Cottage holiday rentals in Hillcrest

Cottage in Normal Heights

The spacious bedroom features a vaulted-beamed ceiling and an inviting California King-size bed, draped with a light blanket. Decorative elements include a wooden headboard, a vintage bench at the foot of the bed, and tasteful wall art. Natural light enters through the frosted window.

4.96 out of 5 average rating, 139 reviews

LOFT: Detached Cottage with Patio

Located in the heart of Normal Heights, where everything is walkable; pubs, markets, cafes. Local’s favorite! The LOFT is a spacious open-space studio loft, in a stand-alone cottage. Whether you fall in love with the vaulted-beamed ceilings, the Loft-style open kitchen, the clawfoot tub, the art & decor, or the lush landscaping, you won’t likely forget this place any time soon. Everywhere you turn is a feast for your eyes. We’ve ensured that comfort is as much of a priority as is beauty.

A charming cottage with a welcoming porch is showcased. A colorful red umbrella provides shade over a patio table surrounded by several chairs on the paved outdoor area. Lush greenery accents the space, contributing to a relaxed atmosphere.

4.97 out of 5 average rating, 123 reviews

It’s so Lovely on Larkspur Adorable Cottage in OB

Relax in our remodeled and sunshine filled 1 bed, 1 bath cottage with easy access to the beach, parks, restaurants, coffee shops, grocery and more. Uniquely away from the hustle and bustle, our charming neighborhood has limited through traffic and that friendly OB vibe you are looking for. We live next door and are Superhosts and ambassadors of Ocean Beach; to prove it, check out our reviews before our remodel by going to my profile or searching for "Charming OB Cottage with Private Patio".

4.97 out of 5 average rating, 244 reviews

A bright living area features a comfortable light gray sofa adorned with decorative pillows. A round coffee table sits on a patterned rug, and a wall-mounted television is visible. Natural light filters through a large window beside the front door, which is framed with greenery.

Cottage in Hillcrest

Canyon Views w/ Outdoor Seating & Parking

Prime location! Within walking distance to Trader Joe’s, Whole Foods, Ralph’s, cafes, gyms, amazing restaurants, great nightlife, and Sunday's Farmer's Market! This newly restored historic cottage is in the heart of Hillcrest, San Diego. Originally located in Balboa Park, it housed workers for the 1915 Panama–California Exposition. Perched on a canyon, the cottage blends modern amenities with farmhouse charm. Book now for a San Diego stay that fuses the past with modern comforts!

Cottage in Greater North Park

A well-lit interior features a spacious bed with a multi-striped blanket. Two wooden chairs are positioned beside a small table with a bottle and vase of flowers. Large windows provide natural light, and a subtle color palette creates a serene ambiance.

4.86 out of 5 average rating, 321 reviews

Private Cottage near Balboa Park

Welcome to this stylish, romantic, and quiet casita situated in a private garden setting! Located in exciting North Park, you can walk just blocks to some of San Diego's best restaurants, cafes, and breweries, as well as the Observatory for concerts and Morley Field, home to a beautiful outdoor public pool and tennis facility. You are a five minute drive to the San Diego Zoo and Balboa Park, a 10 minute drive to downtown/airport, and a 15 minute drive to beautiful beaches.

The living room features a comfortable sofa and inviting chairs arranged around a low coffee table. A large TV is positioned against a white wall, complementing the artistic decor. Natural light enters through the windows, creating a welcoming ambiance in the cozy space.

4.94 out of 5 average rating, 429 reviews

Fabulous Cottage at the Beach

Newly remodeled 1940's cottage just 50 steps to the sand with fabulous beach and ocean views. Enjoy the ocean breeze from your front porch and watch people walk by. Go sunbathing and swimming, take a bike ride or a stroll on the beach, have a glass of wine and witness the most beautiful sunsets. We are located in a quiet residential neighborhood of Ocean Beach. This bright and cozy cottage has everything you'll need to feel at home.

4.86 out of 5 average rating, 518 reviews

A light-filled living area features a comfortable sofa adorned with patterned pillows. A round coffee table sits atop a decorative rug. A flat-screen TV is positioned on a console, while a dining nook with chairs and a small table is visible in the background.

Cottage in Hillcrest

Dragonfly Cottage - In the Heart of San Diego

Cozy cottage located in HIllcrest, the heart of San Diego. Private entrance with a full kitchen and shared patio/BBQ area and Hot Tub. Super close to Balboa Park, The San Diego Zoo, Beaches and Downtown. Walking distance to an amazing array of restaurants and bars. A great place to relax and enjoy all that San Diego has to offer.

Cottage in Sherman Heights

4.95 out of 5 average rating, 263 reviews

Historic Charmer Steps to Downtown

Charming, fully renovated cottage located in an Historic District on the edge of Downtown San Diego. This is a safe, QUIET historic neighborhood. Not a tourist area. Most guests drive or ride share. There is one off-street parking spot for you. There no coffee shops or restaurants in the immediate few blocks.

4.93 out of 5 average rating, 349 reviews

A panoramic view of rolling green hills meets a shimmering bay, dotted with residential areas. Lush trees frame the foreground, while the coastline stretches into the distance under a clear blue sky.

Cottage in Pacific Beach

Family and Pet Friendly Beach Bungalow

Our newly renovated beach bungalow has 2 bedrooms, a large comfy couch and a full bath. It is located 1 mile from the beach, 0.2 miles to Vons, Starbucks, Trader Joe's, restaurants and bars. Bikes, beach chairs and a beach umbrella are available for use. Private gated parking. Pets welcome.

The exterior of the cottage is presented with a bright yellow facade and a welcoming entrance. A white bench with cushions is situated on a pathway of stone slabs, surrounded by artificial grass and greenery, enhancing the cottage's charm.

4.98 out of 5 average rating, 628 reviews

Cozy Cottage -3 blocks from beach+parking+bikes

Private cottage for your Ocean Beach getaway. Includes secure parking, keyless entry, TV with streaming apps and local channels, high-speed internet, and an outdoor shower to freshen up after a day at the beach just three blocks away. Dining and shopping are conveniently located nearby.

Cottage in La Jolla Shores

A charming cottage exterior features a brick pathway leading to the front door, surrounded by well-kept grass and shrubs. The wooden siding is complemented by a welcoming porch and a prominent chimney, set against a clear blue sky.

4.99 out of 5 average rating, 258 reviews

La Jolla Shores redwood beach cottage

Redwood cottage 3 blocks walking distance to beautiful La Jolla Shores beach. Large serene back yard with patio, hot tub, outdoor shower and beautiful plants and trees. Near shopping and restaurants but in a quiet setting. In 2025, 45% of our bookings were from repeat guests.

The living area features a comfortable dark sofa and a light wooden dining table surrounded by white chairs. Natural light enters through large windows, highlighting decorative elements such as plants and colorful cushions. A ceiling fan adds to the airy atmosphere, creating a relaxed space.

4.87 out of 5 average rating, 467 reviews

Steps from the beach

Charming cottages that are steps from the ocean & beach. Enjoy sunsets and ocean views from your private patio. Located within walking distance (less than 3 min) from all that Ocean Beach has to offer. Enjoy the food, numerous cafes, sun, and beach life.

Cottage in Greater North Park

A comfortable living area features a sectional sofa with decorative pillows, offering a cozy seating option. A sleek TV stand holds a flat-screen television, while two windows allow natural light to brighten the space. The wood floor adds warmth to the environment.

4.88 out of 5 average rating, 893 reviews

Quaint Cottage Heart of North Park, Location A+!

Fully remodeled in 2022, beautiful studio cottage in the heart of North Park, San Diego's most vibrant urban neighborhood. Near to Balboa Park & Zoo and many cafes, bars, and restaurants nearby. Explore San Diego from the heart of a great community!

Popular amenities for cottage rentals in Hillcrest

Kitchen

Wifi

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

4.92 out of 5 average rating, 242 reviews

A private entryway is framed by lush greenery and colorful plants. A rustic wooden gate provides access, set against a clean, beige wall. Blue pots filled with vibrant foliage are positioned at either side of the path leading to the entrance.

Cottage in Pacific Beach

Crown Point Gem with Salt Water Pool

A spacious outdoor patio features a dining table with an umbrella and four chairs. Potted palm trees line the edges, and the red decking adds a vibrant touch. The ocean is visible in the distance, enhancing the relaxing beachfront atmosphere.

4.9 out of 5 average rating, 417 reviews

Ocean front Paradise– see waves from Jacuzzi!

Cottage in College East

4.86 out of 5 average rating, 28 reviews

Cute, modern, private back house w/ free parking

Superhost

A spacious balcony overlooks a shared backyard featuring lush greenery and a glimpse of the neighboring homes. Adirondack chairs invite relaxation while a clear blue sky complements the vibrant landscape below.

Cottage in Bay Park

4.78 out of 5 average rating, 27 reviews

1bd large backyard with spa, firepit, dining, pets

Pet-friendly cottage rentals

The living area features a light grey sofa and a circular glass coffee table, positioned on a soft area rug. A ceiling fan hangs above, and light wood flooring complements the space. Natural light enters through windows adorned with minimalistic treatments, enhancing the room's welcoming feel.

4.93 out of 5 average rating, 165 reviews

Charming Cottage: Parking, Bikes & Walk to Sand!

4.93 out of 5 average rating, 173 reviews

The living room features a spacious, soft sectional sofa adorned with decorative pillows. A round coffee table is centered on a colorful area rug, while a bright window allows natural light. The room is connected to a dining area with a visible ceiling fan and wooden furniture.

Cottage in Pacific Beach

Cheerful & Sunny-3BR House in Pacific Beach CA

4.88 out of 5 average rating, 390 reviews

Last-Minute Discount at Green Door Cottage!

A cozy sleeping area is presented with a spacious bed featuring blue and white striped linens. Mirrored walls enhance the room's brightness. A ceiling fan hangs above, providing airflow. A small dresser is positioned beside the bed, and a compact washer and dryer set is discreetly tucked away.

4.87 out of 5 average rating, 300 reviews

Ocean Beach ~ Your dream vacation!

4.96 out of 5 average rating, 102 reviews

An outdoor patio features a large stone sun design at its center, surrounded by a mosaic of differently shaped stones. Bright murals depicting a sun and nature adorn the cottage wall, while a cozy seating area includes a wooden bench and lounge chairs amidst lush greenery.

Cottage in La Jolla

EcoTopia: Beach, Art, Surf, & Ceremony Cottage

4.94 out of 5 average rating, 204 reviews

A welcoming entrance features a white front door framed by large windows, offering natural light. Two blue chairs are positioned on a small grassy area, ideal for outdoor relaxation. Surrounding plants enhance the calm and inviting setting.

Cottage in El Cajon

Private cozy cottage

A sunny outdoor deck is shown, featuring a glass table surrounded by chairs. A large umbrella provides shade, while teal bar stools are positioned nearby. An American flag adds a festive touch against the light-colored exterior of the cottage.

4.96 out of 5 average rating, 146 reviews

2 Bedroom Beach Cottage - Literally Steps to Sand

4.9 out of 5 average rating, 230 reviews

Grant's Getaway, cottage 1 block to beach w/AC

Private cottage rentals

A cozy living room features a soft leather sofa adorned with textured cushions. A round rattan coffee table sits in front of a white faux brick fireplace, with light streaming through sheer curtains. Decorative elements include a wall mirror and a small plant on a side table.

4.85 out of 5 average rating, 489 reviews

Boho Bungalow | Cozy Hideaway | Walk Everywhere!

A bright living area features a spacious sectional sofa opposite a wooden coffee table, with a large world map artwork mounted on the wall. Natural light floods the space through sliding glass doors that lead to the outdoor area. Potted plants add a touch of greenery.

4.95 out of 5 average rating, 202 reviews

Renovated Central Beach House w AC, Steps to Beach

4.89 out of 5 average rating, 261 reviews

The entrance to the cottage is framed by a white picket fence, leading to a spacious patio area. Lush trees provide shade, while outdoor seating arrangements invite relaxation. The exterior features pastel hues, with decorative windows and charming accents enhancing the inviting appearance of the home.

Cottage in Encanto

Hilltop Cottage - Incredible views of San Diego!

A modern living area features a comfortable gray couch with accent pillows, paired with two upholstered chairs and a small dining table in the background. A natural wood coffee table is positioned in front, alongside plush ottomans on a striped rug. Bright sunlight streams through the window.

4.87 out of 5 average rating, 227 reviews

726 Steps to the Sand-Upscale Beach Cottage

A light-filled living room showcases a comfortable grey sofa adorned with patterned cushions. A simple wooden coffee table sits atop a textured area rug. The space is enhanced by a ceiling fan and warm-toned walls, providing a calm atmosphere. A dining area is visible through an opening.

4.86 out of 5 average rating, 343 reviews

Charming Beach Cottage Steps to Sand + Bikes & A/C

The exterior of the cottage features a welcoming front porch with comfortable seating. A white railing surrounds the porch, enhancing its charm. Lush greenery lines the walkway, and the entrance showcases a decorative sign, inviting guests to enjoy the serene beachside atmosphere.

4.87 out of 5 average rating, 181 reviews

Perfection! Steps to the Sand w/ Air Conditioning!

4.94 out of 5 average rating, 453 reviews

The entrance to the cottage features a light blue door framed by a neutral-colored stucco exterior. Two large windows are visible on either side, adorned with potted green plants, while a white trellis extends overhead, providing shade.

Cottage in La Jolla

Pearl 1 Cottage - La Jolla Village All sanitized

A private outdoor space features a grassy area surrounded by tall hedges. A large patio umbrella provides shade over a dining table with chairs, while additional seating chairs are arranged on the lawn. The space offers a peaceful environment for relaxation.