Holiday rentals with a pool in Shelter Island

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.

4.99 out of 5 average rating, 179 reviews

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

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.

4.99 out of 5 average rating, 100 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!

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, 283 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.

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.

4.93 out of 5 average rating, 138 reviews

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.

4.99 out of 5 average rating, 209 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.

Apartment in San Diego

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 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, 110 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.

4.97 out of 5 average rating, 156 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 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.

4.98 out of 5 average rating, 201 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 San Diego

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.

Superhost

An aerial view of a backyard pool area showcases a uniquely shaped pool surrounded by colorful floaties. A hot tub sits nearby, forming part of a spacious entertainment space under a shaded gazebo and featuring comfortable lounge chairs arranged neatly along the side.

4.82 out of 5 average rating, 100 reviews

Clairemont•Scenic View•Pool•HotTub•Spacious

🌤️Look no further! Welcome to our Sunny San Diego getaway🌤️ Our spacious, stylist 4bedroom, 3bath home is the perfect family getaway. Located in a peaceful neighborhood, this spacious retreat has everything you need for a relaxing and fun stay. Unwind on the patio, take a dip in the blue pool, and enjoy breathtaking uphill view from the backyard. The expansive yard is ideal for family activities, including a life-sized chess game. Your ideal San Diego experience awaits! 🏡✨

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.

4.93 out of 5 average rating, 285 reviews

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 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, 192 reviews

Luxury Family Home Near Dining, Shops + Zoo

Welcome to Casa Clandestino🎋 Located in North Park, this fully remodeled 1914 Craftsman offers the perfect blend of location, privacy, and style. Enjoy a stunning outdoor area with a new 30 ft. Trex deck, heated pool/hot tub, resort furniture, 65-inch outdoor TV, market lights, and a 6-burner gas grill. Inside, find 4 beds, 2.5 baths, a chef’s kitchen, Carrera marble bathrooms, original hardwood floors, and coffered ceilings.

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.