
Vacation rentals with a pool in Little Italy
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Little Italy
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Private 1 BR Paradise retreat
Private, yet central. It is your exclusive paradise retreat to enjoy from your spacious 1 bedroom guest house located on the lower level of our home. Hang out in the expansive and private backyard with pool, different sitting areas and covered BBQ room. Or maybe a workout in the gym. Centrally located in the Village of La mesa. Just a 1/4 mile jaunt into the quaint village with its numerous assortments of dining options, stores and trolley station. Freeway close to beaches, downtown and airport

Custom Guesthouse, Balboa Park/Zoo/Hillcrest& pool
2021 CUSTOM guesthouse with pool in Hillcrest/San Diego Zoo/Balboa Park /Marston Hill area.Full kitchen , a queen bed, a queen sleeper sofa & crib. Full bath, indoor/outdoor dining, WiFi, smart TV, pool, AC/heating, BBQ& free parking. Walking to restaurants/bars/shops/stores (Trader Joe's, Ralph's & Whole Foods). Under a mile to Farmers Market. Minutes' drive to all San Diego beaches. No rent for children under 3, only $95/stay. High chair, Pack & Play Crib, crib mattress & cover are provided

On park. 1 bed apt.has air & small kitchen+w&d
Apt is UPSTAIRS on park side. Queen bed in bedroom. 2 XL twin beds in living room. OLD unit. NOT for those who want modern perfection. TIGHT parking for 1 small car. Walk to brewery, bars, restaurants &coffee shops. Close to zoo, downtown and Hillcrest. Dogs considered. Tempurpedic Bed and 2 Twin beds. Full kitchen, W&D, , WiFi and free smaller size car parking ..not big trucks yes limit 2 dogs and they must be sociable dogs visiting must be walked not left alone all day or all night

The Endless Summer Condo!
Let your worries drift away at this 6th floor corner condo with panoramic ocean views! With floor to ceiling windows throughout, you'll feel like you're floating above the sea! Leave your toes in the sand or walk to PB's best restaurants and attractions in minutes! When you're done exploring, put on a Beach Boys record while having dinner with the family amid a golden sunset..ah the good life! Create cherished memories that will linger long after the sun sets, here, at The Endless Summer Condo!

Mission Hills Charming suite, walkable to all.
Heart of Mission Hills, upscale area, this private suite, separate from the house, is perched above the pool (separate from main house), own entrance, room has walkin closet, small fridge, swivel TV, electric fireplace to warm you up. We are minutes from airport, walking distance to coffee & restaurants and central to all of SD. Please note this property is wiped down after each visit and steamed, as well as all linens washed. We also don’t rent back to back giving time for thorough cleaning.

Midcentury Lux 4BR home w Pool/Spa/Cabana/Firepit
VERY PRIVATE, COMPLETELY RENOVATED 4BR 3 Bath mid-century home with heated saltwater pool, hot tub and fire pit in totally private backyard retreat. Redone top-to-bottom, inside/out with everything new. The beds are top of the line with very high quality 100% cotton sheets and bath towels. Conveniently we are centrally located in a safe, friendly neighborhood with beautiful mountain views in the back. We never charge any fees - as we want to provide the experience we hope to get when traveling.

Designer Luxury Rental With Pool
Welcome to Wander Haven, a luxury central rental. With it’s on trend design, custom built stock tank pool, array of amenities and thoughtful touches throughout, you won’t ever want to leave. But when do you do decide to venture out and explore all that beautiful San Diego has to offer, you will find the central location gets you to anywhere you want to be in minutes. You’re 15 minutes or less from beaches, downtown, balboa park, sea world, the zoo and hundreds of amazing bars and restaurants.

Luxury Oceanfront Condo with Unbelievable Views
Welcome to your oasis! Prepare to be awestruck by the breathtaking views at Sunset Pacifica. This fully renovated condo features two ensuite bedrooms with the beachy SoCal vibe you desire. Ideally located on the boardwalk, you're minutes from La Jolla, Downtown, the San Diego Zoo, Embarcadero, and top restaurants, bars, and entertainment spots. Whether you're in the mood for exploration or relaxation, you'll find it here- lounging poolside or on the sandy shores of the stunning Pacific Ocean.

Beautifully remodeled 10th floor oceanfront condo
Located on the 10th floor of the beautiful Capri by the Sea in Pacific Beach, this beautifully remodeled one bedroom condo has unbelievable views through its floor to ceiling windows. All kitchen amenities, beach toys, big screen TV, Cable, WiFi, one parking spot in gated lot with option for more. Steps to beach, short walk to lots of restaurants and bars. Resort style complex offering 360 degree view roof deck, gas BBQ, secure private pool and spa, hot water beach shower, and 24-hr security.

Casa De Colores
Need some color in you life? Come stay in our one of a kind home- groovy wall mural, bright decor, rainbow speckled floors. Tucked back in the peaceful neighborhood of University Heights, this home includes a lusciously landscaped yard with a: - Pool -Hottub - BBQ -Outdoor patio furniture Our property also offers the ultimate in convenience: - Acclaimed restaurants and cafes are just minutes away - Close to the Airport, Zoo, Balboa Park, and Downtown - Close to many world-class beaches

Hillcrest canyon home casita with pool access
Stay in a private canyon home in Hillcrest with pool access -just a few miles to the airport, downtown and little Italy. Walk to your favorite bars and restaurants in Hillcrest and Mission Hills, or explore Balboa Park, the world famous San Diego Zoo, and many of the nearby beaches, which are only a 10 -20 minute drive away. You will be 3 miles away from the Convention Center. My home is centrally located within 2 miles from the airport and almost everything is a 10 minute drive away.

Vacation Paradise-Heated Pool+Hot Tub+FirePit+EV
This is your perfect Guest House with a salt & heated pool & hot tub. We are located in a super quiet & very safe neighborhood in beautiful San Diego, 15 minutes drive to beaches, Downtown, La Jolla, Zoo, Stadiums, Sea World, Convention Center + more. Hike next door at Mission Trails & Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo and top quality finishes and furniture. Everything you need for memorable vacation! No smoking or vaping on the property.
Popular amenities for Little Italy rentals with a pool
House rentals with a pool

3BR Urban Oasis with Pool and Hot Tub in San Diego

Bright Contemporary 5-Bedroom Oasis, Pool and Yard

Casa Bahia Beautiful San Diego Home with Pool

Entertainers Dream Pool Home

Eco-Friendly Mount Soledad Pad with Views and Heated Pool

Bright and spacious home with views, pool & spa.

Dream Vacation! Sunny 3 Bedroom Home!

BEACH 5 MINS | Heated Salt Water Pool+Spa+Firepit
Condo rentals with a pool

Bay View Condo in Pacific Beach

Ocean front condo heart of pacific beach

Centrally located n UCSD/ utc-laJolla

One Bedroom Ocean Front Condo!

Enchanted Ocean Sunsets

Spacious 2 BR w/ Free Parking & WiFi

Cozy clean 1 bedroom centrally located by beaches

Oceanfront Elegant Condo - Remarkable Amenities
Other vacation rentals with a pool

Studio | King Bed, Pool, AC, Attractions

Treehouse Retreat in Mission Hills

Bright 2BR | Views &Walkability

Oceanfront Sky View - Pacific Beach Condo

North Park Craftsman Oasis with Pool

Amazing Apartment, Free downtown parking!

Breathtaking Ocean, Bay, City & Petco Park Views

Stunning 2BR/2BA| Plunge Pool, AC, Private
When is the best time to visit Little Italy?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$39,333 GYD | G$52,304 GYD | G$52,304 GYD | G$47,492 GYD | G$40,170 GYD | G$37,868 GYD | G$47,283 GYD | G$48,329 GYD | G$45,191 GYD | G$45,400 GYD | G$41,006 GYD | G$41,634 GYD |
| Avg. temp | 15°C | 15°C | 16°C | 17°C | 18°C | 20°C | 21°C | 22°C | 22°C | 20°C | 17°C | 14°C |
Quick stats about vacation rentals with a pool in Little Italy

Total vacation rentals
Explore 130 vacation rentals in Little Italy

Nightly prices starting at
Little Italy vacation rentals start at G$14,645 GYD per night before taxes and fees

Verified guest reviews
Over 1,050 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wi-Fi availability
130 of Little Italy vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Little Italy rentals

4.9 Average rating
Little Italy stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
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- Rosarito Beach
- Oceanside City Beach
- LEGOLAND California
- San Diego Convention Center E Ent
- SeaWorld San Diego
- University of California-San Diego
- San Diego Zoo Safari Park
- Petco Park
- Ocean Front Walk
- Torrey Pines State Beach
- Tijuana Beach
- Coronado Beach
- Pacific Beach
- Balboa Park
- San Diego Zoo
- Moonlight State Beach
- La Misión Beach
- Liberty Station
- Belmont Park
- Oceanside Harbor
- Sesame Place San Diego
- Coronado Shores Beach
- Black's Beach
- Torrey Pines Golf Course




