Guesthouse holiday rentals in San Diego

Lovely La Jolla Cottage Minutes from the Beach

Awesome location! Right in the heart of Bird Rock/La Jolla close to some of Southern California's best beaches! The Beach Cottage is detached and located towards the rear of our property. You will have your own private entrance with key-less entry. To access The Cottage, walk down the drive way, up the stairs to your suite. The Cottage was custom built with luxury in mind. This one-of-a-kind space provides the ultimate beach getaway! Custom doors and lighting, private balcony off your bedroom, black-out curtains, amazing shower with heated tile flooring, new super-comfortable Eastern King bed with luxury memory foam topper, remote controlled A/C and heating unit, bar sink and mini fridge, Nespresso coffee maker, tea kettle, Direct TV, closet, beach chairs and towels, and more. Unrestricted street parking. Local surf board and bike rental around the corner and if traveling with your four-legged friend, check out online sites for in-home doggie care within blocks. Walk to Bird Rock Coffee Roasters in the morning, Wayfarer Bakery and around the corner for amazing sunsets at the ocean. We are available to help with any questions or concerns during your stay. We look forward to having you! The cottage is a 4-minute walk from the ocean that has a lovely park and benches to enjoy the view, the sunrise and sunset, and clean ocean air. Just steps away from some of the best coffee shops, bakery and cuisine in the Bird Rock, LaJolla neighborhood. Enjoy great bars, shops and casual dining. It’s within a very short ride to Wind n'Sea Beach as well as the sand and surf of Pacific Beach and Mission Bay. LaJolla Cove is an 8-minute car ride. Walking is the BEST way to see La Jolla! Explore the neighborhood and its architecture, see the sea lions in the Cove, shop downtown La Jolla or just hang by the beach! If you want to explore more, Uber is the best way to get around! Pacific beach is 5-min away, Mission beach is 8-min away and downtown San Diego is only 15-min away! Access to The Cottage is down the driveway, and up the stairs. No smoking on property, including private balcony and deck. Southern California is known for being especially dry and fires can spread easily. Thanks for understanding!

Location · Value · Kitchen

Anna's Historic Stone Cottage w/panoramic View!

Welcome to Anna's Historic Stone Cottage! The 110 year old cottage has been transformed into the perfect combination of romantic and rustic for a dream-worthy getaway. The 280sq ft cottage features stunning, panoramic views of the San Diego skyline while offering rooftop seating for sunrise and sunset viewing. The Cottage is conveniently located 20 minutes from the world famous San Diego zoo and most other must-see, tourist spots. Amenities for special occasions offered too. Check out our menu!

Location · Value · Kitchen

Posh Guest House ~ Pool, Spa, Pickleball & Tennis

Stunning Guest House with Pickleball/Tennis and Pool/Spa~ Serene, upscale guest house designed for comfort and fun. Nestled in a prime Rancho Santa Fe location, this retreat offers stunning views, resort style amenities and easy access to the best of Southern CA. Ultra comfortable California King Bed Fully equipped Chefs Kitchen Smart TV with Cable & WiFi Designated work area with garden views Expansive Outdoor Space – perfect for dining, lounging, soaking in the peaceful surroundings and sun

Location · Value · Access

Beautiful Bright Coastal Gem w Patio & Free Bikes

Beautiful bright, centrally located spacious studio unit. 2 Beach Cruisers come with Unit. Smoking/420 allowed on private patio which overlooks our little zen garden. Spa like shower. Easily find safe street parking right in front of property. Fireplace use for Winter, AC for Summer. Hop on the beach cruisers head to the beach 1.3 miles away or the great bars of PB. Pillow Top Luxury Mattress. 55 inch Sony TV w Apple TV. Snacks, Water, Coffee. Beach Towels, cooler and beach chairs provided.

Family · Value · Outdoor spaces

Sunny garden casita in vibrant North Park

Enjoy peaceful, sunny San Diego days as palms sway above this private garden retreat tucked behind a 1925 Craftsman. Designed with a love of nature and simple beauty, the guest house opens onto lush greenery and dappled light — a calm, creative hideaway in the heart of one of San Diego’s most charming neighborhoods. Just a short stroll brings you to great restaurants, world-class breweries, and cozy coffee shops, while Balboa Park, the Zoo, the beaches, and downtown are all only minutes away.

Family · Value · Condition

The Golden Hill mosaic "casita"

This is a boutique guesthouse that is part of a 1913 duplex which has been extensively remodeled, and yet maintains its essence in historic Golden Hill. It is a solar-powered 1-bedroom 1-bathroom featuring custom Mexican furniture, french doors, a view of the San Diego Skyline, and a private patio area. Feel the cool breeze on top of Golden hill, a centrally located up and coming neighborhood with lots of walkable destinations. The home is exquisitely decorated with custom Chilean mosaics.

Value · Family · Check-in

Vacation Paradise-Heated Pool+Hot Tub+FirePit+EV

Welcome to your personal resort! This is your private Guest House with a salt & heated pool + hot tub. Located in a very quiet & safe neighborhood in beautiful San Diego. Drive 15 minutes to the beach, downtown, La Jolla, Zoo, stadiums, Sea World, Convention Center + more. Hike next door at Cowell Mountain or Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo, top quality finishes & furniture. Everything you need for memorable vacation! No smoking or vaping on the property.

Family · Location · Long stay

Cozy Casita in Heart of Normal Heights

Private parking with automatic gate opener Perfect for two, this casita has everything you need in a walkable, central location Located in Normal Heights, 3 blocks from Adams Ave Walk to restaurants, coffee shops, and bars 5 min to North Park, Kensington & University Heights 10 min to Downtown San Diego Full kitchen with all essential cookware and utensils Washer & Dryer on site under carport Kids welcome! Pack n Play and toys available for children under 3 (must be requested).

Value · Location · Amenities

Beautiful Historic Home and Gardens Near Downtown!

Location, Location, Location...Welcome to Union Street Gardens. We are dedicated to providing a peaceful, serene atmosphere in which our guests can relax after a long day of exploring beautiful, sunny San Diego. This unique historic craftsman bungalow is just minutes from downtown, Balboa Park, the Zoo, beaches, and includes a Chef's kitchen, outdoor deck, gardens, fire pit and spa! Perfect for a family of 4 or two couples. Sorry no parties or large groups and no external guests please.

Value · Family · Shared spaces

Carrie’s North Park Casita, in Heart of San Diego

Fully renovated stand-alone guesthouse in North Park, consistently voted one of the coolest neighborhoods in the US. Just a few blocks from all the action at 30th and University, but tucked away in a quiet, historically designated residential neighborhood. Walk to Balboa Park or The World Famous San Diego Zoo. Get to Downtown San Diego, San Diego International Airport, Old Town, Little Italy, Coronado, La Jolla, Sea World, multiple beaches & so much more in under 15 minutes.

Value · Family · Nearby

La Casita - Fully Updated Casita in Mission Hills

This well designed, fully updated detached studio casita is located in one of the most sought after neighborhoods in San Diego - Mission Hills. Surrounded by a serene garden courtyard with private entry and quiet patio. Close to great dining, grocery stores and shopping, and a mere 10 minutes or less to most of San Diego’s main attractions. If you are coming by car, there is plenty of free street parking - otherwise Ubers are plentiful and reasonably priced.

Value · Family · Laundry

Peaceful Garden Getaway-Near Downtown & Beaches

Welcome to your private San Diego escape—a stylish, designer guesthouse set in a peaceful garden in the heart of walkable, centrally-located Kensington. With its relaxed coastal vibe, this cozy casita is perfect for couples, solo travelers, or remote work stays. Enjoy your own lush patio—perfect for morning coffee or evening wine—and walk just minutes to Kensington’s cafés, restaurants, and shops. ⭑ CONTACT US FOR SEASONAL DISCOUNTS ⭑

Family · Location · Decor