Holiday rentals with a pool in Shelter Island

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Top-rated rentals with a pool in Shelter Island

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Top Guest favourite
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.
Home in San Diego
4.99 out of 5 average rating, 171 reviews

Custom Guesthouse, Balboa Park/Zoo/Hillcrest& pool

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

Guest favourite
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.
Guesthouse in San Diego
4.91 out of 5 average rating, 486 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.

Top Guest favourite
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
4.98 out of 5 average rating, 194 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.

Top Guest favourite
A person stands beside floor-to-ceiling windows that offer a view of the ocean during sunset. The seating area is furnished with a leather recliner, and a vibrant artwork adorns the wall. Soft lighting from two lamps enhances the warm ambiance.
Condo in San Diego
4.94 out of 5 average rating, 512 reviews

Oceanfront Elegant Condo - Remarkable Amenities

Spectacular Oceanfront, 8th Floor. Hear the surf as you slide open the floor-to-ceiling glass door. The Boardwalk and beautiful safe swimming beach are at the foot of your building. Join the surfers using our wet suits and our beach cruiser bikes for an easy ride along the Ocean and Mission Bay or stroll along for vibrant people watching. Return to your elegantly appointed, romantic condo provisioned to meet your every need. Everything you need is in 10 blocks along beautiful California coast!

Top Guest favourite
A bright living area features a large window with ocean views and light blue skies. A wooden coffee table rests on a patterned rug, surrounded by comfortable seating. A flat-screen TV is located on a white media console, enhancing the room's modern look.
Condo in San Diego
4.97 out of 5 average rating, 183 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.

Superhost
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.
Condo in San Diego
4.85 out of 5 average rating, 181 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.

Guest favourite
A spacious living area is showcased with a comfortable leather sofa and a decorative rug. A dining table with four chairs is positioned near floor-to-ceiling windows, offering natural light. Art pieces adorn the walls, complementing the inviting atmosphere.
Condo in San Diego
4.92 out of 5 average rating, 191 reviews

Windows to the Ocean

Located by the Ocean in Pacific Beach, few blocks from the Crystal Pier, this luxurious 2-bedroom condo is steps away from restaurants, cafes, bars, nightlife, shopping and of course, the beach! Floor-to-ceiling windows from every room are perfect for enjoying unobstructed views of the ocean, either while sipping a morning cup of coffee or staring at a stunning sunset. Whether you are looking to experience an active beach-front lifestyle or just have a relaxing break, you will find it here!

Guest favourite
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.
Guesthouse in San Diego
4.97 out of 5 average rating, 193 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.

Top Guest favourite
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
4.96 out of 5 average rating, 140 reviews

Vacation Paradise-Heated Pool+Hot Tub+FirePit+EV

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

Top Guest favourite
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.
Home in San Diego
4.97 out of 5 average rating, 155 reviews

University Heights Oasis Getaway

Tucked back in the peaceful neighborhood of University Heights, this home includes a lusciously landscaped yard with a: - Pool -Hottub - BBQ -Outdoor patio furniture Perfect for both families and professionals, our property also offers the ultimate in convenience: - Acclaimed restaurants and cafes are just minutes away - Close to the Airport, Zoo, Balboa Park, and Downtown - Close to many world-class beaches

Top Guest favourite
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.
Home in San Diego
4.96 out of 5 average rating, 112 reviews

Luxe Home w. Serene Backyard Spa

Escape to the heart of San Diego in our chic and luxurious 3-bed oasis, where upscale meets laid-back California cool. Steps from vibrant eateries, buzzing bars, and unique boutiques, this retreat offers a serene backyard with a soothing spa. Experience local attractions, beaches, and the San Diego Zoo, all a short drive away. Your ultimate San Diego adventure awaits!

Guest favourite
A cozy living room features a comfortable gray couch adorned with a woven throw, complemented by a small circular table and a patterned area rug. Natural light floods the space through glass sliding doors that lead to a balcony with seating, framed by soft curtains.
Condo in San Diego
4.92 out of 5 average rating, 165 reviews

Cozy home central to beaches & attractions

Cozy and stylish 1-bedroom condo. Centrally located, with quick access to freeways and on-site parking, nearby popular shopping malls, travelers can easily drive to San Diego Downtown, Beaches, San Diego Zoo, SeaWorld, Balboa Park and La Jolla in under 15 minutes. This place has new furniture and amenities and only 5 minutes’ walk to the trolley station.

Popular amenities for Shelter Island rentals with a pool

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