
Holiday rentals with a pool in Hillcrest
Find and book unique homes with a pool on Airbnb
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

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.

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.

Luxe Point Loma Oasis w/ Pool, Spa & Fire Pit
The vacation of your dreams awaits at the luxury 3BR Point Loma oasis. Each of the posh bedrooms has an en-suite bathroom and access to the exquisite backyard oasis-which is complete with a pool, spa, outdoor kitchen, and fire pit area. Enjoy outdoor dining by the pool or the lovely succulent gardens throughout the property. Sleeps 8. Washer/dryer, complimentary Wi-Fi, Netflix and parking are included. Hotel quality sheets and fresh duvets are also included with your stay. No parties.

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, record player with albums. 19 speakers in the ceilings with connection to your phone for optimal happiness. Plug and play!

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!
Popular amenities for Hillcrest rentals with a pool
House rentals with a pool

Luxury Pool Haven with Views and Fireworks

The Queen House

Airbnb Luxe: The Perfect Blend of Access & Escape

Bright and spacious home with views, pool & spa.

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

Oasis with ocean views/Pool/Hot tub! Sleeps 10!

Tropical Oasis: spa, solar heated pool, waterslide

San Diego Luxury Villa: 6-BR, Pool, Hot Tub, Patio
Apartment 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

Spacious 2 BR w/ Free Parking & WiFi

Cozy clean 1 bedroom centrally located by beaches
Other holiday rentals with a pool

Literal neighbor to Balboa Park!

Treehouse Retreat in Mission Hills

Spanish Retreat! Enjoy private pool and views

Breathtaking Ocean, Bay, City & Petco Park Views

Casita Arroyo - 1 BR guesthouse with pool/hot tub

Luxury High-Rise | Downtown SD

Stunning 2BR/2BA| Plunge Pool, AC, Private

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 | $287 SGD | $260 SGD | $260 SGD | $260 SGD | $284 SGD | $297 SGD | $308 SGD | $299 SGD | $291 SGD | $258 SGD | $342 SGD | $329 SGD |
| 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 holiday rentals with a pool in Hillcrest

Total holiday rentals
Explore 70 holiday rentals in Hillcrest

Nightly prices starting at
Hillcrest holiday rentals start at $104 SGD per night before taxes and fees

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Over 2,010 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
70 of Hillcrest holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Hillcrest rentals
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- Rosarito Beach
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- SeaWorld San Diego
- LEGOLAND California
- San Diego Zoo Safari Park
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- Liberty Station
- Sesame Place San Diego
- Belmont Park
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- Torrey Pines Golf Course
- USS Midway Museum




