Vacation rentals with a pool in Hillcrest, San Diego

Find and book unique homes with a pool on Airbnb

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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Superhost

Home in San Diego

4.85 out of 5 average rating, 184 reviews

Spacious, Heated Pool, Kid Paradise & Near It All!

Spacious family oasis w/ tons to do for the kids! Enjoy a large backyard (rare in San Diego!) & year-round heated pool or spread out inside w/ tons of games. Perfectly located near top attractions like the Zoo & SeaWorld. Ideal for families seeking a getaway in paradise! ⭐ “If you want a pool you can swim at any time of the day this place is it...the house is near everything you want to do around San Diego!” 🏖 HIGHLIGHTS ✓ Newly remodeled ✓ Heated pool (free) ✓ Centrally-located

Guest favorite

Home in La Mesa

4.84 out of 5 average rating, 191 reviews

Sunny SD l Pool l BBQ l Pool Loungers l Sleeps 10

Escape to a fresh 4-bedroom retreat for family and friends (10 ppl max). Updated in January of 2024 with new furniture, and fixtures. Bask in the sun on the deck, take a dip in the pool. Enjoy the private and fenced backyard, BBQ, or the recently renovated and modern Kitchen. This home is perfect for vacations or remote work. Explore San Diego beaches and all the area has to offer, the most popular tourist destinations are all within a 20-30 minute drive. 20 minutes to the beach! Book with us!

Superhost

Home in Mira Mesa

4.87 out of 5 average rating, 163 reviews

LOVE~POOL~RELAXING~CHARMING~Stylish~SD Central.

Stunning vacation home with pool ( unheated) , centrally located in a lovely Mira Mesa neighborhood, just steps from dining & nightlife and close to SD beaches, airport, SD Zoo, Safari, Legoland, SeaWorld, shopping and attractions. Completely remodeled, open concept living as large dual pane windows light up the great room. An oversized island highlights a dream kitchen w/ quartz counters, SS appliances Enjoy private fully landscaped front yard and backyard with unheated pool and with patio.

Top guest favorite

Home in Mission Hills

4.93 out of 5 average rating, 240 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

Home in San Carlos

4.87 out of 5 average rating, 186 reviews

Bright and spacious home with views, pool & spa.

This beautiful and recently remodeled, open-floor plan home is conveniently located directly across from Cowles Mountain, one of San Diego's most visited hiking trails. Each bedroom has its own full bathroom. Perfectly located for the outdoorsy family. Tons of hiking and mountain bike trails are just across the street. Only 15 min. away from beaches, zoo, & Sea World. Gaslamp/Downtown is only 20 min. by car. After a day of exploring, come home to a newly-built, salt-water pool and spa.

Top guest favorite

Home in Bay Park

4.98 out of 5 average rating, 269 reviews

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

Resort style home with a solar heated pool, hot tub, outdoor entertaining space, bay and ocean 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 included. 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

Home in North Park

5 out of 5 average rating, 107 reviews

3 BR Urban Oasis with Pool and Spa in Great Area

This special place is close to everything, making it easy to plan your visit. The charming, walkable, and historic neighborhood of University Heights provides a wonderful park, restaurants, coffeehouses, ice cream shop, bars, and markets nearby. Within 2 miles from the San Diego Zoo and historic Balboa Park. 15 minutes by car to Sea World, beaches, or downtown. The open plan of the communal areas of the house makes it a great space for spending quality time with friends or family.

Superhost

Home in Allied Gardens

4.89 out of 5 average rating, 233 reviews

San Diego Retreat / Cal King x 2 / Pool, Parking!

Welcome to our charming single-story, 1,205 sq ft vacation retreat, centrally located in San Diego! Professionally cleaned for your comfort, the home is perfect for outdoor living with a pool, deck, and fire pit. Enjoy fast Wi-Fi, 4 smart TVs, a California King bed in the primary and second bedrooms, and double bunk beds in the third. Off-street parking is available, and it's a short walk to restaurants, grocery stores, coffee shops, and breweries. Pets are welcome fee applies.

Guest favorite

Home in San Diego

4.95 out of 5 average rating, 186 reviews

Stunning San Diego Home w/Pool,Spa,Outdoor Oasis

Soak up the sun at this 4 bedroom, 2 bathroom, fully gated estate with great amenities making it an entertainers delight.. Boasting a large pool for enjoying the California sunshine in addition to a 6 person jetted therapy spa and a outdoor inferred sauna. Home has a game room with a beautiful pool table and there is a ping pong table in the large laundry room. Backyard also has a large beach type area with a fire pit and outdoor seating areas.

Top guest favorite

Home in Mira Mesa

4.96 out of 5 average rating, 134 reviews

Retreat vacation with salt water pool & hot tub

Your San Diego get-away vacation start easily from this well-placed Mira Mesa comfy home: 🚗 15 mins to UCSD, La Jolla and Del Mar beaches 🚗 25 mins to Sea World , Balboa park, San Diego Zoo, Downtown 🚗 30 mins to Legoland, Carlsbad We’ve got everything you need for a great stay! Relax and enjoy in a resort-style saltwater pool and spa. The pool is solar-heated, so temperature may vary depending on sunlight received.

Guest favorite

Bungalow in El Cajon

4.85 out of 5 average rating, 100 reviews

Stylish Relaxation-Panoramic Views-Private OASIS!

~BRAND NEW DRIVEWAY~Perched high on granite hills, our comfy, stylish bungalow is perfect for a quiet getaway in San Diego. Brew your morning coffee and stroll to the pool to let the expansive views of the city fuel your daily adventures. Host a barbeque in the spacious, private backyard after your day at the beach. Cozy up in the recliner loveseat and enjoy the big screen 4k smart TV (with cable). 420 Friendly!

Guest favorite

Home in University Heights

4.99 out of 5 average rating, 116 reviews

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

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What guests are saying

Solar-Heated Pool w/View, 15 mins to Everything!

5 out of 5 average rating, 19 reviews7 months ago

Shane’s place was above and beyond fantastic! Everything was perfect from the outside oasis, to the immaculate cleanliness throughout, to great location! Also - Shane’s communication was sublime and we had absolutely no issues! I couldn’t recommend Shane’s place enough and if we are ever needing a place to stay in the area we wouldn’t hesitate to book!

Home in Allied Gardens

What guests are saying

Modern Oasis - Pool, Spa, Great Location 5BR/4BA

4.92 out of 5 average rating, 147 reviews2 weeks ago

We had a wonderful stay! The house and backyard were incredibly spacious—plenty of room for both kids and pets to play and enjoy themselves. It was such a treat to have both a hot tub and a pool, especially since the weather was on the chillier side during our weekend. The neighbors have dogs, but they were friendly and didn’t bother us or our pup, which we appreciated. We loved that the home was walking distance to a grocery store, a pharmacy, and Hilltop Park which is dog-friendly. The neighborhood itself is very walkable and pet-friendly, something our whole family truly enjoyed. Overall, this was a memorable and comfortable place to stay for our multigenerational family vacation. We’d definitely return!

Home in Chula Vista

What guests are saying

Casita w/Private Pool, King Bed, Full Kitchen!

4.93 out of 5 average rating, 153 reviews1 month ago

Jayne's place was the perfect launching pad to explore San Diego and the surrounding area! We were 15 minutes from places like the zoo and Coronado, and we even took a day trip up to Laguna Beach. It was amazingly well outfitted, too: sunscreen, beach towels, a cooler, beach blankets & chairs--all of which made it so easy to spend a day at the beach without needing to lug our things across the country for a short trip! The airbnb itself is absolutely lovely and even more spacious than it appeared in pictures. Though it was too chilly to enjoy the pool, we had some lovely mornings sitting outside with our coffee. Thank you, Jayne!

Guesthouse in Mission Hills

What guests are saying

Private Pool & Hot Tub-walk to beach, pet friendly

4.69 out of 5 average rating, 32 reviews2 weeks ago

Kimberley’s place was amazing! A group of us came out for a bachelor party and we felt right at home. Fantastic sleeping arrangements, a cozy back yard area, and all the amenities we needed! I recommend Kimberley’s place to anyone looking for a peaceful stay in beautiful San Diego.

Home in Point Loma Peninsula

What guests are saying

Modern Retreat w Pool, Game Room

5 out of 5 average rating, 6 reviews3 months ago

This has to be my favorite Airbnb of all time, and I’ve been staying in them for almost a decade. Communication was proactive, prompt, and the host was always available. The house was very clean and had everything listed and more. The kitchen, bathrooms, and linens were well stocked, they had everything I needed for a week stay with my family. I really appreciated the host’s willingness to accommodate all my requests. I highly recommend and would stay again. There was a little street and neighbor noise but nothing that kept me up, and as a plus I didn’t have to feel bad about having guests chatting around the wonderful fire pit and game room in the evenings.

Home in San Diego

What guests are saying

An Oasis,Heated Pool, JQZ,Grill,Ocean&MTN View

4.9 out of 5 average rating, 123 reviews1 month ago

Property was accurate to the pics and description. Very close to a plaza with grocery, restaurants, coffee, etc. Highway access was a breeze and only 2 minutes from the property. This made it easy for our ventures around San Diego. The house was private and outside area with pool and hot tub were sublime. We enjoyed most afternoons hanging outside soaking in a great view of San Diego skyline in the distance. Navid was an excellent host. Very prompt to reply and proactive with many recommendations for our family. If we travel to San Diego in the future, I would not hesitate to book this property again.

Home in Chula Vista

What guests are saying

Recently Renovated - Pool, Spacious, Kitchen

4.88 out of 5 average rating, 72 reviews1 week ago

Very accommodating for a huge group (around 10-12 people) and the perfect setting to bring your family or friends for a weekend getaway in San Diego. I brought my college friends here to celebrate my birthday weekend and it was perfect to have a place that has a warm, secure, clean, and homey feel. Backyard is also an amazing chillout spot with a firepit and a pool. Definitely would return here in the future if I were to book an Airbnb in San Diego again.

Home in San Diego

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