Holiday rentals in Pleasure Point

4.98 out of 5 average rating, 244 reviews

Luxury Beach House - Game Room & Hot Tub

Rebuilt from the ground up in 2018. European oak hardwood floors and custom finishes throughout. During the day, enjoy walking to the beaches, surfing, and shops only minutes away. After a day of fun in the sun, BBQ with friends and family. Then, gather around the fire pit, hang out in the game room shooting pool and then take a soak in the hot tub. Bikes, boogie boards, surfboards, beach chairs included for guests use. No visitors or outside guests at any time. Only 8 registered guests max.

Superhost

Treehouse in Aptos

4.9 out of 5 average rating, 545 reviews

Peaceful Treehouse with Ocean View

Featured by Sunset Magazine as a “chic escape.” Inside, mid-century furniture and architectural details are made of natural materials like wood and stone setting a calming, sanctuary tone throughout. Curl up with a good read by the light streaming through floor to ceiling windows and under soaring wooden beams or tuck in for the evening by closing the sliding doors inspired by Japanese screens. Please note that during the winter months, our 1960s artistically unique treehouse may get chilly. H

Guest suite in Scotts Valley

4.96 out of 5 average rating, 728 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!

Superhost

4.92 out of 5 average rating, 341 reviews

Relaxed Luxury by the Beach

Escape to a stunning modern retreat in the heart of Santa Cruz, where contemporary design meets relaxed coastal living. This beautifully designed eco-home offers a peaceful and private getaway. Just a short walk to beach access and surf spots, this home provides the perfect balance of seclusion and convenience. Whether you're here to relax, reconnect, or adventure, you’ll have everything you need—ocean views, a serene backyard, and easy access to Santa Cruz’s best restaurants, cafés, and shops.

Guest suite in Santa Cruz

4.94 out of 5 average rating, 183 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.

5 out of 5 average rating, 108 reviews

Beach Front Dream House! Hottub/E-Bikes/Surfboards

Permit# 231467 Incredible modern home just steps from the best beach in all of Santa Cruz! Ocean and sand views, listen to the waves as you sleep on designer beds, cook in the chefs kitchen, and soak in the hot tub. Perfect central location, less than 5 minutes to boardwalk and downtown. 5 minutes to colorful Capitola village. 9 minutes to UC Santa Cruz Campus. 4 Electric bikes, 4 surfboards, and a kayak to take out and play in the waves! Plus the beach is right out front to enjoy!

Guest suite in Santa Cruz

4.82 out of 5 average rating, 1,029 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.

Guest suite in Santa Cruz

4.98 out of 5 average rating, 209 reviews

Studio Cruz - One mile to Sunny Cove Beach!

Studio Cruz is a private, fully furnished abode above our garage. Private entrance & key code lock for your convenience. Queen sized bed, loveseat, reclining chair, kitchenette with sink, fridge, hot/cold water dispenser, microwave & your own private bath. Wifi, TV with Netflix (no cable) and Sonos Sound Entertainment. The yard is fully fenced. Two friendly dogs & a crazy cat live on the property. Electric car charging available. (240 Volt ChargePoint) for a fee.

5 out of 5 average rating, 176 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!

4.98 out of 5 average rating, 164 reviews

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.

4.97 out of 5 average rating, 726 reviews

26th Ave Beach Home. 1 block to beach.

New construction completed in May of 2017! Immaculate 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.

4.9 out of 5 average rating, 471 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

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Popular amenities for Pleasure Point holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Pleasure Point

5 out of 5 average rating, 59 reviews

Cottage in Santa Cruz

The blue house at the beach

HaileyRating, 5 stars4 days ago

Anne’s cottage on the beach was absolutely wonderful! It’s such a special place—my family and I had a peaceful, relaxing stay. The views of the ocean are beautiful, and the beach is just steps away. We also loved having a few local restaurants within walking distance. Anne was the sweetest host—so kind, responsive, and attentive. She made sure we were well taken care of throughout our stay. The house was spotless, and the bed was very comfortable. We truly hope to stay here again someday.

Guest house in Santa Cruz

4.95 out of 5 average rating, 58 reviews

The Point Cottage

BrookRating, 5 stars1 month ago

This was such a great rental! Everything was perfect. Host VERY helpful and communicative. Beds were AMAZING! Linen was awesome. Everything was spotless. Quiet at night, even though the house is close to great food, ice cream and coffee. I would absolutely stay here again and I highly recommend this place. Perfect for 2 couples or 2 couples with a child or a family of four. One of the best places for it's size in the area. And one of the best hosts as well.

4.96 out of 5 average rating, 27 reviews

Hottub, Firepit, Outdoor TV | Walk to Beach

HeidiRating, 5 stars3 weeks ago

My 17 year-old daughter found this AirBnb and, as usual, her taste was spot on. The house reminded us of the Eichler we stayed in Palm Springs: light, airy, and well appointed. I loved the bedroom with the low, beamed ceilings, and it was fun borrowing the Schwin to bike to the VW car show. My daughter and her friends enjoyed the hot tub and making s’mores. Nova is a lovely street and close to everything - the only slight drawback is common neighborhood noise like we get at home (sanders, lawn mowers) but that’s just par for the course and a very narrow driveway which was tricky to get the cans around (we checked out on a Sunday). We hope to return soon to this lovely home!! We felt cozy and we all slept well. Thanks for hosting us.

5 out of 5 average rating, 30 reviews

Charming Pleasure Point Home-1 Block to beach

AliceRating, 5 stars1 month ago

It’s our first trip with our one month old son and we had an amazing time! We are familiar with the area which is why we picked Erin’s place since it’s so close to privates! Also Erin provided bikes with surfboard rack that we used to ride to surf at jacks which is a huge plus! The house is super well decorated and beds are comfortable. We love the hot tub as well! Everything is perfect! Highly recommended

5 out of 5 average rating, 54 reviews

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

AngelaRating, 5 stars2 weeks ago

We enjoyed this place for our kickoff to summer break. 3 adults, 6 kids; the place had plenty of space for all of us. The only thing that could've made it better would be for guest to somehow see how loud we are. Veronica did a great job communicating the expectations about noise ordinance but if you're not familiar with noise levels it might be hard to gage, especially with kids. Veronica had reach out to me on our first day but she was kind, respectful and responsive. I hope to book this place again.

4.93 out of 5 average rating, 69 reviews

Cabin in Felton

Santa Cruz A-Frame

YangRating, 5 stars1 week ago

The Santa Cruz A-frame was such a serene retreat into the mountains for us, and an antidote to our overly digital and urban lives. Things we appreciated: easy parking, both an upstairs and downstairs bathroom, full kitchen supplies, private balcony, gorgeous forest views, creek in the back, and easy access to Loch Lomond (peddle boating on the lake was so peaceful), the redwood state park (hiking in the largely shaded trail was great on an otherwise sunny day), and local groceries and food (enjoyed the cute outdoor patio in the back of The Grove cafe and bakery). We had a wonderful rest!

4.97 out of 5 average rating, 68 reviews

Immaculate Beach House one block from Pleasure Poi

AjayRating, 5 stars3 weeks ago

Lovely place! Exactly as pictured, short walk to the beach, and very clean :)