while string lights add gentle illumination to the space. Comfortable seating arrangements are present along one side, providing a relaxing area.

4.94 out of 5 average rating, 123 reviews

The Leafy Lounge-Large Home w/ Heated Indoor Pool

4.92 out of 5 average rating, 106 reviews

An open floor plan living area is highlighted by vaulted ceilings and natural light. A cozy beige sofa faces a modern entertainment center, while a large dining table and breakfast bar provide ample seating. Stylish ceiling fans and decorative wall accents add character to the space.

Cottage in Magnolia

Magnolia Cottage/Near Renaissance Festival

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 59 reviews

Lost Pines Poolside Paradise | Outdoor Fire Pit

An outdoor space features a sizable pool surrounded by lush artificial turf. A mini-golf course is set along the perimeter, complemented by several small flags. A shaded seating area with a pergola stands nearby, providing a welcoming space for relaxation.

5 out of 5 average rating, 83 reviews

Houston Huge Pool, miniGolf, Katy Asian Town, King

5 out of 5 average rating, 14 reviews

Giddyup Getaway: Western Oasis w/ Pool! 4bd 9 beds

An inviting pool area features a stylish shape with a rock waterfall and a spa. Two red umbrellas provide shade over lounge chairs, surrounded by lush greenery and a wooden fence. A clear sky enhances the serene atmosphere of this outdoor space.

4.95 out of 5 average rating, 84 reviews

Home Away From Home: Cypress Luxury + Pool & Spa

5 out of 5 average rating, 117 reviews

A sunset casts a warm glow over a ranch house, framed by large oak trees. The spacious porch features a swing and rocking chairs, providing a cozy spot to enjoy the view. Expansive windows allow for ample natural light, enhancing the warm ambiance.

Farm stay in Waller

Beautiful Country Farmhouse

A well-maintained outdoor space is highlighted by a refreshing swimming pool, surrounded by a stone coping and grassy area. The two-story house features a covered balcony with seating, while stairs provide access to the upper level. Lush trees and blue skies frame the serene setting.

4.89 out of 5 average rating, 125 reviews

HOUSE w/private POOL

4.92 out of 5 average rating, 13 reviews

Casa Larissa, Grill & Chill Retreat Heated Pool

A private outdoor space is featured with a swimming pool and a spa, surrounded by a patio area. Comfortable seating is positioned nearby, and string lights above enhance the ambiance. Lush greenery complements the space, providing a serene environment for relaxation.