Holiday rentals with a pool in Hillcrest

4.99 out of 5 average rating, 149 reviews

Two red Adirondack chairs are positioned under a covered patio, facing a serene backyard with a pool. Lush greenery surrounds the area, creating a tranquil atmosphere. A BBQ room and various seating arrangements are visible beyond the pool, enhancing the outdoor retreat experience.

Guest house in La Mesa

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

4.99 out of 5 average rating, 175 reviews

A bright living space features a warm wooden ceiling and large windows. A comfortable orange sofa is paired with a wooden coffee table on a patterned area rug. The kitchen, visible in the background, includes modern appliances and white cabinetry, enhancing the cozy atmosphere.

Home in Hillcrest

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

Flat in University Heights

A serene bedroom features a queen bed with a light-colored quilt. Two bedside tables with lamps are positioned on either side. The walls are adorned with various framed artworks and a large mirror, reflecting natural light from the windows.

4.79 out of 5 average rating, 468 reviews

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

Guest house in Mission Hills

A cozy sleeping area features a spacious bed with a striped throw blanket adorned with decorative tassels. A flat-screen TV is mounted on the wall, and a small table is positioned beside the bed. Soft lighting is provided by wall sconces, creating a calm ambiance.

4.9 out of 5 average rating, 493 reviews

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.

5 out of 5 average rating, 264 reviews

A private outdoor area features a heated pool surrounded by lush green grass and modern loungers. An inviting fire pit is centrally located, with two stylish chairs positioned nearby. The backdrop includes well-maintained shrubbery and tall trees, enhancing the tranquil ambiance.

Home in Serra Mesa

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.

4.93 out of 5 average rating, 132 reviews

A living room features a luxury hanging chair suspended from the ceiling. Natural light filters through sheer curtains, illuminating a cozy seating area with a plush sofa and wooden coffee table. A 50” television is mounted above an elegant fireplace, enhancing the room's comfort.

Home in City Heights

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.

4.98 out of 5 average rating, 223 reviews

The beautifully illuminated pool area features a saltwater pool and hot tub under a starry sky. Lush tropical plants surround the space, enhancing the ambiance. A bottle of champagne and flutes are ready for celebration, while cozy seating is visible in the background.

Guest house in Talmadge

Lovely Guesthouse in garden setting

Centrally located guesthouse on quarter acre lot in a beautiful community 5 minutes drive from restaurants, pubs, shops, library, SDSU. 15 minute drive to beaches, downtown, military bases, zoo, Balboa Park. 800sq’ cottage with great outdoor space- patio, gas grill, salt water/solar heated pool & hot tub, fruit trees for sharing, gardens. Central A/C and heat. Books and games for fun down time. Relax w/SMORS and drinks in the evening around the fire pit table : ) Street parking available.

Home in University Heights

A colorful living area features a vibrant blue couch adorned with decorative pillows. A round white coffee table sits prominently on a multi-colored rug, while a television is mounted above a red cabinet. Artwork and framed prints decorate the pink walls, enhancing the playful ambiance.

4.94 out of 5 average rating, 105 reviews

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

4.89 out of 5 average rating, 123 reviews

A private patio area is visible, adorned with a wooden structure and comfortable seating arrangements. The sparkling pool is set at a distance, surrounded by greenery. Sunlight casts gentle shadows, highlighting the textured concrete and wooden elements in the outdoor space.

Guest suite in Hillcrest

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.

Guest house in Lake Murray

The poolside area features a well-maintained saltwater pool reflecting the colors of the sunset. Comfortable seating arrangements, including lounge chairs and a cozy fire pit, are visible. Large umbrellas provide shade, and lush greenery adds to the serene ambiance.

4.97 out of 5 average rating, 144 reviews

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.

4.97 out of 5 average rating, 116 reviews

A serene backyard oasis features a small spa surrounded by lush greenery and decorative plants. The space is framed by an open wooden structure with a sloped roof, providing a cozy seating area with soft cushions. Unique pendant lights hang above, adding a touch of elegance.

Home in Normal Heights

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!

Home in University Heights

The outdoor space features a solar-heated pool with soft lighting, alongside a hot tub glowing in green. A dining area with a table and chairs is shaded by a red umbrella. Warm string lights enhance a cozy atmosphere in the evening.

4.99 out of 5 average rating, 143 reviews

3BR Urban Oasis with Pool and Hot Tub in San Diego

Escape to our 3BR/2BA Urban Oasis in walkable University Heights! Perfect for families & friends, this stylish home features a private pool, hot tub, and a cozy fireplace. Enjoy a fully equipped kitchen, dedicated workspace, and a magical backyard ambiance. Just minutes from the San Diego Zoo, Balboa Park, and downtown. Your perfect San Diego getaway awaits!

Popular amenities for Hillcrest rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.89 out of 5 average rating, 197 reviews

A view of the inviting swimming pool surrounded by a spacious patio. Natural rock elements and vibrant landscaping enhance the outdoor area. The multi-level deck is visible, offering seating options and picturesque canyon surroundings under a clear blue sky.

Home in La Mesa

The Queen House

4.89 out of 5 average rating, 110 reviews

An open-concept living space features a modern kitchen with a large island and bar seating for four. A light-colored sofa is positioned nearby, with a stone fireplace adding warmth to the room. Natural light streams through the skylight and windows, enhancing the airy feel.

Home in La Mesa

Bright Contemporary 5-Bedroom Oasis, Pool and Yard

4.94 out of 5 average rating, 128 reviews

A modern living room features a light wooden floor and white walls, complemented by a pink accent wall. A flat-screen TV is mounted above a stylish cabinet, with two potted plants on top. A comfortable seating area includes a rattan chair and a coffee table.

Home in Chula Vista

Casa Bahia Beautiful San Diego Home with Pool

4.9 out of 5 average rating, 193 reviews

An open-concept living space features a brown leather sectional sofa, providing comfortable seating against a backdrop of light wood ceilings. A dining table with wooden chairs is visible, complemented by a sleek kitchen equipped with modern appliances and bright white cabinetry.

Home in Pacific Beach

Eco-Friendly Mount Soledad Pad with Views and Heated Pool

Superhost

A serene outdoor space features a salt-water pool surrounded by a concrete patio and manicured grass. An umbrella provides shade over the poolside area, with lush greenery and mountains visible in the background under a partly cloudy sky.

Home in Lake Murray

4.88 out of 5 average rating, 216 reviews

Bright and spacious home with views, pool & spa.

4.91 out of 5 average rating, 211 reviews

A private pool is surrounded by natural stone and lush greenery. Palm trees provide shade, while a bamboo privacy fence enhances the secluded atmosphere. The clear blue water invites relaxation, showcasing gentle ripples under the sunlight.

Home in Chula Vista

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

4.96 out of 5 average rating, 191 reviews

A dining space features a round table with four white chairs, complemented by a potted plant. Large glass doors slide open to reveal expansive views of the backyard, pool, and surrounding hills, with soft evening light illuminating the scene.

Home in Spring Valley

Upscale Resort House /Views, Saltwater Pool/Spa !

4.9 out of 5 average rating, 342 reviews

The spacious exterior of the home features a large wooden deck, surrounded by lush greenery and a well-maintained yard. A brick pathway leads to a private pool area, where the sunlight reflects off the water, creating a serene outdoor setting.

Home in La Jolla

LJ Village Home with private pool & spa

Apartment rentals with a pool

An arched window frames a serene view of palm trees and distant hills at dusk. The soft hues of a fading sunset create a calming atmosphere. Neighborhood rooftops are visible below, with twinkling lights in the distance hinting at urban life.

4.98 out of 5 average rating, 126 reviews

Bay View Condo in Pacific Beach

An aerial view captures the oceanfront condo alongside the sandy beach, with an expansive coastline stretching below. The surrounding neighborhood features a mix of residential and commercial structures, interconnected by roads and pathways, creating a vibrant coastal community.

4.86 out of 5 average rating, 188 reviews

Ocean front condo heart of pacific beach

Apartment in University City

The kitchen features modern appliances, including a stainless steel refrigerator, microwave, and range. A spacious granite countertop offers ample workspace, while cabinets provide organized storage. The area is brightly lit with recessed lighting, enhancing the clean and functional design.

4.96 out of 5 average rating, 256 reviews

Centrally located n UCSD/ utc-laJolla

A spacious living area features large windows offering panoramic ocean views and allowing natural light to fill the room. A comfortable blue couch is positioned near a glass coffee table, with a television mounted above a dark wooden entertainment unit.

4.9 out of 5 average rating, 186 reviews

Enchanted Ocean Sunsets

A bright and airy living room features large floor-to-ceiling windows showcasing expansive ocean views. Comfortable seating arrangements consist of a plush sofa and armchairs, accented by light decor. A coffee table sits at the center, complemented by side tables with lamps, fostering a relaxing atmosphere.

5 out of 5 average rating, 107 reviews

The Endless Summer Condo!

A bright living room features large glass doors opening to breathtaking ocean views. A comfortable white sectional sofa is surrounded by two plush armchairs. Wall art and a round coffee table enhance the inviting atmosphere, while a potted plant adds a touch of greenery.

4.98 out of 5 average rating, 197 reviews

Luxury Oceanfront Condo with Unbelievable Views

A bright living area features a large window with ocean views and light blue skies. A wooden coffee table rests on a patterned rug, surrounded by comfortable seating. A flat-screen TV is located on a white media console, enhancing the room's modern look.

4.97 out of 5 average rating, 185 reviews

Beautifully remodeled 10th floor oceanfront condo

Apartment in Spring Valley

A comfortable living area features a light-toned sofa adorned with colorful cushions and a wooden coffee table. A green chair complements the space, while a decorative wall art piece and potted plant add interest. A dining area is visible in the background.

4.79 out of 5 average rating, 154 reviews

Spacious 2 BR w/ Free Parking & WiFi

Other holiday rentals with a pool

A dining area features a round table with high wooden stools, set against a large arched window showcasing views of the neighborhood. A chalkboard on the wall offers a welcoming message, complemented by light-colored walls and wooden flooring.

4.98 out of 5 average rating, 97 reviews

Ocean-Bay-Sunset View Condo in Pacific Beach!

5 out of 5 average rating, 60 reviews

A spacious living area is highlighted by large glass windows allowing natural light to fill the room. Modern furniture, including a curved white sofa and a dark coffee table, is complemented by various indoor plants. Artworks and decorative items add a touch of character to the space.

Flat in Balboa Park

Literal neighbor to Balboa Park!

Superhost

A modern living area features a cozy sofa with green accent pillows, situated beside a light wood coffee table. A large wall mirror reflects the open space, while a fully equipped kitchen is visible in the background. Warm wood flooring enhances the inviting atmosphere.

Flat in Downtown San Diego

4.77 out of 5 average rating, 30 reviews

NEW DT Luxe King Suite with Sauna & Pool Access

4.94 out of 5 average rating, 50 reviews

The living room displays a blend of modern decor and comfort, featuring a gray sofa, an orange accent chair, and a circular coffee table on a vibrant area rug. A large flat-screen television is mounted on the wall, while natural light filters in through sheer drapes.

Apartment in San Diego

Luxury Living Near the Beach

5 out of 5 average rating, 31 reviews

Home in Kensington

Spanish Retreat! Enjoy private pool and views

Home in Greater North Park

An inviting outdoor space is framed by a wooden pergola, showcasing a clear blue sky above. The heated saltwater pool reflects sunlight, while comfortable lounge chairs are positioned nearby. A covered area with an umbrella offers shade, enhancing relaxation in this tranquil retreat.

4.94 out of 5 average rating, 17 reviews

North Park Craftsman Oasis with Pool

Flat in Downtown San Diego

A modern living room is presented, featuring a large sectional sofa adorned with soft cushions. Two wooden coffee tables are centered in the space, which is illuminated by natural light from floor-to-ceiling windows. Neutral tones and minimalist decor create a welcoming environment.

4.97 out of 5 average rating, 37 reviews

Luxury High-Rise | Downtown SD