Vacation rentals with a pool in Hillcrest

Find and book unique homes with a pool on Airbnb

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 ﺩ.ﺇ 257 per night before taxes and fees

  • Verified guest reviews

    Over 2,430 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 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

  • 4.7 Average rating

    Hillcrest stays receive an average rating of 4.7 out of 5 from guests

Top-rated rentals with a pool in Hillcrest

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite
A bright living space features a warm wooden ceiling and large windows. A comfortable orange sofa is paired with a wooden coffee table on a patterned area rug. The kitchen, visible in the background, includes modern appliances and white cabinetry, enhancing the cozy atmosphere.
Home in Hillcrest
4.99 out of 5 average rating, 191 reviews

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

Guest favorite
A cozy sleeping area features a spacious bed with a striped throw blanket adorned with decorative tassels. A flat-screen TV is mounted on the wall, and a small table is positioned beside the bed. Soft lighting is provided by wall sconces, creating a calm ambiance.
Guesthouse in Mission Hills
4.91 out of 5 average rating, 511 reviews

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.

Top guest favorite
A private outdoor area features a heated pool surrounded by lush green grass and modern loungers. An inviting fire pit is centrally located, with two stylish chairs positioned nearby. The backdrop includes well-maintained shrubbery and tall trees, enhancing the tranquil ambiance.
Home in Serra Mesa
5.0 out of 5 average rating, 299 reviews

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.

Guest favorite
A serene bedroom features a queen bed with a light-colored quilt. Two bedside tables with lamps are positioned on either side. The walls are adorned with various framed artworks and a large mirror, reflecting natural light from the windows.
Apartment in Greater North Park
4.79 out of 5 average rating, 484 reviews

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

Guest favorite
A living room features a luxury hanging chair suspended from the ceiling. Natural light filters through sheer curtains, illuminating a cozy seating area with a plush sofa and wooden coffee table. A 50” television is mounted above an elegant fireplace, enhancing the room's comfort.
Home in City Heights
4.94 out of 5 average rating, 147 reviews

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.

Guest favorite
Home in Mission Hills
4.95 out of 5 average rating, 246 reviews

Resort Living: Hoops, Outdoor Bar, Views, Pool+Spa

Why stay at an ordinary vacation rental when you could make memories somewhere EXTRA-ordinary? When you and your crew pull up to Casa Paradiso, typical expressions might include “Whoa!”, “OMG!” and “Can you believe this place?!” Casa Paradiso by Rental With A View in San Diego is a one-of-a-kind luxury resort home located in the ♥ of the city! Enjoy unlimited bikes, surfboards, and paddleboards—your adventure begins here. If you know San Diego, you know Mission Hills is the best place to be.

Top guest favorite
A spacious outdoor patio showcases a private pool and hot tub, surrounded by comfortable seating and a fire pit. An activity area features games such as foosball and cornhole, with lounge chairs positioned for relaxation. Lush green landscaping complements the inviting space.
Home in Bay Park
4.92 out of 5 average rating, 128 reviews

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.

Top guest favorite
The poolside area features a well-maintained saltwater pool reflecting the colors of the sunset. Comfortable seating arrangements, including lounge chairs and a cozy fire pit, are visible. Large umbrellas provide shade, and lush greenery adds to the serene ambiance.
Guesthouse in La Mesa
4.97 out of 5 average rating, 176 reviews

Vacation Paradise-Heated Pool+Hot Tub+FirePit+EV

Welcome to your personal resort! This is your private Guest House with a salt & heated pool + hot tub. Located in a very quiet & 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.

Top guest favorite
An aerial view highlights a spacious backyard featuring a solar heated pool, hot tub, and tropical landscaping. Lounge chairs are arranged around the pool, and a palapa style cabana with seating is visible, offering an inviting outdoor space for relaxation and entertainment.
Home in Bay Park
4.97 out of 5 average rating, 316 reviews

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

Resort style home with pool (unheated), hot tub (with hot tub heating fee), outdoor entertaining space, bay views, multiple patios, modern amenities, comfortable beds, and more. Convenient location to freeways, Seaworld, Mission Bay, Beaches, Downtown, Balboa Park, Airport, La Jolla and other attractions. Perfect for families and groups. Two car garage parking. 2300 square feet of indoor living and much more outdoors. Your ideal home base for enjoying all that San Diego has to offer.

Top guest favorite
A private patio area is visible, adorned with a wooden structure and comfortable seating arrangements. The sparkling pool is set at a distance, surrounded by greenery. Sunlight casts gentle shadows, highlighting the textured concrete and wooden elements in the outdoor space.
Guest suite in Hillcrest
4.89 out of 5 average rating, 141 reviews

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.

Guest favorite
A vibrant heated pool is surrounded by minimalistic landscaping, featuring tall cacti and a clean white fence. Soft lounge chairs are positioned nearby for relaxation. The clear water reflects the blue sky, creating a refreshing setting for leisure and enjoyment.
Home in Mission Hills
4.93 out of 5 average rating, 293 reviews

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.

Guest favorite
An outdoor living space is showcased, featuring a circular pool surrounded by wooden decking. Comfortable lounge seating with dark cushions and a fire pit is positioned under string lights. Umbrellas provide shade while a gas grill is visible nearby, creating an inviting atmosphere.
Home in Greater North Park
4.95 out of 5 average rating, 198 reviews

Stylish Family Home I Near Dining, Shopping + Zoo

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