
Vacation 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.

Private 1 BR Paradise retreat
Private, yet central. It is your exclusive paradise retreat to enjoy from your spacious 1 bedroom guest house located on the lower level of our home. Hang out in the expansive and private backyard with pool, different sitting areas and covered BBQ room. Or maybe a workout in the gym. Centrally located in the Village of La mesa. Just a 1/4 mile jaunt into the quaint village with its numerous assortments of dining options, stores and trolley station. Freeway close to beaches, downtown and airport

Custom Guesthouse, Balboa Park/Zoo/Hillcrest& pool
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.

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.

Luxury Oceanfront Condo with Unbelievable Views
Welcome to your oasis! Prepare to be awestruck by the breathtaking views at Sunset Pacifica. This fully renovated condo features two ensuite bedrooms with the beachy SoCal vibe you desire. Ideally located on the boardwalk, you're minutes from La Jolla, Downtown, the San Diego Zoo, Embarcadero, and top restaurants, bars, and entertainment spots. Whether you're in the mood for exploration or relaxation, you'll find it here- lounging poolside or on the sandy shores of the stunning Pacific Ocean.

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.

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, record player with albums. 19 speakers in the ceilings with connection to your phone for optimal happiness. Plug and play!

Vacation Paradise-Heated Pool+Hot Tub+FirePit+EV
This is your perfect Guest House with a salted & 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.

Tranquil Poolside Studio
Quiet Poolside Studio Suite! Perfect for visiting family in La Mesa or enjoying everything San Diego has to offer! Please note: this is not a party house. Private side entrance to a relaxing poolside studio. Very quiet with TV, and full kitchen. Comfortable queen size bed and sofa that can sleep one more person comfortably. We are 20 min to the beach, or relax and enjoy the pool! Close to SDSU and easy freeway access to anywhere in San Diego.

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

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.
Popular amenities for Hillcrest rentals with a pool
House rentals with a pool

The Queen House

Bright Contemporary 5-Bedroom Oasis, Pool and Yard

Casa Bahia Beautiful San Diego Home with Pool

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

Mid-Century Modern and Contemporary House

Modern Hilltop Home: Roomy, Views, Family-Friendly

Oasis with ocean views/Pool/Hot tub! Sleeps 10!

Dream Vacation! Sunny 3 Bedroom Home!
Condo rentals with a pool

Best Beach in seconds! AC Luxury KING Beds!

Bay View Condo in Pacific Beach

Ocean front condo heart of pacific beach

One Bedroom Ocean Front Condo!

Enchanted Ocean Sunsets

Sweet Little La Mesa Condo(pool+hot tub) NEAR SDSU

Spacious 2 BR w/ Free Parking & WiFi

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

Literal neighbor to Balboa Park!

Treehouse Retreat in Mission Hills

Spanish Retreat! Enjoy private pool and views

Breathtaking Ocean, Bay, City & Petco Park Views

Casita Arroyo - 1 BR guesthouse with pool/hot tub

Downtown Dream 3

Luxury High-Rise | Downtown SD

1BR Coronado Pool Ocean E
When is the best time to visit Hillcrest?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$46,270 GYD | G$41,873 GYD | G$41,873 GYD | G$41,873 GYD | G$45,851 GYD | G$47,945 GYD | G$49,620 GYD | G$48,154 GYD | G$46,898 GYD | G$41,664 GYD | G$55,064 GYD | G$52,970 GYD |
| 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 vacation rentals with a pool in Hillcrest

Total vacation rentals
Explore 70 vacation rentals in Hillcrest

Nightly prices starting at
Hillcrest vacation rentals start at G$16,749Â GYD per night before taxes and fees

Verified guest reviews
Over 2,010 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
70 of Hillcrest vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Hillcrest rentals
Destinations to explore
- House rentals Hillcrest
- Condo rentals Hillcrest
- Rentals with a fire pit Hillcrest
- Rentals with a patio Hillcrest
- Family-friendly rentals Hillcrest
- Rentals with beach access Hillcrest
- Rentals with a fireplace Hillcrest
- Rentals with outdoor seating Hillcrest
- Guesthouse rentals Hillcrest
- Rentals with a hot tub Hillcrest
- Hotel rooms Hillcrest
- Apartment rentals Hillcrest
- Rentals with breakfast Hillcrest
- Rentals with a washer and dryer Hillcrest
- Pet-friendly rentals Hillcrest
- Cottage rentals Hillcrest
- Rentals with an EV charger Hillcrest
- Fitness-friendly rentals Hillcrest
- Rentals with pools San Diego
- Rentals with pools San Diego County
- Rentals with pools California
- Rentals with pools United States
- Rosarito Beach
- Oceanside City Beach
- Torrey Pines State Beach
- LEGOLAND California
- SeaWorld San Diego
- Tijuana Beach
- Pacific Beach
- University of California-San Diego
- San Diego Zoo Safari Park
- Balboa Park
- Coronado Beach
- Pechanga Resort Casino
- San Onofre Beach
- La MisiĂłn Beach
- Oceanside Harbor
- Moonlight State Beach
- Liberty Station
- Coronado Shores Beach
- Belmont Park
- Sesame Place San Diego
- Black's Beach
- Law Street Beach
- Strand Beach
- Torrey Pines Golf Course




