Holiday rentals with a pool in Shelter Island

4.86 out of 5 average rating, 332 reviews

Guesthouse in Coronado

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:

4.96 out of 5 average rating, 132 reviews

Retreat vacation with salt water 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, UCSD 🚗 25 mins to Sea World , Balboa park, San Diego Zoo, Downtown 🚗 30 mins to Legoland, Carlsbad 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, and pool temperature will vary depending on the sun light received.

Superhost

4.85 out of 5 average rating, 182 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

4.84 out of 5 average rating, 188 reviews

Home in La Mesa

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!

4.88 out of 5 average rating, 140 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.

4.93 out of 5 average rating, 238 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!

4.88 out of 5 average rating, 183 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.

4.98 out of 5 average rating, 268 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.

4.92 out of 5 average rating, 149 reviews

Villa in El Cajon

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!

5 out of 5 average rating, 105 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.

4.96 out of 5 average rating, 139 reviews

Home in Spring Valley

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)