Holiday rentals with a pool in Shelter Island

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.

4.94 out of 5 average rating, 101 reviews

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

Modern 2 bed|2 full bath in the heart of San Diego. Featuring trendy interiors, stock tank pool, and thoughtful amenities, this space is designed for relaxation & comfort. Enjoy seamless indoor-outdoor living with cozy touches that make you feel at home. Casa Luna is perfectly located minutes from North Park, Downtown, Balboa Park, the zoo, close to beaches & a vibrant dining scene. Whether you’re here to unwind or explore, Casa Luna is your ideal home for an unforgettable San Diego experience.

4.98 out of 5 average rating, 121 reviews

Heart of San Diego in Old Town. Private Oasis 6

This Redesigned 4000-SF private oasis located in the heart of San Diego’s historic Old Town is the best on the market. Renovated with every possible option: chef’s kitchen, in/outdoor entertaining, lounges&en-suite bathrooms. This property boasts sophisticated living with just the right amount of edge. Converted garage doors flood each living space with light and character. This location is just steps from dining & nightlife and close 2 San Diego beaches, airport, shopping, attractions plus more

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, 105 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, 289 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 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, 119 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.

4.96 out of 5 average rating, 166 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.

4.94 out of 5 average rating, 108 reviews

Beach<15min,Heated Pool,New Central AC, 4Br Family

Escape to a tranquil haven in the vibrant neighborhood of Serra Mesa. This spacious 4-bedroom, 2-bathroom home offers whole home AC, recently remodeled finishes and a custom built heated pool with deck. Ideal for families, the home has a welcoming ambiance and a backyard for outdoor gatherings, with comfortable furniture and 20ft outdoor Mural by a local artist. Location is convenient, with the Airport, Downtown SD, SD Zoo, and an array of attractions just a short 15-minute drive.

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, 290 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.

4.96 out of 5 average rating, 113 reviews

An outdoor seating area is equipped with a sectional couch surrounding a stone fire pit, with flames flickering invitingly. A large dining table offers ample seating. The heated pool glistens in the background, surrounded by lounge chairs and shaded umbrellas.

Home in El Cajon

Family Fun Oasis Pool Spa and Game Room

Exceptional home w/heated pool and spa in a quiet neighborhood; kitchen has everything you need and more! Perfect for families with kids of various ages or multiple families. What to Expect: - Heated pool w/safety cover - Hot tub - Game Room - Trampoline - Jungle gym - Baby/toddler supplies (pack N play/High Chair) - Spacious master suite. - 20 mins to the beach, the San Diego Zoo, Balboa Park, Sea World, Little Italy and downtown San Diego and all that it has to offer!

4.93 out of 5 average rating, 697 reviews

Guest house 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!

An inviting outdoor space is highlighted by a swimming pool with a water feature, surrounded by lounge chairs and a wooden deck. A movie screen is set up for outdoor viewing, while landscaped areas add greenery to the scene.

4.97 out of 5 average rating, 115 reviews

SD Group Retreat | Pool, Hot Tub, Theater, near DT

Welcome to Casa Leon — a private, resort-style group retreat in San Diego. Perfect for bachelorette & bachelor trips, birthdays, family gatherings, and group getaways, this newly remodeled home blends privacy, space, and unforgettable experiences. Enjoy hot tub movie nights under the stars, poolside hangs, and fireside evenings—all just minutes from Downtown, Gaslamp, Balboa Park, the Airport, SeaWorld, and the SD Zoo.

A serene backyard is framed by colorful sunset skies, featuring a cozy hammock in the foreground and a comfortable seating area with grey couches. String lights add warmth to the outdoor space, complemented by lush greenery throughout the neatly landscaped yard.