Pleasure Point vacation rentals

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Top-rated vacation rentals in Pleasure Point

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

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Guest favorite

Guesthouse in Santa Cruz

4.98 out of 5 average rating, 480 reviews

Garden Oasis Guesthouse 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. Detached guesthouse & spacious lush yard, fully furnished, outdoor area and more. 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.

Jul 19 – 26

G$33,689 GYD per night

Guest favorite

Home in Santa Cruz

4.99 out of 5 average rating, 216 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.

Sep 28 – Oct 5

G$186,392 GYD per night

Guest favorite

Guest suite in Santa Cruz

4.82 out of 5 average rating, 998 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. Garden hot tub, meditation & QiGong instruction, bicycle loan, allergy-free, healing sessions, and low-EMF option--renewing for heart, body & soul. Sunrise/sunset at beach.

Oct 8 – 15

G$26,700 GYD per night

Guest favorite

Guest suite in Santa Cruz

4.92 out of 5 average rating, 141 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.

Sep 1 – 8

G$25,036 GYD per night

Guest favorite

Home in Santa Cruz

4.98 out of 5 average rating, 151 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

Apr 17 – 24

G$78,017 GYD per night

Guest favorite

Home in Santa Cruz

4.97 out of 5 average rating, 256 reviews

@visitpleasurepoint

Location. Location. Location. This new to the market, freshly-updated 900 sqft beach house is located in the heart of Pleasure Point on a quiet residential street. Only 200 feet from the beach and the famed Jack O'Neill surf spot. The house is directly between surfing spots at The Point and The Hook, a 3 minute walk. It is also a short stroll along the beach to shopping and restaurants. If you are looking to live “The Point” lifestyle, there is no better location. You can walk everywhere!

May 16 – 23

G$75,894 GYD per night

Guest favorite

Cottage in Santa Cruz

4.99 out of 5 average rating, 120 reviews

Surf Cottage in Pleasure Point

Tucked into a tree lined corner of charming Pleasure Point you'll find the Surf Cottage, a relaxing escape from the everyday hustle. Located just a short walk from ocean views, sandy beaches and world famous surf, the home is decorated in a coastal-modern style which includes rare vintage finds, Moroccan rugs, and a collection of found objects and artwork from around the world. Come feel the breeze, slow down, and enjoy all that the Surf Cottage and Santa Cruz have to offer.

Jul 9 – 16

G$97,917 GYD per night

Guest favorite

Guest suite in Santa Cruz

4.97 out of 5 average rating, 170 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.

Feb 8 – 15

G$31,169 GYD per night

Guest favorite

Home in Santa Cruz

5.0 out of 5 average rating, 127 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!

Mar 26 – Apr 2

G$104,635 GYD per night

Guest favorite

Apartment in Santa Cruz

4.89 out of 5 average rating, 763 reviews

Christine's Cottage

Christine's Cottage is a cozy and very quiet space. It is 1.3 miles from the ocean and has a queen-sized bed, full bath, small kitchen, patio and a private entrance. There is high-speed Wi-fi, Directv and Roku streaming services are included . A laundry room is available on the property. Guests love the quiet neighborhood, the close proximity to the ocean, local restaurants, shopping, and The Boardwalk. Dogs are very welcome. There is no extra charge.

Sep 24 – Oct 1

G$30,658 GYD per night

Guest favorite

Bungalow in Santa Cruz

4.97 out of 5 average rating, 208 reviews

Vintage Charm Close to Downtown and Beaches

This beautifully & recently renovated studio with separate entry and private bathroom is in the middle of everything Santa Cruz has to offer: downtown, beaches, boardwalk, West Cliff Drive, bike paths, etc. are an easy walk or bike-ride. The studio is also a quiet area for remote work. We are pleased to host you and help make your experience great. You may also access the common-space gardens and hot tub in the spa-like back yard (upon request).

Oct 13 – 20

G$27,420 GYD per night

Guest favorite

Home in Santa Cruz

4.98 out of 5 average rating, 604 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.

Feb 7 – 14

G$62,555 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Pleasure Point vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Pleasure Point's top sights

Seabright State Beach59 locals recommend

Verve Coffee Roasters220 locals recommend

Moran Lake County Park23 locals recommend

Taqueria Vallarta34 locals recommend

Aloha Island Grille21 locals recommend

Pleasure Pizza East Side Eatery51 locals recommend

Other great vacation rentals in Pleasure Point

Guest favorite

Guest suite in Scotts Valley

4.96 out of 5 average rating, 629 reviews

Snug and Cozy between the Skyline and the Sea

Oct 9 – 16

G$15,819 GYD per night

Guest favorite

Apartment in Santa Cruz

4.94 out of 5 average rating, 328 reviews

Charming West-Side Pied-a-Terre

Aug 5 – 12

G$33,522 GYD per night

Guest favorite

Guest suite in Santa Cruz

4.93 out of 5 average rating, 564 reviews

Mini Guest Suite with Private Entrance

G$26,209 GYD per night

Guest favorite

Home in Santa Cruz

4.98 out of 5 average rating, 158 reviews

Magnolia Garden Bungalow :)Dogs/Hot Tub

Nov 5 – 12

G$93,095 GYD per night

Guest favorite

Guest suite in Santa Cruz

4.97 out of 5 average rating, 347 reviews

New Modern Light filled Studio

Mar 15 – 22

G$29,375 GYD per night

Guest favorite

Guest suite in Santa Cruz

4.96 out of 5 average rating, 225 reviews

Sunny Private Studio Near Harbor & Beach

May 31 – Jun 7

G$30,479 GYD per night

Superhost

Home in Santa Cruz

4.93 out of 5 average rating, 323 reviews

Modern Designer: Amazing Location

Oct 8 – 15

G$129,737 GYD per night

Guest favorite

Home in Santa Cruz

4.88 out of 5 average rating, 487 reviews

Town-and-Nature

Oct 8 – 15

G$20,903 GYD per night

Show all

Other great vacation rentals in Pleasure Point

Guest favorite

Guesthouse in Santa Cruz

4.89 out of 5 average rating, 606 reviews

Sunny Harborside Bungalow

Oct 22 – 29

G$31,250 GYD per night

Guest favorite

Guesthouse in Santa Cruz

4.97 out of 5 average rating, 626 reviews

Upper WS Guesthouse-2mi. from UC, Downtown & Beach

Apr 17 – 24

G$33,465 GYD per night

Guest favorite

Home in Santa Cruz

4.95 out of 5 average rating, 131 reviews

Escape to "Enseñada Del Sol" Beach House

Oct 31 – Nov 7

G$117,460 GYD per night

Guest favorite

Guest suite in Santa Cruz

4.89 out of 5 average rating, 356 reviews

Savasana Surfer's Retreat

Jul 27 – Aug 3

G$31,012 GYD per night

Guest favorite

Guest suite in Aptos

4.89 out of 5 average rating, 163 reviews

Aptos-Seacliff Beach Studio by Yves

Sep 1 – 8

G$27,752 GYD per night

Guest favorite

Guest suite in Santa Cruz

4.93 out of 5 average rating, 644 reviews

Cozy garden westside king suite STR18-0122

Oct 12 – 19

G$31,542 GYD per night

Guest favorite

Home in Santa Cruz

4.95 out of 5 average rating, 176 reviews

Quiet Beach Cottage in the heart of Capitola

Sep 12 – 19

G$85,647 GYD per night

Guest favorite

Home in Santa Cruz

4.89 out of 5 average rating, 218 reviews

Santa Cruz Casita, Near Beaches, Private & Sweet!

Jul 22 – 29

G$35,688 GYD per night

Show all

Quick stats about vacation rentals in Pleasure Point

Total rentals
150 properties
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Pet-friendly rentals
60 properties allow pets
Family-friendly rentals
110 properties are a good fit for families
Total number of reviews
17K reviews
Nightly prices starting at
G$12,509 GYD before taxes and fees

Frequently Asked Questions

Are there pet-friendly vacation rentals in Pleasure Point?
Four-legged friends are welcome in Pleasure Point. Choose from more than 60 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Pleasure Point?
Yes! Work meets play with ease at over 80 vacation rentals in Pleasure Point featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Pleasure Point have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Pleasure Point. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Pleasure Point have a bbq area?
Absolutely! We offer over 60 house rentals with a bbq area in Pleasure Point. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Pleasure Point?
Pleasure Point has more than 90 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in cottage rentals in Pleasure Point?
Experience the best of Pleasure Point with our cottage rentals, starting at about $190 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cottage rentals in Pleasure Point have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Pleasure Point. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Pleasure Point?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 100 homes with wifi, over 60 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Pleasure Point vacation rentals

Top-rated vacation rentals in Pleasure Point

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Pleasure Point vacation rentals

Stay near Pleasure Point's top sights

Other great vacation rentals in Pleasure Point

Guest suite in Scotts Valley

Apartment in Santa Cruz

Guest suite in Santa Cruz

Home in Santa Cruz

Guest suite in Santa Cruz

Guest suite in Santa Cruz

Home in Santa Cruz

Home in Santa Cruz

Other great vacation rentals in Pleasure Point

Guesthouse in Santa Cruz

Guesthouse in Santa Cruz

Home in Santa Cruz

Guest suite in Santa Cruz

Guest suite in Aptos

Guest suite in Santa Cruz

Home in Santa Cruz

Home in Santa Cruz

Quick stats about vacation rentals in Pleasure Point

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there pet-friendly vacation rentals in Pleasure Point?

Are there vacation rentals with a dedicated workspace in Pleasure Point?

Do house rentals in Pleasure Point have air conditioning?

Do house rentals in Pleasure Point have a bbq area?

Are there family-friendly house rentals in Pleasure Point?

How much does it cost to stay in cottage rentals in Pleasure Point?

Do cottage rentals in Pleasure Point have wifi?

What are the most popular amenities for House Rentals in Pleasure Point?

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