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

Home in La Mesa

4.84 out of 5 average rating, 182 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

4.88 out of 5 average rating, 186 reviews

Palisades by the Bay Whole House Rental!

Whether it's lounging by the pool, or catching some sun at San Diego's famous beaches, this house has you covered. This whole house rental has plenty of space with 4 Bedrooms and 2.5 bath and is centrally located in the Bay Ho neighborhood of Clairemont, with views of Mount Soledad. Features costal vibe interior, pool, and fire pit. Top San Diego destinations such as La Jolla, Pacific Beach, Mission bay, and Mission beach, SeaWorld, and the World Famous San Diego Zoo are all within 10 min.

Superhost

Home in San Diego

4.9 out of 5 average rating, 246 reviews

Fire Victims We Want to Help - Just Send Inquiry

A lavishly furnished home with heated year round pool in the very heart of San Diego! The shops (including Target a 5 minute walk) and restaurants are all newly gentrified and the drive to Del Mar, La Jolla, Sea World, Zoo, Pacific Beach are 10 minutes away. This fantastic 4/2 has an open floor plan with full wall windows and french doors to the private backyard pool and patio. Chic furnishings complimented by charming large round dining table that seats 7+. And Lyft/Uber are just 3 min wait!

Guest favorite

Home in San Diego

4.87 out of 5 average rating, 135 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.

Guest favorite

Home in San Diego

4.93 out of 5 average rating, 229 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!

Superhost

Cottage in San Diego

4.93 out of 5 average rating, 204 reviews

Crown Point Gem with Salt Water Pool

This Cottage home is a beautiful Oasis in San Diego's Crown Point neighborhood. Our home is 2 blocks from Mission Bay with access to bike paths, water sports, and playgrounds for the kids. Easily walk to great restaurants, coffee shops, night life and shopping. With our cool saltwater pool, hot tub, grill and relaxing patio space you wont even need to leave the house to get that vacation feeling. Please let us know if you would like the pool heated, we charge $75/night for this service.

Superhost

Home in San Diego

4.87 out of 5 average rating, 175 reviews

Bright and spacious home with views, pool & spa.

This beautiful and recently remodeled, open-floor plan home is conveniently located directly across from Cowles Mountain, one of San Diego's most visited hiking trails. Each bedroom has its own full bathroom. Perfectly located for the outdoorsy family. Tons of hiking and mountain bike trails are just across the street. Only 15 min. away from beaches, zoo, & Sea World. Gaslamp/Downtown is only 20 min. by car. After a day of exploring, come home to a newly-built, salt-water pool and spa.

Guest favorite

Home in San Diego

4.98 out of 5 average rating, 262 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.

Guest favorite

Villa in El Cajon

4.91 out of 5 average rating, 139 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!

Guest favorite

Home in Spring Valley

4.95 out of 5 average rating, 126 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)

Guest favorite

Home in San Diego

4.97 out of 5 average rating, 115 reviews

Retreat vacation with solar heating pool & hot tub

The home is centrally located in the Mira Mesa neighborhood of San Diego. You will be close to many attractions in San Diego. 15 mins to La Jolla and UCSD. 25 mins to Sea World , old town or downtown. We have all you need for your stay! Enjoy a private fenced yard, with salt water pool and a jacuzzi that are built for entertainment and relaxation. The pool is solar heated, pool temperature will vary depending on the sun light received.

Guest favorite

Home in San Diego

5 out of 5 average rating, 105 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