Vacation rentals with a patio in Pleasure Point

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.

Cozy Coastal Redwood Cabin

Rest and connect in this warm, cozy, and private cabin that is nestled in the redwoods. Only minutes away from Henry Cowell State Park, where you can enjoy world class mountain biking trails, hiking, or swimming in the river. Or, enjoy the beach 15 minutes away. This is a perfect place to refresh in the magic of the Coastal Redwoods. Music fills most nights either from the Felton Music Hall or from the chorus of frogs. And wake up in the mornings to the mist in the trees when the fog rolls in.

Modern Coastal Home|Central Location|Private Patio

Spend your coastal vacation in this newly designed 1940’s Cottage. Thoughtfully designed with a mix of both modern and traditional elements, this Cottage feels warm and inviting from the moment you enter the space. Enjoy the beautiful California weather in the private patio featuring native coastal landscaping. Whether you are spending your days at the beach, surfing, exploring the Redwoods or looking to simply unplug and unwind we look forward to hosting you at our Coastal Cottage. P# 221094

Oceanview Family Playground

Family-friendly oceanview home at Pleasure Point. This inviting retreat offers a backyard play area, including a water table and climbing structure for the little ones. Enjoy outdoor dining, the BBQ grill, the hot tub, hammocks. Inside, take in two living areas, two en-suite bedrooms, toys, playhouse, and baby amenities. EV charger in garage. Nearby, find great surfing spots, a coastal bike trail, Capitola Village, and Santa Cruz Beach Boardwalk. Create memories at your Pleasure Point home!

Peaceful Coastal Mountain Cabin

Nestled among the towering trees in the Santa Cruz mountains, our A-frame, "Redwood Skye," offers a peaceful retreat where you can escape, unwind, and enjoy nearby hiking, biking, beaches, parks and more — all of which got us featured on the Emmy award-winning TV series, “Staycation.” Conveniently located: 5 mins to Henry Cowell State Park, Roaring Camp Railroad & Felton Music Hall; 15 mins to Santa Cruz with its famous boardwalk and spectacular beaches; 45 mins to San Jose; ~1 hr to SFO.

Custom Cabin Retreat in the Redwoods

This retreat offers guests a unique experience of living in a well designed, minimalist space while having all one really needs. From the nautically-inspired curved ceiling w/ skylights to the custom redwood trim, this cozy retreat will inspire. Relax on the private deck with the fire pit, walk to the river or enjoy the local trails thru the towering redwoods. Santa Cruz beaches are just 35 min away, 25 min to Big Basin and Henry Cowell, and 35 min to fine dining in Saratoga.

Mermaid Cottage - Walk to Beach+Boardwalk+Downtown

Welcome to the Mermaid Cottage located in the heart of Santa Cruz! This cute and cozy retreat is the perfect place to unwind and soak up the sun. Just a short walk away, you'll find yourself on the sandy shores of Cowell's Beach, where you can swim, surf, or just relax and soak up the sun. And if you're looking for some excitement, the famous Santa Cruz Beach Boardwalk is also just a short stroll away. Short-term rental permit (STR22-0024) Transient Occupancy Tax No. 002482

Serene luxury beach bungalow in Pleasure Point

Just steps away from the breathtaking Santa Cruz coast lies Bungalow318. This 1940's bungalow has been meticulously renovated and is ready for your relaxing retreat, romantic getaway, surfing adventure or family vacation. Relax in the open concept family room, enjoy a day at the beach or surfing world-class surf breaks, lounge in the hot tub and spend a cozy evening on the patio lounge in front of a warm fire. The ways to enjoy this special property are endless!

Santa Cruz Beach House - Steps to Boardwalk/Beach

Escape to Beach Hill Hideaway, a light-filled, 2,000 sq ft coastal home in Santa Cruz. Perfect for families and friends, this stylish retreat comfortably fits your group and is just steps from the Beach Boardwalk, Wharf, and downtown. Enjoy a fully-equipped kitchen, free on-site parking, EV charger, air conditioning, outdoor shower, BBQ and fire pit, TV with Roku, piano, books/games, yoga mats, and dedicated workspace. Walk everywhere from this prime location!

Redwood Cottage & Hot Tub

Enjoy this quaint, peaceful redwood retreat tucked away in the Santa Cruz Mountains. This small private cottage comes with a private hot tub, outdoor shower, propane fire pit and hammock. You'll be 10 minutes to downtown Felton and 25 minutes to Santa Cruz beaches. The cottage is on a shared property and next door to the main house. Please note there is no indoor shower (outdoor only) and the road is one lane with a steep driveway. Permit #211304

Beach View Cottage - Hot Tub

Gorgeous, newly remodeled, home with amazing views of the ocean, beach, and lagoon. Hot tub, bikes, surfboards, kayak. Everything you could possibly want for a Santa Cruz trip in a spectacular setting VR PERMIT # 191354 Just 200 yards from the beach, this tranquil beach view cottage is your perfect beachside escape. Located on a quiet, private street in Pleasure Point, this charming and newly updated two-story home offers stunning ocean views.

Robin’s Nest in the Redwoods

Welcome to Robin's Nest in the Redwoods (Permit #181415) Tucked into the scenic foothills of the Santa Cruz Mountains, this charming, quaint cabin offers the perfect blend of peace and convenience. Enjoy easy access to stunning local beaches and serene hiking trails through the majestic redwoods - all just 35 miles from San Jose. This tranquil retreat feels both secluded and centrally located, offering the best of both worlds!