Vacation 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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Superhost

Guesthouse in San Diego

4.91 out of 5 average rating, 247 reviews

Green Door Cottage

Enjoy our new, fully renovated (2021) tiny Cottage which holds a timeless charm and is also filled with a modern touch. Close to all the wonderful things San Diego has to offer - beaches, downtown, the zoo, Padres games, SeaWorld, SAN airport, Old Town, SDSU, you name it! Nice sized turf yard with total privacy and an amazing back deck! Outside table and fire pit are perfect for the cool nights of San Diego. If you need more space, check out our other listing, Pink Door Craftsman (sleeps 7)!

Aug 25 – Sep 1

€ 147 per night

Guest favorite

Condo in San Diego

4.93 out of 5 average rating, 427 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 condo provisioned to meet your every need. Everything you need is within 8 blocks along the beautiful California coast!

Aug 9 – 16

€ 422 per night

Guest favorite

Guesthouse in San Diego

4.93 out of 5 average rating, 123 reviews

Modern Guest House with pool, steps to SDSU

Casita within easy walking distance to SDSU, Viejas Arena, Cal Coast Credit Union Open Air Theatre, shops, and transit. Casita includes Tempur-Pedic Queen bed and a love seat which converts to twin bed. Enjoy the peaceful canyon side garden, firetpit and pool, or relax in the hammock. Panoramic door opens completely to let in our wonderful weather and the view. Note: Pool is heated with a solar cover, comfy for swimming APR-OCT. Max 3 guests, no children/infants due to unfenced pool.

Aug 31 – Sep 7

€ 134 per night

Guest favorite

Guesthouse in La Jolla

4.97 out of 5 average rating, 158 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.

Apr 6 – 13

€ 421 per night

Guest favorite

Home in Point Loma Peninsula

4.93 out of 5 average rating, 120 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.

Jun 1 – 8

€ 1,106 per night

Guest favorite

Guesthouse in Mission Hills

4.94 out of 5 average rating, 118 reviews

Central Guesthouse w/ Private Pool & Full Kitchen

Perfect poolside retreat suitable for small families and couples! This 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 option, accompanied by many 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.

Oct 6 – 13

€ 300 per night

Guest favorite

Home in Bay Park

4.98 out of 5 average rating, 241 reviews

Resort Style Living with Pool, Spa, and Bay Views!

Resort style home with a solar heated pool, hot tub, outdoor entertaining space, bay and ocean views, multiple patios, modern amenities, comfortable beds, and more. Convenient location to freeways, Seaworld, Mission Bay, Beaches, Downtown, Balboa Park, Airport, La Jolla and other attractions. Perfect for families and groups. Two car garage parking included. 2300 square feet of indoor living and much more outdoors. Your ideal home base for enjoying all that San Diego has to offer.

Jan 4 – 11

€ 742 per night

Guest favorite

Condo in Pacific Beach

4.99 out of 5 average rating, 108 reviews

Luxury Oceanfront Condo with Unbelievable Views

Welcome to your Oasis! You will be completely in awe of the breathtaking views that Sunset Pacifica has to offer. This fully renovated condo features two ensuite bedrooms decorated with the beachy SoCal vibe you are looking for. Centrally located on the boardwalk and just minutes to La Jolla, Downtown, the famous SD Zoo, Embarcadero, restaurants, bars and entertainment. There is so much to do here or just lounge around poolside or on the sandy shores of the beautiful Pacific Ocean.

Oct 20 – 27

€ 677 per night

Superhost

Condo in North Ocean Beach

4.84 out of 5 average rating, 228 reviews

Swell Times Beach Studio

Need a cozy, affordable beachside getaway located steps from the sand in world famous Ocean Beach? Come chill at The Swell Times Beach Studio with sprawling beach views - just steps from the sand. Great for solo travelers, small families, or anyone looking to enjoy all OB has to offer. Ocean Beach is the closest beach area to the San Diego Airport, and there are tons of great restaurants, bars, coffee shops, and more within easy walking distance - totally pet friendly too :)

Aug 11 – 18

€ 216 per night

Guest favorite

Guesthouse in Mission Hills

4.91 out of 5 average rating, 415 reviews

Mission Hills Charming suite, walkable to all.

Heart of Mission Hills, upscale area, this private guest suite, separate from the house, is perched above the pool (separate building from main house), own entrance; sure to provide privacy. 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 with Clorox as well as all linens washed. We also don’t rent back to back giving time for thorough cleaning.

Oct 26 – Nov 2

€ 107 per night

Guest favorite

Guesthouse in San Diego

4.89 out of 5 average rating, 430 reviews

Pool house at Sunset Cliffs, Ocean Beach, Downtown

This is a unique property at the top of Sunset Cliffs within a mile to Ocean Beach! Close to Downtown Gaslamp. The property has a phenomenal entertaining backyard, great for relaxing by the pool during the day, Hot Tub, or sitting by the fire or rooftop bar at night with a glass of wine! Walk down to the bottom of the street and you will find 2 miles of walking trails next to the ocean cliffs!

Nov 30 – Dec 5

€ 320 per night

Guest favorite

Guesthouse in San Diego

4.94 out of 5 average rating, 333 reviews

The BEST NEST Clean, peaceful, private, affordable

This lovely private & separate unit is comfortable, clean and convenient. Your completely private suite is accessible via your own entrance. Minutes from major attractions, away from the hustle and bustle. Full kitchen for easy meal preparation. Located in a nice usually quiet neighborhood, close to major freeways. Enjoy the gorgeous San Diego weather in the quaint outdoor patio area.

Feb 24 – Mar 3

€ 122 per night