Holiday rentals in Pleasure Point
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Top-rated holiday rentals in Pleasure Point
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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
Peaceful Treehouse with Ocean View
Permit 171035 Featured by Sunset Magazine as a “chic escape,” this Peaceful Treehouse-style retreat blends mid-century design with natural materials like wood and stone for a calming, sanctuary feel. Light pours through floor-to-ceiling windows beneath soaring wooden beams, and Japanese-inspired doors add to the architectural charm. Set high in the trees with ocean views, the home offers three elevated decks including one with a hammock. Perfect for relaxing and enjoying the surrounding canopy.
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!
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!
Quiet Beach Cottage in the heart of Capitola
Nestled into the heart of Capitola, this beach cottage is walking distance to the best of Capitola (Rental Permit #261046). Newly remodeled stunning two bedroom home, two bath, with a Pottery Barn pull out couch, this home is built for comfort and relaxation. Walking distance to Capitola Village(1 mile) and pleasure point (.5). Just blocks to the beach, local breweries, restaurants, shopping and iconic surfing. This home was designed for a peaceful getaway!
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.
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.
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
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.
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!
Stunning Oceanfront - Sunset Magazine Home
Welcome to this award-winning 3-bedroom home (Permit 171346)! Featured in the prestigious Sunset Magazine, this stunning property offers breathtaking ocean views and the perfect blend of modern amenities and coastal charm, providing a comfortable stay just a 5-minute walk from the beach, with a cul-de-sac next door that’s a local favorite viewpoint and gathering spot.
Romantic Retreat with hot tub near the beach!
Are you looking for a restful, meditative or romantic retreat? This fantastically located, atmospheric and private guest house boasts a sleeping loft with skylights from which to listen to the surf, and a comfy hot tub set under a pepper tree. We are a block and a half from the beach, so it’s a perfect spot for surfers and guests who love to be outside.
Popular amenities for Pleasure Point holiday rentals
Other great holiday rentals in Pleasure Point
2BR Pleasure Point Getaway
Surf Loft just blocks from Pleasure Point!
Bella Notte by the beach Studio 8
The Point Cottage
Surf & Soak: Coastal Cottage w/ Hot Tub I Bikes
Pleasure Point/Santa Cruz House, 1 Block to Beach!
Cozy Beach Home
Designer Inspired Cottage One Block from the Beach
When is the best time to visit Pleasure Point?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $420 SGD | $419 SGD | $449 SGD | $458 SGD | $437 SGD | $509 SGD | $548 SGD | $532 SGD | $457 SGD | $447 SGD | $455 SGD | $462 SGD |
| Avg. temp | 11°C | 12°C | 13°C | 14°C | 15°C | 16°C | 17°C | 18°C | 18°C | 17°C | 13°C | 11°C |
Frequently Asked Questions
What are the best places to stay in Pleasure Point?
Pleasure Point has a variety of accommodations, including family homes, beach cottages, and rentals with ocean views. Many places are conveniently located near beaches, surf spots, and casual dining, making it easy to enjoy everything the neighborhood has to offer.
What are the best things to do in Pleasure Point with kids?
Kids often enjoy beach outings, exploring tide pools, and playing at local parks in Pleasure Point. Consider renting bikes, flying kites, or joining a family-friendly surf lesson for an engaging outdoor experience.
What are some of the best things to do in Pleasure Point?
Explore the beach, try surfing at popular breaks, or enjoy the local café scene around Pleasure Point. Art galleries, tide pools, and seaside walking paths provide relaxing ways to connect with the neighborhood’s surf and community heritage.
How is the weather in Pleasure Point?
Pleasure Point has a mild coastal climate, with winter temperatures around 41–62°F (5–17°C) and summer highs reaching 74°F (24°C). Rain is more common in winter, while late spring and summer bring clearer skies and warmer afternoons.
When is the best time to visit Pleasure Point?
Late spring through early fall is often recommended for its mild temperatures, more daylight, and a lively calendar of community events. Cooler months see fewer crowds and dramatic coastal views, appealing to those who prefer a quieter visit.
What are the best places to visit in Pleasure Point?
Frequently suggested spots in Pleasure Point include the seaside cliffs, local surf breaks, and small art galleries. The neighborhood also has parks and gathering spaces for picnics and relaxing by the water.
What are some hiking trails in Pleasure Point?
Pleasure Point has scenic cliffside paths and access to neighborhood trails overlooking the ocean. For more wooded terrain, nearby state parks frequently suggested by locals have forested and coastal hiking options.
What are some family activities we can do in Pleasure Point?
Families can enjoy beach days, tide pooling, or walking neighborhood trails in Pleasure Point. Surf lessons, bike rentals, and local parks provide interactive experiences for visitors of all ages.
What are some of the best day trip ideas from Pleasure Point?
Around Pleasure Point, explore neighboring coastal towns, forested state parks, or local farmers markets for distinct day adventures. Popular options include visiting redwood groves, tasting regional wines, or discovering marine life at an aquarium nearby.
Are there any pet friendly accommodations available in Pleasure Point?
Many vacation rentals around Pleasure Point welcome pets, and the neighborhood has a friendly atmosphere for travelers with animals. Several beaches and outdoor cafés accommodate dogs, making it comfortable for those exploring with pets.
What are some local tips for visiting Pleasure Point?
Locals often suggest visiting in the early morning for peaceful beach walks and catching the changing tides. Enjoy the area’s independent shops and consider chatting with surf enthusiasts for tips about the best breaks or tide pool spots.
What is Pleasure Point known for?
Pleasure Point is known for its vibrant surf culture, picturesque coastline, and relaxed community atmosphere. The area has popular surf spots, scenic ocean overlooks, and a history rooted in beach life.
What are the best hidden gems to explore in Pleasure Point?
Explore tucked-away surf breaks, small coffee shops, and local art galleries around Pleasure Point. Parks and scenic tide pools are often suggested for a quieter experience along the coast.
What are the best foods to try in Pleasure Point?
Pleasure Point is known for fresh seafood, locally made burritos, and creative café fare. Many visitors also enjoy fresh pastries, acai bowls, and street tacos from neighborhood favorites.
What should I bring for a trip to Pleasure Point?
Pack comfortable layers, as mornings can be cool and afternoons warmer, with temperatures ranging from 41–74°F (5–24°C) during the year. Beachwear, sun protection, and a light jacket are often suggested, especially for those planning to explore the shoreline or try surfing.
What is the nightlife in Pleasure Point like?
Pleasure Point’s nightlife has a laid-back energy, with casual bars, local breweries, and spots for live music around the area. Evening gatherings often center on beach bonfires and neighborhood hangouts rather than club scenes.
What are the most popular events or festivals in Pleasure Point?
Pleasure Point celebrates its surf culture with surf competitions and beachside events throughout the year. Community gatherings, art fairs, and outdoor music are often recommended, especially during the summer and early fall.
Are there family friendly vacation rentals in Pleasure Point?
Pleasure Point has a range of vacation rentals, including options thoughtfully equipped for families. Many homes feature open living spaces, private yards, and easy access to the beach, creating a relaxed environment for guests of all ages.
Quick stats about holiday rentals in Pleasure Point
Total holiday rentals
Explore 180 holiday rentals in Pleasure Point
Nightly prices starting at
Pleasure Point holiday rentals start at $64 SGD per night before taxes and fees
Verified guest reviews
Over 17,940 verified reviews to help you choose
Family-friendly holiday rentals
130 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 80 rentals that welcome pets
Rentals with dedicated workspaces
90 properties have a dedicated workspace
Wifi availability
180 of Pleasure Point holiday rentals include wifi access
Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Pleasure Point rentals
4.9 Average rating
Pleasure Point stays are highly rated by guests – averaging 4.9 out of 5!
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