Holiday rentals with a pool in Downtown

4.99 out of 5 average rating, 134 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

Guest house in Mission Hills

A private patio area is depicted, featuring comfortable seating and a coffee table surrounded by plants. A bright blue umbrella provides shade by the pool, while sunlight reflects off the water, enhancing the relaxed atmosphere. Colorful cushions add a touch of warmth to the seating.

4.94 out of 5 average rating, 179 reviews

Casita w/Private Pool, King Bed, Full Kitchen!

Perfect poolside retreat suitable for small families and couples! The pool house boasts a fully-equipped kitchen, a private pool, front patio and sunbathing deck! You'll enjoy a luxurious king-size bed and a convenient full-size fold-out couch, perfect for kids! Plus, all the amenities necessary for a memorable stay. Located in one of San Diego's most central neighborhoods of Mission Hills, you're just a stroll away from restaurants, Old Town, the light rail, and easy access to the I-5 highway!

4.99 out of 5 average rating, 167 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 guest home with pool in Hillcrest/San Diego Zoo/Balboa Park area. Full kitchen, a queen bed, a queen sleeper sofa, and a 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 Sprouts. Minutes' drive to San Diego beaches. No rent for children under 3, only $95/stay. High chair, Pack & Play/Crib, crib mattress, and cover are provided.

4.93 out of 5 average rating, 121 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.

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, 181 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 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, 178 reviews

Beautifully remodeled 10th floor oceanfront condo

Located on the 10th floor of the beautiful Capri by the Sea in Pacific Beach, this beautifully remodeled one bedroom condo has unbelievable views through its floor to ceiling windows. All kitchen amenities, beach toys, big screen TV, Cable, WiFi, one parking spot in gated lot with option for more. Steps to beach, short walk to lots of restaurants and bars. Resort style complex offering 360 degree view roof deck, gas BBQ, secure private pool and spa, hot water beach shower, and 24-hr security.

4.98 out of 5 average rating, 217 reviews

The beautifully illuminated pool area features a saltwater pool and hot tub under a starry sky. Lush tropical plants surround the space, enhancing the ambiance. A bottle of champagne and flutes are ready for celebration, while cozy seating is visible in the background.

Guest house in Talmadge

Lovely Guesthouse in garden setting

Centrally located guesthouse on quarter acre lot in a beautiful community 5 minutes drive from restaurants, pubs, shops, library, SDSU. 15 minute drive to beaches, downtown, military bases, zoo, Balboa Park. 800sq’ cottage with great outdoor space- patio, gas grill, salt water/solar heated pool & hot tub, fruit trees for sharing, gardens. Central A/C and heat. Books and games for fun down time. Relax w/SMORS and drinks in the evening around the fire pit table : ) Street parking available.

4.93 out of 5 average rating, 260 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

Heated pool, spa, cabana and views. Boutique hotel vibes in San Diego. Palm Springs meets South Beach with a splash of groovy. Location is perfect for Downtown, conventions, shows in town. Highway friendly. Private backyard for bbq, food, drinks and relaxing. Pool is heated with cozy spa to relax and watch the planes take off. Hi speed Wifi, smart TV's, HBO, NFL Package, record player with albums. 19 speakers in the ceilings with connected to your phone for optimal happiness. Plug and play!

4.97 out of 5 average rating, 191 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.

4.95 out of 5 average rating, 164 reviews

The exterior showcases a modern home adjacent to a serene pool, featuring a waterfall feature. Sun loungers and chairs are positioned around the pool area, with landscaped gardens providing a backdrop of greenery and colorful succulents.

Home in San Diego

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.

4.95 out of 5 average rating, 120 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

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, 128 reviews

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

This is the 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 Downtown, La Jolla, Beaches, Zoo, Sea World & Convention Center. Hike next door at Mission Trails & Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo and top quality finishes await you inside. Everything you need for memorable vacation! No smoking or vaping on the property.

Popular amenities for Downtown 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.

5 out of 5 average rating, 137 reviews

3BR Urban Oasis | Pool & Spa | University Heights

4.89 out of 5 average rating, 187 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

4.98 out of 5 average rating, 294 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!

4.95 out of 5 average rating, 115 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

4.84 out of 5 average rating, 219 reviews

A spacious outdoor area features a clear blue pool surrounded by palm trees. Lounge chairs are positioned nearby, and a shaded table with chairs offers a spot for relaxation. The backyard showcases a privacy fence and ample sunlight.

Home in La Mesa

Sunny SD l Pool l BBQ l Pool Loungers l Sleeps 10

4.82 out of 5 average rating, 126 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

Home in Greater North Park

4.91 out of 5 average rating, 105 reviews

5m to Zoo & pool- The San Diego Poolside Paradise

4.91 out of 5 average rating, 200 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!

Apartment rentals with a pool

Apartment in Mission Beach

Aerial view captures a vibrant sunset over the ocean, with golden hues reflecting on the water's surface. The beachfront is framed by palm trees and residential buildings, while a sandy shore gently meets the water. Nearby, grassy park areas and a parking lot are visible.

4.87 out of 5 average rating, 127 reviews

Best Beach in seconds! Luxury 3Bd/2Ba KING Beds!

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, 93 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.

4.98 out of 5 average rating, 123 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.

4.85 out of 5 average rating, 175 reviews

Ocean front condo heart of 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, 250 reviews

Centrally located n UCSD/ utc-laJolla

4.93 out of 5 average rating, 42 reviews

The living room displays a blend of modern decor and comfort, featuring a gray sofa, an orange accent chair, and a circular coffee table on a vibrant area rug. A large flat-screen television is mounted on the wall, while natural light filters in through sheer drapes.

Apartment in San Diego

Luxury Living Near the Beach

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.

4.86 out of 5 average rating, 191 reviews

One Bedroom Ocean Front Condo!

4.79 out of 5 average rating, 217 reviews

A clear blue swimming pool is surrounded by a spacious deck. Several lounge chairs are arranged around the pool, with picturesque landscaping visible in the background. The area is secured with fencing, ensuring a safe environment for guests.

Apartment in San Diego

Comfortable & convenient accommodation @ San Diego

Other holiday rentals with a pool

5 out of 5 average rating, 58 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, 11 reviews

Home in La Mesa

Airbnb Luxe: The Perfect Blend of Access & Escape

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, 65 reviews

Breathtaking Ocean, Bay, City & Petco Park Views

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, 25 reviews

Luxury High-Rise | Downtown SD

4.72 out of 5 average rating, 58 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

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, 25 reviews

Downtown Escape I Free Garage Parking

5 out of 5 average rating, 12 reviews

An inviting pool area is shown with a clear blue pool surrounded by tan decking. Lounge chairs are placed nearby, and a pergola offers shaded seating. Lush greenery and distant hillside views enhance the outdoor space under a bright blue sky.

Guest house in El Cajon

Casa sunset

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.