Vacation rentals with a pool in Hillcrest, San Diego

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Top-rated rentals with a pool in Hillcrest, San Diego

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

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Guest favorite

Home in San Diego

4.97 out of 5 average rating, 119 reviews

Luxe Home - Heated Pool - Steps to Best Dining

In the heart of North Park, have it all, location, privacy & space, w/ this sophisticated & completely remodeled 1914 craftsman style home. Featuring a stunning outdoor paradise w/ a brand new 30 ft. Trex deck, heated pool/hot tub, resort lounge furniture, 65-inch outdoor tv, market lights & 6-burner gas grill. An open concept, 4 bed, 2.5 bath home is a true hidden gem - including a dreamy chef’s kitchen, stunning Carrera marble bathrooms, original hardwood floors & coffered boxed beam ceilings.

Guest favorite

Guesthouse in San Diego

4.97 out of 5 average rating, 188 reviews

Lovely Guesthouse in garden setting

Centrally located guesthouse on quarter acre lot in a beautiful community 5 minutes drive from restaurants, pubs, shops, library, SDSU. 15 minute drive to beaches, downtown, military bases, zoo, Balboa Park. 800sq’ cottage with great outdoor space- patio, BBQ, salt water/solar heated pool & hot tub, gardens and free range pet bunnies. Central A/C and heat. Books and games for fun down time. Relax w/SMORS and drinks in the evening around the fire pit table : ) Street parking always available.

Superhost

Guesthouse in San Diego

4.91 out of 5 average rating, 250 reviews

Green Door Cottage

Enjoy our new, fully renovated (2021) tiny Cottage which holds a timeless charm and is also filled with a modern touch. Close to all the wonderful things San Diego has to offer - beaches, downtown, the zoo, Padres games, SeaWorld, SAN airport, Old Town, SDSU, you name it! Nice sized turf yard with total privacy and an amazing back deck! Outside table and fire pit are perfect for the cool nights of San Diego. If you need more space, check out our other listing, Pink Door Craftsman (sleeps 7)!

Guest favorite

Home in San Diego

4.94 out of 5 average rating, 204 reviews

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!

Guest favorite

Guesthouse in San Diego

4.93 out of 5 average rating, 123 reviews

Modern Guest House with pool, steps to SDSU

Casita within easy walking distance to SDSU, Viejas Arena, Cal Coast Credit Union Open Air Theatre, shops, and transit. Casita includes Tempur-Pedic Queen bed and a love seat which converts to twin bed. Enjoy the peaceful canyon side garden, firetpit and pool, or relax in the hammock. Panoramic door opens completely to let in our wonderful weather and the view. Note: Pool is heated with a solar cover, comfy for swimming APR-OCT. Max 3 guests, no children/infants due to unfenced pool.

Guest favorite

Guesthouse in San Diego

4.94 out of 5 average rating, 118 reviews

Central Guesthouse w/ Private Pool & Full Kitchen

Perfect poolside retreat suitable for small families and couples! This suite 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 option, accompanied by many 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, cocktail bars, the light rail, and easy access to the I-5 highway.

Guest favorite

Condo in San Diego

4.99 out of 5 average rating, 108 reviews

Luxury Oceanfront Condo with Unbelievable Views

Welcome to your Oasis! You will be completely in awe of the breathtaking views that Sunset Pacifica has to offer. This fully renovated condo features two ensuite bedrooms decorated with the beachy SoCal vibe you are looking for. Centrally located on the boardwalk and just minutes to La Jolla, Downtown, the famous SD Zoo, Embarcadero, restaurants, bars and entertainment. There is so much to do here or just lounge around poolside or on the sandy shores of the beautiful Pacific Ocean.

Guest favorite

Guesthouse in San Diego

4.91 out of 5 average rating, 415 reviews

Mission Hills Charming suite, walkable to all.

Heart of Mission Hills, upscale area, this private guest suite, separate from the house, is perched above the pool (separate building from main house), own entrance; sure to provide privacy. 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 with Clorox as well as all linens washed. We also don’t rent back to back giving time for thorough cleaning.

Superhost

Home in San Diego

4.95 out of 5 average rating, 100 reviews

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.

Guest favorite

Guesthouse in San Diego

4.94 out of 5 average rating, 335 reviews

The BEST NEST Clean, peaceful, private, affordable

This lovely private & separate unit is comfortable, clean and convenient. Your completely private suite is accessible via your own entrance. Minutes from major attractions, away from the hustle and bustle. Full kitchen for easy meal preparation. Located in a nice usually quiet neighborhood, close to major freeways. Enjoy the gorgeous San Diego weather in the quaint outdoor patio area.

Guest favorite

Home in San Diego

5.0 out of 5 average rating, 140 reviews

Midcentury Lux 4BR home with Pool, Spa & Cabana

COMPLETELY renovated 4BR 3 Bath mid-century home with heated pool, hot tub and fire pit! We renovated the house top-to-bottom, inside and out and everything is brand new. The beds are top quality with 100% cotton sheets. 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.

Guest favorite

Guest suite in Bonita

4.86 out of 5 average rating, 289 reviews

Resort-Style Living, Pool, Close to All San Diego

Large, private air-conditioned studio attached to beautiful ranch-styled, executive home with amazing pool. Resort-style living. Unwind & relax by the pool and gardens. Close to downtown SD, Comic Con, major attractions, beaches, airport & Mexico. Coffee, tea and snacks are provided in the room for your enjoyment! Lots of off street parking. Safe neighborhood.