Holiday rentals with a pool in Cypress

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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 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.
Apartment in Houston
4.98 out of 5 average rating, 257 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!

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.
Guesthouse in Neartown - Montrose
4.96 out of 5 average rating, 335 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
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, 151 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
Apartment in Addicks Park Ten
5 out of 5 average rating, 5 reviews

Lodgeur | Sunset-view 1BR | Energy Corridor

Stylish, comfortable, and beautifully designed furnished 1-bedroom apartment (608 SF, 9th floor) in Houston’s Energy Corridor. Chef-ready kitchen, blazing fast WiFi, in-unit laundry, and premium amenities such as a pool and 24/7 gym. Family-friendly. Includes free parking. There’s everything you need for both short and extended stays! Steps from the Texas Children's Hospital West Campus and Houston Methodist West Hospital, with easy access to Energy Corridor offices and Katy via I-10.

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.
Guesthouse in Houston
4.78 out of 5 average rating, 120 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
The living room features a modern yet cozy design, showcasing a white sectional sofa adorned with soft blue throws. A neutral area rug lies on the dark hardwood floor, while natural light floods the space through a set of large windows. A television is mounted above a stone fireplace.
Home in Houston
4.98 out of 5 average rating, 59 reviews

The Velvet Nest-Prime Location-2 King bd 1Queen bd

Welcome to The Velvet Nest, your cozy modern retreat tucked away in a peaceful, tree-lined neighborhood. From the moment you step inside, you’ll be greeted by soft tones, elegant decor, and sunlight pouring through oversized windows. This dreamy home was made for resting, recharging, and simply breathing. Whether you’re here for a romantic weekend, a family getaway, or just need to rest your soul — The Velvet Nest is your little corner of calm. We’d be honored to host your stay 💖

Guest favourite
An inviting outdoor space features a saltwater pool surrounded by lounge chairs and tables made of rich wood. Potted plants and colorful decorations add a vibrancy, while tall trees provide shade. A calming atmosphere is created, perfect for relaxation and enjoyment.
Guest suite in Greenway / Upper Kirby Area
4.89 out of 5 average rating, 1,478 reviews

2Montrose/Med Center/Galleria2

Experience the best of Space City when you stay at this centrally located, cozy and quiet 500sq ft. loft. Hosting 1 bedroom 1 full bath, with modern comforts. Upstairs of bungalow home with your own entrance (no shared indoor space) shared salt pool & garden, allows you to relax with ease after a day at nearby museums, medical Center, Memorial park, Rice University, shopping at the Galleria or exploring downtown attractions. No guests allowed at any time(pool/ hot tub not heated)

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, 162 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

Top Guest favourite
The living area features a sleek, modern sofa and a plush accent chair, paired with stylish marble-top coffee tables. An artistic wall pattern enhances the space, while soft lighting from a nearby lamp complements the open layout that connects to the kitchen.
Apartment in Medical Center Area
4.96 out of 5 average rating, 118 reviews

Spacious Modern Apt in TMC | MD Anderson

Experience Houston in a spacious modern apartment with great vibes and amenities. The Unit: → Lightning Fast Wi-Fi → Comfortable King Bed → Dedicated Workspace + Monitor → 55" Living Room Smart TV → 50” Bedroom Smart TV → Fully Stocked Kitchen → Washer & Dryer → Private Parking (Park at your own risk) The Amenities: → View and Lounge → Pool + Spa → Full Size Gym Ideal for Texas Medical Center visitors, healthcare trainees/workers, travel nurses, and business travelers.

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.
Guesthouse in The Woodlands
4.89 out of 5 average rating, 277 reviews

Lakefront Guesthouse: Pool, BBQ, Bike, Paddle Boat

Welcome to your lakefront escape - a spacious (~900 sq ft) private guesthouse suite with gorgeous Lake Paloma views, infinity pool access, and all the comfort you need for an easy, memorable stay. Perfect for families or small groups - up to 4 adults (or 5 guests including kids). NOTE: The guesthouse is attached to our home, where we live. Guests have a private entrance and private guesthouse space (not shared). The only shared areas are the driveway and backyard

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!

Top Guest favourite
Tiny home in Houston
4.96 out of 5 average rating, 24 reviews

Tiny Home Oasis in the City!

Escape to our cozy tiny home, a haven in the heart of the city! Enjoy exclusive access to your own refreshing pool, a lush tropical garden, perfect for relaxation. Key Features 🐾 Pet-Friendly 💦 Private Pool 🌺 Tropical Garden 🍽️ Close to Shopping & Restaurants 📍 Guest Access: You’ll have complete access to the entire home, the private pool, and the garden. Enjoy urban convenience while basking in nature

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 150 holiday rentals in Cypress

  • Verified guest reviews

    Over 3,020 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    150 of Cypress holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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