
Holiday rentals with a pool in Hillcrest
Find and book unique homes with a pool on Airbnb
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
2021 CUSTOM guesthouse with pool in Hillcrest/San Diego Zoo/Balboa Park /Marston Hill area.Full kitchen , a queen bed, a queen sleeper sofa & crib. Full bath, 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). Under a mile to Farmers Market. Minutes' drive to all San Diego beaches. No rent for children under 3, only $95/stay. 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.

Resort Style Living with Pool, Spa, and Bay Views!
Resort style home with pool, hot tub (with heating fee), 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.

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.

Vacation Paradise-Heated Pool+Hot Tub+FirePit+EV
This is your perfect Guest House with a salt & heated pool & hot tub. We are located in a super quiet & very safe neighborhood in beautiful San Diego, 15 minutes drive to beaches, Downtown, La Jolla, Zoo, Stadiums, Sea World, Convention Center + more. Hike next door at Mission Trails & Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo and top quality finishes and furniture. Everything you need for memorable vacation! No smoking or vaping on the property.

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

La Jolla Beach House-Family Focused-3min to Beach
Escape to our boho-inspired Bird Rock/La Jolla beach house, perfect for families! This serene La Jolla retreat features a private pool, large hot tub, and cozy fire pit. Enjoy a private oasis with hammocks and a BBQ. Recently upgraded with modern decor and new appliances, this home comfortably accommodates your group for the ultimate relaxing getaway just minutes from La Jolla Cove and famous beaches.

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.

Lionhead - Private Boutique Home
Experience boutique hotel vibes where Palm Springs meets South Beach. This "plug-and-play" retreat features a private backyard resort with a heated pool ($50/day for stays 5 days or less), Jacuzzi, cabana, and BBQ—perfect for watching planes take off over the city. Enjoy high-speed Wi-Fi, Smart TVs, and a vintage record player, all minutes from Downtown, conventions, and easy highway access.
Popular amenities for Hillcrest rentals with a pool
House rentals with a pool

Heated Pool, XXL Spa, Mini-Golf & Chef’s Kitchen!

3 bedroom home with pool 15 minutes from beaches

Travelers Oasis w/ Private Pool + Hot Tub

Surf Cottage w/Pool & Firepit 10min from the beach

Family Oasis: Private Pool, Game Room, Garden View

Bright and spacious home with views, pool & spa.

Upscale Resort House /Views, Saltwater Pool/Spa !

Private House in the Hills, Pool, Pickleball court
Apartment rentals with a pool

Bay View Condo in Pacific Beach

Centrally located n UCSD/ utc-laJolla

One Bedroom Ocean Front Condo!

The Endless Summer Condo!

Beautifully remodeled 10th floor oceanfront condo

Cozy clean 1 bedroom centrally located by beaches

Spacious 2 BR w/ Free Parking & WiFi

Sweet Little La Mesa Condo(pool+hot tub) NEAR SDSU
Other holiday rentals with a pool

Fun and relaxation in the same location.

Downtown SD 1BR King · Walkable Gaslamp District

Iconic Waterfall House

Bright 2BR | Views &Walkability

Breathtaking Ocean, Bay, City & Petco Park Views

Luxury High-Rise | Downtown SD

Stunning 2BR/2BA| Plunge Pool, AC, Private

Sunset house
When is the best time to visit Hillcrest?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $284 SGD | $257 SGD | $257 SGD | $257 SGD | $281 SGD | $294 SGD | $304 SGD | $295 SGD | $288 SGD | $272 SGD | $299 SGD | $322 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 80 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 2,110 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
80 of Hillcrest holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Hillcrest rentals
Destinations to explore
- Rentals with a washing machine and dryer Hillcrest
- Flat rentals Hillcrest
- Cottage rentals Hillcrest
- Rentals with a patio Hillcrest
- Serviced apartment rentals Hillcrest
- Apartment rentals Hillcrest
- Guest house rentals Hillcrest
- Fitness-friendly rentals Hillcrest
- Rentals with a hot tub Hillcrest
- House rentals Hillcrest
- Rentals with a fireplace Hillcrest
- Family-friendly rentals Hillcrest
- Rentals with outdoor seating Hillcrest
- Rentals with beach access Hillcrest
- Pet-friendly rentals Hillcrest
- Rentals with a firepit Hillcrest
- Hotel rooms Hillcrest
- Rentals with an EV charger Hillcrest
- Rentals with breakfast Hillcrest
- Rentals with pools San Diego
- Rentals with pools San Diego County
- Rentals with pools California
- Rentals with pools United States
- Rosarito Beach
- LEGOLAND California
- SeaWorld San Diego
- San Diego Convention Center E Ent
- Oceanside City Beach
- University of California-San Diego
- San Diego Zoo Safari Park
- Petco Park
- Ocean Front Walk
- Tijuana Beach
- Torrey Pines State Beach
- Pacific Beach
- Balboa Park
- Coronado Beach
- San Diego Zoo
- Pechanga Resort Casino
- Liberty Station
- Moonlight State Beach
- La Misión Beach
- San Onofre Beach
- Belmont Park
- Oceanside Harbor
- San Diego State University
- Sesame Place San Diego




