Guesthouse holiday rentals in San Diego

Guesthouse in Mission Hills

A curving staircase is visible, flanked by white walls and adorned with vibrant blue tiles. Handrails provide support along the ascent, leading to a bright upper space. A potted plant enhances the serene ambiance at the top of the stairs.

5 out of 5 average rating, 249 reviews

Santorini-Inspired Cottage w/ Hot Tub + Views

*CHECK OUT OUR OTHER AIRBNB* Travel 16 steps up a Greek-inspired curving stairway with 2-story high walls to your tucked-away cottage built into the hillside villa of Alta Colina. With spectacular views, step onto the balcony to watch planes take off & boats sail around the harbor. End the night in front of your secluded back patio fireplace or climb the steps of your spiral staircase to the rooftop Jacuzzi. European-inspired design & details, it'll be hard to believe you’re still in San Diego!

The exterior of a historic stone cottage showcases a rounded structure with large, circular windows. Native plants and decorative rocks surround the entrance, highlighting the natural landscape. The name 'Anna' is displayed on a rustic wooden sign, further enhancing the cottage's character.

4.9 out of 5 average rating, 437 reviews

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!

Guesthouse in Pacific Beach

A spacious studio unit features a large bed adorned with crisp white linens. Natural light fills the room through two windows. A kitchenette is visible to the left, and a dining area is set against the wall. A cozy area rug adds warmth to the wooden floor.

4.92 out of 5 average rating, 1,059 reviews

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.

Guesthouse in Sherman Heights

A private garden is illuminated at night, featuring various seating areas surrounded by lush greenery and colorful plants. Lanterns provide soft light, casting a warm glow on the outdoor space. A patterned rug and dark wooden furniture complete the serene atmosphere, inviting relaxation.

4.96 out of 5 average rating, 569 reviews

Romantic Private Garden Studio Near Downtown

A magical private garden surrounds a tiny studio (240 sq ft) with kitchenette in historic residential district, 10 blocks to East Village and Petco BallPark, near Gaslamp Quarter, and one mile to Convention Center and downtown. Easy access to freeways, very close to Balboa Park, San Diego Zoo, and Coronado Island. Airport and train station less than 15 min. We offer a safe, sweet, and contemplative getaway near the city, with WiFi but no TV. One pet OK only with prior approval. 420 friendly.

A light-filled living area features two comfortable sofas facing a modern entertainment unit. A large screen television is mounted on the wall. Sunlight streams through windows, illuminating decorative plants and a neutral-colored coffee table, enhancing the serene ambiance.

4.97 out of 5 average rating, 195 reviews

Free Bikes. 5 min walk to Windensea Beach La Jolla

Charming one-bedroom guesthouse in La Jolla, California. Just a 6 minute walk from windensea beach. Private entrance with self check in. Newly renovated living, dinning and kitchenette. The bedroom features a plush California king-size bed. sleeper sofa pulls out to a comfortable full-size bed. The modern bathroom is spacious, clean and inviting. Amenities for the beach will be ready for you. Chairs, umbrellas, cooler, beach toys and boogie boards and 2 bikes Relax on your private porch.

Guesthouse in Lake Murray

The poolside area features a well-maintained saltwater pool reflecting the colors of the sunset. Comfortable seating arrangements, including lounge chairs and a cozy fire pit, are visible. Large umbrellas provide shade, and lush greenery adds to the serene ambiance.

4.97 out of 5 average rating, 154 reviews

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.

Guesthouse in Mission Hills

The open studio loft features a spacious queen bed draped with light fabric. A small blue sofa with decorative cushions sits opposite a wooden coffee table. Natural light streams in through a well-placed window, illuminating the soft carpet and simple decor.

4.98 out of 5 average rating, 204 reviews

Mission Hills-Entire Guest House-Center of it All

Enjoy a stylish experience at this centrally-located studio loft. Detached Guest House is striking distance of the best SanDiego has to offer. Walk to the best restaurants in town. Zoo, Coronado, Gaslamp & Downtown it’s all at your fingertips. Minutes from Airport. Soaring 15 foot ceilings and comfy queen bed with canopy and small futon. A stones throw from the airport, train, I5 & bay. Perched at the summit of Mission Hills stunning views of the bay, Coronado Island and the Pacific beyond!

Guesthouse in Mission Hills

A spacious living area features a large sectional sofa adorned with decorative pillows, complemented by a wooden coffee table. A vibrant wall art piece with colorful surfboards is displayed above the couch, while natural light fills the room through expansive windows.

4.98 out of 5 average rating, 285 reviews

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.

The tropical pool features gentle waterfalls cascading into vibrant blue water. Surrounding palm trees and lush greenery enhance the serene environment. A tiki bar and a hot tub grotto provide inviting leisure options. A second-story balcony overlooks this tranquil outdoor space, illuminated by soft evening lights.

4.98 out of 5 average rating, 200 reviews

Luxury Tropical Private Guesthouse in La Jolla

Beautiful private guesthouse on $5 million property with stunning views and luxury amenities. Take a dip in the tropical pool with waterslide, tiki bar, and hot tub grotto. Enjoy indoor or outdoor dining. Gated property, vaulted ceilings, marble bathroom, private balcony, parking, and trail for guests. Guesthouse has 1 bedroom with a queen bed and can accommodate an extra twin bed on the loft. House has closet, bathroom with beautiful stone shower, modern kitchen, two patios, WiFi, TV.

Guesthouse in Pacific Beach

The open living area features a modern dining table with four white chairs, accompanied by a small black side table. Light wood tile flooring creates a warm atmosphere. Large windows provide natural light and a view of the outdoors, while soft curtains frame the space.

4.98 out of 5 average rating, 335 reviews

Charming Modern Apartment with private terrace

The apartment is above our home with its own private entry with a nice ocean view terrace. Plenty of street parking, tile Floors throughout. 15 mins walking to the beach or 5 mins bike ride (2 bikes free to use). Walking distance to Garnet Ave, restaurants, bar, grocery stores. 1 King size bedroom with 45" smart TV, dvd , WIFI free, Netflix free, 2 full baths with bidet and shower, full kitchen, living room with a queen bed sleeper sofa and smart TV Blackout cellular shades.

5 out of 5 average rating, 184 reviews

The entrance to the casita is framed by lush greenery, featuring a pathway lined with stone leading to a white door. A mature tree provides shade alongside colorful shrubs and a well-maintained garden, offering a welcoming entry to the private retreat.

Guesthouse in San Diego

Renovated Beach Casita: AC, Lux King Bed, Patio

Escape to our newly renovated, coastal-modern beach casita on a quiet street in vibrant Ocean Beach. Just 2.5 blocks from the beach and steps to cafes, restaurants, and bars, it’s perfect for couples, families, or small groups. Relax on the private patio, enjoy a premium king bed and queen pullout, and cool off with rare AC. With a full kitchen, walk-in closet, desk, and beach gear, it’s the ideal retreat near San Diego’s top attractions for a perfect beach or city getaway.

A modern loft space features warm wood flooring and a plush area rug. A gray sofa faces a sleek entertainment center. A desk and stool are situated by a window, offering views of the surrounding landscape. Natural light fills the room through large windows.

4.95 out of 5 average rating, 221 reviews

Mountain top view getaway loft

This loft is completely sound proof! VIEWS, VIEWS, VIEWS!! Do not miss this stunning contemporary loft, located in the highly desired Mt. Helix community. The guest house faces west, giving you phenomenal 270-degree views of the ocean, Downtown, Point Loma, Coronado islands, Coronado bridge, and more! Designed and built by an acclaimed San Diego home designer, this property was featured in Dream Homes Magazine and is well known for its incredible design and construction.

Popular amenities for San Diego guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

A well-maintained putting green is surrounded by lush greenery, featuring multiple flags indicating different holes. A sand trap is positioned nearby, and a winding path made of stone leads through the garden space, enhancing the serene outdoor environment.

4.94 out of 5 average rating, 150 reviews

Pool Side Safari Cabin-On the backend of our Home

4.93 out of 5 average rating, 123 reviews

An open kitchen and living area is presented with modern furnishings. A large island with four bar stools centers the space, complemented by pendant lighting. A round mirror and a plant add decor, while a living area with a cozy sofa invites relaxation.

Guesthouse in Encinitas

Coastal Casita - Your Rad Cali Getaway

4.99 out of 5 average rating, 186 reviews

A bright living area is characterized by large windows that invite natural light and provide views of greenery outside. A wall-mounted TV is positioned opposite a comfortable sofa, while a colorful dining chair adds a playful touch to the space.

Guesthouse in Del Cerro

The Happy Family * 2 playhouses near SDSU!

4.89 out of 5 average rating, 647 reviews

Guesthouse in South Park

Private South Park Bungalow - Large Yard & Parking

Guesthouse in Pacific Beach

A welcoming living area features a futon and coffee table set on polished hardwood floors. Bright natural light fills the room through the window. A dining area with a table for four is visible, along with kitchen access through an open doorway.

4.83 out of 5 average rating, 402 reviews

Pacific Beach Guest House With Garage and A/C

4.99 out of 5 average rating, 217 reviews

A welcoming entrance features a textured walkway leading to a front door, framed by a wooden railing. Colorful flowers bloom along the sloped landscape, enhancing the natural appeal of the surroundings. Clear skies and distant homes provide a serene backdrop.

Guesthouse in El Cajon

Modern mountain guest house. Incredible views

Guesthouse in Ocean Beach

A cozy studio space is highlighted by a spacious bed adorned with soft pillows. A minimalist round dining table sits beside the bed, accompanied by two chairs. Modern decor is complemented by a ceiling fan and a wall-mounted TV. Natural light fills the area through a nearby window.

4.91 out of 5 average rating, 182 reviews

Detached Guest Suite · Private · Walk to Beach

4.98 out of 5 average rating, 247 reviews

A spacious living area is equipped with a plush sofa and light-colored chairs, accented by decorative pillows. A wooden coffee table rests on a colorful area rug. Natural light fills the room through two windows, highlighting a work desk and welcoming artwork on the wall.

Guesthouse in El Cajon

Fletcher Hills - modern 1 BR.Easy, no step access.

Guesthouses with a patio

A charming exterior of a white house is framed by vibrant green plants and orange flowers. A stone pathway leads to an inviting front door, flanked by decorative lanterns. A small dog stands on the path, adding a sense of welcoming to the scene.

4.98 out of 5 average rating, 106 reviews

Mt. Helix Casita private petite home

4.97 out of 5 average rating, 114 reviews

Guesthouse in Bonita

Adorable 1- bedroom guesthouse/Casita

4.98 out of 5 average rating, 137 reviews

A private outdoor patio presents comfortable seating with two chairs and a sofa surrounding a coffee table. An umbrella provides shade, and greenery is visible alongside the patio. The paved surface features decorative stones, creating a cozy area for relaxation.

Guesthouse in Poway

Gorgeous Guesthouse Poway w/Private Yard

A sunset view captures the coastline with gentle waves and a curved beach extending toward the horizon. The scene features vibrant hues of orange and pink in the sky, with palm trees in the foreground and distant hills framing the landscape.

4.98 out of 5 average rating, 266 reviews

La Jolla Oasis: Ocean, City and Fire Works Views

A spacious deck is visible, furnished with a table and four wicker chairs. A decorative bowl sits at the center of the table. The panoramic view of the surrounding landscape and city skyline stretches into the distance under a clear blue sky.

4.96 out of 5 average rating, 243 reviews

Da Hui Hut - La Mesa’s best view and spa

A cozy living area features a sectional sofa and wooden coffee table, complemented by a television mounted on the wall. Several light sources illuminate the space, including a ceiling fan. Decorative wall art adds a personal touch, while windows allow natural light to brighten the room.

4.99 out of 5 average rating, 344 reviews

SDCannaBnB #1 *420 *parking *dog-friendly *hot tub

A private deck features a fire table with flames, surrounded by outdoor seating, including a striped lounge chair and a wicker settee. Lush greenery frames the stunning ocean view, while the sunset casts a soft glow across the sky.

4.97 out of 5 average rating, 105 reviews

Smashing Recently-Built Ocean/Bay/City Views

A vibrant sunset casts shades of orange and pink across the sky, viewed from a residential street. Palm fronds frame the scene, while neighboring homes and trees are softly silhouetted against the colorful backdrop.

4.95 out of 5 average rating, 184 reviews

San Diego Newly Built Private Guesthouse (Sleep 4)

Guest house rentals with a washing machine and dryer

4.96 out of 5 average rating, 337 reviews

A cozy sleeping area features a spacious bed adorned with a textured blanket and decorative pillows. Natural light filters through windows with shutters. A light-colored armchair and circular wooden table complement the inviting ambiance of the room.

Guesthouse in San Diego

Private beach guesthouse w/ private parking

A private deck is shown, featuring a red umbrella over a round table with four chairs. The entrance to the guest house is framed by glass doors and accompanied by a vibrant red door. Lush greenery and flowerbeds enhance the outdoor space.

4.99 out of 5 average rating, 218 reviews

Stunning Guest House 15 min. from Zoo, Downtown

An outdoor living space is featured, showcasing a stone fireplace with a flickering fire. A cozy seating arrangement is present nearby, and a television is visible through a glass door, contributing to a relaxed atmosphere perfect for gathering.

4.98 out of 5 average rating, 448 reviews

Beautiful Private Villa walk to beach

Guesthouse in Greater North Park

The exterior of a renovated guesthouse is presented, featuring a white stucco facade with decorative tiles along the steps. A green door, large windows, and a charming walkway leading to the stairs enhance the inviting appearance of the property.

4.99 out of 5 average rating, 187 reviews

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

Guesthouse in Golden Hill

A charming exterior of a boutique guesthouse is presented, featuring a vibrant yellow door and large windows. Lush greenery with various plants and flowers adorns the landscape, while a crafted stone pathway leads to the entrance. A warm, inviting atmosphere is conveyed through well-maintained landscaping.

4.87 out of 5 average rating, 543 reviews

The Golden Hill mosaic "casita"

4.97 out of 5 average rating, 201 reviews

Guesthouse in Hillcrest

Luxury Studio W/ Garden View in Heart of Hilcrest

Guesthouse in Greater North Park

A spacious bedroom features a king bed with neutral bedding and decorative pillows. French doors provide natural light and open to a balcony overlooking lush greenery. A modern ceiling fan and soft lighting complement the hardwood floor and simple decor, creating a comfortable and inviting space.

4.96 out of 5 average rating, 212 reviews

New Guest House - North Park