Holiday rentals with a pool in Downtown San Diego

4.99 out of 5 average rating, 193 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

1 bedroom, 1 bath /Hillcrest/San Diego Zoo/Balboa

One bedroom, one bath with a pool in the Hillcrest/San Diego Zoo/Balboa Park /Marston Hill area. Full kitchen, queen bed, queen sleeper sofa & crib. 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). Walking to the Farmers Market. Minutes' drive to all San Diego beaches. No rent for children under 3, only a $95/stay flat fee. High chair, Pack & Play Crib, crib mattress & cover are provided

FamilyLocationParks

4.98 out of 5 average rating, 124 reviews

Home in Old Town

Heart of San Diego in Old Town. Private Oasis 6

This Redesigned 4000-SF private oasis located in the heart of San Diego’s historic Old Town is the best on the market. Renovated with every possible option: chef’s kitchen, in/outdoor entertaining, lounges&en-suite bathrooms. This property boasts sophisticated living with just the right amount of edge. Converted garage doors flood each living space with light and character. This location is just steps from dining & nightlife and close 2 San Diego beaches, airport, shopping, attractions plus more

LocationFamilyAir conditioning

5.0 out of 5 average rating, 303 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.

ValueFamilyCleanliness

4.94 out of 5 average rating, 151 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.

LocationFamilyGetting around

4.92 out of 5 average rating, 131 reviews

A spacious outdoor patio showcases a private pool and hot tub, surrounded by comfortable seating and a fire pit. An activity area features games such as foosball and cornhole, with lounge chairs positioned for relaxation. Lush green landscaping complements the inviting space.

Home in Bay Park

Modern Central SD Home w/ Pool & Spa Near Beach

Experience luxury at Bay Breeze Retreat, an exclusive oasis in the heart of Mission Bay, San Diego. This stunning residence features a private salt pool, outdoor jacuzzi spa, elegant fire pit, whole house water filter system and a state-of-the-art grill and kitchen. Inside, revel in contemporary upgrades which makes the place perfect for family gatherings of up to 8 guests. Walk to Luce Bar & Kitchen and Bird Rock Coffee. Minutes from downtown and top attractions, your perfect escape awaits.

FamilyLocationEV charging

4.96 out of 5 average rating, 180 reviews

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.

Guest house in La Mesa

Vacation Paradise-Heated Pool+Hot Tub+FirePit+EV

Welcome to your personal resort! This is your private Guest House with a salt & heated pool + hot tub. Located in a very quiet & safe neighborhood in beautiful San Diego. Drive 15 minutes to the beach, downtown, La Jolla, Zoo, stadiums, Sea World, Convention Center + more. Hike next door at Cowell Mountain or Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo, top quality finishes & furniture. Everything you need for memorable vacation! No smoking or vaping on the property.

LocationFamilyNearby

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.

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

FamilyLocationCheckout

4.96 out of 5 average rating, 136 reviews

A dining area is highlighted by a round wooden table surrounded by six wooden chairs. A cozy blue sofa is positioned nearby, with large glass doors opening to a pool area. Natural light enhances the space, complemented by a modern pendant light overhead.

4.92 out of 5 average rating, 102 reviews

San Diego Oasis- A Retro Retreat w/ King Size Bed!

Welcome to San Diego Oasis, a retro retreat--a mid-century modern oasis in sunny San Diego! This stylish home combines classic charm with all the modern upgrades you desire. Unwind by the sparkling pool, enjoy a friendly game of air hockey or corn hole, board games or enjoy s'mores around the gas fire pit . The retro retreat is the perfect blend of comfort, convenience, and timeless design. SD's most popular attractions are all within a 20-30 minute drive. Only 20 minutes to the beach!

FamilyLocationComfort

4.89 out of 5 average rating, 143 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.

FamilyLocationOutdoor spaces

4.94 out of 5 average rating, 198 reviews

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.

ValueLocationIndoor spaces

4.93 out of 5 average rating, 293 reviews

A vibrant heated pool is surrounded by minimalistic landscaping, featuring tall cacti and a clean white fence. Soft lounge chairs are positioned nearby for relaxation. The clear water reflects the blue sky, creating a refreshing setting for leisure and enjoyment.

Home in Mission Hills

Lionhead - Private Boutique Home

Unwind in your private backyard resort, featuring a heated pool, complimentary Jacuzzi, cabana, and BBQ—perfect for watching planes soar over the city skyline. Amenities: High-speed Wi-Fi, Smart TVs, and a vintage record player. Location: Minutes from Downtown, the Convention Center, and easy highway access. 🏊🏼‍♀️🛟Optional pool heat is available for $50/day (stays under 5 days). To ensure the best experience, heating is applied to the full duration of your stay only.

LocationFamilyDecor

A spacious backyard is showcased with a glistening pool surrounded by a concrete deck. Green grass offers a soft contrast, while lounge chairs and a shaded seating area are positioned for relaxation. String lights illuminate the space, enhancing the outdoor ambiance during twilight.

4.95 out of 5 average rating, 110 reviews

San Diego Pool House with Luxury King/Queen Suites

Indulge in this luxurious 4-bed 3-bath home! The perfect escape for families and groups of friends seeking comfort and style. Accommodating up to 10 people, this stunning home is complete with king and queen suites plus a backyard pool oasis. Located just 10 minutes from downtown San Diego, whether you seek relaxation or excitement, you'll find it all right here! Book now for a truly extraordinary experience.

LocationFamilyHospitality

Popular amenities for Downtown San Diego rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 125 reviews

Home in Normal Heights

Family Oasis w/ Heated Pool

FamilyValueOutdoor spaces

4.97 out of 5 average rating, 317 reviews

An aerial view highlights a spacious backyard featuring a solar heated pool, hot tub, and tropical landscaping. Lounge chairs are arranged around the pool, and a palapa style cabana with seating is visible, offering an inviting outdoor space for relaxation and entertainment.

Home in Bay Park

Resort Style Living with Pool, Spa, and Bay Views!

ValueFamilyHiking

4.89 out of 5 average rating, 223 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

ValueFamilyAir conditioning

4.83 out of 5 average rating, 173 reviews

Relax in Style! 4BR Pool/Spa/Firepit – SuperHost

ValueFamilyWalkability

4.96 out of 5 average rating, 138 reviews

Travelers Oasis w/ Private Pool + Hot Tub

LocationFamilyCheckout

The outdoor space features a private heated pool surrounded by five lounge chairs, each positioned for sun exposure. Colorful floaties are seen in the water. A shaded patio area is visible in the background, providing an inviting space for relaxation.

4.98 out of 5 average rating, 120 reviews

Heated Pool + Hot Tub | Games | 10 min to Beach

LocationValueIndoor spaces

A serene outdoor space showcases a sparkling pool adjacent to a jetted hot tub, with canyon views stretching in the background. A glass fence enhances the vista, and the surrounding landscape features palm trees and gentle hills under a clear blue sky.

4.98 out of 5 average rating, 116 reviews

ModernCoastal I View I Pool ITub

LocationFamilyQuiet

4.94 out of 5 average rating, 109 reviews

A welcoming living area features a leather sofa and a round coffee table, complemented by a modern electric fireplace. Natural light filters through sheer curtains, illuminating decorative vases along the floor. A cozy hanging chair and a potted plant add warmth to the space.

Home in City Heights

Stunning 2BR/2BA| Plunge Pool, AC, Private

FamilyLocationComfort

Apartment rentals with a pool

A spacious living area features large glass sliding doors that reveal an expansive ocean view with a sunset. Comfortable seating includes a modern gray sectional and two accent chairs, inviting relaxation. The room is illuminated with warm, natural light, enhancing the serene coastal atmosphere.

4.94 out of 5 average rating, 336 reviews

Beach Front Condo - Capri by the Sea - Remodeled

FamilyValueKitchen

4.86 out of 5 average rating, 232 reviews

Oceanfront/Oceanview Modern and Comfy Condo

ValueLocationLong stay

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.

Spacious 2 BR w/ Free Parking & WiFi

LocationValueWifi

4.78 out of 5 average rating, 170 reviews

A spacious living area is showcased with a comfortable leather sofa and a decorative rug. A dining table with four chairs is positioned near floor-to-ceiling windows, offering natural light. Art pieces adorn the walls, complementing the inviting atmosphere.

4.92 out of 5 average rating, 217 reviews

Windows to the Ocean

LocationValueAccuracy

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.

4.97 out of 5 average rating, 143 reviews

Bay View Condo in Pacific Beach

ValueLocationAccuracy

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, 225 reviews

Luxury Oceanfront Condo with Unbelievable Views

LocationValueSleep quality

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, 208 reviews

Beautifully remodeled 10th floor oceanfront condo

FamilyValueGetting around

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, 112 reviews

Ocean-Bay-Sunset View Condo in Pacific Beach!

FamilyValueHospitality

Other holiday rentals with a pool

4.97 out of 5 average rating, 100 reviews

Breathtaking Ocean, Bay, City & Petco Park Views

FamilyValueIndoor spaces

4.96 out of 5 average rating, 28 reviews

Top Floor Views of Ocean, Bay, City & Petco Park

ValueFamilyComfort

5.0 out of 5 average rating, 27 reviews

Downtown Studio, Luxury High-Rise, View, Parking

LocationViewQuiet

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.

4.93 out of 5 average rating, 58 reviews

Luxury High-Rise | Downtown SD

ValueLocationCondition

Townhouse in Bankers Hill - Park West

A spacious living area features a large sectional sofa, a cozy bean bag, and a coffee table on a soft area rug. A mounted television and a modern fireplace add a focal point to the room, which is illuminated by natural light from large windows.

Modern 3 bed/ 3.5 bath Townhome in Little Italy

FamilyLocationNearby

4.96 out of 5 average rating, 72 reviews

4.83 out of 5 average rating, 18 reviews

High-Rise Luxury Retreat • Pickleball • Parking

ValueLocationAccuracy

4.87 out of 5 average rating, 39 reviews

Fun and relaxation in the same location.

ValueFamilyNearby

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.