Holiday rentals with a pool in Shelter Island

Find and book unique homes with a pool on Airbnb

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 favourite

Guesthouse in San Diego

4.93 out of 5 average rating, 144 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!

Guest favourite

Guest suite in San Diego

4.97 out of 5 average rating, 352 reviews

Groovy canyon studio pool & spa blocks from SDSU

It’s a groovy studio splashed with color :) Enjoy this slice of paradise hosted by Airbnb super hosts. You can splendor in their thrifty take on the San Diego stay. Bask in the blissful views, and spoil yourself in the spa! If it gets too hot, hop in the pool! No worries allowed at this groovy getaway. We have unique booking methods! Short term stays less than 28 days are available for booking 1 month in advance. If it's over a month before your visit, our calendar only allows longterm booking

Guest favourite

Guesthouse in San Diego

4.78 out of 5 average rating, 379 reviews

Law Street Retreat

RENOVATED…Studio with separate entrance in gated property 6 blocks from beach in Pacific Beach. Bikes now available! Ask host for details. Sleeps 3, amenities include a queen bed and a fold single bed couch with full bath, small fridge, microwave, smart TV, 100mbps WiFi and air conditioning. Guests are welcome to enjoy the pool, outside shower and BBQ. Pets are welcome. There is a $50 fee per pet per stay. The studio is attached to the pool house. The pool pump is behind 2 doors & runs daily.

Superhost

Condo in San Diego

4.85 out of 5 average rating, 143 reviews

Ocean front one bedroom condominium

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

Home in San Diego

4.93 out of 5 average rating, 224 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!

Guest favourite

Condo in San Diego

4.91 out of 5 average rating, 134 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!

Guest favourite

Guesthouse in San Diego

4.98 out of 5 average rating, 169 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.

Guest favourite

Guesthouse in San Diego

4.91 out of 5 average rating, 433 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.

Guest favourite

Home in San Diego

5 out of 5 average rating, 185 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!

Guest favourite

Guesthouse in San Diego

4.89 out of 5 average rating, 459 reviews

Pool house at Sunset Cliffs, Ocean Beach, Hot Tub!

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!

Guest favourite

Guesthouse in San Diego

4.95 out of 5 average rating, 368 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.

Guest favourite

Condo in San Diego

4.93 out of 5 average rating, 281 reviews

Beach Front Condo - Capri by the Sea - Remodeled

Ocean Front Unobstructed Views! Beachfront Living at its Finest! From the second you walk into 9th floor condo, the Breathtaking Views will remain with you for a Lifetime! We completed a Full High End Remodel including Furniture & Many Amenities! Located just North of Crystal Pier in Pacific Beach, San Diego. The Best View & Location in the Area!!!