
Holiday rentals with a pool in Hillcrest
Find and book unique homes with a pool on Airbnb
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 $118 NZD per night before taxes and fees

Verified guest reviews
Over 2,250 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
70 of Hillcrest holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Hillcrest rentals
Top-rated rentals with a pool in Hillcrest
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

1 bedroom, 1 bath /Hillcrest/San Diego Zoo/Balboa
One bedroom, one bath with a pool in the Hillcrest/San Diego Zoo/Balboa Park /Marston Hill area. Full kitchen, queen bed, queen sleeper sofa & crib. 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). Walking to the Farmers Market. Minutes' drive to all San Diego beaches. No rent for children under 3, only a $95/stay flat fee. High chair, Pack & Play Crib, crib mattress & cover are provided

Vacation Paradise-Heated Pool+Hot Tub+FirePit+EV
Welcome to your personal resort! This is the perfect Guest House with a salt & heated pool + hot tub. Located in a super quiet & very safe neighborhood in beautiful San Diego. Drive 15 minutes to the beach, downtown, La Jolla, Zoo, stadiums, Sea World, Convention Center + more. Hike next door at Cowell Mountain or Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo, top quality finishes & furniture. Everything you need for memorable vacation! No smoking or vaping on the property.

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.

Family Oasis w/ Heated Pool
A family-friendly SD home with a private heated pool and spacious backyard for relaxing and playing. The Home ⁘ 3 Bedrooms & 2 Bathrooms ⁘ Personal A/C & Heat in Every Room ⁘ Complimentary Washer & Dryer ⁘ 2 Rollaway Beds Available Upon Request Outdoor Space ⁘ Private Heated Pool (inquire about fee) ⁘ Outdoor Shower & Wood Burning Fire Pit ⁘ Fenced Backyard ⁘ Pool Toys, Loungers, & Umbrellas Family-Friendly ⁘ Pack n’ Play & Games ⁘ Pets Welcome upon Request ⁘ Quiet Residential Neighborhood

Modern Central SD Home w/ Pool & Spa Near Beach
Experience luxury at Bay Breeze Retreat, an exclusive oasis in the heart of Mission Bay, San Diego. This stunning residence features a private salt pool, outdoor jacuzzi spa, elegant fire pit, whole house water filter system and a state-of-the-art grill and kitchen. Inside, revel in contemporary upgrades which makes the place perfect for family gatherings of up to 8 guests. Walk to Luce Bar & Kitchen and Bird Rock Coffee. Minutes from downtown and top attractions, your perfect escape awaits.

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
Unwind in your private backyard resort, featuring a heated pool, complimentary Jacuzzi, cabana, and BBQ—perfect for watching planes soar over the city skyline. Amenities: High-speed Wi-Fi, Smart TVs, and a vintage record player. Location: Minutes from Downtown, the Convention Center, and easy highway access. 🏊🏼♀️🛟Optional pool heat is available for $50/day (stays under 5 days). To ensure the best experience, heating is applied to the full duration of your stay only.

Your Modern Lux Pool Resort in the Heart of SD
Welcome to our canyon front, mountain-modern home in Hillcrest & University Heights. Just 3 blocks from the adored Vermont St. Bridge, you'll be right in the heart of Hillcrest and able to escape the city when it's time to relax. Enjoy spa-like accommodations, modern amenities, premium linens & toiletries, and sprawling outdoor spaces. Whoever you are, we are committed that you LOVE your stay.

Luxe Home w. Serene Backyard Spa
Escape to the heart of San Diego in our chic and luxurious 3-bed oasis, where upscale meets laid-back California cool. Steps from vibrant eateries, buzzing bars, and unique boutiques, this retreat offers a serene backyard with a soothing spa. Experience local attractions, beaches, and the San Diego Zoo, all a short drive away. Your ultimate San Diego adventure awaits!
Popular amenities for Hillcrest rentals with a pool
House rentals with a pool

La Jolla Beach House-Family Focused-3min to Beach

Resort Style Living with Pool, Spa, and Bay Views!

Surf Cottage w/Pool & Firepit 10min from the beach

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

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

Upscale Resort House /Views, Saltwater Pool/Spa !

Pacific Beach-Amazing Panoramic View-Heated Pool

Vacation Getaway w/ Gas Grill, Hot Jacuzzi, Pool
Condo rentals with a pool

Bay View Condo in Pacific Beach

Centrally located n UCSD/ utc-laJolla

One Bedroom Ocean Front Condo!

Enchanted Ocean Sunsets

The Endless Summer Condo!

Luxury Oceanfront Condo with Unbelievable Views

Beautifully remodeled 10th floor oceanfront condo

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

Fun and relaxation in the same location.

Treehouse Retreat in Mission Hills

Iconic Waterfall House

Breathtaking Ocean, Bay, City & Petco Park Views

Luxury High-Rise | Downtown SD

Whimsical Artist’s Retreat | Heated Pool + Spa

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

Top Floor Views of Ocean, Bay, City & Petco Park
When is the best time to visit Hillcrest?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $374 NZD | $338 NZD | $338 NZD | $338 NZD | $370 NZD | $387 NZD | $401 NZD | $389 NZD | $379 NZD | $359 NZD | $394 NZD | $425 NZD |
| 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 |
Destinations to explore
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- Rentals with pools San Diego
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- Rentals with pools United States
- Rosarito Beach
- SeaWorld San Diego
- San Diego Convention Center E Ent
- University of California-San Diego
- Petco Park
- Oceanside City Beach
- San Diego Zoo Safari Park
- Ocean Front Walk
- Pacific Beach
- Tijuana Beach
- Torrey Pines State Beach
- Balboa Park
- Coronado Beach
- San Diego Zoo
- Pechanga Resort Casino
- San Diego State University
- Liberty Station
- La Misión Beach
- Moonlight State Beach
- San Onofre Beach
- Belmont Park
- Oceanside Harbor
- Sesame Place San Diego
- Black's Beach




