Holiday rentals with a pool in Downtown San Diego

4.99 out of 5 average rating, 192 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

LocationFamilyBathroom

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

LocationFamilyCheck-in

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.

FamilyLocationCheckout

4.94 out of 5 average rating, 150 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.

FamilyLocationNearby

4.98 out of 5 average rating, 125 reviews

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

FamilyLocationLaundry

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.

LocationFamilyAir conditioning

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.

LocationValueHeating

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.

LocationValueIndoor 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.

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Home in University Heights

An aerial view captures the spacious outdoor area, featuring a rectangular pool surrounded by sun loungers and umbrellas. Lush greenery is visible alongside neatly arranged pathways and stone retaining walls, complementing the mountain-modern design of the home in the background.

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.

FamilyLocationKitchen

4.9 out of 5 average rating, 189 reviews

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

Welcome to Endless Summer, your ideal family retreat! This beautiful 4-bedroom, 2.5-bath home is just 15 minutes from Downtown San Diego, near attractions like Petco Park, the San Diego Zoo, and local beaches. Located in Mount Helix, La Mesa, enjoy stunning canyon views and a refreshing swimming pool with a waterfall. Experience a unique stay at a home that has it all!

ValueLocationIndoor spaces

Popular amenities for Downtown San Diego rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.97 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!

LocationFamilyComfort

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!

LocationFamilyParking

5.0 out of 5 average rating, 124 reviews

Home in Bay Park

Resort-Style Villa - Pool, Spa & Views

LocationFamilyNearby

Home in Greater North Park

3BR Urban Oasis with Hot Tub, Pool & Private Deck

ValueFamilyAccuracy

4.99 out of 5 average rating, 174 reviews

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, 118 reviews

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

FamilyLocationTV

An inviting outdoor space is highlighted by a swimming pool with a water feature, surrounded by lounge chairs and a wooden deck. A movie screen is set up for outdoor viewing, while landscaped areas add greenery to the scene.

4.96 out of 5 average rating, 124 reviews

SD Group Retreat | Pool, Hot Tub, Theater, near DT

ValueFamilyOutdoor spaces

4.92 out of 5 average rating, 235 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 Bonita

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

FamilyLocationLaundry

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

LocationFamilyAir conditioning

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

ValueLocationWalkability

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

LocationValueQuiet

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

ValueLocationComfort

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.

5.0 out of 5 average rating, 143 reviews

The Endless Summer Condo!

ValueLocationSleep quality

Superhost

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.

Apartment in Spring Valley

Spacious 2 BR w/ Free Parking & WiFi

LocationFamilyComfort

4.78 out of 5 average rating, 170 reviews

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

ValueLocationAir conditioning

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

LocationFamilyWifi

4.86 out of 5 average rating, 232 reviews

Oceanfront/Oceanview Modern and Comfy Condo

ValueFamilyBiking

Other holiday rentals with a pool

4.97 out of 5 average rating, 99 reviews

Breathtaking Ocean, Bay, City & Petco Park Views

LocationFamilyHot tub

4.96 out of 5 average rating, 28 reviews

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

LocationFamilyNearby

5.0 out of 5 average rating, 27 reviews

Downtown Studio, Luxury High-Rise, View, Parking

LocationIndoor spacesCheckout

Superhost

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

LocationValueQuiet

A bright living room features a green accent wall adorned with foliage, enhancing the natural feel. A large smart TV is mounted on the wall, with a comfortable white sofa and coffee table arranged around a woven area rug. Expansive windows allow natural light to fill the space.

4.94 out of 5 average rating, 17 reviews

Modern Sky Oasis in Downtown SD

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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

FamilyValueIndoor spaces

4.96 out of 5 average rating, 72 reviews

Superhost

4.83 out of 5 average rating, 18 reviews

High-Rise Luxury Retreat • Pickleball • Parking

LocationValueNearby

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.