
Vacation 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.

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.

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.

Quiet Spa-like Oasis in the City
Relax! This guest suite is a small & cozy oasis with a private keyless-lock entry. Enjoy the comfy Queen-size bed with an attached private shower/bath. Stroll down an outdoor walkway to an expansive patio area with gorgeous canyon views, BBQ with a Mini-Fridge, and a cabana with an additional shower. Vacation or business trips. 10-15 minutes to most SD activities, Zoo, Balboa Park, beach, malls. 15-minute walk to breweries, restaurants, music, coffee, etc. Plz, read House Rules BEFORE booking!

Casa De Colores
Need some color in you life? Come stay in our one of a kind home- groovy wall mural, bright decor, rainbow speckled floors. Tucked back in the peaceful neighborhood of University Heights, this home includes a lusciously landscaped yard with a: - Pool -Hottub - BBQ -Outdoor patio furniture 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

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.

Luxe Point Loma Oasis w/ Pool, Spa & Fire Pit
The vacation of your dreams awaits at the luxury 3BR Point Loma oasis. Each of the posh bedrooms has an en-suite bathroom and access to the exquisite backyard oasis-which is complete with a pool, spa, outdoor kitchen, and fire pit area. Enjoy outdoor dining by the pool or the lovely succulent gardens throughout the property. Sleeps 8. Washer/dryer, complimentary Wi-Fi, Netflix and parking are included. Hotel quality sheets and fresh duvets are also included with your stay. No parties.

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.

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!

Casa Bahia Beautiful San Diego Home with Pool

Entertainers Dream Pool Home

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

Eco-Friendly Mount Soledad Pad with Views and Heated Pool

Bright and spacious home with views, pool & spa.

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

Mid-Century Modern and Contemporary House
Condo 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

Cozy and relaxing beach vibe 1 bedroom condo

Gated community, parking, 250 Mbps. Save 10%/month

Luxury Living Near the Beach

One Bedroom Ocean Front Condo!

Modern 2BD/2BA w/Pool in Heart of Pacific Beach
Other vacation rentals with a pool

Fun and relaxation in the same location.

Treehouse Retreat in Mission Hills

Literal neighbor to Balboa Park!

North Park Craftsman Oasis with Pool

*KING BED* Adorable 2bd 2ba condo, very Central

Luxury High-Rise | Downtown SD

Downtown Escape I Free Garage Parking

Stunning 2BR/2BA| Plunge Pool, AC, Private
When is the best time to visit Hillcrest?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$46,202 GYD | G$41,812 GYD | G$41,812 GYD | G$41,812 GYD | G$45,784 GYD | G$47,874 GYD | G$49,547 GYD | G$48,083 GYD | G$46,829 GYD | G$44,320 GYD | G$48,711 GYD | G$52,474 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 80 vacation rentals in Hillcrest

Nightly prices starting at
Hillcrest vacation rentals start at G$14,634 GYD per night before taxes and fees

Verified guest reviews
Over 2,110 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

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

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




