
Holiday rentals with a pool in Monterey Bay
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Monterey Bay
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Snug and Cozy between the Skyline and the Sea
Super private, peaceful, and quiet; an excellent place for the traveler who is excited about exploring the Santa Cruz mountains and coast. Completely private In-law unit with extras needed to make it cozy. Snuggled between Scotts Valley, Felton, and Santa Cruz it's near Henry Cowell Redwoods State Park, 1440 Multiversity, and Mount Hermon Conference Center yet less than an hour from Silicon Valley. The Airbnb cleaning handbook is followed making this one of the cleanest places you’ll stay at!

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.

Royal Villa - Ocean View - Heated Pool - Seascape
If you're looking for the best, you've found it. There's not a larger or better 1 bedroom condo in the main building at Seascape. It is the only 864 sq ft end unit with ocean view balcony and lots of windows to let the light in! Oh, and has a actual kitchen with a full size fridge and dishwasher. No matter what special occasion brings you to town, this is the condo you will want stay in! Seascape Beach Resort has amazing sunsets, a soft sandy beach, top notch restaurants, and so many amenities.

Oceanfront beach house with private hot tub
This home has a spacious layout with private beach access . Only a half minute walk to the natural beach with panoramic views of Monterey Bay. Relax in the private hot tub as waves crash in the background( WE JUST INSTALLED NEW Hot tub )There are beautiful ocean views from all rooms. Breathtaking sunsets are an evening routine. Whales and dolphins can be seen from the comforts of the bed or couch. The house is a perfect setup for one big family, or two families with small children .

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.

Old Amesti Schoolhouse mid-bay amidst farmland
This 100 year old school house surrounded by organic farms in the Pajaro Valley is a great starting point for your adventures in the Monterey Bay. From here you can reach Santa Cruz to the North or Monterey to the south in 30 minutes. When you are finished sightseeing come back to this comfortable home. A major renovation was recently completed to update the electrical, heating and plumbing yet preserving as much of the past as possible. Outside enjoy the pool, spa or game areas.

Aptos Condo with Spectacular Ocean Views
Enjoy stunning full ocean and sand views from Monterey to Santa Cruz at this beautifully located beach retreat. Watch whales and dolphins from the deck, relax by the ocean-view swimming pool just steps away, or take a short walk to the beach. Santa Cruz Beach & Boardwalk is just 15 minutes away, world famous Monterey Bay Aquarium and Pebble Beach 45 minutes, and Levi’s Stadium only 30 miles. This oceanfront escape is the perfect blend of location, comfort, and unforgettable views.

The Hilltop Venue w/pool, fire pits & views-241155
Take it easy at this unique and tranquil getaway. Located on 9 acres in a non touristy area. Surrounded by farmland and 5 min drive to u-pick organic produce. 75’ lap pool w/lounge shelf & hot tub. Views include a glimpse across the bay, Regan Vineyard and SC Mountains. Queen bed and futon. It is located beneath main house with private entrance. Pool /hot tub/ lawn is a shared space with 3 other neighbor units that live on property. Ideal for 2 guests but we allow up to 4

Monterey Dunes Oceanfront Beach House
The Monterey Dunes Colony is a picturesque gated community on the beach sitting between Monterey and Santa Cruz. This house features 3 bedrooms and 2 bathrooms with a beautiful ocean view and private beach access. The Master, main living area, and kitchen have beautiful views of the Pacific Ocean. You can watch dolphins and whales from the comfort of the kitchen table. Beautiful sunsets are a daily occurrence. This house is great for a large family or 2 smaller families.

Spectacular Ocean View- Heated Pool & Spa Seascape
Relax at this beautiful, peaceful place to stay with an amazing ocean view! This 1 bedroom condo at Seascape Resort is the perfect getaway if you're looking to go to the beach, check out amazing restaurants, enjoy the boardwalk, or hit up nearby beach towns shops. This condo has been updated and is prepared spotless each time. Seascape Resort is located nicely at the center of Monterey Bay making it easy to visit Santa Cruz, Capitola, Monterey, Carmel and more!

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!

Cabana (ca-ba-na);a private retreat next to a pool
Located in a historical neighborhood dating to the early 1930's. The cabana has lots of natural light. Privacy walls. A private patio and entrance. The spacious cabana features a stone fireplace, a grand queen bed, large bathroom with a shower for 2. The vibe is of peace and serenity. The colors are muted and sparsely decorated. The bed sheets, pillow and mattress protectors and blanket are changed after each stay. The bath towels are warm. ZEN!
Popular amenities for Monterey Bay rentals with a pool
House rentals with a pool

2 bedroom Rio Del Mar Apt - Stunning Ocean Views

Beautiful Large 4BR Home with POOL

Adorable Country Cottage WITH POOL!

Santa Cruz Beach House with Pool & Spa

Serene Vineyard Chateau with Pool, Hot Tub, BBQ

La Selva Seaside Sanctuary

Private Carmel Valley Retreat

Toro Park Sunshine | Pool & Hot Tub
Condo rentals with a pool

Seascape Ocean View Condo

Luxury Garden View - Relax and Unwind - Seascape

Seascape Resort Villa Beautiful Ocean View Sleep 6

OCEAN Views and Steps from the BEACH, New & Modern

Monterey Bay Sanctuary Beach resort

Beach Front Villa at Seascape Resort

Oceanview Villa w/ 2 Decks, ONE Pool & Fireplace

Rare Oceanview Studio Seascape Resort!
Other holiday rentals with a pool

Seascape Oceanview Luxury 2B w/theater walk2beach

Seascape Ocean Front Villa

Ocean View at Seascape with Private Balcony

Redwood Oasis - Private Heated Pool by State Park!

Huckleberry Woods Sanctuary: Pool and Spa

3823 Sand Dollar House - Oceanfront on the Beach

Luxury Villa - Flora View - Ground Level -Seascape

Nuby's Bed & Breakfast (SCC Permit #251085)
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- Stanford University
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