Holiday rentals with a pool in Old Town

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

4.95 out of 5 average rating, 221 reviews

The property features a spacious backyard with a heated pool surrounded by lounge chairs. Palm trees line the perimeter, and soft lighting illuminates the outdoor area during sunset. The two-story house overlooks the pool, creating an inviting atmosphere for relaxation and gatherings.

Home in La Mesa

XTRA 10% OFF until Nov: Pool, outdoor fire pits, c

Find your family's dream spot in San Diego! Our cozy house sits on a quiet hill, offering privacy and amazing sunset views. Dive into our pool year-round (heating at an additional cost), roast marshmallows by the fire, and cook up fun meals together. With 3 bedrooms and 2 bathrooms, it’s perfect for families, accommodating up to 9 guests. Plus, we're close to all the best attractions. Want a vacation you'll always remember? Send us a message to make it happen! 🌅🏠 We have 3 comfy beds that can

Guest house in Mission Hills

A cozy sleeping area features a spacious bed with a striped throw blanket adorned with decorative tassels. A flat-screen TV is mounted on the wall, and a small table is positioned beside the bed. Soft lighting is provided by wall sconces, creating a calm ambiance.

4.91 out of 5 average rating, 486 reviews

Mission Hills Charming suite, walkable to all.

Heart of Mission Hills, upscale area, this private suite, separate from the house, is perched above the pool (separate from main house), own entrance, room has walkin closet, small fridge, swivel TV, electric fireplace to warm you up. We are minutes from airport, walking distance to coffee & restaurants and central to all of SD. Please note this property is wiped down after each visit and steamed, as well as all linens washed. We also don’t rent back to back giving time for thorough cleaning.

5 out of 5 average rating, 254 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.

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, 183 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.

4.97 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.

4.93 out of 5 average rating, 272 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, record player with albums. 19 speakers in the ceilings with connection to your phone for optimal happiness. Plug and play!

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.

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

Tucked back in the peaceful neighborhood of University Heights, this home includes a lusciously landscaped yard with a: - Pool -Hottub - BBQ -Outdoor patio furniture Perfect for both families and professionals, 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

4.96 out of 5 average rating, 112 reviews

A serene backyard oasis features a small spa surrounded by lush greenery and decorative plants. The space is framed by an open wooden structure with a sloped roof, providing a cozy seating area with soft cushions. Unique pendant lights hang above, adding a touch of elegance.

Home in Normal Heights

Luxe Home w. Serene Backyard Spa

Escape to the heart of San Diego in our chic and luxurious 3-bed oasis, where upscale meets laid-back California cool. Steps from vibrant eateries, buzzing bars, and unique boutiques, this retreat offers a serene backyard with a soothing spa. Experience local attractions, beaches, and the San Diego Zoo, all a short drive away. Your ultimate San Diego adventure awaits!

Apartment in Mission Valley

A cozy living room features a comfortable gray couch adorned with a woven throw, complemented by a small circular table and a patterned area rug. Natural light floods the space through glass sliding doors that lead to a balcony with seating, framed by soft curtains.

4.92 out of 5 average rating, 165 reviews

Cozy home central to beaches & attractions

Cozy and stylish 1-bedroom condo. Centrally located, with quick access to freeways and on-site parking, nearby popular shopping malls, travelers can easily drive to San Diego Downtown, Beaches, San Diego Zoo, SeaWorld, Balboa Park and La Jolla in under 15 minutes. This place has new furniture and amenities and only 5 minutes’ walk to the trolley station.

Popular amenities for Old Town 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

4.89 out of 5 average rating, 195 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

4.97 out of 5 average rating, 298 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!

4.94 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

4.85 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

4.9 out of 5 average rating, 192 reviews

An open-concept living space features a brown leather sectional sofa, providing comfortable seating against a backdrop of light wood ceilings. A dining table with wooden chairs is visible, complemented by a sleek kitchen equipped with modern appliances and bright white cabinetry.

Home in Pacific Beach

Eco-Friendly Mount Soledad Pad with Views and Heated Pool

4.88 out of 5 average rating, 213 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.

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!

Apartment 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!

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

4.94 out of 5 average rating, 47 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.

4.85 out of 5 average rating, 198 reviews

One Bedroom Ocean Front Condo!

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

Apartment in Mission Valley

4.8 out of 5 average rating, 60 reviews

NEW by Seaworld, Mission Beach, Balboa Park

Apartment in Mission Beach

A bright and modern living space features a large window offering views of palm trees and Mission Bay. A comfortable blue sofa is paired with stylish wooden chairs, and a glass coffee table sits in the center. A wall-mounted TV and decorative wall lighting enhance the inviting ambiance.

4.85 out of 5 average rating, 84 reviews

Steps to Mission BEACH & BAY View Paradise Retreat

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

Other holiday rentals with a pool

Treehouse in Mission Hills

A light-filled open living space features a spacious bed complemented by a soft area rug. A kitchenette with a countertop and two wooden stools is positioned beside a seating area with a gray sofa. Large windows provide views of the surrounding greenery.

4.91 out of 5 average rating, 22 reviews

Treehouse Retreat in Mission Hills

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

5 out of 5 average rating, 11 reviews

Flat in San Diego

King Bed + Free Parking • Near SeaWorld & Beaches

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

4.95 out of 5 average rating, 75 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 Cherokee Point

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