
Holiday rentals with a pool in Half Moon Bay
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Quick stats about holiday rentals with a pool in Half Moon Bay

Nightly prices starting at
Half Moon Bay holiday rentals start at €147 per night before taxes and fees

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Over 20 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Half Moon Bay rentals

4.8 Average rating
Half Moon Bay stays are highly rated by guests – averaging 4.8 out of 5!
Top-rated rentals with a pool in Half Moon Bay
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Private Queen Suite-Pool & Hot Tub, private entry
This is your Getaway spot! Enjoy your private suite, bathroom and large smart TV, pool and hot tub outside your door. Located within 3 miles of downtown Los Gatos and Campbell with great food options. Levi's Stadium/49ers 9.5 miles, Mountain Winery Concerts 7.5 miles, San Jose International Airport 6.5 miles, SFO 35 miles, SAP Center/NCAA/Sharks 4.6 miles. We have professional cleaning. Check-out like a hotel, no starting laundry! Hot tub and Pool are a perfect way to relax and end the evening.

3 BR Home on Vineyard nr Palo Alto & Stanford
Professionally cleaned detached home nestled among an oak grove, waterfall & vineyard in the hills above Stanford (10 min), Palo Alto (20 min), Menlo Park (10-20 min), Mountain View (25 min) and San Francisco and San Jose. Perfect for families and groups; staycations, off-sites or startups visiting Silicon Valley . See resort-style amenities below. LATEST UPGRADES: better AC, faster internet & WiFi6 for lots of devices & bandwidth. Pickleball lines on tennis court; putting green w/ remote tees.

Beautiful 4 Bedroom Hillside Retreat
Peaceful retreat on top a hill with breathtaking views of Pinole Valley and surrounded by nature. 4 bedroom 2.5 bathroom home comes with huge backyard, swimming pool*, gazebo, private driveway, beautiful panoramic views. circular driveway. View of the sunset every night. May see the turkey and herd of deer during your stay. 30 minutes away from San Francisco, 15 mins away from Berkeley, and 30 mins away from Napa. *Pool is available but NOT HEATD *Jacuzzi available, NOT HEATED and NOT WORKING

Relax + Unwind in Brand New 2BD Modern Bch Retreat
Sea breezes and unobstructed 180-degree ocean views greet you from the private deck of RdM Lookout, a brand-new beach property with a bright open, mid-century modern beach design complete with a cozy fireplace hardwood floors, and quartz counters. A comfortable, chic space, guests tell us they love the amazing beds, soft linens, fluffy towels, and our gourmet kitchen with a stocked coffee bar with to-go cups for long beach walks. Come home to a relaxing, beach vacation in a charming beach town.

Rustic Cabin in the Redwoods
Tucked among the redwood trees on top of King's Mountain, this 1 bedroom cabin offers both rustic charm and modern luxury. Property owners live onsite in the main house about 30 feet away from the cabin. Located just 20 minutes off HWY 280, this cabin is the perfect weekend retreat for those looking to get away from the bay area without actually leaving. Spend time relaxing in the pool, hiking or biking one of the nearby trails, or just reading a book while sitting among the redwood trees.

The Hacienda- Santa Cruz Mountain Ridgetop Retreat
"Welcome to the Hacienda", a modest mid-century retreat located in the beautiful Santa Cruz Mountains. The Hacienda is located just 5 minutes from Ben Lomond town, 10 minutes from Henry Cowell State Park and only a 20 minute drive from Santa Cruz beaches. Our unique private home includes a pool & hot tub which sits on the ridgetop overlooking the gorgeous San Lorenzo Valley. If you're looking for peace & tranquility or simply need to relax and recharge, the Hacienda awaits your arrival.

The Willow Cottage
Modern Farmhouse Cottage, walking distance to downtown Walnut Creek. Recently renovated unit sits on a sprawling 5 Acres, which feels like the country but also close to shopping and amazing restaurants. Includes full access to a pool, Chef style kitchen and an outdoor lounge area. Private entrance and plenty of free parking. If Interested, please contact me with: - Occupancy (total amount of guests, pets, cars, etc) - A bit about yourself and your interest in renting

Cabana in Sierra Azul Open Space Preserve
Nestled in the Sierra Azul Mountain Range in Los Gatos, we enjoy AMAZING unobstructed views of the Entire Silicon Valley... San Francisco to Gilroy from 1700ft altitude! This private retreat is perfect for relaxing and rejuvenating, surrounded by forest, streams and wildlife! Relax in complete solitude, refresh with chemical-free, great tasting spring water and crisp clean air high above the smog of Silicon Valley! Great Hiking/Biking Trails at your backdoor!

Luxury Silicon Valley Wellness and Work Oasis
Ideal for business travelers, couples, and nature lovers, while staying in a quiet residential setting. Peaceful upscale exclusive use 1,500 sq ft Los Altos Hills retreat beside Rancho San Antonio Preserve. Private trail access. Fast fiber Wi-Fi, workspace, fireplace, sauna, pool table, full kitchen, plush queen bed. Year-round hot tub, BBQ patio, saline pool. Minutes to Stanford, Los Altos, Palo Alto, and major tech campuses, dining and shops.

Private Suite w/ Views – Near SF & Wine Country
Escape to a private 620 sq ft Sonoma Suite in an upscale Marin neighborhood, ideally located between San Francisco and Wine Country. This modern retreat for two features a private entrance, designer furnishings, a spa-style bathroom, ultra-fast Wi-Fi, and EV charging. Perfect for a romantic getaway or work-from-anywhere stay with serene views and privacy. Seasonal access to a nearby community lap pool (guest access available; fee may apply).

Stay Alpha Home • Modern Redwood Retreat with Pool
Permit 231266 - Nestled in the Santa Cruz mountains is this serene oasis, rustic with modern touches and a stunning pool (the upper pool and main pool are not heated). Embrace yourself with the lush tropical setting and gorgeous redwood groves in this mesmerizing, unique villa. With distance between you and the closest neighbor, it’s perfect for families and nature enthusiasts seeking a rejuvenating retreat. Your redwood getaway awaits!

Hillside Wellness Retreat | Pool, Gym & A/C
Escape to your own private hillside wellness retreat in Marin. Recharge with sweeping views, a heated saltwater pool, fitness studio, air conditioning, and a peaceful standalone guesthouse all to yourselves. Perfect for couples, solo travelers, remote workers, and small families seeking relaxation, outdoor adventure, or a refreshing getaway. Minutes drive from San Francisco, Napa, Sonoma, hiking, yoga, spas, and farm-to-table dining.
Popular amenities for Half Moon Bay rentals with a pool
House rentals with a pool

Pool, Hot tub SFO, Napa, Clean Home

Private cul-de-sac home in Marin with pool

Private Pool Villa for family getaways

Luxury 4-Suite Carbon-Neutral Home With Pool

Waterfront home w/ private dock and pool

Old Amesti Schoolhouse mid-bay amidst farmland

Private Oasis with Pool and Fire Pit

Craftman’s Castle
Apartment rentals with a pool

Walk to the beach, panoramic ocean view, and pool!

Seascape Resort Villa Beautiful Ocean View Sleep 6

Spectacular Ocean View- Heated Pool & Spa Seascape

OCEAN Views and Steps from the BEACH, New & Modern

Beach Front Villa at Seascape Resort

Oceanview Villa w/ 2 Decks, ONE Pool & Fireplace

Rare Oceanview Studio Seascape Resort!

Seascape Oceanf 1 bdr suite hottub Aptos SantaCruz
Other holiday rentals with a pool

*Official Resort Listing*DLX Ocean View 2 BD Villa

Romantic Mtn Studio - Pool, Sauna, Views!

Private Garden Cottage Belmont Hills*Pool*HotTub*

Separate entry room near Stanford

Heated Pool, Jacuzzi, Sauna, Huge Views, Chic ADU!

Cozy BUS on Farm Animal Rescue with CITY VIEW

Tropical Garden Cottage +HOT TUB &POOL by Downtown

MCM Waterfront Pool/Hot Tub between SF and Napa
Destinations to explore
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- Stanford University
- Santa Cruz Beach Boardwalk
- Golden Gate Park
- Santa Cruz Beach
- Muir Woods National Monument
- Capitola Beach
- Moscone Center
- Golden Gate Bridge
- Oracle Park
- University of California-Berkeley
- Levi's Stadium
- SAP Center
- Henry Cowell Redwoods State Park
- Rio Del Mar Beach
- Mission Dolores Park
- Pier 39
- Chase Center
- Six Flags Discovery Kingdom
- University of California San Francisco
- California’S Great America
- Oakland Arena
- Palace of Fine Arts
- Seacliff State Beach
- Big Basin Redwoods State Park





