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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Guest favorite

Guesthouse in Coronado, California, US

4.85 out of 5 average rating, 270 reviews

Coronado Island Pool Cottage

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

Sep 24 – Oct 1

R3,055 ZAR 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!

Mar 15 – 22

R6,117 ZAR per night

Guest favorite

Guesthouse in San Diego

4.93 out of 5 average rating, 122 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.

Sep 5 – 12

R2,272 ZAR per night

Guest favorite

Guesthouse in San Diego, California, US

4.97 out of 5 average rating, 157 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.

Nov 27 – Dec 4

R7,540 ZAR per night

Guest favorite

Home in San Diego, California, US

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.

May 31 – Jun 7

R20,763 ZAR per night

Guest favorite

Guesthouse in San Diego, California, US

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 23 – 30

R5,248 ZAR per night

Guest favorite

Home in San Diego, California, US

4.98 out of 5 average rating, 240 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.

Oct 23 – 30

R15,254 ZAR per night

Guest favorite

Condo in San Diego

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.

Sep 20 – 27

R13,652 ZAR per night

Guest favorite

Guesthouse in San Diego, California, US

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.

Sep 2 – 9

R1,833 ZAR per night

Guest favorite

Home in San Diego

4.94 out of 5 average rating, 203 reviews

Boutique home with view, heated pool, spa + cabana

Heated pool, spa, cabana and view. 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 audio hub plug in.

Dec 1 – 8

R10,557 ZAR 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 27 – Dec 2

R5,614 ZAR 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.

Jan 11 – 18

R2,093 ZAR per night