
Holiday 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.

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

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.

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.

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.

Family Oasis w/ Heated Pool
A family-friendly SD home with a private heated pool and spacious backyard for relaxing and playing. The Home ⁘ 3 Bedrooms & 2 Bathrooms ⁘ Personal A/C & Heat in Every Room ⁘ Complimentary Washer & Dryer ⁘ 2 Rollaway Beds Available Upon Request Outdoor Space ⁘ Private Heated Pool (inquire about fee) ⁘ Outdoor Shower & Wood Burning Fire Pit ⁘ Fenced Backyard ⁘ Pool Toys, Loungers, & Umbrellas Family-Friendly ⁘ Pack n’ Play & Games ⁘ Pets Welcome upon Request ⁘ Quiet Residential Neighborhood

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.

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.

Beach<15min,Heated Pool,New Central AC, 4Br Family
Escape to a tranquil haven in the vibrant neighborhood of Serra Mesa. This spacious 4-bedroom, 2-bathroom home offers whole home AC, recently remodeled finishes and a custom built heated pool with deck. Ideal for families, the home has a welcoming ambiance and a backyard for outdoor gatherings, with comfortable furniture and 20ft outdoor Mural by a local artist. Location is convenient, with the Airport, Downtown SD, SD Zoo, and an array of attractions just a short 15-minute drive.

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.

Mountain View• Solar-heated Pool •HotTub •GameRoom
☀️Welcome to our fun, newly updated home in a quiet, secure neighborhood in La Mesa ☀️ 🌊Swim in our beautiful blue, solar-heated pool while enjoying an elevated mountain view, perfect for relaxation and fun. Unwind in our fantastic game room, equipped with a pool table, arcade machines and pop-a-hoop, offering endless entertainment for guest at all age. End the day in our in-home movie theater, where you can enjoy your favorite films in ultimate comfort. ☀️

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

Bright and spacious home with views, pool & spa.

Upscale Resort House /Views, Saltwater Pool/Spa !

Pacific Beach-Amazing Panoramic View-Heated Pool

Tropical Oasis: spa, solar heated pool, waterslide

Beach House w/ Private Pool & Spa mins to beach!

Vacation Getaway w/ Gas Grill, Hot Jacuzzi, Pool

Mid-Century Style Family House with Spa

Ocean View Private Pool & Spa Home w/Putting Green
Apartment rentals with a pool

Ocean-Bay-Sunset View Condo in Pacific Beach!

Bay View Condo in Pacific Beach

Ocean front condo heart of pacific beach

Centrally located n UCSD/ utc-laJolla

Enchanted Ocean Sunsets

The Endless Summer Condo!

Beautifully remodeled 10th floor oceanfront condo

Cozy clean 1 bedroom centrally located by beaches
Other holiday rentals with a pool

NEW! Hot Tub/Pool/Fire Pit/10 Mins to Beach

Fun and relaxation in the same location.

Bright 2BR | Views &Walkability

Iconic Waterfall House

Heated Pool | Steps to Bay | Roofdeck & Parking

San Diego Pool Home Oasis | Large Backyard Retreat

Breathtaking Ocean, Bay, City & Petco Park Views

Stunning 2BR/2BA| Plunge Pool, AC, Private
When is the best time to visit Hillcrest?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $376 SGD | $296 SGD | $292 SGD | $256 SGD | $280 SGD | $293 SGD | $303 SGD | $294 SGD | $287 SGD | $271 SGD | $298 SGD | $321 SGD |
| 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 holiday rentals with a pool in Hillcrest

Total holiday rentals
Explore 70 holiday rentals in Hillcrest

Nightly prices starting at
Hillcrest holiday rentals start at $90 SGD per night before taxes and fees

Verified guest reviews
Over 2,250 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
70 of Hillcrest holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Hillcrest rentals
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- Rentals with pools San Diego
- Rentals with pools San Diego County
- Rentals with pools California
- Rentals with pools United States
- Rosarito Beach
- San Diego Convention Center E Ent
- SeaWorld San Diego
- Oceanside City Beach
- San Diego Zoo Safari Park
- Ocean Front Walk
- Pacific Beach
- Coronado Beach
- Tijuana Beach
- Torrey Pines State Beach
- Balboa Park
- San Diego Zoo
- Pechanga Resort Casino
- San Diego State University
- Moonlight State Beach
- Mission Beach
- La Misión Beach
- Oceanside Harbor
- San Onofre Beach
- Liberty Station
- Belmont Park
- LEGOLAND California
- Sesame Place San Diego
- Black's Beach





