Waterfront holiday 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 favourite

Guest suite in Point Loma Peninsula

4.98 out of 5 average rating, 143 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.

Top guest favourite

Guest suite in Bay Park

5 out of 5 average rating, 347 reviews

Luxury Bay/Ocean view suite-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.

Top guest favourite

Bungalow in Mission Hills

4.9 out of 5 average rating, 216 reviews

☀️26’ SunDeck w/Ocean VIEWS SUNSETS! - Fast Wifi

• Perfect location • Keyless entry • Private 26’ SunDeck w/Harbor + Endless views • 902Mbps Wifi • 65” HDTV Netflix fuboTV • 2 KING Beds • Fully equipped kitchen + Kemflo h2o filtration • Easy access to nearby beaches • Private yard + BBQ • Fireplace • AC + Central Heating • Onsite washer-dryer → Minutes to scenic beaches, Little Italy, Zoo, Balboa Park NOTE: Nightclub style events and/or unauthorized large gatherings are strictly prohibited and may result in immediate cancellation.

Superhost

Guest suite in Point Loma Peninsula

4.92 out of 5 average rating, 215 reviews

Bay View Suite • Rooftop Deck + Indoor Jacuzzi

Wake up to breathtaking views of the San Diego skyline and bay from your private rooftop deck. Relax in a stylish suite with a king-size adjustable bed, spa-style indoor Jacuzzi for two, and exclusive access to a rooftop fire pit and garden corner—perfect for a romantic night under the stars. Nestled in Point Loma, one of San Diego’s most exclusive and quiet neighborhoods, just minutes from Little Italy, the airport, and the beach. Ideal for romantic getaways or peaceful stays with a view.

Guest favourite

Home in Mission Hills

4.91 out of 5 average rating, 264 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.

Superhost

Home in Downtown

4.85 out of 5 average rating, 184 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!

Top guest favourite

Guest suite in Point Loma Peninsula

4.97 out of 5 average rating, 100 reviews

Modern Ocean View Sunset Cliffs/Point Loma by PLNU

Huge 1 BR/BA + queen sofa bed, private guest suite in Sunset Cliffs area of PL/OB w/private entry, ocean/sunset views, 10 min walk to ocean. 1,000 sq ft of modern design w/glass wall garage door, large queen BR, walk-in closet, portable desk/chair & 2 patios w/1,200 sq ft! Great for couples, remote work, beach, PLNU visit/Thurs Club event! Amenities: private fire pit, fast Wifi, cable/stream apps, A/C, fans, swing, quiet neighborhood, eBikes for rent & ample free street parking.

Top guest favourite

Apartment in Mission Beach

5 out of 5 average rating, 297 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.

Top guest favourite

Loft in Downtown

4.98 out of 5 average rating, 130 reviews

Waterfront Loft | 1BR | Little Italy | Downtown

The local neighborhood is highly walk-able and perched along the San Diego Bay in Little Italy. Little Italy is the most vibrant neighborhood in downtown San Diego with a main street that abounds with restaurants, boutiques, craft beer, and wine bars all at your doorstep. This is a very urban location which brings a lot of urban noise. The unit sits adjacent the train and trolley line in the urban core. No parking provided, Ideal for guests without a car.

Guest favourite

Home in Pacific Beach

4.97 out of 5 average rating, 121 reviews

Stunning Beach House! 2 Tubs & Outdoor Shower New!

Located steps from the sand in Pacific Beach, on a serene street with gated parking, this stunning Villa redefines the word Oasis. Amazing Amenities: Hot Tub, Soaking Tub, Outdoor shower, sun lounger, Outdoor fireplace and TV, and more. All amenities are exclusively for your private use. The interior is equally impressive, featuring a Posturepedic mattress, chef's kitchen, AC, high end washer and dryer and more. Your Vacation is going to be Magic!

Guest favourite

Home in Pacific Beach

4.96 out of 5 average rating, 167 reviews

New! Bayside Bungalow - Upscale Beach Retreat!

Wake up every morning and enjoy a stroll along the water when staying at our new Bayside Retreat in Crown Point. Our recently remodeled (2022) guest house is just 1 block to the Bay and within walking distance to restaurants, bars, shopping and, nightlife. The guest house is bright and open with vaulted ceilings and brand new everything! Enjoy 600 thread count luxury cotton linens, a silky-soft down alternative duvet, and air conditioning.

Guest favourite

Cottage in North Ocean Beach

4.93 out of 5 average rating, 381 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.