
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

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

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.

Quiet Spa-like Oasis in the City
Relax! This guest suite is a small & cozy oasis with a private keyless-lock entry. Enjoy the comfy Queen-size bed with an attached private shower/bath. Stroll down an outdoor walkway to an expansive patio area with gorgeous canyon views, BBQ with a Mini-Fridge, and a cabana with an additional shower. Vacation or business trips. 10-15 minutes to most SD activities, Zoo, Balboa Park, beach, malls. 15-minute walk to breweries, restaurants, music, coffee, etc. Plz, read House Rules BEFORE booking!

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.

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.

University Heights Oasis Getaway
Tucked back in the peaceful neighborhood of University Heights, this home includes a lusciously landscaped yard with a: - Pool -Hottub - BBQ -Outdoor patio furniture Perfect for both families and professionals, 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

Lionhead - Private Boutique Home
Experience boutique hotel vibes where Palm Springs meets South Beach. This "plug-and-play" retreat features a private backyard resort with a heated pool ($50/day for stays 5 days or less), Jacuzzi, cabana, and BBQ—perfect for watching planes take off over the city. Enjoy high-speed Wi-Fi, Smart TVs, and a vintage record player, all minutes from Downtown, conventions, and easy highway access.

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

The Queen House

Casa Bahia Beautiful San Diego Home 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

Modern Hilltop Home: Roomy, Views, Family-Friendly

Upscale Resort House /Views, Saltwater Pool/Spa !
Condo rentals with a pool

Ocean-Bay-Sunset View Condo in Pacific Beach!

Cozy and relaxing beach vibe 1 bedroom condo

Centrally located n UCSD/ utc-laJolla

Luxury Living Near the Beach

Gated community, parking, 250 Mbps. Save 10%/month

One Bedroom Ocean Front Condo!

Enchanted Ocean Sunsets

NEW by Seaworld, Mission Beach, Balboa Park
Other vacation rentals with a pool

Fun and relaxation in the same location.

Treehouse Retreat in Mission Hills

Literal neighbor to Balboa Park!

NEW DT Luxe King Suite with Sauna & Pool Access

*KING BED* Adorable 2bd 2ba condo, very Central

Luxury High-Rise | Downtown SD

Downtown Dream 4

Stunning 2BR/2BA| Plunge Pool, AC, Private
When is the best time to visit Hillcrest?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ812 | ﺩ.ﺇ735 | ﺩ.ﺇ735 | ﺩ.ﺇ735 | ﺩ.ﺇ804 | ﺩ.ﺇ841 | ﺩ.ﺇ870 | ﺩ.ﺇ845 | ﺩ.ﺇ823 | ﺩ.ﺇ731 | ﺩ.ﺇ966 | ﺩ.ﺇ929 |
| 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 80 vacation rentals in Hillcrest

Nightly prices starting at
Hillcrest vacation rentals start at ﺩ.ﺇ257 per night before taxes and fees

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Over 2,110 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
80 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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