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Holiday rentals with a pool in Cypress

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Cypress

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Top guest favourite
A serene backyard features a heated pool and spa surrounded by a textured patio. The two-story home showcases multiple windows, inviting natural light. A shaded seating area with an umbrella and lounge chairs offers comfortable outdoor relaxation, with a fenced area providing privacy.
Home in Houston
4.97 out of 5 average rating, 137 reviews

Gorgeous Home W/Heated POOL/SPA & Fun GAME ROOM!

WELCOME TO OUR BEAUTIFUL HOME! Enjoy endless entertainment w/Pool Table, Pac-Man Arcade & Heated Pool/Spa feature in your own private backyard oasis! Conveniently located w/easy access to HWYs & exciting attractions Houston offers! This spacious 2-story features an open layout/4 Beds, 2.5 Baths w/Queen beds & TV’s. A fully equipped kitchen, office/library stocked w/tons of books & games! Step outside to the backyard retreat w/ample outdoor seating, BLACKSTONE GRILL, lounge, cabana & fire-pit!

Top guest favourite
A cozy living area features a plush couch adorned with decorative pillows and a textured rug. Lush plants are displayed throughout, adding a vibrant touch. Large windows provide a bright backdrop with views of the downtown skyline, and a mounted TV is positioned on the wall.
Flat in Houston
4.98 out of 5 average rating, 255 reviews

Tranquil Studio, Pool, Downtown View, Work-Ready

Relax in this super vibey, plant-filled studio with a private downtown view balcony and access to a 24/7 rooftop pool. Guests rave about the calming energy, greenery, décor, and peaceful atmosphere, perfect for unwinding or working. Centrally located and safe, this dog-friendly quiet retreat also features high-speed Wi-Fi and is ideal for solo travelers, couples, or business. With a host who goes above and beyond, experience the peaceful energy that makes this space unforgettable. Book now!

Superhost
The exterior of the building features a well-defined entrance with a large number '3' displayed prominently. The layout includes a staircase leading to the upper level, flanked by neat landscaping and gravel pathways.
Flat in Braeswood
4.83 out of 5 average rating, 103 reviews

Bright Studio Across from NRG | Med Center + Pool

Welcome to your perfect Houston getaway! Perfectly located across from NRG Stadium and steps from the Texas Medical Center, this bright, modern studio offers comfort and convenience whether you're here for medical appointments, exploring, or just relaxing. Location Med Center/NRG 0.8 mi to NRG stadium 1.2 mi to MD Anderson 2.2 mi to Zoo 1.7 mi to Rice University 3.1 mi to Museum District Steps away from grocery store & Starbucks. Safety odds paramount, this is a secure gated community.

Top guest favourite
A secluded backyard features a glistening swimming pool surrounded by potted plants. A cozy guest house is visible, complemented by shaded areas and circular hanging seats. A dining table with striped umbrella can be seen nearby, enhancing the outdoor living space.
Guest house in Neartown - Montrose
4.96 out of 5 average rating, 334 reviews

Under the Oak Montrose

Welcome to Under the Oak Montrose! This property is my home and I’d love to share my guest house and gorgeous backyard santuary with you. Ya'll! The Michelin Guide for Texas came out early 2025. Located within 1 mile radius of 3 Hou restaurants with a Michelin Star, and near so many others recommended. As if you needed another reason to book... Want to stay just one night? Message me! It's not allowed by default in my calendar but I'm happy to accomodate with a little communication.

Guest favourite
A spacious living area is highlighted by a large flat-screen TV mounted on the wall. A modern glass coffee table sits on a soft carpet, flanked by a plush gray couch with bright orange accent pillows. A decorative plant adds a touch of greenery, while a stylish fan circulates overhead.
Flat in Braeswood
4.91 out of 5 average rating, 122 reviews

Your Home away From Home

Very clean 1 bedroom with a fully equipped kitchen, gym, pool & FREE gated parking for your safety! This is the perfect location whether you are working or relaxing! Just a few minutes from the medical center and everything our wonderful downtown area has to offer! 5 Minutes to NRG Stadium 8 Minutes to Zoo 10 Minutes to The Galleria Mall 15 Minutes to Toyota Center 15 Minutes to Minute Maid Park 30 Minutes from both IAH & HOU Airport Close to all the clubs, lounges & much much more!

Guest favourite
An outdoor oasis features a free-standing hot tub bubbling with water, surrounded by a patio with lounge chairs adorned with bright red cushions. A spacious swimming pool is visible in the background, complemented by a covered seating area providing shade.
Home in Cypress
4.88 out of 5 average rating, 149 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.

Superhost
A cozy sleeping area features a spacious bed with neutral bedding and a decorative yellow pillow. A soft blanket drapes over the bed. The small kitchenette is visible in the background, showcasing a coffee maker, mini fridge, and cabinets.
Guest house in Houston
4.77 out of 5 average rating, 118 reviews

*Tiny home in Spring Branch/Houston*

Cute, clean, and functional pool house. 150 square feet. Perfect for 1 or 2 people MAX. 20 min. from downtown. Wifi,mini fridge w/freezer & microwave provided. The best taco trucks are around the corner. We offer pool passes for $20 per day. Read guest book for food options in area. Note: this is similar to a studio. Pool house is separated from the main house. You have your own private entrance, fenced in green space, free parking, and keyless entry. Thanks for booking!😊 Cheers!

Top guest favourite
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
4.91 out of 5 average rating, 160 reviews

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

Guest favourite
An inviting living area is featured with a plush white sofa paired with decorative pillows in neutral tones. A cozy, rounded armchair complements the space, while a round coffee table holds a decorative arrangement. Natural light streams in through large glass doors leading to an outdoor balcony.
Flat in Downtown Houston
4.97 out of 5 average rating, 181 reviews

Lavish King 1BDR Skyline Views: Pool, Free Parking

Experience downtown Houston luxury in this cozy apartment adorned in soothing neutral tones, promising both comfort & aesthetic appeal. Close to major attractions, including the George R. Brown Convention Center, Toyota Center, Med-Center and Minute Maid Park. You’ll get skyline views from the balcony. Accommodates all types of travellers. Located just minutes away from popular dining spots like The Breakfast Klub, Turkey Leg Hut, Taste Bar & Kitchen, Lost & Found, & more.

Guest favourite
A two-story lakefront guesthouse is featured, showcasing expansive windows and a tiled roof. Lush greenery surrounds the property, and a patio area with outdoor seating is visible along the water's edge. The tranquil setting offers a serene view of the lake.
Guest suite in The Woodlands
4.89 out of 5 average rating, 277 reviews

Lakefront Guesthouse: Pool, BBQ, Bike

Lakefront Guesthouse with private access to the Lake. Spacious 1-Bed Suite (900sft) for peaceful and comfortable stay for your family (1 King Bed and 1 Queen Bed). Can accommodate up to 4 adults or 5 people including kids Enjoy the Lakeview, Pool, Sunrise/Sunset, Grill and Patio. Please note, the Guesthouse is attached to the main house where we live. All the interior pictures are from the Guesthouse. Guests don’t share any space with us except the driveway and backyard.

Superhost
A serene outdoor pool area is framed by a brick exterior. Comfortable lounge chairs are positioned beside the crystal-clear water, surrounded by greenery and landscaping. A patio extends from the house, providing a view of the pool and a tranquil atmosphere.
Home in Houston
4.79 out of 5 average rating, 146 reviews

NEW! Luxurious Stay with Beautiful Pool + Backyard

A great escape from the city! Quiet neighborhood, not too far from the city but far enough to relax and enjoy the quiet neighborhood with an outdoor pool. Only 30 minutes from downtown Houston. Come relax or enjoy the house with family and friends. Perfect for a weekend getaway. This is not an ideal place to have parties because we want to be respectful to our neighbors. We have 5 official beds (1 king bed, 2 queen beds and 2 full size beds).

Guest favourite
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.
Home in Cypress
4.91 out of 5 average rating, 258 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!

Popular amenities for Cypress rentals with a pool

When is the best time to visit Cypress?

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Quick stats about holiday rentals with a pool in Cypress

  • Total holiday rentals

    Explore 140 holiday rentals in Cypress

  • Verified guest reviews

    Over 2,730 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wifi availability

    140 of Cypress holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Cypress rentals

  • 4.7 Average rating

    Cypress stays receive an average rating of 4.7 out of 5 from guests

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  7. Rentals with pools