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.

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, 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

5 out of 5 average rating, 255 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.

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.

4.98 out of 5 average rating, 107 reviews

A serene backyard features a heated pool surrounded by palm trees and lounge chairs. The space is designed for relaxation and outdoor enjoyment, showcasing a clean landscape with concrete pathways and decorative gravel.

Home in Normal Heights

Private Heated Pool | Sleeps 10

A family-friendly SD home with a private heated pool and spacious backyard for relaxing and playing. The Home ⁘ 3 Bedrooms & 2 Bathrooms ⁘ Personal A/C & Heat in Every Room ⁘ Complimentary Washer & Dryer ⁘ 2 Rollaway Beds Available Upon Request Outdoor Space ⁘ Private Heated Pool (inquire about fee) ⁘ Outdoor Shower & Wood Burning Fire Pit ⁘ Fenced Backyard ⁘ Pool Toys, Loungers, & Umbrellas Family-Friendly ⁘ Pack n’ Play & Games ⁘ Pets Welcome upon Request ⁘ Quiet Residential Neighborhood

4.88 out of 5 average rating, 215 reviews

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

Bright and spacious home with views, pool & spa.

This beautiful and recently remodeled, open-floor plan home is conveniently located directly across from Cowles Mountain, one of San Diego's most visited hiking trails. Each bedroom has its own full bathroom. Perfectly located for the outdoorsy family. Tons of hiking and mountain bike trails are just across the street. Only 15 min. away from beaches, zoo, & Sea World. Gaslamp/Downtown is only 20 min. by car. After a day of exploring, come home to a newly-built, salt-water pool and spa.

4.88 out of 5 average rating, 377 reviews

A solar-heated pool glimmers in the sunlight, surrounded by inviting lounge chairs and a shaded umbrella. A cozy outdoor dining area with a table is visible in the background, framed by lush greenery and large eucalyptus trees.

Guest suite in Bonita

Resort-Style Living, Pool, Close to All San Diego

Nestled in a quiet, discreet neighborhood, our private air-conditioned studio offers a safe & serene retreat. Attached to a stunning ranch-style executive home, it features an amazing pool for your relaxation. We are conveniently located a short distance away from the Gaylord Convention Center, the Olympic Training Center, downtown San Diego, Comic-Con, major attractions, concert venues, beaches, airport & Mexico. Enjoy a complimentary butler tray that includes coffee, tea & snacks.

4.97 out of 5 average rating, 193 reviews

The tropical pool features gentle waterfalls cascading into vibrant blue water. Surrounding palm trees and lush greenery enhance the serene environment. A tiki bar and a hot tub grotto provide inviting leisure options. A second-story balcony overlooks this tranquil outdoor space, illuminated by soft evening lights.

Guest house in La Jolla

Luxury Tropical Private Guesthouse in La Jolla

Beautiful private guesthouse on $5 million property with stunning views and luxury amenities. Take a dip in the tropical pool with waterslide, tiki bar, and hot tub grotto. Enjoy indoor or outdoor dining. Gated property, vaulted ceilings, marble bathroom, private balcony, parking, and trail for guests. Guesthouse has 1 bedroom with a queen bed and can accommodate an extra twin bed on the loft. House has closet, bathroom with beautiful stone shower, modern kitchen, two patios, WiFi, TV.

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.

4.96 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.

4.93 out of 5 average rating, 133 reviews

A spacious living area is highlighted by vaulted ceilings and floor-to-ceiling windows offering expansive city views. Modern seating includes a light grey sofa, orange armchairs, and a round white coffee table. The open kitchen is visible in the background, featuring bar seating and contemporary finishes.

Home in Mission Hills

Heated Pool-Jacuzzi-King Bed-City Views-Chic Decor

⚜ Stunning wrap-around balcony with panoramic city views ⚜ Heated pool with jacuzzi ($100/day to heat — request in advance) ⚜ 2,500 sq-ft of interior space with vaulted ceilings & open floor plan ⚜ Chic modern décor throughout ⚜ Two fully stocked kitchens ⚜ 4 king beds, 1 sofa bed & 1 couch ⚜ Poolside sun loungers & outdoor lounge areas ⚜ Complimentary washer & dryer ⚜ Attached studio suite with private access (included) ⚜ Located in Historic Mission Hills, San Diego

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.

Popular amenities for San Diego rentals with a pool

Kitchen

Wifi

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

4.94 out of 5 average rating, 122 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

4.86 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

4.85 out of 5 average rating, 101 reviews

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

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

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

4.81 out of 5 average rating, 127 reviews

The outdoor area showcases a clear pool surrounded by a spacious patio. Lounge chairs, a poolside table, and an umbrella are positioned for relaxation. The backdrop features low landscaping with cacti and a glimpse of the house, enhancing the tranquil setting.

Home in Lake Murray

Mid-Century Modern and Contemporary House

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!

4.96 out of 5 average rating, 188 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 !

Apartment rentals with a pool

4.94 out of 5 average rating, 215 reviews

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.

Apartment in Oceanside

*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

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, 254 reviews

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 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.

4.91 out of 5 average rating, 181 reviews

Enchanted Ocean Sunsets

Apartment in Solana Beach

A spacious living area showcases a large coffee table centered among plush couches. A fireplace and a mounted television are present, while a colorful painting adds a vibrant touch. Natural light fills the room through expansive windows, offering views of the surrounding landscape.

4.96 out of 5 average rating, 127 reviews

Del Mar Ocean View! Walk to the Beach!

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, 149 reviews

Spacious 2 BR w/ Free Parking & WiFi

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.

Apartment 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!

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!

5 out of 5 average rating, 16 reviews

Home in La Mesa

Airbnb Luxe: Designer Pool, Fitness and Office

Flat in Downtown San Diego

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

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.

5 out of 5 average rating, 33 reviews

Luxury High-Rise | Downtown SD

A shared swimming pool is surrounded by lounge chairs and tropical greenery. The building features multiple balconies, providing views of the pool area. The pool area is bathed in sunlight, enhancing the resort-like feel of the space.

4.84 out of 5 average rating, 32 reviews

Modern 2BD/2BA w/Pool in Heart of Pacific Beach

4.76 out of 5 average rating, 72 reviews

A round wooden dining table occupies the center of the room, accompanied by black chairs. A decorative planter rests on the table, featuring vibrant green succulents. Large glass doors lead to a cozy lounge area, enhancing the open feel of the space adorned with natural materials.

Flat in Gaslamp Quarter

Downtown Dream 4