Holiday rentals with a pool in Sail Bay

4.9 out of 5 average rating, 124 reviews

Condo in San Diego

Oceanfront Condo

Private parking, a relaxing pool & jacuzzi, and direct beachfront living- all in one stunning retreat. HIGH LEVEL condo (Best Views!) Wake up to waves and breathtaking ocean views. Enjoy coffee with a sunrise over Crystal Pier, then walk to the sand in seconds. Lounge by the pool, grill outdoors, or unwind on the rooftop terrace with a sunset. Newly renovated kitchen & bathrooms. No cleaning fees—just a stress-free, luxury stay. Fall asleep to the sound of waves. Your beachfront escape awaits.

LocationFamilyShared spaces

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.

5 out of 5 average rating, 294 reviews

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.

ValueFamilyComfort

4.79 out of 5 average rating, 450 reviews

A private entrance is surrounded by lush green foliage, providing a sense of seclusion. The entrance door, painted in a calm blue, leads to the interior space. A paved walkway extends toward the pool area, enhancing the overall tranquil setting.

Guesthouse in San Diego

Law Street Retreat

RENOVATED…Studio with separate entrance in gated property 6 blocks from beach in Pacific Beach. Bikes now available! Ask host for details. Sleeps 3, amenities include a queen bed and a fold single bed couch with full bath, small fridge, microwave, smart TV, 100mbps WiFi and air conditioning. Guests are welcome to enjoy the pool, outside shower and BBQ. Pets are welcome. There is a $50 fee per pet per stay. The studio is attached to the pool house. The pool pump is behind 2 doors & runs daily.

LocationFamilyIndoor spaces

4.97 out of 5 average rating, 203 reviews

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.

Condo in San Diego

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.

FamilyValueParking

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.

4.92 out of 5 average rating, 124 reviews

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.

LocationFamilyAmenities

4.91 out of 5 average rating, 211 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.

Condo in San Diego

Windows to the Ocean

Located by the Ocean in Pacific Beach, few blocks from the Crystal Pier, this luxurious 2-bedroom condo is steps away from restaurants, cafes, bars, nightlife, shopping and of course, the beach! Floor-to-ceiling windows from every room are perfect for enjoying unobstructed views of the ocean, either while sipping a morning cup of coffee or staring at a stunning sunset. Whether you are looking to experience an active beach-front lifestyle or just have a relaxing break, you will find it here!

ValueLocationCheckout

4.97 out of 5 average rating, 173 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 San Diego

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.

LocationValuePool

4.92 out of 5 average rating, 255 reviews

A private entryway is framed by lush greenery and colorful plants. A rustic wooden gate provides access, set against a clean, beige wall. Blue pots filled with vibrant foliage are positioned at either side of the path leading to the entrance.

Cottage in San Diego

Crown Point Gem with Salt Water Pool

This Cottage home is a beautiful Oasis in San Diego's Crown Point neighborhood. Our home is 2 blocks from Mission Bay with access to bike paths, water sports, and playgrounds for the kids. Easily walk to great restaurants, coffee shops, night life and shopping. With our cool saltwater pool, hot tub, grill and relaxing patio space you wont even need to leave the house to get that vacation feeling. Please let us know if you would like the pool heated, we charge $75/night for this service.

ValueFamilyCheck-in

An outdoor entertaining area features a large sectional sofa with rich cushions surrounding a glowing fire pit. Two shaded umbrellas offer comfort, while a backdrop of city lights twinkles across the horizon during twilight.

4.98 out of 5 average rating, 123 reviews

Pacific Beach-Amazing Panoramic View-Heated Pool

LAJOLLA / PACIFIC BEACH - Mt. Soledad Spectacular Luxury View Home - 180 Degree Amazing Panoramic Views. Upgraded home located on Mt. Soledad - unobstructed views of Mission Bay, Downtown, Ocean & Mountains from every room. Over 1000 ft of outdoor entertaining decks. - Heated Pool - Jacuzzi - Sauna - Viking BBQ - Outdoor Fire Pit - Luxury bedding - 2 outdoor LED Tv's - 6 total large screen LED Tv's - iPad Remotes - Indoor / Outdoor Music -Direct TV, Apple Tv, Netflix, High Speed WiFi

ValueFamilyView

4.94 out of 5 average rating, 195 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.

ValueLocationKitchen

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.

4.9 out of 5 average rating, 203 reviews

Eco-Friendly Mount Soledad Pad with Views and Heated Pool

Savor the ocean tang from the front patio while taking in 180+ degree views of the downtown city lights, peek-a-boo's of Pacific Beach, Crystal Pier, Mission Beach, Ocean Beach & Ocean Beach Pier all while staring directly over Mission Bay and the Sea World Fireworks. The interior features mid-century modern touches, and has been designated as a "Demonstration Home" and won the coveted "Excellence Award" from SDG&E for its energy and water efficiency, plus indoor air quality.

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