Condo holiday rentals in Gilroy

New! Stylish Condo on Santana Row

Enjoy an indulgent experience at this stylish and centrally-located condo in the heart of Santana Row. "The Row" is a premium blend of residential, retail, and dining spaces in the center of Silicon Valley. Revel in gourmet restaurants, upscale shops, cinemas and a lively atmosphere with outdoor concerts and seasonal festivals. Take a short stroll to Westfield Valley Fair to continue your journey in fine dining, entertainment and shopping venues Located right off of highways 17, 280, and 880.

Oceanview Villa w/ 2 Decks, ONE Pool & Fireplace

Spectacular ocean view condo with views towards Monterey AND Santa Cruz. Yes, you have the sunrise and sunset from both decks. Two story Seascape Villa, South Bluff. Very well designed space with living room, kitchen, deck & powder room on first floor, two bedrooms, two bathrooms, and a second deck upstairs. WiFi, free parking, ONE heated pool on the NORTH BLUFF, short walk down to the beach on a special path. L’Occitane Shampoo/Conditioner/Lotion, Nespresso for coffee. Bartesian Cocktail Maker.

Art-Inspired Respite in the Heart of Oldtown

Enjoy a stylish experience at this centrally-located upstairs unit. This two bedroom apartment is one of three units on the same property. Unique and interesting art fill the walls from travels and collecting. This colorful and bright apartment is spacious and private. A newly remodeled kitchen make this open space a convenient place to prepare a meal. Two large bedrooms and a new and updated bathroom provide comfort and tranquility. A large shared yard with BBQ, couch, tables and lawn games.

Beach Front Villa at Seascape Resort

The newly remodeled unit offers a beautiful fireplace, hardwood flooring, a new kitchen with stainless steel appliances, bathrooms, stairs, a laundry system, and more. Beautiful villa just a 10-15 min walk to the beach. Bring your family and friends to enjoy this quaint place with an expensive ocean view and the best view of the resort. Live spaciously in 2 luxurious master suites upstairs and an open concept living room and kitchen downstairs. It will surely be an unforgettable experience!

Cozy Apartment Right Downtown

If your looking for a quality centrally located place to stay. Fifth Street Retreat is your choice. RIGHT DOWNTOWN. We are also close to other cities. If you want the ocean Monterey and Carmel Valley and Santa Cruz is right next door. If you want the city, San Francisco is above us. If your interested in hiking, Pinnacle National Park is in our back yard. Hollister Hills if you are a motorcycle enthusiast. Walking and bicycling trails. So many great restaurants, bakeries and bars. #enjoyus

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.

Fully Equipped OceanView Ground Villa &Heated Pool

Breathtaking ocean & beach views facing Monterey Bay, Capitola Beach & Santa Cruz. This luxurious, ground level, 2-BR villa has the convenience of amazing sunsets, a direct 5-min path to the soft sandy beach, & a furnished patio facing open lawn space. Enjoy the views of the white water surf right from the living room, patio or bedroom; take a dip in the heated pools/hot tub just steps from your front door; or dine at Sanderlings Restaurant. Why choose one when you can do it all?

Warm and Cozy Two-Story Loft Overlooking Santana Row

Welcome! We have worked hard to create a beautiful, relaxing atmosphere for the business traveler who has been traveling/working all day or for families who are visiting and want a comfortable “home base”. Our beautiful, clean and comfortable 2 story loft overlooks the main “Row” with popular restaurants and shops or you can take an easy walk across the street to Valleyfair Mall. Our 2 bedroom 1.5 bathroom is equipped with everything you need for a comfortable stay!

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!

Luxury Santana Row Loft, Balcony & Parking

Stay directly on Santana Row in this luxury 2-story loft with 22-ft ceilings, floor-to-ceiling windows, and a private balcony overlooking the Row. Sleeps 4 with a full kitchen, fast Wi-Fi, in-unit washer/dryer, and free reserved parking (rare for Santana Row). Walk to top dining, shopping, and nightlife, with Westfield Valley Fair across the street. A quiet, comfortable retreat and ideal Silicon Valley home base for business or weekend stays.

Flora Belle, Perfect Carmel-by-the-Sea Getaway

Flora Belle is your perfect Carmel- by- the- Sea get away. This ground floor condo is in a superb location just steps to Ocean Avenue with its world class restaurants, shopping, and white sand beaches. There is one off street designated parking spot ideal for a compact car. The bedroom has a queen bed and petite walk in closet. The bathroom, accessed through the bedroom, boasts a roomy corner shower. Carmel Belle awaits your visit!

Your Coastal Sanctuary - Far from the Craziness

A calming oceanfront condo at Pajaro Dunes on Monterey Bay, perfect for couples, families, and coastal getaways. Enjoy beach access, ocean views, and a peaceful California coast escape. Your personal retreat on Monterey Bay made for slow mornings, barefoot beach walks, and quiet moments that linger. Unplug, unwind, and rediscover the joy of simple pleasures in a space designed for calm, comfort, and connection.