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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Guest favourite
A cozy living area is featuring a spacious, light gray sectional sofa adorned with decorative pillows. Framed artwork lines the walls, and a ceiling fan gently stirs the air. An open dining space with a wooden table and chairs is visible in the background.
Townhouse in Energy Corridor
4.82 out of 5 average rating, 248 reviews

Energy Corridor 1 Level Home Assigned Parking

Enjoy this remodeled 2 bedroom Townhome. With easy access to everything Houston has to offer. It is steps from public transportation, has a reserved parking spot,swimming pool for the summer months, a lovely outdoor eating area, quiet location. The unit has 2 bedrooms, one and a half bathrooms, a TV in the living room and each bedroom. The kitchen is outfitted with everything you need and Houston has every kind of dining and nightlife you could ask for. Right here in the Energy Corridor and close to every major road way.

Superhost
A spacious living area is highlighted by a high open ceiling and large windows allowing for natural light. A dark leather sofa and two accent chairs are positioned around a decorative rug. A media console holds a flat-screen TV, creating a comfortable lounge environment.
Farm stay in Conroe
4.88 out of 5 average rating, 238 reviews

Country Retreat close to The Woodlands w/Pool

Stay 5 Min from The Woodlands in this one-of-a-kind retreat next to the Jones State Forest. 1/2 mile to walking, biking, or horseback riding on forest trails. At night you’ll gaze at twinkling constellations poolside or relax in our massage chair or jetted garden tub. Attend an outdoor concert at the nearby Cynthia Woods Mitchell Pavilion, one of the top amphitheaters in America. We are 5 min from The Woodlands Medical Center, and 10 min from The Woodlands Mall where you can shop till you drop.

Guest favourite
An aerial view captures a serene waterfront community, featuring well-maintained homes with varied roof styles. Lush green lawns and palm trees border a calm lake, where fountains create gentle water displays. Paved paths and boats can be seen along the water's edge, inviting leisurely activities.
Villa in Cypress
5 out of 5 average rating, 15 reviews

Finest Luxury Resort-Style Home!

Experience Luxury Vacation HOME w/SPACIOUS LIVING overlooks PANORAMIC WATERFRONT PRIVATE LAKE SHORE@Ur backyard! 1-1000 night, Sophisticated vibe & ample seating 2mingle & entertain, supplying U W/every amenity needed 4a tranquil vacation, plenty of rooms 2enjoy precious time w/Ur family & friends in Ur outdoor kitchen, w/Ur boat4relaxing ride around the lake from Ur DOCK@Ur backyard, can accommodate up to 10+adult, Excellent schools & tons of shopping & dining nearby! Don't wait! GET IT TODAY!

Top guest favourite
A serene outdoor space is highlighted by a heated pool with fountain features, surrounded by lush greenery and colorful flowers. A stylish gazebo provides shaded seating, with comfortable lounge chairs positioned nearby. The natural landscape is enhanced by tall trees, creating a private and tranquil ambiance.
Home in Conroe
4.99 out of 5 average rating, 168 reviews

Country Sanctuary-5*Lux King Bed-2,400+ Sq Ft

This beautiful, custom-built 2,400+ sq ft home, that sits on 1 acre, is surrounded by the woods and the many deer, giving you all of the privacy you will need for a relaxing retreat. If you want to feel peace and tranquillity while listening to the birds chirping, you want to stay here. Please make the Country Sanctuary a favorite in your search by clicking on the RED HEART in the upper right hand corner, this will help you find it again and share with others. Christmas Tree for the Holidays

Guest favourite
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
4.8 out of 5 average rating, 115 reviews

*Spring Branch/Houston tiny home*

Cute, clean, and functional pool house. 150SF Perfect for 1 or 2 people. 20 min. from down town. 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, and is 150SQFT. Guest house is separated from the main house. You have your own private entrance, large fenced in green space, free parking, and keyless entry. Thanks for booking!😊 Cheers!

Guest favourite
A shaded outdoor space is featured, housing a sectional seating area with plush cushions. A hanging chair adds charm alongside a coffee table. The private saltwater pool is visible, surrounded by neatly arranged landscaping and a carpet of green grass.
Home in Midtown
4.89 out of 5 average rating, 175 reviews

Midtown Oasis w/ Private Heated Pool

Make memories at this unique and beautiful house in the heart of Midtown Houston! This home features a large private pool situated on an oversized lot in a great area of Houston. You get the convenience of the Midtown location with the space of a suburban home. Midtown is one of the BEST areas to stay in Houston if you want to see all the city has to offer. You can easily get to the NRG/Rodeo via the Lightrail Station, which is a 9 min walk. Avoid limited parking or traffic with Ubers/taxi!

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, 250 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!

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, 145 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.

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, 155 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, 173 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, 275 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.

Popular amenities for Cypress rentals with a pool

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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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