Holiday rentals with a pool in Downtown San Diego

4.99 out of 5 average rating, 187 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

4.94 out of 5 average rating, 101 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

Modern 2 bed|2 full bath in the heart of San Diego. Featuring trendy interiors, stock tank pool, and thoughtful amenities, this space is designed for relaxation & comfort. Enjoy seamless indoor-outdoor living with cozy touches that make you feel at home. Casa Luna is perfectly located minutes from North Park, Downtown, Balboa Park, the zoo, close to beaches & a vibrant dining scene. Whether you’re here to unwind or explore, Casa Luna is your ideal home for an unforgettable San Diego experience.

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, 105 reviews

ModernCoastal I View I Pool ITub

Spectacular canyon views are the backdrop to this stunning, modern newly renovated San Diego home! The jetted hot tub with water falling in the sparkling pool, the natural light streaming through the french doors, huge screened folding door, and skylights, the beautiful Great Room with the inviting living room, gourmet kitchen, indoor/outdoor dining, comfy beds, spectacular rooms & bath, sunset vista point, outdoor BBQ & backyard loungers and daybed are all designed to get you in vacation mode!

5 out of 5 average rating, 289 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.

4.94 out of 5 average rating, 143 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.

4.97 out of 5 average rating, 92 reviews

Breathtaking Ocean, Bay, City & Petco Park Views

It’s all about the VIEWS in this Luxury Downtown residence featuring top Italian grain leather futuristic smart furniture with BREATHTAKING VIEWS of the Bay, Ocean, Petco Park from every room & the sunny balcony, Coronado Bridge, Point Loma and the City. Steps to Convention Center, Rady Shell, Seaport Village, Embarcadero, and Gaslamp Quarter with restaurants, music venues, coffee shops, rooftops, and sprawling nightlife. Little Italy, Balboa Park, San Diego Zoo, Beaches and Shopping nearby.

4.92 out of 5 average rating, 119 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.

4.96 out of 5 average rating, 167 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.

Guesthouse 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.

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.

4.88 out of 5 average rating, 229 reviews

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.

4.94 out of 5 average rating, 108 reviews

Home in Serra Mesa

Beach<15min,Heated Pool,New Central AC, 4Br Family

Escape to a tranquil haven in the vibrant neighborhood of Serra Mesa. This spacious 4-bedroom, 2-bathroom home offers whole home AC, recently remodeled finishes and a custom built heated pool with deck. Ideal for families, the home has a welcoming ambiance and a backyard for outdoor gatherings, with comfortable furniture and 20ft outdoor Mural by a local artist. Location is convenient, with the Airport, Downtown SD, SD Zoo, and an array of attractions just a short 15-minute drive.

4.93 out of 5 average rating, 290 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.

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.

4.97 out of 5 average rating, 115 reviews

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

Welcome to Casa Leon — a private, resort-style group retreat in San Diego. Perfect for bachelorette & bachelor trips, birthdays, family gatherings, and group getaways, this newly remodeled home blends privacy, space, and unforgettable experiences. Enjoy hot tub movie nights under the stars, poolside hangs, and fireside evenings—all just minutes from Downtown, Gaslamp, Balboa Park, the Airport, SeaWorld, and the SD Zoo.

Popular amenities for Downtown San Diego rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 123 reviews

Travelers Oasis w/ Private Pool + Hot Tub

4.96 out of 5 average rating, 102 reviews

Luxury SD Retreat • Pool • Hot Tub • EV Charger

4.89 out of 5 average rating, 209 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

Home in Greater North Park

An outdoor living space is showcased, featuring a circular pool surrounded by wooden decking. Comfortable lounge seating with dark cushions and a fire pit is positioned under string lights. Umbrellas provide shade while a gas grill is visible nearby, creating an inviting atmosphere.

4.95 out of 5 average rating, 197 reviews

Luxury Family Home Near Dining, Shops + Zoo

5 out of 5 average rating, 104 reviews

A landscaped backyard features a pathway of concrete pavers lined with gravel, leading to a seating area with modern outdoor furniture. To one side, a wooden deck provides elevated space with views of the surrounding area and palm trees, complemented by open sky.

Home in Del Cerro

Modern Hilltop Home: Roomy, Views, Family-Friendly

4.91 out of 5 average rating, 223 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!

4.96 out of 5 average rating, 213 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 !

Superhost

The outdoor area features a sparkling pool with a curved design, surrounded by lush greenery and palm trees. A spacious patio allows for relaxation and sunbathing, with a clean, contemporary aesthetic highlighting the inviting southern California weather.

4.75 out of 5 average rating, 122 reviews

Tranquil Canyon Oasis + Private Pool + Sunset View

Condo 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, 106 reviews

Ocean-Bay-Sunset View Condo in Pacific Beach!

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.

4.96 out of 5 average rating, 136 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, 207 reviews

Ocean front condo heart of pacific beach

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.

4.99 out of 5 average rating, 216 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, 199 reviews

Beautifully remodeled 10th floor oceanfront condo

Superhost

A spacious living area is presented with a large blue sofa facing a mounted flat-screen TV. The kitchen features white cabinetry with modern appliances and a decorative backsplash. A dining area with two high-backed stools is positioned at the counter, alongside a coffee table adorned with a decorative arrangement.

Condo in San Diego

4.83 out of 5 average rating, 206 reviews

Cozy clean 1 bedroom centrally located by beaches

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, 539 reviews

Oceanfront Elegant Condo - Remarkable Amenities

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, 335 reviews

Beach Front Condo - Capri by the Sea - Remodeled

Other holiday rentals with a pool

Superhost

4.92 out of 5 average rating, 38 reviews

Fun and relaxation in the same location.

A spacious living area features a large sectional sofa with light-colored throw blankets. A glass coffee table sits on a soft area rug, while a flat-screen TV is mounted on the wall. Large windows allow natural light to fill the room, highlighting wooden flooring.

4.93 out of 5 average rating, 28 reviews

Bright 2BR | Views &Walkability

Bungalow in Bankers Hill - Park West

A private dipping pool is surrounded by sleek wooden beams and potted greenery. Red outdoor seating offers a comfortable space for lounging, while the fire pit provides warmth. White drapery creates shade over the area, enhancing the tranquil ambiance.

4.93 out of 5 average rating, 54 reviews

San Diego Oasis Middle of DT

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.

4.98 out of 5 average rating, 49 reviews

Luxury High-Rise | Downtown SD

5 out of 5 average rating, 22 reviews

Walk to Comic-Con, Luxury High-Rise, View, Parking

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, 46 reviews

Downtown Escape I Free Garage Parking

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.

4.93 out of 5 average rating, 14 reviews

Modern Sky Oasis in Downtown SD