Holiday rentals near Shelter Island

We found 3,257 holiday rentals — enter your dates for availability

Scroll through and discover holiday rentals within easy reach of Shelter Island that provide the perfect home base for your trip. Whether you're travelling with a group or just with your pet, holiday homes have the amenities that you need and want for your stay, which might include a hot tub and a washer and dryer. At the end of the day, you'll find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Shelter Island

Showing deals for:17 July - 24 July

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What are the best holiday rentals near Shelter Island?
The best holiday rentals near Shelter Island are typically located in the scenic Point Loma area of San Diego. You will find a great selection of properties here, including many private homes and comfortable apartments. The best holiday rentals near Shelter Island often provide easy access to the waterfront and local attractions. If you are willing to drive a bit further, renting in nearby areas can be an affordable option, providing more choice.

Many top-rated rentals feature amenities such as a deck or patio for outdoor enjoyment, laundry facilities, and the option for pets to be permitted, which is great for those travelling with animals. These homes are ideal for families or groups looking for a relaxing coastal stay.
Are there any cheap holiday rentals near Shelter Island?
There are several affordable holiday rentals near Shelter Island, especially if you are flexible with location and travel dates. Budget-friendly stays typically start around AU$235 per night. Some stays even drop below this price in January and February during the off-season, making it a great option for guests looking to experience the area without overspending. These rentals often include free amenities such as WiFi, toiletries, and self-parking, and can range from cosy studio apartments to modest family homes, providing a clean, comfortable base for adventure.

To get the best value, consider staying slightly outside major hubs. If you're willing to drive a bit further, renting around nearby areas can be an affordable option. With a little planning, it is absolutely possible to find a comfortable stay near Shelter Island while keeping costs down.

*Pricing data are based on past 12 months data.
What are the best pet-friendly holiday rentals near Shelter Island?
There are hundreds of pet-friendly holiday rentals near Shelter Island, ensuring a comfortable stay for guests and their animal companions. Over 390 properties, primarily private holiday houses and apartments, are available in areas such as Point Loma. These rentals frequently feature amenities like food and water bowls, private outdoor spaces, and comfortable living areas, suiting both the needs of pets and the convenience of guests.

When searching for the best pet-friendly holiday rentals near Shelter Island, always review individual property rules regarding pet size, breed restrictions, and any additional fees. Shelter Island itself is welcoming to pets, offering paved paths and open green areas for walking.
What are the top holiday rentals with pools near Shelter Island?
There are approximately 71 holiday rentals near Shelter Island that offer access to swimming pools, with a mix of private, shared, indoor, and outdoor options available. Properties such as private holiday houses and condos are prevalent, many featuring private backyard pools or communal pool access. These properties are concentrated in areas like Point Loma and the surrounding San Diego neighbourhoods. Guests can expect standard amenities such as fully equipped kitchens, Wi-Fi, and often include features like heated pools or dedicated children's pools, making them suitable for families and groups.

When selecting your ideal stay, consider whether a private pool, offering seclusion, or a shared pool, which might come with additional facilities like hot tubs, best suits your preferences. For cooler months, many properties offer heated or indoor pool options. It is always wise to check the specific pool type and heating availability when making your reservation to ensure it aligns with your travel plans, particularly for peak summer dates.
What are the best family holiday rentals near Shelter Island?
There are over 560 family-friendly holiday homes available near Shelter Island, primarily private holiday houses and apartments, offering ample space and comfort for groups of all sizes. These properties often boast multiple bedrooms and bathrooms, full kitchens, and generous living areas, all designed with families in mind. With such a wide selection, you can find stays with outdoor play areas like yards or patios where kids can play, and amenities like highchairs, travel cribs, and even toys for children. Many also include washer/dryers, making laundry convenient during your stay.

When choosing the best fit for your family, focus on properties that offer separation of space, allowing adults and kids to unwind comfortably. Look for homes with practical amenities such as well-equipped kitchens to prepare meals, and outdoor areas for children to play safely. Staying nearby means less travel time and more time enjoying Shelter Island and its surroundings.
Are there any luxury holiday rentals near Shelter Island?
There are several luxury holiday rentals near Shelter Island, combining natural scenery with modern comfort. These properties often feature amenities such as private heated pools, gourmet kitchens with private chef services, spa-style bathrooms with designer toiletries and bathrobes, and stunning lake or mountain views. Many homes also include a fireplace for cooler evenings.

These homes are ideal for families or larger groups, offering amenities like air conditioning and entertainment spaces. Many of these top-tier stays are managed by highly rated Stayz hosts, ensuring a professional and premium experience.
How much is a holiday rental near Shelter Island?
Holiday rentals near Shelter Island offer a wide range of options to suit different budgets, making it easy for guests to enjoy a memorable stay. Budget-friendly properties typically start around AU$235 per night, providing an affordable option. Mid-range rentals, including private homes, are generally around AU$480 per night, offering more comfort and privacy. Upscale options can cost AU$790 or more per night, especially for properties with premium amenities or desirable locations.

Enter your destination, travel dates, and number of guests on search to see the best options. You can use filters to set a minimum and maximum nightly price range along with other preferences. Rates may vary based on the season and specific amenities, but with a little planning, guests can find a rental that perfectly balances convenience and value.

*Pricing data are based on past 12 months data.
Where should I stay when visiting Shelter Island?
When visiting Shelter Island, Point Loma offers a fantastic selection of holiday rentals. This area is known for its beautiful marinas and proximity to the coastline, providing properties with excellent views and easy access to the water activities around Shelter Island. It's a great choice for guests seeking a relaxed coastal experience.

Another excellent option is the Ocean Beach neighbourhood, a short distance from Shelter Island. Ocean Beach boasts a classic, laid-back beach town feel, with a variety of holiday rentals close to its famous pier and surf spots. This area is great for those who appreciate a more bohemian vibe and easy access to the beach.

For those seeking a slightly more secluded feel with convenient access to Shelter Island, areas further along the Point Loma peninsula towards Cabrillo National Monument offer properties that provide stunning ocean views and a peaceful setting.
What is the cheapest month to stay near Shelter Island?
The cheapest time to find holiday rentals near Shelter Island is typically during the late Winter (January to February). January is frequently the cheapest month, often providing the best deals on properties, with rates often 15-25% lower compared to the peak summer season. Guests can often find various savings and greater availability for homes and condos during these months.
Are there any lakefront holiday rentals near Shelter Island
Lakefront holiday rentals near Shelter Island offer a great mix of comfort, scenery, and outdoor adventure. Many are located along quiet lakes in the wider San Diego area, such as Lake Hodges or Lake Murray. These properties are a short drive from Shelter Island, offering convenient access to water activities such as kayaking, fishing, or simply relaxing by the shore.

These homes often feature spacious decks, fire pits, hot tubs, and full kitchens, making them ideal for families and larger groups. Guests can enjoy mountain and lake views, spot wildlife, and unwind in peaceful surroundings after exploring local trails.
Are there any top beachfront holiday rentals near Shelter Island
Beachfront holiday rentals near Shelter Island are primarily located along the waterfront, offering direct access to the sand or stunning water views over the bay. Many properties boast ocean-view balconies, providing a great spot to relax. While Shelter Island itself offers a quieter, more relaxed environment, the proximity to lively dining, nightlife, and shopping areas in nearby Point Loma is excellent for guests seeking more activity.

Guests can enjoy a range of amenities such as beach towels, water sports equipment, and beach umbrellas. Accommodation types vary, including private holiday houses and apartments, many with ocean-facing rooms or private terraces. These rentals cater to different group sizes and preferences, from intimate units to multi-bedroom properties.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Stayz customer service and Stayz™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare customer service is available 24/7 to support you every step of the way.

Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.