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Holiday rentals in Hillcrest

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Top-rated holiday rentals in Hillcrest

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
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.
Guest house in Mission Hills
5 out of 5 average rating, 234 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!

Top guest favourite
An outdoor seating area features a rustic fireplace, surrounded by lush greenery. Wooden chairs are arranged around a rectangular table on a spacious patio, inviting relaxation in a natural setting. The area is neatly landscaped, with a blend of grass and garden elements.
Flat in Hillcrest
4.99 out of 5 average rating, 119 reviews

San Diego at your doorstep

Relax with the family at this peaceful place to stay. Studio apartment furnished with queen bed and queen sofa sleeper enhanced w/ a fully enclosed outdoor living space which includes an outdoor kitchen, fireplace, washer and dryer. Child and dog friendly. Located in a quiet neighborhood a fifteen minute stroll from the SD Zoo, Balboa Park and Hillcrest. Close to public transportation. A fifteen minute drive to beaches, downtown SD, the airport, harbor, and little Italy. Free parking and WiFi.

Top guest favourite
A light-toned sofa is accompanied by decorative pillows featuring textured patterns. A small side table holds stacked books, and a brass lamp with a fabric shade provides soft lighting. Natural light filters in through the window, enhancing the cozy atmosphere of the living space.
Bungalow in Hillcrest
4.96 out of 5 average rating, 363 reviews

Spanish Revival 1920s Bungalow - Patio - Alcazar Court

• 1924 Spanish Revival Bungalows - Alcazar Court - Nestled in the heart of the city in historic Hillcrest - with cafes, bars, and shops • Fully equipped 1 bd 1 ba bungalows complement shady olive tree-lined patios - guests can enjoy coffee in the morning - glass of wine in the afternoon. Enjoy the charm and tranquility of a bygone era and convenience of modern amenities, • Explore nearby Balboa Park, home to 16 museums and performing arts venues, as well as the world-famous San Diego Zoo.

Top guest favourite
A charming cottage is set within a lush garden, featuring a variety of tropical plants and vibrant flowers. The pathway leads to the entrance, framed by palm and cacti, inviting guests to explore the serene outdoor space.
Guest suite in University Heights
4.98 out of 5 average rating, 813 reviews

MIKE'S PLACE - A PRIVATE COTTAGE

The cottage features full amenities that include: Tempurpedic™ queen-size bed. Wi-Fi, Smart TV, air conditioning, refrigerator, microwave, wet bar, coffee maker, toaster, and iron. Window seat for sitting, reading or lounging. Private entrance and patio connecting to a courtyard and Japanese garden. Spacious bathroom with 12 foot high tiled shower. French doors open to a private sitting area. If the days are booked in the cottage we might have an opening at, Mikes House and Garden.

Superhost
The open-concept living area presents a modern design with high ceilings and large windows offering views of the outdoors. A comfortable couch is accompanied by a chair and coffee table, while a dining table accommodates four. Natural light fills the space, highlighted by polished concrete floors.
Loft in Hillcrest
4.8 out of 5 average rating, 231 reviews

Modern Penthouse -Walk to Everything in Hillcrest

Penthouse loft in recently built ultra-modern building. Minimal and clean, but with all of the essentials. Gorgeous Sunset and neighborhood views from large private terrace. Paid reserved parking available. Conveniently located in the heart of Hillcrest, only 2 blocks to Whole Foods, Trader Joes, Ralphs grocery store, and many great restaurants, bars and boutique shops. Other nearby attractions include Balboa Park, Downtown San Diego, SeaWorld, The San Diego Zoo, and Mission Beach.

Guest favourite
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
4.97 out of 5 average rating, 230 reviews

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!

Top guest favourite
A cozy living area features a navy blue sofa adorned with yellow and white cushions. Natural light floods in through two windows, illuminating the warm wooden floors. Decorative elements include a gold-framed mirror and a stylish floor lamp, enhancing the space's modern appeal.
Home in San Diego
4.95 out of 5 average rating, 438 reviews

Mid-Century Retreat Hillcrest, Parking, A/C

This 2nd floor retreat sits in a prime location of Hillcrest, a highly desirable area in San Diego. It is very bright, quiet, and private and sits directly behind our house(pictured) with no common walls. You are within walking distance to "The Heart of Hillcrest" where you will discover many fabulous restaurants, coffee and boutique shops, and so much more. We are a short Uber drive to downtown and everywhere else San Diego has to offer. We hope you stay with us soon!

Guest favourite
An outdoor patio is surrounded by lush greenery, featuring vibrant flowers and ferns. A rustic wooden feature stands to one side, complementing the warm-toned brick flooring. A large glass door provides access to the interior, inviting natural light into the space.
Guest house in Hillcrest
4.9 out of 5 average rating, 229 reviews

Relaxing Oasis - short walk to shops & recreation

The Zen Den- This small oasis boasts a location that offers the best of both worlds: a quiet sanctuary for some tranquil R&R, and close proximity to San Diego’s best nightlife, sightseeing, and recreation. The studio opens up to an outdoor patio perfect for San Diego’s sunny and 70 weather. Your blissful retreat is located one block from the bustling metro district of Hillcrest with coffee shops, restaurants, parks, walking/running trails, and more.

Guest favourite
A serene courtyard features a prominent tree with sprawling branches, offering shade over a wooden deck. A Zen Buddha statue sits peacefully on the deck, surrounded by lush greenery and decorative plants, creating a calming atmosphere. Stairs lead to the upper levels of the property.
Flat in Hillcrest
4.96 out of 5 average rating, 523 reviews

Hillcrest #2 Cozy Private Balcony ZenGarden Garage

Heat up the cherry red kettle or complementary coffee and indulge in a morning snack from your private balcony, overlooking the serene Zen garden, and listening to the zen fountain, creating a chilled ambience. Zen Buddha, awaits your exit and every arrival to the property, whether retuning from the eclectic Hillcrest nightlife, or a scenic stroll through Balboa Park, with its many museums, gardens, fountains, restaurant and coffee shops.

Top guest favourite
The inviting entrance features a covered porch adorned with a vibrant yellow door. Succulents and greenery enhance the landscape, complemented by a palm tree nearby. The porch area includes seating, providing a welcoming atmosphere for relaxation.
Home in San Diego
4.96 out of 5 average rating, 139 reviews

The Cozy Craftsman

Escape to this serene, stylish retreat. Built in 1935, this Craftsman-style home exudes timeless San Diego charm. Perfectly situated in University Heights, bordering Hillcrest and North Park, you’ll be close to restaurants, cafés, grocery stores, public transportation, the San Diego Zoo, and Balboa Park. This 650 sq ft home has been renovated inside and out, and equipped with everything you need for a comfortable stay!

Guest favourite
A spacious living area features a comfortable sofa and a large mirror reflecting the room. A coffee table with a decorative tablecloth and a vase of pink flowers serves as a focal point. Natural light streams in through the nearby window, illuminating the wooden floor and light-colored walls.
Home in Hillcrest
4.92 out of 5 average rating, 713 reviews

Beautiful Quiet 1 Bedroom Flat w/ A/C in Hillcrest

- A beautiful & quiet/peaceful street - Early Luggage drop off - Walking distance to Balboa Park, trendy restaurants, gym, hiking trails, San Diego Zoo, Grocery store - Central A/C - Bright unit, large private patio deck - Brand new high end appliances -Easy freeway access: 10 min to SeaWorld, Downtown, Airport, MCAS, MCRD -Free dedicated parking -Streaming services subscription

Guest favourite
Guest house in Hillcrest
4.97 out of 5 average rating, 193 reviews

Luxury Studio W/ Garden View in Heart of Hilcrest

Charming Hidden Gem Studio in the Heart of Hillcrest Discover this hidden gem – a cozy, French-inspired studio casita with elegant furnishings and a private, furnished patio. Enjoy a fully equipped kitchen, a spacious open living and sleeping area, and an attached deck overlooking the tranquil canyon. Perfect for a peaceful retreat just steps from the vibrant Hillcrest scene.

Popular amenities for Hillcrest holiday rentals

When is the best time to visit Hillcrest?

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Avg. price$179 SGD$178 SGD$175 SGD$179 SGD$184 SGD$196 SGD$227 SGD$201 SGD$173 SGD$182 SGD$191 SGD$199 SGD
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Quick stats about holiday rentals in Hillcrest

  • Total holiday rentals

    Explore 480 holiday rentals in Hillcrest

  • Nightly prices starting at

    Hillcrest holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 40,030 verified reviews to help you choose

  • Family-friendly holiday rentals

    180 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 140 rentals that welcome pets

  • Holiday rentals with a pool

    80 properties feature pools

  • Rentals with dedicated workspaces

    270 properties have a dedicated workspace

  • Wifi availability

    480 of Hillcrest holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Hillcrest rentals

  • 4.8 Average rating

    Hillcrest stays are highly rated by guests – averaging 4.8 out of 5!

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