
Vacation rentals with a pool in Hillcrest
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Top-rated rentals with a pool in Hillcrest
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

Casita w/Private Pool, King Bed, Full Kitchen!
Perfect poolside retreat suitable for small families and couples! The pool house boasts a fully-equipped kitchen, a private pool, front patio and sunbathing deck! You'll enjoy a luxurious king-size bed and a convenient full-size fold-out couch, perfect for kids! Plus, all the amenities necessary for a memorable stay. Located in one of San Diego's most central neighborhoods of Mission Hills, you're just a stroll away from restaurants, Old Town, the light rail, and easy access to the I-5 highway!

Custom Guesthouse, Balboa Park/Zoo/Hillcrest& pool
2021 CUSTOM guest home with pool in Hillcrest/San Diego Zoo/Balboa Park area. Full kitchen, a queen bed, a queen sleeper sofa, and a 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 Sprouts. Minutes' drive to San Diego beaches. No rent for children under 3, only $95/stay. High chair, Pack & Play/Crib, crib mattress, and cover are provided.

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.

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.

Heated Pool | Renovated 3BR Home | Backyard Oasis
⁘ Heated Pool in Secluded Backyard (*see notes*) ⁘ Newly Renovated Craftsman Home ⁘ Outdoor Shower & Wood Burning Fire Pit ⁘ 3 Private Bedrooms & 2 Bathrooms ⁘ Green, Modern Decor ⁘ Free Local Coffee ⁘ Pack n’ Play ⁘ Personal A/C & Heat in Every Room ⁘ Fully Stocked Kitchen ⁘ Outdoor Lounge Areas ⁘ Complimentary Washer & Dryer ⁘ 5 min Walk to local Coffee, Bars, Restaurants ⁘ 1 Block to Grocery and Liquor Stores ⁘ 3 Miles to SD Zoo & Balboa Park ⁘ 3 Miles to Gaslamp/DT ⁘ 8 Miles to Ocean Beach

Lionhead - Private Boutique Home
Heated pool, spa, cabana and views. Boutique hotel vibes in San Diego. Palm Springs meets South Beach with a splash of groovy. Location is perfect for Downtown, conventions, shows in town. Highway friendly. Private backyard for bbq, food, drinks and relaxing. Pool is heated with cozy spa to relax and watch the planes take off. Hi speed Wifi, smart TV's, HBO, NFL Package, record player with albums. 19 speakers in the ceilings with connected to your phone for optimal happiness. Plug and play!

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.

La Jolla Beach House-Family Focused-3min to Beach
Welcome to the Bird Rock Beach House! This delightful boho beach-inspired house is the perfect home for your San Diego/ La Jolla family getaway. You're minutes from La Jolla Cove, Windansea Beach, Mission Bay, and Mission Beach. You can explore downtown La Jolla & Garnet Avenue, which both offer a variety of restaurants, nightlife, and shops. Or you can head 5 minutes north to the world-renowned La Jolla Cove to see the playful seals who also call this place home. No parties/events

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

Midcentury Lux 4BR home w Pool/Spa/Cabana/Firepit
COMPLETELY renovated 4BR 3 Bath mid-century home with heated pool, hot tub and fire pit in totally private backyard retreat. We renovated the house top-to-bottom, inside and out and everything is brand new. The beds are top quality with very high quality 100% cotton sheets and bath towels. The house is centrally located in a safe, friendly neighborhood and has beautiful mountain views in the back. Additionally, we do not charge any fees for anything!

Spacious North Park Home - Walk to Dining & Shops
Welcome to Casa Clandestino🎋 Located in North Park, this fully remodeled 1914 Craftsman offers the perfect blend of location, privacy, and style. Enjoy a stunning outdoor area with a new 30 ft. Trex deck, heated pool/hot tub, resort furniture, 65-inch outdoor TV, market lights, and a 6-burner gas grill. Inside, find 4 beds, 2.5 baths, a chef’s kitchen, Carrera marble bathrooms, original hardwood floors, and coffered ceilings.
Popular amenities for Hillcrest rentals with a pool
House rentals with a pool

Modern Central SD Home w/ Pool & Spa Near Beach

Bright Contemporary 5-Bedroom Oasis, Pool and Yard

The Queen House

North Park Craftsman Oasis with Pool

Eco-Friendly Mount Soledad Pad with Views and Heated Pool

Bright and spacious home with views, pool & spa.

Mid-Century Modern and Contemporary House

5m to Zoo & pool- The San Diego Poolside Paradise
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!

Comfortable & convenient accommodation @ San Diego

Enchanted Ocean Sunsets

Beautifully remodeled 10th floor oceanfront condo

Spacious 2 BR w/ Free Parking & WiFi
Other vacation rentals with a pool

Treehouse Retreat in Mission Hills

Literal neighbor to Balboa Park!

Breathtaking Ocean, Bay, City & Petco Park Views

Casita Arroyo - 1 BR guesthouse with pool/hot tub

Luxury High-Rise | Downtown SD

Modern Sky Oasis in Downtown SD

Designer Penthouse | 41st Floor | 2 Kings + Views

Modern 3 bed/ 3.5 bath Townhome in Little Italy
When is the best time to visit Hillcrest?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | 
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$46,227 GYD | G$41,834 GYD | G$41,834 GYD | G$41,834 GYD | G$45,809 GYD | G$47,900 GYD | G$46,018 GYD | G$45,181 GYD | G$41,834 GYD | G$41,625 GYD | G$55,012 GYD | G$52,920 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 Hillcrest

Total vacation rentals
Explore 70 vacation rentals in Hillcrest

Nightly prices starting at
Hillcrest vacation rentals start at G$16,734 GYD per night before taxes and fees

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

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
70 of Hillcrest vacation rentals include wi-fi access

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