Vacation rentals with a pool in Shelter Island

4.86 out of 5 average rating, 340 reviews

The outdoor area features a spacious salt-water pool surrounded by natural rock formations and tropical palm trees. A jacuzzi is located nearby, and the peaceful setting offers ample space for relaxation and enjoyment of the sun.

Guesthouse in Coronado

Coronado Island Pool Cottage

2 blocks from the Beach, the Cottage offers a peaceful, clean & private stay with exclusive use of the pool, jacuzzi, bikes, beach items, surfboards, deck chairs, Cable TV & Wifi. 3 rooms: QUEEN BEDROOM has AC, heater, ironing, hangers & 8 foot mirrors. LOUNGE ROOM has AC, heater, QUEEN sofa-bed, Cable TV, microwave, fridge/freezer, toaster, cutlery, coffee/tea, & bottled water. BATHROOM has walk-in shower, all toiletries & towels. BEFORE BOOKING, please click/read the “SHOW MORE" details here:

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.

4.94 out of 5 average rating, 157 reviews

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, cocktail bars, the light rail, and easy access to the I-5 highway!

A cozy sleeping area features a spacious bed with a striped throw blanket adorned with decorative tassels. A flat-screen TV is mounted on the wall, and a small table is positioned beside the bed. Soft lighting is provided by wall sconces, creating a calm ambiance.

4.91 out of 5 average rating, 458 reviews

Mission Hills Charming suite, walkable to all.

Heart of Mission Hills, upscale area, this private suite, separate from the house, is perched above the pool (separate from main house), own entrance, room has walkin closet, small fridge, swivel TV, electric fireplace to warm you up. We are minutes from airport, walking distance to coffee & restaurants and central to all of SD. Please note this property is wiped down after each visit and steamed, as well as all linens washed. We also don’t rent back to back giving time for thorough cleaning.

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.

5 out of 5 average rating, 149 reviews

Custom Guesthouse, Balboa Park/Zoo/Hillcrest& pool

2021 CUSTOM guest home with a pool in the heart of Hillcrest/San Diego/Zoo/Balboa Park area. Full kitchen, a queen bed & a queen sleeper sofa. Full bath, indoor & outdoor dining, WiFi, smart TV, pool, AC/heating, BBQ& free parking. Short walk to restaurants/shops/stores (Trader Joe's, Ralph's & Whole Foods). Minutes' drive to San Diego's beaches. It accommodates 1-4 guests. No rent for children under 3, but $95/stay. A high chair, Pack & Play/Crib with a crib mattress and cover are provided.

4.98 out of 5 average rating, 161 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.

Condo 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 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, 243 reviews

Lionhead - Private Boutique Home

Heated pool, spa, cabana and views. Boutique hotel vibes in San Diego. Palm Springs meets South Beach with a splash of groovy. Location is perfect for Downtown, conventions, shows in town. Highway friendly. Private backyard for bbq, food, drinks and relaxing. Pool is heated with cozy spa to relax and watch the planes take off. Hi speed Wifi, smart TV's, HBO, NFL Package, record player with albums. 19 speakers in the ceilings with connected to your phone for optimal happiness. Plug and play!

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.

4.98 out of 5 average rating, 180 reviews

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

A city skyline is displayed at dusk, featuring tall modern buildings and a vibrant sky transitioning from purple to orange. Outdoor seating areas are visible below, illuminated by warm lights, creating a lively urban atmosphere.

Condo in San Diego

4.91 out of 5 average rating, 103 reviews

SKYLINE VIEW 4U

Picturesque views from this studio loft with queen bed and floor to ceiling windows looking over downtown! Enjoy a cup of coffee or evening dinner on your private patio. The Convention center, Horton Plaza, Sea Port Village, Gaslamp, and Petco Park just a block away. Experience San Diego living in one of the best location in downtown. Accommodates 2-4 comfortably and is ideal for a couples getaway or traveling business professionals. *free garage parking available during Comic Con

An inviting outdoor area features a crystal-clear pool alongside a spa with a waterfall feature. Relaxing lounge chairs are positioned by the water, surrounded by lush landscaping and stone accents, creating a serene atmosphere for enjoyment.

4.94 out of 5 average rating, 149 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 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.

4.99 out of 5 average rating, 151 reviews

La Jolla Beach House-Family Focused-3min to Beach

Welcome to the Bird Rock Beach House! This delightful boho beach-inspired house is the perfect home for your San Diego/ La Jolla family getaway. You're minutes from La Jolla Cove, Windansea Beach, Mission Bay, and Mission Beach. You can explore downtown La Jolla & Garnet Avenue, which both offer a variety of restaurants, nightlife, and shops. Or you can head 5 minutes north to the world-renowned La Jolla Cove to see the playful seals who also call this place home. No parties/events

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.

4.95 out of 5 average rating, 106 reviews

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.