Vacation rentals with a pool in Monterey

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Monterey

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in Scotts Valley

4.96 out of 5 average rating, 699 reviews

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!

Superhost

Rental unit in Santa Cruz

4.84 out of 5 average rating, 191 reviews

Canopy Tours Thrills| Amusement Park. Pool

Striking the perfect balance between natural beauty and urban design, this Santa Cruz hotel challenges the typical experience with a bold blend of contradictions. Attractions await you: ✔ Spectacular nature experience on steam engine trains at Roaring Camp Railroad ✔ Seals at Año Nuevo State Park ✔ Astonishing views at California's oldest state park, Big Basin Redwoods State Park ✔ Redwood Canopy Tours with suspension bridges and zip lines ✔ Iconic views at Natural Bridges State Park

Guest favorite

Guesthouse in Monte Sereno

4.98 out of 5 average rating, 413 reviews

Quiet Poolside Cottage for Solitude

New construction 800 sq. ft. Cottage 1.1 miles to downtown Los Gatos. Off-street parking for one car. Cathedral ceilings with skylight (morning sun, nightly stars). Comfortable pillow top King bed. Single bed in same space for extra guest (extra $25 for third guest/night). Kitchenette with basics. Dining table for work spaces. Pool available for guests. Jacuzzi not available. Many quiet places on property to relax. We do not accept third party reservations. Add your guests on reservation.

Guest favorite

Home in Aptos

4.92 out of 5 average rating, 533 reviews

Relax Watch Waves Crash Chic + Modern 3BD

Sea breezes and beautiful ocean views greet you from your 40-foot deck at RdM Lookout, a newer property with hardwood floors, quartz counters, and a bright, modern open beach design with a cozy fireplace which was featured on the design website Houzz. A comfortable, chic space, guests tell us they love the amazing beds, soft linens, fluffy towels, and our gourmet kitchen-stocked coffee bar with to-go cups for beach walks. Come home to a relaxing, beach vacation in a charming beach town.

Guest favorite

Home in Castroville

4.96 out of 5 average rating, 180 reviews

Oceanfront Retreat w/Private HotTub

Beachfront oasis with majestic views of the Pacific Ocean and stunning sunsets! Recently remodeled & and conveniently located halfway between Santa Cruz & Monterey/Carmel. We love our split-level home layout with the dining & living rooms on upper levels for the best ocean views over the dunes. Enjoy privacy in our secure gated community with family fun amenities: tennis, pool, ping-pong, Pop-A-Shot basketball, etc. *** BEWARE OF SCAMS! WE DO NOT OFFER LOWER RATES ON CRAIGSL _ _ T!

Guest favorite

Townhouse in Castroville

4.95 out of 5 average rating, 270 reviews

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.

Guest favorite

Guesthouse in Almaden Valley

4.97 out of 5 average rating, 940 reviews

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!

Guest favorite

Guesthouse in Monte Sereno

4.89 out of 5 average rating, 199 reviews

Greenwood Guest House, a Peaceful Oasis

Welcome to Greenwood Guest House, a 1 bedroom, 1 bath private house situated in a peaceful and expansive backyard with a pool, tennis court, and beautiful scenery. Our space is a good fit for business trips, couple vacations, and family visits. The kitchenette and laundry room make longer stays quite enjoyable. Easy access to Highway 17 and 85, 15 minute drive to San Jose airport (SJC) and 2 minute drives to either downtown Los Gatos or Saratoga.

Guest favorite

Guest suite in Salinas

4.95 out of 5 average rating, 368 reviews

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!

Superhost

Guest suite in Carmel Valley

4.81 out of 5 average rating, 108 reviews

Cozy Studio in Carmel Valley w/ pool!

Designed to feel like you're on a boat, our small Studio is available in Carmel Valley with private entrance & access to the pool with its own private patio. This room is below our main house and the ceilings are low (please take note if you are taller than 6’2). We are located 2 miles from CV Village & 12 miles from downtown Carmel. Pool is open July-October. Spa is open year round, please message me to turn on the hot tub jets and heater.

Guest favorite

Townhouse in Castroville

4.94 out of 5 average rating, 327 reviews

28 Seconds Walk to Beach

Pacific ocean is the backyard with private beach access right from our decks in 28 seconds. One of the closest units to the beach with no mound in dunes blocking your view. You have the beach to yourself. Gated community with secluded beach, panoramic view of majestic sun sinking into the vast ocean, sound of waves pounding the sandy beach from right inside the house. 20-minute drive to Monterey Bay Aquarium, 17-mile, Carmel-by-the-sea.

Superhost

Guest suite in Gilroy

4.82 out of 5 average rating, 101 reviews

Private guest suite with pool and stunning views

We welcome you to stay at our humble little guest suite nestled in the Santa Cruz mountains. Enjoy the serenity and stillness between the towering redwoods and bustling wildlife. This guest suite is located off the “wine trail” between Gilroy and Morgan Hill (around 15 minute drive from both), and directly next to Martin Ranch Winery. Here you can enjoy your privacy on your getaway from the hustle and bustle of daily life.