Holiday rentals with a pool in San Diego

4.99 out of 5 average rating, 147 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.

Guesthouse 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, 172 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

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, 100 reviews

The Endless Summer Condo!

Let your worries drift away at this 6th floor corner condo with panoramic ocean views! With floor to ceiling windows throughout, you'll feel like you're floating above the sea! Leave your toes in the sand or walk to PB's best restaurants and attractions in minutes! When you're done exploring, put on a Beach Boys record while having dinner with the family amid a golden sunset..ah the good life! Create cherished memories that will linger long after the sun sets, here, at 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, 194 reviews

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.

A person stands beside floor-to-ceiling windows that offer a view of the ocean during sunset. The seating area is furnished with a leather recliner, and a vibrant artwork adorns the wall. Soft lighting from two lamps enhances the warm ambiance.

4.94 out of 5 average rating, 513 reviews

Oceanfront Elegant Condo - Remarkable Amenities

Spectacular Oceanfront, 8th Floor. Hear the surf as you slide open the floor-to-ceiling glass door. The Boardwalk and beautiful safe swimming beach are at the foot of your building. Join the surfers using our wet suits and our beach cruiser bikes for an easy ride along the Ocean and Mission Bay or stroll along for vibrant people watching. Return to your elegantly appointed, romantic condo provisioned to meet your every need. Everything you need is in 10 blocks along beautiful California coast!

5 out of 5 average rating, 173 reviews

A green, manicured lawn is highlighted with a white gazebo and ornamental garden seating. Towering palm trees flank the scene, while a staircase leads up to a spacious home nestled in the background. Shadows create a gentle pattern on the grass from surrounding elements.

Guesthouse in Kit Carson

French Garden Poolside Retreat -Wine & Safari Park

170+ Perfect 5.0 Reviews – Amazing views, peaceful and beautiful apartment on a French estate in San Diego Wine Country close to the Wild Animal Park. A perfect setting to celebrate a special occasion and create memories. Amazing sweeping views of the vinyards/mountains situated on the golf course with full access to the pool, spa, covered parking, EV chg. and private European garden park. Beautiful luxury apartment suite with a kitchen, sitting room, bathroom, steam shower/sauna and bedroom.

The image captures a panoramic view of the beach, featuring a vibrant blue sky and sunlit ocean. Palm trees line the shore, while the Oceanside Pier extends into the water. The rooftops of nearby buildings are visible in the foreground.

4.94 out of 5 average rating, 129 reviews

Upscale condo with Rooftop Deck & Ocean View!

Our upscale unit is a 3rd floor 'penthouse' in the "A" building on the south side of North Coast Village. It has a fantastic view of the surf, sand and the Oceanside Pier from your large dedicated rooftop balcony! There's a beautiful, fully upgraded kitchen, a king in the master and a queen sleeper sofa in the LR. Upstairs is a large & open loft bedroom with a queen Murphy bed, a breakfast nook and a 75” TV. And did we mention your new happy place, that fabulous rooftop deck?

Guesthouse 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.

4.96 out of 5 average rating, 140 reviews

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.

4.89 out of 5 average rating, 109 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 with Pool and

Welcome to our 5-bedroom, 3-bathroom home, offering ample space for your entire group. With a myriad of amenities, games, and relaxation areas, you may find yourself wanting to spend your entire stay simply enjoying the comforts of this exceptional home. Whether that be opting for a pool day relaxing in San Diego's mediterranean climate, or cozying up next to the fireplace with your fav movie on. This spacious rental will ensure a memorable San Diego experience! 🌄

4.89 out of 5 average rating, 253 reviews

A serene pool area features crystal-clear water, with striped lounge floats anchored in the center. Surrounding palm trees offer shade, while natural stone accents decorate the pool's edge. The sound of a waterfall can be faintly heard, contributing to a calming atmosphere.

Guest suite in La Mesa

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.

4.98 out of 5 average rating, 485 reviews

Home in Encinitas

Lux Casita with Pickleball & Resort Amenities

Escape to this inviting Casita, where bright white walls and French doors fill each room with light and warmth. Thoughtfully furnished and full of charm, it offers a serene retreat with private resort-style amenities, including a tennis court, pool, and lush gardens. Step outside to hiking and biking trails, then return to cozy comfort. An optional second suite provides extra space for a relaxed, luxurious stay.

4.99 out of 5 average rating, 199 reviews

A serene backyard is framed by colorful sunset skies, featuring a cozy hammock in the foreground and a comfortable seating area with grey couches. String lights add warmth to the outdoor space, complemented by lush greenery throughout the neatly landscaped yard.

Home in La Jolla

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 backyard 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.

Popular amenities for San Diego rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 141 reviews

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

4.86 out of 5 average rating, 101 reviews

The outdoor area features a private pool surrounded by lush greenery and palm trees. A fire pit area with woven seating provides a relaxed gathering spot. A shaded deck extends the living space, while colorful pool floats add a playful touch to the inviting scene.

Home in La Mesa

Entertainers Dream Pool Home

Superhost

The private pool area is surrounded by palm trees and cacti, with lounge chairs positioned for relaxation. A shaded dining area is visible in the background, complemented by the warm glow of a sunset sky. The scene creates a serene outdoor retreat.

Home in San Diego

4.85 out of 5 average rating, 101 reviews

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

4.9 out of 5 average rating, 192 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

4.99 out of 5 average rating, 145 reviews

An aerial view of a private estate nestled among lush greenery and mature trees is showcased. The clear saltwater pool is surrounded by a beautifully landscaped patio, highlighting the natural beauty of the surrounding hills and valleys.

Home in Valley Center

Secluded View Home •Saltwater Pool&Spa •Sleeps 10

Home in University Heights

A tranquil pool area is surrounded by lush landscaping, featuring palm trees and various plants. Two lounge chairs with an umbrella are positioned beside the pool, reflecting a serene evening sky with hues of pink and purple.

4.97 out of 5 average rating, 155 reviews

University Heights Oasis Getaway

4.93 out of 5 average rating, 128 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

4.91 out of 5 average rating, 208 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!

Condo rentals with a pool

An ocean view from the balcony reveals sandy beaches and gentle waves lapping at the shore. Coastal vegetation frames the scene, with the iconic Oceanside Pier visible in the distance against a clear blue sky.

4.94 out of 5 average rating, 215 reviews

*Beach Break* Oceanfront/Balcony/Walk Everywhere

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, 125 reviews

Bay View Condo in Pacific Beach

A private balcony features a small table and two woven chairs, offering views of palm trees and the ocean. Nearby, the pool area is visible, surrounded by lush greenery and the white structures of the complex against a clear blue sky.

4.9 out of 5 average rating, 228 reviews

Beachfront 1BR Condo | Pool | Hot Tub | Sleep 4

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.

4.85 out of 5 average rating, 182 reviews

Ocean front condo heart of pacific beach

4.96 out of 5 average rating, 254 reviews

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.

Condo in University City

Centrally located n UCSD/ utc-laJolla

A wooden deck provides a vantage point overlooking the sandy beach and ocean. The distant condo buildings line the shore, with pedestrians enjoying the beach and pier visible in the background. The scene is illuminated by warm sunset light, enhancing the coastal atmosphere.

4.85 out of 5 average rating, 198 reviews

One Bedroom Ocean Front Condo!

A view from the balcony showcases a sandy beach dotted with umbrellas and people enjoying the sun. Palm trees line the shore, while gentle waves roll towards the beach. The iconic pier stretches into the ocean, framed by a clear blue sky.

4.92 out of 5 average rating, 207 reviews

Couples Retreat Beachside Studio, King Bed

4.95 out of 5 average rating, 255 reviews

The inviting pool area features a bright blue swimming pool surrounded by lush greenery and vibrant flower beds. Umbrellas provide shade for the seating area, with patio furniture arranged for relaxation. Decorative tiles adorn the edge of the pool, enhancing the tranquil atmosphere.

Condo in Guajome

✻Beautiful & Spacious Oside Oasis Family Retreat✻

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, 96 reviews

Ocean-Bay-Sunset View Condo in Pacific Beach!

4.95 out of 5 average rating, 21 reviews

Fun and relaxation in the same location.

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.

Apartment in Balboa Park

Literal neighbor to Balboa Park!

A modern living room is highlighted by a large sectional sofa in contrasting black and white, situated near expansive floor-to-ceiling windows. The stunning views of the bay and city skyline are captured in natural light, with a sleek coffee table positioned in front of the sofa.

4.98 out of 5 average rating, 66 reviews

Breathtaking Ocean, Bay, City & Petco Park Views

Superhost

A living area is presented with a vibrant yellow sofa complemented by decorative cushions. A circular table sits on a striped rug, surrounded by a leather armchair. A small potted plant adds a touch of greenery, and large glass doors lead to a balcony, offering natural light.

Apartment in Gaslamp Quarter

4.85 out of 5 average rating, 98 reviews

Downtown Dream 3

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, 35 reviews

Luxury High-Rise | Downtown SD

A spacious living area features large floor-to-ceiling windows showcasing a partial city and bay view. A comfortable navy blue sofa, adorned with an orange throw pillow, faces a mounted 65-inch smart TV. A round coffee table and stylish dining area are visible, enhancing the contemporary feel.

5 out of 5 average rating, 28 reviews

Downtown Escape I Free Garage Parking