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, 190 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

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.

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, 110 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, 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.

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.

4.94 out of 5 average rating, 144 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.

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.

4.9 out of 5 average rating, 164 reviews

Ocean Front at La Jolla Shores

This ocean front home is situated in the popular La Jolla Shores beach community. With its incredible seaside location, staggering views of the surf, wide sandy beach, and breathtaking sunsets this La Jolla Shores beach house is a vacation home you'll want to visit. Boasting nearly 3,000 square feet of living space with 4 bedrooms, 3 full baths, chef's kitchen with views, spacious great room with ocean views, fireplace, outdoor kitchen with built in BBQ, pool and 3 expansive outdoor decks.

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.

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.

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, 291 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.

4.93 out of 5 average rating, 705 reviews

Guesthouse in San Diego

OB studio, ocean views, hot tub & garage parking!

Casita De 7 Palmeras is an open floor plan studio located in Ocean Beach which is a central location to explore San Diego's best beaches and attractions. Spend the day at the beach, zoo, Sea World, or wherever, and then come back and unwind in the amazing hot tub or on the view terrace to enjoy the amazing sunset! Garage parking, top quality Cal King bed, ocean / bay views, fast & reliable WIFI, premium Direct TV HD channel package, and Fujitsu split air-conditioning!