Vacation rentals in Pleasure Point

4.95 out of 5 average rating, 105 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

4.99 out of 5 average rating, 239 reviews

A cozy, dark green cabin is nestled among towering trees, showcasing a large window and a glass-paneled door. Three steps lead to the entrance, surrounded by a natural landscape of redwoods.

Guest suite in Felton

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.

A serene backyard is illuminated by string lights, creating a peaceful atmosphere. Pathways made of stones meander through well-maintained greenery, including low-growing plants and clustered shrubs. A seating area is visible in the background, providing an inviting space for relaxation under the evening sky.

4.98 out of 5 average rating, 232 reviews

Adorable Capitola/Pleasure Pt Beach House

Awesome location, just steps to Pleasure Point, the famous "Hook" surf spot, Privates Beach & the vibrant 41st Ave eateries & breweries, surf shops & eclectic shopping district or a short 15 min walk to Capitola Village. Stroll/ cruise (4 bikes provided) along the cliff, grab a beach chair & towel & hit the beach or just relax in the backyard oasis. Nearby is golf, wineries, Big Trees State Park, Santa Cruz Beach Boardwalk. Home is not child proofed so use caution booking for kiddos under 2

A bright studio features a spacious bed with light bedding against a green accent wall. A small dining table with yellow and black chairs is present, along with a small couch and an entertainment area with a wall-mounted TV. Natural light enters through a window overlooking a grassy backyard.

4.95 out of 5 average rating, 204 reviews

Cute Pleasure Point Studio - Walk to the Surf

In the heart of Pleasure Point, this remodeled, private studio is a short walk to the best surf spots in Santa Cruz. 3-minute walk to the stairs by O'Neill's house, and ~6 different breaks also within walking distance. Short stroll to coffee shops, restaurants and more. Walk or ride bikes (2 provided) almost everywhere. Quick drive to Capitola, Boardwalk & downtown Santa Cruz. Open to singles or couples (baby OK) that understand that our family lives in adjoining property. No pets allowed.

Place to stay in Santa Cruz

A private garden patio is featured, containing a round table with two chairs. Each chair is accompanied by a throw pillow. A small vase with flowers sits on the table, and colorful signage is visible on the fence in the background.

4.97 out of 5 average rating, 122 reviews

Melton Beach House. Private entry,space and patio.

Space is not suitable or safe for children under 5 years of age. Great location.We are conveniently a 10-15 minute walk to the Hook and Pleasure Point surf breaks.And in the other direction you have a 15 minute walk down to the adorably charming Capitola village and very lovely beach.There you'll find quaint boutique shops and many restaurants/bar choices along the beach esplanade. With in a 5 minute walk you'll find New Leaf market,Whole foods, Penny's ice cream,and 6 other restaurant's.

A tranquil garden space features a wooden picnic table surrounded by lush greenery and vibrant orange trees. Various shrubs and plants create a secluded feel, while a stone border adds a natural element to the serene environment.

4.83 out of 5 average rating, 1,068 reviews

Birdsong Studio by Beach-Jasmine Gardens

Jasmine Garden Oasis Retreat House—3 block walk to quiet beaches. Ideal for individuals, couples, or families seeking serenity. SC Permit # 231326. Two upstairs independent guest studios inside our home, each with queen bed and extra beds for $25 charge: Jade Studio with private deck, and Birdsong Studio overlooking garden and hot tub. Meditation & QiGong instruction, bicycle rental nearby, allergy-free, healing sessions, low-EMFs--renewing for heart, body & soul. Sunrise/sunset at beach.

The entrance to the guest suite is framed by lush greenery and decorative pots. A pathway of stones leads to a white door, adorned by charming string lights. The evening sky adds depth to the scene, enhancing the welcoming ambiance of the space.

4.98 out of 5 average rating, 604 reviews

Garden Oasis for Guests to Relax, Surf & Adventure

Welcome to our Artistic Garden retreat! Centrally located in the heart of Santa Cruz, 1 mile from Sunny Cove Beach and Pleasure Point. Close to the boardwalk, yacht harbor, Downtown Santa Cruz & Capitola. Enjoy the suite & spacious lush yard, fully furnished, outdoor area . Our 1/2 acre farmhouse lot is a garden oasis with lush palms, proteas, bamboo & succulents weaving throughout. Our garden and private lot have it all! 1 night stay ok when available just ask. No animals allowed.

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.

4.99 out of 5 average rating, 191 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, 187 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.

4.91 out of 5 average rating, 812 reviews

A green yurt is nestled among tall trees, featuring a wooden deck with a set of two outdoor chairs and small tables. Colorful prayer flags drape from the yurt's awning, framing the entrance where double French doors invite guests inside.

Yurt in Watsonville

Mountain Top Yurt in the Redwoods

Peaceful, clean, spacious, beautifully decorated and quiet 24' Yurt completely surrounded by Redwoods on top of the Santa Cruz Mountains. Spend a couple days meditating, reading or writing the next chapter of your memoir. Walking distance to Mount Madonna Retreat Center (open now through reservation only). County Park hiking and horseback riding trails located within 3 miles. Ideal place for photography and mountain/road biking.

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, 765 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.

4.94 out of 5 average rating, 147 reviews

A spacious room features a high wooden ceiling with exposed beams, complemented by large windows that allow natural light. A comfortable sofa and a cozy bed are arranged around a central area, with a small rug adding texture to the polished floor.

Bungalow in Santa Cruz

Gorgeous Bungalow 3 blocks to beach

Welcome to the Gladys house! Local permit #231060—Situated in the Jewel Box above Capitola, sleeps 5/6 , has 2 full baths, 2 bedrooms and a convertible workspace. Enclosed yard, koi pond.. walk to anything. Dogs ok (but please read on..) Quiet neighborhood,- outdoor shower/bath, bikes to borrow, parking for 3 vehicles. EV charger, BBQ- everything you need to enjoy the area!

Popular amenities for Pleasure Point vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Pleasure Point

A spacious bed is dressed in neutral bedding, flanked by two modern lamps on wooden nightstands. Two windows allow natural light to flood the room, highlighting the new hardwood floors. A closet and bathroom entrance are visible in the background.

5 out of 5 average rating, 28 reviews

Pleasure Point Surf Studio

The exterior of the home is showcased at sunset, highlighting a contemporary design with wooden accents. A spacious driveway leads to the entrance, complemented by lush greenery. Two bicycles are parked neatly, inviting outdoor exploration.

5 out of 5 average rating, 21 reviews

Surf Loft just blocks from Pleasure Point!

5 out of 5 average rating, 66 reviews

An outdoor deck area features a wooden table with two chairs and a lantern. Sunlight filters through a green umbrella, highlighting a view of Twin Lakes State Beach in the distance. Lush greenery borders the deck, creating a serene seaside atmosphere.

Cottage in Santa Cruz

The blue house at the beach

4.95 out of 5 average rating, 74 reviews

A comfortable living room features a brown leather sofa and two chairs arranged around a round ottoman. A large area rug adds color underfoot, while natural light filters through sheer curtains. A television is mounted above a stone fireplace, complemented by potted plants.

Guesthouse in Santa Cruz

The Point Cottage

5 out of 5 average rating, 54 reviews

A private yard is surrounded by tall trees, featuring a hot tub with bubbles rising to the surface. A hammock is visible to the side of the yard, alongside two Adirondack chairs. The cabin's entrance is shown, with a window allowing natural light to enter.

Cabin in Boulder Creek

Forest Cabin & Hot Tub

4.86 out of 5 average rating, 311 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

4.89 out of 5 average rating, 99 reviews

The exterior of the two-story home showcases a modern design with a combination of wood and gray siding. A large window allows natural light to enter, while a tree provides shaded greenery in the front. A walkway leads to the entrance, and parking spaces are visible.

Home in Capitola

Capitola Village Wind + Sea Home