Pirate Cove Cottages - Vacation Rentals in Little Italy

Remodeled 1BD 1920s Craftsman Pet Friendly From US $191
         

1920's Remodeled Cottage in the Heart of Little Italy From US $198
         

7.3 (7 Reviews)
House
  • Parking
  • Security/Safety
  • Child Friendly
PRIVATE COTTAGE IN BEAUTIFUL BANKER’S HILL!!! From US $319
         

4.7 (7 Reviews)
Cottage
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
1920 Remodeled Craftsman Cottage Heart of Little Italy From US $138
         

3.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Home-y Cottage In The Heart of Little Italy From US $250
         

Luxury Places to Stay in Little Italy

Over 272+ Luxury Places to Stay in or Near Little Italy
Elegant 5BR with BBQ Balcony & City Views From US $1,661
         

New
House
  • Air Conditioner
  • Parking
  • Security/Safety
1900's Victorian Home Sleeps 22 8BDRM 3Bath From US $1,536
         

8.0 (2 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Little Italy

Over 38+ Top-Rated Vacation Rentals with a Pool in or Near Little Italy
Rooftop Villa - Little Italy From US $363
         

10.0 (1 Review)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Courtyard by Marriott San Diego Downtown Little Italy From US $161
         

Hilton Garden Inn San Diego Downtown/Bayside From US $218
         

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8.6 (1274 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Courtyard by Marriott San Diego Downtown Little Italy From US $258
         

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8.5 (253 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Homewood Suites by Hilton San Diego Downtown/Bayside From US $223
         

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8.4 (1074 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Residence Inn by Marriott San Diego Downtown From US $252
         

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8.4 (1002 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Residence Inn by Marriott San Diego Downtown From US $460
         

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8.3 (476 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Hampton Inn San Diego-Downtown From US $171
         

8.2 (2472 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Little Italy

Over 68+ Pet-Friendly Vacation Rentals in or Near Little Italy
Ocean View Loft in Little Italy near Downtown-Gaslamp From US $315
         

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9.9 (12 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
301 Amazing Sky Loft in Little Italy! From US $349
         

8.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Charming 3 BD Home in the Heart of Little Italy! From US $618
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
2 Modern Units in Heart of Little Italy! From US $442
         

10.0 (2 Reviews)
Condo
  • Air Conditioner
  • Pet Friendly
  • TV
Piccola Italia with free garage parking From US $349
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Little Italy Bungalow From US $271
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern Urban Row Home * 2 Blocks to San Diego Bay * A/C From US $503
         

9.8 (7 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Little Italy

Over 16+ Large Vacation Homes & Villas in or Near Little Italy
RK Hostel From US $80
         

6.9 (154 Reviews)
Hostel
  • Designated Smoking Area
  • TV
  • Balcony/Terrace
5BR (Sleeps 12!) Downtown Little Italy Home w/Outdoor Space From US $1,095
         

4BR (Sleeps 10!)Heart of Little Italy: Walk to Dining & Fun! From US $828
         

Modern 5 BD Rental with Spectacular Rooftop! From US $1,156
         

4BD Home in the Heart of Little Italy From US $681
         

10.0 (12 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
5BD Home with outdoor space in Little Italy! From US $737
         

9.8 (6 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
TuCasa | Luxury 4 Story Villa in Little Italy From US $742
         

Wheelchair Accessible Vacation Homes in Little Italy

Over 86+ Wheelchair Accessible Vacation Homes in or Near Little Italy
The Italian Retreat, Little Italy From US $197
         

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8.2 (11 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
La Pensione Hotel From US $138
         

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8.6 (1921 Reviews)
Hotel
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Urban Loft in Little Italy w/City View and parking From US $390
         

8.8 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
303/C Little Italy double balcony Loft/Parking From US $361
         

7.6 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
302/C Panoramic View Loft parking incl. From US $448
         

2.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Little Italy Vacation Rentals and Airbnb Places to Stay Under $200

Over 54+ Little Italy Vacation Rentals and Airbnb Places to Stay Under $200
Remodeled 1BD 1920s Craftsman 1666 From US $170
         

7.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
PodShare San Diego - Hostel From US $80
         

7.0 (87 Reviews)
Hostel
  • Air Conditioner
  • Parking
  • Security/Safety
Beautiful Little Italy home From US $156
         

New
Apartment
  • Air Conditioner
  • Security/Safety
  • Sports/Activities
2 Bedroom 2 Bath in Little Italy - Walkable to Everything From US $137
         

Little Italy 1 BDR - Cozy & Stylishn From US $165
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Little Italy

Over 137+ Instantly Bookable Vacation Homes in or Near Little Italy
Historic Gem in the Heart of Little Italy! From US $366
         

10.0 (239 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Rooftop w/Views: Modern Little Italy Townhome From US $709
         

Room U at The Dutra Inn - Little Italy From US $226
         

10.0 (11 Reviews)
Apartment
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety
4BR/5BD - Free Parking - Walk to Nightlife! From US $702
         

Room A at The Dutra Inn - Little Italy From US $373
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Stylish Little Italy Loft: Modern Urban Retreat From US $290
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace

About Little Italy Vacation Rentals

With more than 5 Little Italy vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Piratecovecottages and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Little Italy.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Piratecovecottages Little Italy, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Little Italy. Places to stay near Little Italy are 1722.22 ft² on average, with prices averaging $219 a night.

Piratecovecottages makes it easy and safe to find and compare vacation rentals in Little Italy with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Little Italy

Type Count
Cottages 3
Holiday Apartments 1
Vacation Homes 1

Use these Quick Filters to Find a Vacation Rental in Little Italy

Pro Tip: Piratecovecottages makes it easy to compare the best listings on Piratecovecottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Piratecovecottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Little Italy.

Weather in Little Italy

View the weather forecast for Little Italy before booking your Little Italy Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Little Italy Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Little Italy?

There are a lot of options in Little Italy. If you plan on staying in the Little Italy area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Little Italy:

How many vacation rentals are available in Little Italy?

Currently, the total number of properties listed in 2026 is over 5 in the Little Italy area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Little Italy.