Vacation 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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Superhost

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

4.86 out of 5 average rating, 335 reviews

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:

Superhost

An outdoor pool takes center stage, surrounded by lush greenery and evening skies painted in vibrant hues. The pool area features a smooth, concrete edge and a set of steps leading into the inviting water, creating a serene space for relaxation.

Home in San Diego

4.85 out of 5 average rating, 185 reviews

Spacious, Heated Pool, Kid Paradise & Near It All!

Spacious family oasis w/ tons to do for the kids! Enjoy a large backyard (rare in San Diego!) & year-round heated pool or spread out inside w/ tons of games. Perfectly located near top attractions like the Zoo & SeaWorld. Ideal for families seeking a getaway in paradise! ⭐ “If you want a pool you can swim at any time of the day this place is it...the house is near everything you want to do around San Diego!” 🏖 HIGHLIGHTS ✓ Newly remodeled ✓ Heated pool (free) ✓ Centrally-located

Guest favorite

A clear blue swimming pool is surrounded by a spacious deck, featuring lounge chairs and shaded seating. A dining area is visible under a pergola, with additional chairs and a table. The backyard is lined with privacy fencing and greenery, creating a serene outdoor space.

Home in La Mesa

4.84 out of 5 average rating, 192 reviews

Sunny SD l Pool l BBQ l Pool Loungers l Sleeps 10

Escape to a fresh 4-bedroom retreat for family and friends (10 ppl max). Updated in January of 2024 with new furniture, and fixtures. Bask in the sun on the deck, take a dip in the pool. Enjoy the private and fenced backyard, BBQ, or the recently renovated and modern Kitchen. This home is perfect for vacations or remote work. Explore San Diego beaches and all the area has to offer, the most popular tourist destinations are all within a 20-30 minute drive. 20 minutes to the beach! Book with us!

Superhost

Home in San Diego

4.87 out of 5 average rating, 165 reviews

LOVE~POOL~RELAXING~CHARMING~Stylish~SD Central.

Stunning vacation home with pool ( unheated) , centrally located in a lovely Mira Mesa neighborhood, just steps from dining & nightlife and close to SD beaches, airport, SD Zoo, Safari, Legoland, SeaWorld, shopping and attractions. Completely remodeled, open concept living as large dual pane windows light up the great room. An oversized island highlights a dream kitchen w/ quartz counters, SS appliances Enjoy private fully landscaped front yard and backyard with unheated pool and with patio.

Top guest favorite

The outdoor pool glows in the evening light, revealing clear water with a unique shape. Surrounding the pool, lounge chairs and umbrellas create a tranquil space for relaxation. A gas fire pit adds warmth to the area, enhancing the captivating view of the cityscape beyond.

Home in San Diego

4.88 out of 5 average rating, 142 reviews

Ocean View Private Pool & Spa Home w/Putting Green

Welcome to your Private, resort style, pool and spa home with spectacular views day and night! 4 bedrooms, 3 baths (1 bedroom and bathroom with shower on main/ground level). Tropical setting, and just a short drive to major attractions like our world famous Beaches, Zoo, Sea World, Balboa Park, Downtown, Coronado, Outlet Shopping, Sesame Place and even Mexico! Soaring 18 foot ceilings in the Living room and Dining room. Outdoor dining, Putting Green, and lounges for resort-like relaxation.

Top guest favorite

A cozy outdoor lounging area features a spacious daybed with neutral-colored cushions. Nearby, a wooden table holds remote controls. The heated pool is visible in the background, surrounded by palm trees and cacti, under a clear blue sky.

Home in San Diego

4.93 out of 5 average rating, 241 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 favorite

Villa in El Cajon

4.92 out of 5 average rating, 154 reviews

Enchanted Paradise! ♨ Pool+Spa+Outdoor Kitchen ☀

Brand New Property! Massive garden of Eden style resort home with sprawling outdoor entertainment area and spacious open concept inside, perfect for large families with kids and responsible adults. Updated top to bottom with all new outdoor and indoor furniture, modern upgrades in all bedrooms and common areas. Centrally located and 20 minutes from the beach and all of SD's top attractions! 8 person hot tub, sparkling gas heated saltwater pool and new outdoor kitchen. Don't miss out!

Top guest favorite

A serene outdoor space features a curved lounge chair positioned on a wooden deck, overlooking a tranquil pool surrounded by lush greenery. The natural rock formations add texture to the serene atmosphere, while the canopy above provides shade.

Home in San Diego

5 out of 5 average rating, 107 reviews

3 BR Urban Oasis with Pool and Spa in Great Area

This special place is close to everything, making it easy to plan your visit. The charming, walkable, and historic neighborhood of University Heights provides a wonderful park, restaurants, coffeehouses, ice cream shop, bars, and markets nearby. Within 2 miles from the San Diego Zoo and historic Balboa Park. 15 minutes by car to Sea World, beaches, or downtown. The open plan of the communal areas of the house makes it a great space for spending quality time with friends or family.

Guest favorite

Home in Spring Valley

4.96 out of 5 average rating, 141 reviews

Upscale Resort House /Views, Saltwater Pool/Spa !

This home offers Saltwater pool and Spa. Saltwater pools and Spa produce softer-feeling water. breathtaking views from its location high in the hills overlooking Rancho San Diego. In the backyard you can enjoy the sunrise from the private pool or deck or practice your putting on our putting green. The House is a mid-century modern home perched above the City. It's great for groups seeking easy access to San Diego's highlights (15 to 20 minutes to Beaches and Downtown)

Top guest favorite

A solar-heated saltwater pool is surrounded by a spacious patio area, featuring lounge chairs and an umbrella for shade. A privacy fence encloses the backyard, creating a quiet retreat. The sun casts gentle shadows across the water, enhancing the serene setting.

Home in San Diego

4.96 out of 5 average rating, 135 reviews

Retreat vacation with salt water pool & hot tub

Your San Diego get-away vacation starts easily from this well-placed Mira Mesa comfy home: 🚗 15 mins to UCSD, La Jolla and Del Mar beaches 🚗 25 mins to Sea World , Balboa park, San Diego Zoo, Downtown 🚗 30 mins to Legoland, Carlsbad We’ve got everything you need for a great stay! Relax and enjoy in a resort-style saltwater pool and spa. The pool is solar-heated, so temperature may vary depending on sunlight received.

Guest favorite

A refreshing pool is surrounded by a spacious deck, showcasing lounge chairs and a large umbrella. Expansive views of the city and distant hills are visible under clear blue skies, creating a serene outdoor retreat.

Bungalow in El Cajon

4.85 out of 5 average rating, 102 reviews

Stylish Relaxation-Panoramic Views-Private OASIS!

~BRAND NEW DRIVEWAY~Perched high on granite hills, our comfy, stylish bungalow is perfect for a quiet getaway in San Diego. Brew your morning coffee and stroll to the pool to let the expansive views of the city fuel your daily adventures. Host a barbeque in the spacious, private backyard after your day at the beach. Cozy up in the recliner loveseat and enjoy the big screen 4k smart TV (with cable). 420 Friendly!

Top guest favorite

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

4.99 out of 5 average rating, 118 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