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Vacation rentals in Pleasure Point

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Top-rated vacation rentals in Pleasure Point

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
A uniquely designed treehouse is elevated among the trees, showcasing large glass windows and wooden beams. A wooden walkway leads up to the structure, enhancing the connection with the surrounding natural environment.
Treehouse in Aptos
4.91 out of 5 average rating, 601 reviews

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.

Top guest favorite
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.
Guesthouse in Felton
4.99 out of 5 average rating, 308 reviews

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.

Top guest favorite
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.
Home in Santa Cruz
4.98 out of 5 average rating, 255 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

Guest favorite
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
4.86 out of 5 average rating, 330 reviews

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!

Guest favorite
A light-filled living room features a spacious grey sectional sofa and two dark grey armchairs. A coffee table is centered on a natural fiber rug, while large windows invite ample natural light and frame views of a lush garden outside.
Home in Santa Cruz
4.95 out of 5 average rating, 281 reviews

Bel Air Santa Cruz Steps to Beach

Experience coastal living in this peaceful elegant beach home Spacious fully renovated home is clean fresh and modern while keeping its cozy beach life charm Open beam ceilings, ample windows, and sliding doors connect the open kitchen living room to private backyard patio creating a light and free flowing space Warm and tranquil this fully furnished three bedroom home is the ideal place to enjoy beach life Come to the sea Take a few moments to slow down and see the world with a little wonder

Top guest favorite
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.
Place to stay in Santa Cruz
4.95 out of 5 average rating, 154 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.

Guest favorite
A red picnic table is nestled among lush greenery, surrounded by orange trees and flowering plants. A peaceful garden setting is enhanced by a rock perimeter and various shrubs, creating a tranquil retreat perfect for outdoor meals or relaxation.
Guest suite in Santa Cruz
4.84 out of 5 average rating, 1,162 reviews

Jade Studio by Beach at Jasmine Garden Oasis

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.

Top guest favorite
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.
Home in Santa Cruz
5 out of 5 average rating, 210 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!

Top guest favorite
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.
Home in Santa Cruz
4.97 out of 5 average rating, 122 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.

Guest favorite
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.
Home in Santa Cruz
4.96 out of 5 average rating, 112 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.
Home in Santa Cruz
4.82 out of 5 average rating, 123 reviews

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.

Guest favorite
A cedar hot tub is positioned against a vibrant orange wall, offering a private and serene setting. Surrounding the hot tub is a small glass-top table accompanied by four black wicker chairs. A bouquet of flowers adds a touch of color to the table.
Bungalow in Santa Cruz
4.95 out of 5 average rating, 462 reviews

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 vacation rentals

GymBBQ grillLaptop-friendly workspaceWifiAir conditioning

Other great vacation rentals in Pleasure Point

Guest favorite
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.
Home in Santa Cruz
5 out of 5 average rating, 31 reviews

Surf Loft just blocks from Pleasure Point!

Superhost
Apartment in Santa Cruz
5 out of 5 average rating, 3 reviews

Bella Notte by the beach Studio 8

Top guest favorite
The view captures the ocean and sandy beach from a spacious deck, framed by tall trees. Clear blue skies and calm waters are visible, while a dining area with wooden chairs is set up on the deck, inviting relaxation and enjoyment of the surroundings.
Home in Santa Cruz
5 out of 5 average rating, 196 reviews

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

Top guest favorite
An aerial view displays the condo's proximity to the beach, showcasing sandy shores and gentle waves lapping at the coast. Nearby structures include other residences and parking areas, with a clear blue sky above, emphasizing the coastal location.
Apartment in Capitola
4.93 out of 5 average rating, 81 reviews

Oceanview Condo - StepstoBeach Bikes

Guest favorite
Home in Santa Cruz
4.85 out of 5 average rating, 73 reviews

Surf & Soak: Coastal Cottage w/ Hot Tub I Bikes

Guest favorite
A charming exterior of a single-story residence is framed by colorful flowers and shrubs. A pathway leads to a welcoming front porch, accentuated by a teal door and large windows. A white picket fence surrounds the yard, enhancing the home's inviting appearance.
Home in Santa Cruz
5 out of 5 average rating, 19 reviews

Cozy Beach Home

Guest favorite
An aerial view captures the single-family home featuring a well-maintained front yard with shrubs and landscaping. Surrounding residential properties and distant trees are visible, along with a glimpse of the neighborhood and sky. A driveway is adjacent to the home, leading to a garage.
Home in Santa Cruz
4.89 out of 5 average rating, 9 reviews

VB Haus 2BR |4 Blocks to Ocean |FastWiFi | BigYard

Top guest favorite
The exterior of a charming yellow cottage features a double door garage below the residence. Red doors provide a striking contrast to the yellow siding. Three windows above allow natural light to fill the upper space, framed by crisp white trim.
Cottage in Upper Seabright
4.92 out of 5 average rating, 133 reviews

Seabright Cottages

When is the best time to visit Pleasure Point?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$68,409 GYDG$68,200 GYDG$73,220 GYDG$74,685 GYDG$71,128 GYDG$82,844 GYDG$89,329 GYDG$86,609 GYDG$74,476 GYDG$72,802 GYDG$74,057 GYDG$75,312 GYD
Avg. temp11°C12°C13°C14°C15°C16°C17°C18°C18°C17°C13°C11°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 vacation rentals in Pleasure Point

  • Total vacation rentals

    Explore 180 vacation rentals in Pleasure Point

  • Nightly prices starting at

    Pleasure Point vacation rentals start at G$10,460 GYD per night before taxes and fees

  • Verified guest reviews

    Over 17,940 verified reviews to help you choose

  • Family-friendly vacation rentals

    130 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 80 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wi-Fi availability

    180 of Pleasure Point vacation rentals include wi-fi 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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