Vacation 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, 160 reviews

Custom Guesthouse, Balboa Park/Zoo/Hillcrest& pool

2021 CUSTOM guest home with pool in Hillcrest/San Diego Zoo/Balboa Park area. Full kitchen, a queen bed, a queen sleeper sofa, and a 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 Sprouts. Minutes' drive to San Diego beaches. No rent for children under 3, only $95/stay. High chair, Pack & Play/Crib, crib mattress, and cover are provided.

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, 112 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 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, 171 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.

An outdoor dining area is highlighted by a large table surrounded by six black wicker chairs. French doors open to a spacious interior, while potted plants and greenery frame the setting, creating an inviting and open atmosphere for relaxation and gatherings.

4.93 out of 5 average rating, 375 reviews

PB Dream HOUSE Steps to Beach Bay ❤️Modern Private

Located in the heart of Pacific Beach, this modern beach house has been completely remodeled and re-imagined to make your stay unforgettable. Designed with the eye toward comfort and entertainment. *Private Outdoor Retreat w/ Kitchen, 6 Person Hot Tub, Fire Pit *AC w/ independent temp control in each room *Voice Controlled Sound System, 4K TVs in every room *Beautiful bathroom w/ dual showers *Bikes, boards, beach towels and toys *Walk to coffee, yoga & gyms, dining, entertainment, shopping!

A clear blue pool is surrounded by lush palm trees, with lounge chairs positioned along the poolside. The area is paved with bricks, and a spacious pool house is visible in the background, emphasizing a relaxed outdoor environment.

4.97 out of 5 average rating, 173 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.

An aerial view captures the oceanfront condo alongside the sandy beach, with an expansive coastline stretching below. The surrounding neighborhood features a mix of residential and commercial structures, interconnected by roads and pathways, creating a vibrant coastal community.

4.84 out of 5 average rating, 167 reviews

Ocean front condo heart of pacific beach

Gorgeous ocean-front condo with amenities galore. In the heart of bustling Pacific Beach, this 1 BR condo has it all: a magnificent, unobstructed ocean view on the 10th floor; steps from the beach, restaurants, shops, and bars; a roomy, delightful living space with floor-to-ceiling windows; a modern, fully equipped kitchen, and parking spot! Leave your worries behind, soak up the sun, check out San Diego’s many attractions — or just kick back and relax in this peaceful, beach-front oasis.

4.94 out of 5 average rating, 169 reviews

A private patio area is depicted, featuring comfortable seating and a coffee table surrounded by plants. A bright blue umbrella provides shade by the pool, while sunlight reflects off the water, enhancing the relaxed atmosphere. Colorful cushions add a touch of warmth to the seating.

Guesthouse in San Diego

Casita w/Private Pool, King Bed, Full Kitchen!

Perfect poolside retreat suitable for small families and couples! The suite boasts a fully-equipped kitchen, a private pool, front patio and sunbathing deck! You'll enjoy a luxurious king-size bed and a convenient full-size fold-out couch, perfect for kids! Plus, all the amenities necessary for a memorable stay. Located in one of San Diego's most central neighborhoods of Mission Hills, you're just a stroll away from restaurants, Old Town, the light rail, and easy access to the I-5 highway!

A spacious living area features large windows offering panoramic ocean views and allowing natural light to fill the room. A comfortable blue couch is positioned near a glass coffee table, with a television mounted above a dark wooden entertainment unit.

4.91 out of 5 average rating, 163 reviews

Enchanted Ocean Sunsets

Ocean front condo In Pacific Beach with spectacular sunsets and stunning views of Mission Beach and La Jolla. Beach front location just steps away from the sand and waves. Enjoy surfing, paddle boarding, long walks on the boardwalk, bike rentals, boat rentals, volleyball, fabulous restaurants and a vibrant night life! Delightful location close to amazing attractions including Sea World, San Diego Zoo and Balboa park. Come spoil yourself in this newly remodeled luxurious space!

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.

5 out of 5 average rating, 130 reviews

3 BR Urban Oasis with Pool and Spa in Great Area

This special place is close to everything, making it easy to plan your visit. The charming, walkable, and historic neighborhood of University Heights provides a wonderful park, restaurants, coffeehouses, ice cream shop, bars, and markets nearby. Within 2 miles from the San Diego Zoo and historic Balboa Park. 15 minutes by car to Sea World, beaches, or downtown. The open plan of the communal areas of the house makes it a great space for spending quality time with friends or family.

4.96 out of 5 average rating, 119 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

This is the 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 Downtown, La Jolla, Beaches, Zoo, Sea World & Convention Center. Hike next door at Mission Trails & Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo and top quality finishes await you inside. Everything you need for memorable vacation! No smoking or vaping on the property.

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, 231 reviews

Midcentury Lux 4BR home w Pool/Spa/Cabana/Firepit

COMPLETELY renovated 4BR 3 Bath mid-century home with heated pool, hot tub and fire pit in totally private backyard retreat. We renovated the house top-to-bottom, inside and out and everything is brand new. The beds are top quality with very high quality 100% cotton sheets and bath towels. The house is centrally located in a safe, friendly neighborhood and has beautiful mountain views in the back. Additionally, we do not charge any fees for anything!

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.