Holiday rentals with a pool in Santa Cruz County

Guest suite in Scotts Valley

A private entrance is visible, leading into the unit. Lush greenery hangs over the door, while a wooden deck offers space for relaxation. Potted plants surround the area, and BBQ grills are positioned near the poolside, enhancing the outdoor ambiance.

4.96 out of 5 average rating, 855 reviews

Snug and Cozy between the Skyline and the Sea

Super private, peaceful, and quiet; an excellent place for the traveler who is excited about exploring the Santa Cruz mountains and coast. Completely private In-law unit with extras needed to make it cozy. Snuggled between Scotts Valley, Felton, and Santa Cruz it's near Henry Cowell Redwoods State Park, 1440 Multiversity, and Mount Hermon Conference Center yet less than an hour from Silicon Valley. The Airbnb cleaning handbook is followed making this one of the cleanest places you’ll stay at!

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A sunny balcony is seen with two chairs and a small table, surrounded by decorative plants. The ocean can be viewed in the background, with clear skies and sunlight reflecting on the water. A vibrant rug covers the balcony floor.

5.0 out of 5 average rating, 134 reviews

Oceanview Villa w/ 2 Decks, ONE Pool & Fireplace

Spectacular ocean view condo with views towards Monterey AND Santa Cruz. Yes, you have the sunrise and sunset from both decks. Two story Seascape Villa, South Bluff. Very well designed space with living room, kitchen, deck & powder room on first floor, two bedrooms, two bathrooms, and a second deck upstairs. WiFi, free parking, ONE heated pool on the NORTH BLUFF, short walk down to the beach on a special path. L’Occitane Shampoo/Conditioner/Lotion, Nespresso for coffee. Bartesian Cocktail Maker.

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Guest suite in Willow Glen

4.95 out of 5 average rating, 214 reviews

Private Queen Suite-Pool & Hot Tub, private entry

This is your Getaway spot! Enjoy your private suite, bathroom and large smart TV, pool and hot tub outside your door. Located within 3 miles of downtown Los Gatos and Campbell with great food options. Levi's Stadium/49ers 9.5 miles, Mountain Winery Concerts 7.5 miles, San Jose International Airport 6.5 miles, SFO 35 miles, SAP Center/NCAA/Sharks 4.6 miles. We have professional cleaning. Check-out like a hotel, no starting laundry! Hot tub and Pool are a perfect way to relax and end the evening.

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A view captures a multi-story building positioned near the shore, with cars parked along the street. The ocean stretches beyond, featuring calm blue waters and a clear sky above. The beach is visible in the distance, enhancing the coastal atmosphere.

4.88 out of 5 average rating, 108 reviews

Walk to the beach, panoramic ocean view, and pool!

Kick back and relax in this calm, stylish space. With panoramic views of the pacific, chances are you'll see dolphins, otters, and even whales during season. Leave the doors open and nap to the sound of the waves hitting the shore! Heated pool on property & less than a 5-minute walk to the beach, restaurants, drinks, coffee, sandwiches and more! Recently upgraded with brand new flooring throughout condo, fireplace with mounted large smart tv (perf for movie nights!), soaking tub and comfy beds!

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4.96 out of 5 average rating, 181 reviews

A spacious deck is showcased with comfortable seating arrangements, complemented by a dining table. Lush greenery in planters is visible, along with panoramic ocean views under a clear blue sky. A cozy rug anchors the seating area, inviting relaxation.

Home in Aptos

Relax + Unwind in Brand New 2BD Modern Bch Retreat

Sea breezes and unobstructed 180-degree ocean front views greet you from the large private deck of RdM Lookout, a brand-new beach property with a bright open, mid-century modern beach design complete with a cozy fireplace, hardwood floors, and quartz counters. A beautiful, chic space, guests tell us they love the amazing beds, fluffy towels, and our gourmet kitchen with a stocked coffee bar with to-go cups for long beach walks. Come home to a relaxing, beach vacation in a charming beach town.

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A two-story condo with a contemporary exterior features vertical wooden siding in soft blue tones. A wide staircase leads to the entrance, which is sheltered by a canopy. Large windows allow natural light to enter, surrounded by greenery and a small shrub at the front.

4.81 out of 5 average rating, 297 reviews

Sandpiper by the Sea

The condo is located in a tranquil condo community, just two blocks from the longest beach in Santa Cruz County. You can walk in either direction for a couple of miles from this beach. Closely located to Seascape Golf Course and Seascape Resort. With Monterey Bay, Capitola, and Santa Cruz within a short drive, this location is centrally located to many tourist spots, hiking trails, beaches, wineries, and so much more. And, the complex has two beautiful pools, heated April through October.

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4.95 out of 5 average rating, 125 reviews

A scenic pool area is framed by tall pine trees, with a vibrant sunset reflecting in the calm water. The landscape features gentle hills in the background, enhancing the serene environment.

Home in Ben Lomond

The Hacienda- Santa Cruz Mountain Ridgetop Retreat

"Welcome to the Hacienda", a modest mid-century retreat located in the beautiful Santa Cruz Mountains. The Hacienda is located just 5 minutes from Ben Lomond town, 10 minutes from Henry Cowell State Park and only a 20 minute drive from Santa Cruz beaches. Our unique private home includes a pool & hot tub which sits on the ridgetop overlooking the gorgeous San Lorenzo Valley. If you're looking for peace & tranquility or simply need to relax and recharge, the Hacienda awaits your arrival.

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4.78 out of 5 average rating, 597 reviews

Aptos Condo with Spectacular Ocean Views

Enjoy stunning full ocean and sand views from Monterey to Santa Cruz at this beautifully located beach retreat. Watch whales and dolphins from the deck, relax by the ocean-view swimming pool just steps away, or take a short walk to the beach. Santa Cruz Beach & Boardwalk is just 15 minutes away, world famous Monterey Bay Aquarium and Pebble Beach 45 minutes, and Levi’s Stadium only 30 miles. This oceanfront escape is the perfect blend of location, comfort, and unforgettable views.

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4.93 out of 5 average rating, 154 reviews

A spacious outdoor pool lined with a brick border shimmers under the clear sky. Comfortable lounge chairs are positioned beside the pool. Lush green trees and a fenced area provide a serene backdrop to this inviting space.

Villa in Santa Cruz

Luxury garden villa w/ hot tub and game room

Welcome to our Luxury Villa in the Santa Cruz mountains, a paradise where you can relax and make unforgettable memories. Our villa boasts a spacious patio where you can enjoy your meals surrounded by enchanting gardens. Unwind in our pool, relax in the hot tub, or challenge your friends to a game of pool on professional sized pool table, in our brand-new recreation room. The room features a beautiful handmade walnut bar, complete with a commercial ice maker, sink, and fridge.

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4.94 out of 5 average rating, 399 reviews

A balcony features two chairs and a small table, overlooking a bright blue pool and the ocean beyond. Sunlight illuminates the space, enhancing the view of the nearby beach and the landscape of the surrounding resort.

Townhouse in Aptos

2bed OceanFront condo w/Pools+HotTub

Enjoy the comforts of a beach condo with the features of a luxury resort style retreat. This 2 bedroom 2.5 bathroom Villa has two balconies with incredible Ocean Views. Modern kitchen, and beach themed decor make this condo a vacation retreat you cannot miss. Plus pool and hot tub heated year round! Located on 17-miles of secluded beachfront in Aptos California, south of Santa Cruz. Treat yourself to exquisite fine dining at the Sanderlings Restaurant, beach pathways and more!

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