
Holiday houses in Shelter Island
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Top-rated holiday rentals in Shelter Island
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Walk to Balboa Park and Hillcrest from an Immaculate Home
Take a stroll through the park, then unwind with a leisurely dinner under the festoon lights. Classic crown molding, hardwood floors, and pared-back tones of gray and taupe create an air of calm at this elegant haven spread out over 1500 square feet. You will find the space charming & spacious with over 1500 sq. feet. This single level property is the lower level of a historic duplex. Hardwood floors, crown molding, gas fireplace and laundry room. Street parking is usually readily available. This A+ location of Banker's Hill is NOT impacted by air plane noise. Enjoy the entire lower level duplex and use of the back yard with patio set for dining. Please note the upper tenant may also want to use this space so this area could be shared. We would love to greet you but are also fine with allowing you to access with a code on the front door. We live nearby and are happy to make suggestions for dining or things to do. Located near numerous restaurants, and Balboa Park, Hillcrest, the zoo, Downtown, Little Italy, and the Convention Center are all within 10 minutes. Be at the beach in less than 15 minutes. The bus line runs up First Ave for easy access to Downtown and Uptown. Near trolley and train station. We are within 10 minutes to the San Diego International Airport and a quick Uber ride to Downtown, Little Italy. Walk to the heart of Hillcrest, Balboa Park and the Zoo. Be at the beach in less then 15 minutes. Central location near the I-5, I-163 & I-8. Because of the hardwood floors, you will hear the footsteps above. The kitchen is well stocked if your a cook and we have an area where you can set up your laptop. wireless available and 3 smart TV's for your enjoyment. Small market less than 1 block away.

Savor Panoramic Harbor and Skyline Views near Shelter Island
The views in our house are absolutely spectacular! The location is central to great restaurants, downtown SD, SeaWorld, and bay beaches where you can kayak or paddle board. It is a ideal choice for vacations and for business travelers looking for a comfortable place to call home while traveling. Entire House, 3 Patios, and parking for car in garage and driveway We like to stay out of our guests way during their stay, but we will always be accessible either via phone call or text; but if you are so relaxed and you don't want to expend energy to text or call, merely ring the wifi doorbell and it will connect to our cell phone and we can address any questions you may have. The mid-century modern house sits on the side of a hill in the La Playa neighborhood of Point Loma, overlooking the harbor. It is a quiet neighborhood, within walking distance of the harbor, beach, nice restaurants, and amenities. Please note 24 hours before arrival, we will provide you a door code you can use to enter the home, the same code locks the home when you come and go during your stay.

Kellogg’s Beach Cozy Home
Have fun with the whole family at this stylish place just a block away from Kellogg's Beach of San Diego Bay. Relax in our cozy home with a spacious kitchen and peaceful deck and backyard with wonderful trees and lots of space to play or relax. Kellogg's beach is a hidden gem. Enjoy your vacation just a block away from the beach while enjoying our stylish home with a peaceful backyard with beautiful trees just below our deck. The property lot splits between this home and a detached small home

Gorgeous Bay Views, Private Comfy Deck & Much More
Relax on your large, private deck with beautiful views of San Diego Bay, downtown skyline, Coronado, nearby mountains, and the Pacific ocean. Watch the fighter jets take off from North Island and the Navy & cruise ships. You have lovely sunrises and can watch the sunset reflected off the skyline from the same deck chair! Our home is located less than 10 minutes from the airport, Shelter Island, and VERY EASY walking distance to restaurants, shops, yoga, the bay, and FREE pickleball/tennis.

Bayview Paradise
Known as the Huguette House, this luxury private single-family two bedrooms two bathrooms home in La Playa the heart of Point Loma, San Diego offers 180-degree panoramic views of the world-famous San Diego Bay and Downtown Skyline. views of the San Diego bay, marina, and Coronado Island during the day and spectacular views of the Downtown San Diego skyline at night, fully equipped kitchen, and laundry room, 2 bedroom suites with queen beds .2 luxury bathrooms, HDTV, computer desk and WFI

Beautiful New 2BR/2.5BA Coastal Home In Point Loma
*** Point Loma***Each Bedroom Has Its Own Bathroom**First Floor Patio & Second Story Balcony**10 ' Vaulted Ceilings***Washer/Dryer ***BBQ***Fountain***Kohler Black Matte Finished Hardware***Italian Marble Counter Tops***High End Luxury Finishes***European Porcelain Floors**8' Mahogany Solid Core Doors***Assigned Tandem Parking For Two Cars***Walk to Humphries By The Bay Concerts*** The Home Is In A Quiet Neighborhood With A Respectful 10:00 PM Quiet Hours In Place Policy. Not A Party Home.

Upgraded Pt Loma Panoramic Views - 1 Bedroom Suite
Brand new full kitchen installed November 2025. Enjoy your home away from home and beautiful Pt Loma. With an expansive view of the gorgeous San Diego Bay & Shelter Island you can enjoy a comfortable space with luxury amenities. A spacious oasis to escape the hustle and bustle of the city, but close enough for a night out on the town. If you’d rather stay in and enjoy the views, relax on the patio, soak in the hot tub, or have a drink by the fire pit with your fur baby.

Sunset Cliffs Hideaway
Kick back and relax in this peaceful, stylish space. Spacious Bedroom in private residence with private entrance, easy parking, located 1.5 blocks from beautiful Sunset Cliffs. Less than 15 min drive to all of the best San Diego has to offer. Walking distance to Ocean Beach (~1 mi), a funky beach town with its own casual style. Room is "hotel style" with private entrance, small patio, bed, bath, fridge and microwave; no access to main house.

Coast Escape: Walk to Beach, Eats&Docks|2M Airport
Simple studio w/ private entry. Here's what is walkable: Ralphs (~2–3 min) – grocery store Better Buzz (~5 min) – coffee shop H & M Landing (~10 min) – sportfishing, watersport rentals Kellogg Beach (~15 min) – beach on San Diego Bay Sunset Cliffs (~25–30 min) –ocean cliff walks; sunset views OTHER ATTRACTIONS: 1.5 MI to airport, 4 MI to Convention Center, 2.5 MI to Sea World, 4.5 MI to Zoo, 4 MI to Gaslamp Quarter, 2 MI to Pt. Loma Naval base

Cozy remodeled 2 bed apt in Point Loma
Stay in this cute and cozy remodeled 2 bed 1 bath apartment stocked with everything you need for your San Diego visit! Located in a quiet neigborhood of Point Loma, you are just a quick drive from the airport and lots of San Diego attractions. The apartment is newly remodeled and ready to be enjoyed with lots of space in the back patio to enjoy food and games at the picnic table or relax around the fire pit.

🌴Private Guest Suite in Pt. Loma Wooded Area🌞⛱
Located 2 miles from the beach and 1 mile from the bay! Your 2-bedroom private guest suite is the 1st floor of a luxury private residence in the upscale wooded area of Pt. Loma San Diego. Located in a quiet neighborhood, a private entrance opens to a kitchenette, charming lounge area, two well-appointed bedrooms, and one roomy bathroom. Enjoy a private deck and yard for dining, grilling or lounging.

1stResorts.com WATER VIEW FAMILY VILLA A w/ HOTTUB
Brand New FAMILY Villa with Water Views from the kitchen / living area! Special reduction for week long stay!! Two level Villa. Large deck attached. Hot Tub, Barbecue Grill, Fire pit! Beautiful sunsets!! Come stay with us and enjoy all of San Diego's finest. We are located close to Balboa Park, Coronado and so many great venues and experiences or just stay on site and enjoy your very own Oasis!
Popular amenities for Shelter Island holiday rentals
Other great holiday rentals in Shelter Island

Cottage at Cabrillo Cozy garden studio

La Playa | Charming Bayside Bungalow

Spectacular Views | Amazing Escape Point Loma

Cozy Retro Home with Bay & City Views

Point Loma Hideaway - brand new!

Ocean View Retreat • Walk to Beach • Parking

Renovated 1BR in Point Loma Near Harbor & Airport

On The Beach Casita - Bay front access
Destinations to explore
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- SeaWorld San Diego
- Coronado Beach
- Rosarito Beach
- University of California-San Diego
- LEGOLAND California
- San Diego Zoo
- San Diego Zoo Safari Park
- Petco Park
- San Diego Convention Center E Ent
- Pacific Beach
- Balboa Park
- Tijuana Beach
- San Diego State University
- Torrey Pines State Beach
- Mission Beach
- Oceanside City Beach
- Ocean Front Walk
- Moonlight State Beach
- Las Olas Resort & Spa
- La Misión Beach
- Belmont Park
- Sesame Place San Diego
- San Onofre Beach
- Liberty Station





