Family-friendly holiday rentals in Pleasure Point

4.97 out of 5 average rating, 105 reviews

Walk to Beach | Spa, Outdoor Kitchen + TV, Firepit

Welcome to our renovated 1950's style bungalow, perfectly situated in Pleasure Point! Permit #241032 Start your day with a walk to Verve Coffee, a local favorite, and head to one of the nearby world-class surf spots. After a day of adventure, come back to enjoy the large, private yard complete with a hot tub, fire pit, outdoor kitchen, and dining area perfect for al fresco meals. Optional Add-Ons: Early Check In/Late Check Out (when available) - $40 Grocery Shopping - $50 + cost of groceries

4.96 out of 5 average rating, 169 reviews

An A-Frame cabin is surrounded by lush greenery, positioned on elevated ground. A stone pathway leads to the entrance, flanked by wooden railings. The cabin features large glass panels on its façade, allowing natural light to flood the interior. A deck with seating overlooks the nature surroundings.

Cabin in Felton

Santa Cruz A-Frame

This unique A-Frame cabin, in a quiet mountain neighborhood with private creek access, was handbuilt in 1965 and remodeled in the summer of 2024. Now a little slice of heaven on the creek in the redwoods. *5-10 min to Henry Cowell Redwoods State Park, Roaring Camp Railroad, Loch Lomond Recreation Area, the Trout Farm Inn, Quail Hollow Ranch + Felton stores. *20 min to Santa Cruz, beach + Boardwalk. *1 min to Zayante Creek Market (EV charger) Find us on social: Insta @SantaCruzAFrame

4.86 out of 5 average rating, 334 reviews

A cozy cottage exterior is framed by vibrant greenery and colorful flowers. A concrete pathway leads to the front door, which is flanked by attractive window accents. The inviting entrance features a simple doorbell and a number sign, enhancing the welcoming appeal of the home.

Cottage in Santa Cruz

Pleasure Point Beach Cottage

Santa Cruz County Permit# 221116: Enjoy Pleasure Point living in this sweat cottage. Just a few minutes stroll and you’re at the beach and some of Santa Cruz’s best surf. Cruise the cliffs on bikes, hit the waves, or BBQ and soak up the sun! You’re sure to enjoy this special little house and its big back yard. Enjoy the fully stocked kitchen, 50 inch 4k TV, hot outdoor shower, big gas BBQ, 2 beach cruisers, 2 soft surf boards, beach toys, a wagon (great for beach transport), and much more!

An aerial view of the backyard reveals a spacious layout featuring a hot tub, a covered seating area with lounge chairs, and vibrant blue umbrellas. A play area with a climbing structure and water table is visible, surrounded by lush greenery and landscaped pathways.

4.93 out of 5 average rating, 159 reviews

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!

The open-concept kitchen and living area feature a clean design with white cabinetry and a blue-tiled backsplash. A large window allows natural light to fill the space, illuminating the gray sofa and wooden coffee table. Four white bar stools are positioned at the kitchen island.

5 out of 5 average rating, 215 reviews

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!

4.97 out of 5 average rating, 204 reviews

The exterior of the Surf Cottage is framed by a white picket fence and features a lush garden with blooming flowers. A large tree provides shade, while the cottage reveals a charming coastal-modern design. Bright blue skies complete the welcoming atmosphere.

Cottage in Santa Cruz

Surf Cottage in Pleasure Point

Nestled in a tree-lined corner you'll find the Surf Cottage at Pleasure Point, a lovingly curated home by a California native who lived in NYC and Paris. Stay in surf-shack style with vintage finds, Moroccan rugs, and a collection of objects and artwork from around the world. You'll be just steps away from breathtaking ocean views, sandy beaches and world-renowned surf spots. Come for some coastal vibes and experience all that Santa Cruz has to offer.

A spacious deck features comfortable adirondack chairs arranged around a fire pit, with the ocean and lagoon visible in the background. Eucalyptus trees provide shade and a natural ambiance, enhancing the serene atmosphere of this outdoor space.

4.97 out of 5 average rating, 127 reviews

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.

A bright, airy sleeping area with a spacious bed centered beneath a sloped ceiling. Multiple windows allow natural light to fill the room. A wooden desk and chair are positioned against one wall, complemented by a small wicker chair nearby and an accent cabinet.

4.98 out of 5 average rating, 174 reviews

Beach Suite

Welcome to your cozy private space, 1.5 blocks from a great local beach! The space is in a great centrally located neighborhood between downtown Santa Cruz and Capitola Village. Fully private suite with King size bed, living space and bathroom . A great location, charming, classic and cozy space. Many local beaches within walking distance. Soft top longboards, boogie boards, beach chairs, beach accessories available for use. No Animal Allowed!

An aerial view captures the shoreline where waves meet the sandy beach. The coastline curves gently while a road runs parallel, with houses visible along the street. The vibrant colors of the ocean and sand contrast against the greenery nearby.

4.88 out of 5 average rating, 528 reviews

180°OceanView+HotTub+EBikes+Surfboards+SUPS+Kayak

Incredible beach home with sweeping views of the ocean. Watch the waves crash from your bed. Directly in front of Pleasure Point, a world class surf spot. 180° upstairs decks to lounge & enjoy the ocean and views of the ocean from every room in the home. Hot tub, cedar sauna, 4 electric bikes, surfboards, stand-up paddle boards, sea kayak, ping pong table, basketball arcade game, and dart board. permit#191362

An open-concept living area features high vaulted ceilings and large windows allowing natural light to fill the space. A cozy seating arrangement is highlighted by white sofas and a coffee table, while a dining table is set against the backdrop of a lush outdoor view.

4.97 out of 5 average rating, 839 reviews

26th Ave Beach Home. 1 block to beach.

Newer custom built 2 BR/1BA 1,000 square foot home in 26th Ave beach/Pleasure Point area. 2 miles from Capitola Village, downtown Santa Cruz and the Boardwalk. Home is located 1 block away from 26th Ave. beach on a quiet dead end street with very little traffic. Located within walking distance to the best surf spots in Santa Cruz, including Pleasure Point, The Hook and 26th ave. Washer and dryer available.

A hot tub is positioned on a wooden deck, surrounded by lush eucalyptus trees. A potted plant with green leaves sits nearby, with ocean views visible through the wooden fencing. The serene landscape emphasizes the connection to nature.

4.94 out of 5 average rating, 122 reviews

Ocean View Cottage HotTub- Surfboards-Bikes-Kayak

Beautiful private beach home with fantastic views. Beach and lagoon views in a serene setting. Wander down the eucalyptus and cypress grove to the beach or up the the path along the lagoon into Monarch butterfly nesting grounds. Remodeled home with a gorgeous kitchen, two large decks, plenty of front and backyard space. All in the best location imaginable for Santa Cruz!

Superhost

An aerial view showcases the oceanfront setting of the neighborhood, with a panoramic expanse of blue water meeting the horizon. Nearby, coastal homes are positioned along the shore, highlighting the area's vibrant community and proximity to the beach.