Waterfront vacation rentals in Little Italy, San Diego

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Top-rated waterfront rentals in Little Italy, San Diego

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

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Guest favorite

Guest suite in Point Loma Peninsula

4.98 out of 5 average rating, 116 reviews

Point Loma Retreat - Steps to the Bay

Be one of the first to stay in this gorgeous Point Loma brand new house with all new finishes, AC, floor, walls, windows, lights, paintings, kitchen cabinets, counters, appliance, Full bath, walk in closet and new furniture! The space features 1 bedroom, 1 bathroom, 1 walk in storage. Living dinning and kitchen are layed out in a welcoming open space. You'll enjoy incredible access to the scenic harbor front and marina in a calm and peaceful dead end street with no traffic, high end neighbor.

Dec 23 – 30

G$34,333 GYD per night

Guest favorite

Guest suite in Bay Park

5.0 out of 5 average rating, 223 reviews

Luxury Bayview Roost Studio -San Diego/Mission Bay

Welcome to San Diego! The Bayview Roost awaits you - a newly built 465 sq. ft luxury studio with a breathtaking view overlooking Mission Bay and Sea World fireworks! Modern amenities include a full kitchen and bath with a rain shower, quartz counter tops, washer/dryer, central AC/heat, high speed Wifi, Smart TV and your own private entrance! Situated less than 10 minutes to Sea World, Little Italy, Old Town, Gaslamp, San Diego Zoo, Petco Park, La Jolla, beaches, local universities & SD trolley.

Aug 16 – 23

G$56,817 GYD per night

Guest favorite

Home in Point Loma Peninsula

4.98 out of 5 average rating, 111 reviews

Bayview Paradise

Known as the Huguette House, this luxury private single-family two bedrooms two bathrooms home in La Playa the heart of Point Loma, San Diego offers 180-degree panoramic views of the world-famous San Diego Bay and Downtown Skyline. views of the San Diego bay, marina, and Coronado Island during the day and spectacular views of the Downtown San Diego skyline at night, fully equipped kitchen, and laundry room, 2 bedroom suites with queen beds .2 luxury bathrooms, HDTV, computer desk and WFI

Feb 4 – 11

G$86,162 GYD per night

Guest favorite

Home in San Diego

4.9 out of 5 average rating, 150 reviews

Chic 1-Bedroom | Ocean Views | Steps to the Beach

Our sweet beach bungalow is in the heart of mission beach. One story up off the ground floor gives it privacy and a peak to the beautiful pacific. Wake up to waves crashing and a nice cup of coffee to take on your morning walk. Choose your destination, beach or bay: both are 1 one minute walk. This house holds so many memories for us, we know it will for you too! Please note, we do not host animals in this unit. If you would like to bring your furry friend, check out our other unit!

Mar 31 – Apr 7

G$58,806 GYD per night

Guest favorite

Condo in Pacific Beach

4.99 out of 5 average rating, 108 reviews

Luxury Oceanfront Condo with Unbelievable Views

Welcome to your Oasis! You will be completely in awe of the breathtaking views that Sunset Pacifica has to offer. This fully renovated condo features two ensuite bedrooms decorated with the beachy SoCal vibe you are looking for. Centrally located on the boardwalk and just minutes to La Jolla, Downtown, the famous SD Zoo, Embarcadero, restaurants, bars and entertainment. There is so much to do here or just lounge around poolside or on the sandy shores of the beautiful Pacific Ocean.

Jun 5 – 12

G$157,063 GYD per night

Guest favorite

Loft in Downtown San Diego

4.97 out of 5 average rating, 473 reviews

Room T at The Dutra Inn - Little Italy

“I thought about changing this whole thing to just read: Napoleon slept here. Room T is kind of like the little spoon of The Dutra. Or maybe like a precious package tucked under the building’s right arm? But no, despite popular opinion, the T doesn’t stand for tiny. Room T is big enough for your wildest ambitions and your coffee in the morning. There’s approximately 1,000 cupboards here—all presumably concealing tiny French dictators or perhaps, hidden treasures." IG: @the.dutra

Dec 3 – 10

G$48,737 GYD per night

Guest favorite

Home in Mission Hills

4.92 out of 5 average rating, 130 reviews

Modern House In The Hills | Killer Location!

Enjoy a stylish experience at this centrally-located, spacious 2 bedroom top floor retreat in lower Mission Hills, just 2 minutes north of Little Italy. Perched in one of the most prestigious & historic neighborhoods in San Diego. Be close to downtown, only 10 minutes to Mission Beach and centrally located for all the city has to offer. This is the perfect launching point to exploring San Diego, and coming home to this beautifully appointed home in this location is second to none.

Aug 13 – 20

G$108,301 GYD per night

Superhost

Home in San Diego

4.83 out of 5 average rating, 137 reviews

Little Italy 2BR Loft Near Waterfront & Convention

Discover the heart of San Diego from our spacious loft in Little Italy, the culinary gem of downtown. Perfectly situated for both business and leisure travelers, you're steps away from the waterfront, convention center, and vibrant city life. Embrace the urban experience with convenience at your doorstep, including eclectic bars and restaurants. We provide a white noise machine and earplugs, though the lower floor offers a quieter retreat. Experience the best of city living!

Apr 12 – 19

G$69,746 GYD per night

Guest favorite

Condo in Mission Beach

5.0 out of 5 average rating, 239 reviews

Ocean Front Mission Beach Penthouse!

OCEAN FRONT BLISS IN THE HEART OF MISSION BEACH! Relax and Unwind in this 3rd Floor Penthouse End-Unit Ocean Front condo with panoramic views of the Pacific ocean overlooking the Mission Beach Boardwalk! Located equidistant between Belmont Park and Crystal Pier in the HEART of Mission Beach walk to everything including restaurants, bars, nightlife, coffee shops and so much more! Enjoy meals on your private balcony and people-watching with the Pacific Ocean as your front yard.

Jan 13 – 20

G$93,564 GYD per night

Guest favorite

Guest suite in La Jolla

4.83 out of 5 average rating, 282 reviews

Sunset and waves from your private patio

La Jolla oceanfront private entrance master suite (660 sq. ft). No direct access to rocky beach below but access okay from next door park. Hot tub on the cliff tops for you only. There is roofed enclosure space with refrigertor drawers, full sink with no disposal. Restaurants, coffeeshops nearby. Perfect for anniversary celebration. We have another suite just listed, which is similar and at lower rate, and you might find it more exicting. Message us for more information.

Jul 30 – Aug 6

G$88,534 GYD per night

Guest favorite

Home in North Ocean Beach

4.97 out of 5 average rating, 394 reviews

Stunning Ocean View. Beach House. Garage/AC/Heat

Amazing ocean view and easy beach access -- while being in your own private spot with a birds-eye view of beach activity. My home (built in 2008 and well-maintained) is detached and gated-- away from crowds or shared spaces--giving you the opportunity to be safe and relaxed while taking in a stunning ocean view. My ideal guests are early-to-bed and early-to-rise to align with my neighbors in this less touristy beach area of San Diego.

Jan 26 – Feb 2

G$69,714 GYD per night

Guest favorite

Cottage in North Ocean Beach

4.95 out of 5 average rating, 299 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.

Mar 7 – 14

G$43,900 GYD per night