Holiday rentals with a pool in Santa Cruz County

Relax + Unwind in Brand New 2BD Modern Bch Retreat

Sea breezes and unobstructed 180-degree ocean views greet you from the 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 comfortable, chic space, guests tell us they love the amazing beds, soft linens, 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.

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!

Quiet Poolside Cottage for Solitude

New construction 800 sq. ft. Cottage 1.1 miles to downtown Los Gatos. Off-street parking for one car. Cathedral ceilings with skylight (morning sun, nightly stars). Comfortable pillow top King bed. Single bed in same space for extra guest (extra $25 for third guest/night). Kitchenette with basics. Dining table for work spaces. Pool available for guests. Jacuzzi not available. Many quiet places on property to relax. We do not accept third party reservations. Add your guests on reservation.

Beach View Condo - Heated Pool - Seascape Resort

ONE OF THE BEST BEACH AND OCEAN VIEWS AT SEASCAPE. 2 story, 2 bedroom, 2-1/2 bath deluxe condo. Two, private balconies with whitewater and beach views and beautiful sunsets. A well equipped kitchen, a BBQ, access to the North Bluff swimming pool and spa, a resort bar and restaurant, and easy beach l-access. Golf, fitness center and tennis are available at a reasonable cost. The Village includes a coffee shop, pizza parlor, Chinese restaurant, a grocery store, Mexican restaurant and more.

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.

Old Amesti Schoolhouse mid-bay amidst farmland

This 100 year old school house surrounded by organic farms in the Pajaro Valley is a great starting point for your adventures in the Monterey Bay. From here you can reach Santa Cruz to the North or Monterey to the south in 30 minutes. When you are finished sightseeing come back to this comfortable home. A major renovation was recently completed to update the electrical, heating and plumbing yet preserving as much of the past as possible. Outside enjoy the pool, spa or game areas.

Private Queen Suite-Pool & Hot Tub, private entry

This is your Getaway and World Cup spot! Enjoy your private suite, bathroom and large smart TV with all the action. Located within 3 miles of downtown Los Gatos and Campbell great food options. Levi's Stadium 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.

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.

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.

Private Pool Villa for family getaways

Looking for a comfy space to spend time with friends and family? Beach or great outdoors more your thing? 10 minutes from Seacliff State Beach and 12 minutes to Nisene Marks, this sunny locale is your comfortable home base for your next adventure. Why not just hang out by the pool? The water typically stays comfortable for swimming from April-September. Enjoy dining for 8 inside or on the patio. So close to the sea, but above the foggier lower elevations. Family friendly!

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 3 pools, 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!

*Official Resort Listing* Partial View 2 BDR Villa

This listing offers an updated residential-style experience within a luxury resort—the best of both worlds! Featuring a primary bedroom with a king bed and en suite bathroom, a 2nd bedroom with a queen bed, and a separate guest bathroom. Enjoy the comfort of a living room with a gas fireplace, a fully equipped kitchen, and sofa seating. Each villa includes a private patio or balcony with a partial ocean view. Units are individually owned—decor and layout may vary.