Holiday 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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Superhost

Home in San Diego

4.85 out of 5 average rating, 185 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 favourite

Home in La Mesa

4.84 out of 5 average rating, 192 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, 165 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 favourite

Home in Otay Mesa

4.88 out of 5 average rating, 142 reviews

Ocean View Private Pool & Spa Home w/Putting Green

Welcome to your Private, resort style, pool and spa home with spectacular views day and night! 4 bedrooms, 3 baths (1 bedroom and bathroom with shower on main/ground level). Tropical setting, and just a short drive to major attractions like our world famous Beaches, Zoo, Sea World, Balboa Park, Downtown, Coronado, Outlet Shopping, Sesame Place and even Mexico! Soaring 18 foot ceilings in the Living room and Dining room. Outdoor dining, Putting Green, and lounges for resort-like relaxation.

Top guest favourite

Home in Mission Hills

4.93 out of 5 average rating, 241 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 favourite

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.

Guest favourite

Villa in El Cajon

4.92 out of 5 average rating, 154 reviews

Enchanted Paradise! ♨ Pool+Spa+Outdoor Kitchen ☀

Brand New Property! Massive garden of Eden style resort home with sprawling outdoor entertainment area and spacious open concept inside, perfect for large families with kids and responsible adults. Updated top to bottom with all new outdoor and indoor furniture, modern upgrades in all bedrooms and common areas. Centrally located and 20 minutes from the beach and all of SD's top attractions! 8 person hot tub, sparkling gas heated saltwater pool and new outdoor kitchen. Don't miss out!

Top guest favourite

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.

Guest favourite

Home in Spring Valley

4.96 out of 5 average rating, 142 reviews

Upscale Resort House /Views, Saltwater Pool/Spa !

This home offers Saltwater pool and Spa. Saltwater pools and Spa produce softer-feeling water. breathtaking views from its location high in the hills overlooking Rancho San Diego. In the backyard you can enjoy the sunrise from the private pool or deck or practice your putting on our putting green. The House is a mid-century modern home perched above the City. It's great for groups seeking easy access to San Diego's highlights (15 to 20 minutes to Beaches and Downtown)

Guest favourite

Home in Mira Mesa

4.96 out of 5 average rating, 135 reviews

Retreat vacation with salt water pool & hot tub

Your San Diego get-away vacation starts 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 favourite

Bungalow in El Cajon

4.85 out of 5 average rating, 102 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 favourite

Home in University Heights

4.99 out of 5 average rating, 118 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