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.

Guest favorite

Home in Santa Cruz

4.99 out of 5 average rating, 213 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.

Dec 1 – 8

R16,334 ZAR per night
Guest favorite

Guest suite in Santa Cruz

4.92 out of 5 average rating, 137 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 16 – 23

R2,277 ZAR per night
Guest favorite

Home in Santa Cruz

4.98 out of 5 average rating, 145 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

Dec 9 – 16

R7,096 ZAR per night

Popular amenities for Pleasure Point vacation rentals

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 Santa Cruz

4.82 out of 5 average rating, 913 reviews

Birdsong Studio by Beach--Jasmine Gardens

Sep 15 – 22

R2,428 ZAR per night
Guest favorite

Guesthouse in Santa Cruz

4.98 out of 5 average rating, 472 reviews

Garden Oasis Guesthouse Relax, Surf & Adventure

May 31 – Jun 7

R3,089 ZAR per night
Guest favorite

Apartment in Santa Cruz

4.89 out of 5 average rating, 761 reviews

Christine's Cottage

Aug 19 – 26

R3,246 ZAR per night
Guest favorite

Guest suite in Scotts Valley

4.96 out of 5 average rating, 623 reviews

Snug and Cozy between the Skyline and the Sea

Sep 16 – 23

R1,439 ZAR per night
Guest favorite

Home in Santa Cruz

4.95 out of 5 average rating, 127 reviews

Escape to "Enseñada Del Sol" Beach House

Jun 4 – 11

R10,451 ZAR per night
Guest favorite

Apartment in Santa Cruz

4.94 out of 5 average rating, 323 reviews

Charming West-Side Pied-a-Terre

Aug 19 – 26

R3,002 ZAR per night
Superhost

Guest suite in Aptos

4.89 out of 5 average rating, 160 reviews

Aptos-Seacliff Beach Studio by Yves

Sep 3 – 10

R2,538 ZAR per night
Guest favorite

Home in Santa Cruz

4.86 out of 5 average rating, 128 reviews

Aloha Beach House

Sep 24 – Oct 1

R8,069 ZAR per night
Guest favorite

Home in Santa Cruz

4.98 out of 5 average rating, 230 reviews

Steps to Black's Beach

Oct 28 – Nov 4

R4,300 ZAR per night
Guest favorite

Guest suite in Aptos

4.91 out of 5 average rating, 604 reviews

The Hummingbird Haven

Apr 29 – May 6

R2,352 ZAR per night
Guest favorite

Bungalow in Santa Cruz

4.98 out of 5 average rating, 200 reviews

Vintage Charm Close to Downtown and Beaches

Sep 12 – 19

R2,494 ZAR per night
Guest favorite

Home in Santa Cruz

4.98 out of 5 average rating, 157 reviews

Magnolia Garden Bungalow :)Dogs/Hot Tub

Dec 25 – Jan 1

R8,513 ZAR per night

Other great vacation rentals in Pleasure Point

Guest favorite

Home in Santa Cruz

4.95 out of 5 average rating, 172 reviews

Quiet Beach Cottage in the heart of Capitola

Sep 13 – 20

R7,610 ZAR per night
Guest favorite

Cottage in Santa Cruz

4.9 out of 5 average rating, 114 reviews

Cottage At Pleasure Point & Capitola Village

Apr 17 – 24

R4,911 ZAR per night
Guest favorite

Guest suite in Santa Cruz

4.89 out of 5 average rating, 353 reviews

Savasana Surfer's Retreat

Jul 20 – 27

R2,944 ZAR per night
Guest favorite

Home in Santa Cruz

4.88 out of 5 average rating, 301 reviews

Sunny, Spacious, and Modern Home Near The Beach

Oct 6 – 13

R12,730 ZAR per night
Guest favorite

Guesthouse in Santa Cruz

4.97 out of 5 average rating, 619 reviews

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

Mar 20 – 27

R3,044 ZAR per night
Superhost

Apartment in Santa Cruz

4.8 out of 5 average rating, 148 reviews

Relax on the Point

Nov 26 – Dec 3

R4,772 ZAR per night
Guest favorite

Home in Santa Cruz

4.93 out of 5 average rating, 101 reviews

Twin Lakes Santa Cruz Beach Home

Nov 30 – Dec 7

R14,030 ZAR per night
Guest favorite

Guest suite in Santa Cruz

4.95 out of 5 average rating, 219 reviews

Sunny Private Studio Near Harbor & Beach

Jul 19 – 26

R3,078 ZAR per night
Guest favorite

Cottage in Santa Cruz

4.97 out of 5 average rating, 378 reviews

Sea Otter Cottage in Santa Cruz!

Dec 30 – Jan 6

R6,805 ZAR per night
Guest favorite

Cottage in Santa Cruz

4.94 out of 5 average rating, 102 reviews

Relaxing Modern Home|Chefs Kitchen|Private Patio

May 4 – 11

R6,119 ZAR per night
Guest favorite

Home in Aptos

4.95 out of 5 average rating, 418 reviews

The Fox's Den A Relaxing 1 Bedroom Redwood Retreat

Apr 9 – 16

R3,071 ZAR per night
Superhost

Guest suite in Santa Cruz

4.78 out of 5 average rating, 1090 reviews

Beach Suite- HotTub+E-Bikes+Surfboards+Kayak

Jul 12 – 19

R6,399 ZAR per night

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

16K reviews

Nightly prices starting at

R1,138 ZAR 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 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 house rentals in Pleasure Point have wifi?

    Absolutely! We offer over 100 house rentals with wifi in Pleasure Point. Enjoy a tailored experience with all the comforts you desire.

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