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 San Diego

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 20 – 27

R2,937 ZAR 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.

Sep 6 – 13

R3,962 ZAR per night

Guest favorite

Cottage in North Ocean Beach

4.92 out of 5 average rating, 132 reviews

Oceanfront Cottage ON Beach w/ Prvt. Yard & Garage

Imagine waking up to the sound of the ocean and the smell of the ocean air. You are ON the sand, beachfront in this cottage. Enjoy your coffee on the patio or on the front porch as you plan your day of beach fun & relaxation. The private side yard & private garage are yours to enjoy away from other beach goers if you want your own space, or you can get out there on the beach & enjoy the water, waves & sand! The choice is yours. This Ocean Beach property is the perfect location for your holiday!

Dec 1 – 8

R7,647 ZAR per night

Guest favorite

Home in San Diego

4.98 out of 5 average rating, 110 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

Apr 3 – 10

R7,822 ZAR per night

Guest favorite

Home in Mission Beach

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!

Apr 17 – 24

R4,747 ZAR per night

Guest favorite

Condo in San Diego

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.

Sep 20 – 27

R13,416 ZAR 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 4 – 11

R4,332 ZAR per night

Guest favorite

Home in San Diego

4.91 out of 5 average rating, 128 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.

Apr 14 – 21

R8,906 ZAR per night

Superhost

Home in Downtown 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!

Oct 2 – 9

R5,537 ZAR per night

Guest favorite

Condo in San Diego

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.

Dec 9 – 16

R8,210 ZAR per night

Superhost

Loft in Downtown San Diego

4.84 out of 5 average rating, 134 reviews

Amazing 1bd In Heart of Little Italy!

An Urban retreat in San Diego's most walkable neighborhood. This elegant one bedroom loft has high ceilings on the lower floor. Panoramic views from either balcony. Located in the heart of Little Italy surrounded by the city's best bars, breweries, restaurants, and coffee shops. Stroll through the Farmer's Market on a Saturday morning, jump in an uber to Petco Park/Convention Center, or walk down to the waterfront park, Harbor and Downtown.

Oct 27 – Nov 3

R3,883 ZAR per night

Guest favorite

Home in San Diego

4.97 out of 5 average rating, 393 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 1 – 8

R8,014 ZAR per night