Five Islands holiday rentals

We found 792 holiday rentals — enter your dates for availability
Discover a selection of 5 homes and other holiday rentals in Five Islands that are perfect for your trip. Holiday rentals provide the amenities that you need and want for your family, friends or furry companion, such as parking and a washer and dryer. What you'll find is a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Five Islands

Showing deals for:18 Dec - 25 Dec

Celebrate Christmas here with your family.
Living area
Living area
Interior
Exceptional
(54 reviews)

Driftwood Beachfront Luxury Home Magnificent Ocean Views

Phippsburg

8% off
AU$9,906
for 7 nights, 1 home
AU$1,415 per night
includes taxes & fees
Driftwood Beachfront Luxury Home Magnificent Ocean Views
Interior
Property grounds
Dining
Interior
Exceptional
(61 reviews)

Waterfront Cottage on Cove with Private Dock, Kayaks & Fire Pit

Trevett

8% off
AU$2,916
for 7 nights, 1 home
AU$417 per night
includes taxes & fees
Waterfront Cottage on Cove with Private Dock, Kayaks & Fire Pit
Room
Exterior
Private kitchen
Living area
Exceptional
(10 reviews)

Quiet waterfront serenity awaits!

Georgetown

8% off
AU$5,105
for 7 nights, 1 home
AU$729 per night
includes taxes & fees
Quiet waterfront serenity awaits!
Room
Private kitchen
Living area
Private kitchen
Exceptional
(24 reviews)

New home in Boothbay, downtown Boothbay harbor is located about a mile away.

Boothbay

8% off
AU$2,256
for 7 nights, 1 home
AU$322 per night
includes taxes & fees
New home in Boothbay, downtown Boothbay harbor is located about a mile away.
Upstairs master bedroom view
Outdoor dining
Kitchen
Exterior
Exceptional
(36 reviews)

Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.

Boothbay Harbor

8% off
AU$3,827
for 7 nights, 1 home
AU$547 per night
includes taxes & fees
Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.
Living room to kitchen.
Aerial view of condo on the left side.
Kitchen with granite counter top and high top seating.
Living room.
Exceptional
(9 reviews)

Beautiful Condo on Ocean Cove - Easy walk to harbor-side town

Boothbay Harbor

8% off
AU$4,447
for 7 nights, 1 apartment
AU$635 per night
includes taxes & fees
Beautiful Condo on Ocean Cove - Easy walk to harbor-side town
Screen porch
Exterior
Living area
Living area
Exceptional
(9 reviews)

Welcome to Owl House - Your Coastal Retreat in East Boothbay!

East Boothbay

8% off
AU$3,922
for 7 nights, 1 home
AU$560 per night
includes taxes & fees
Welcome to Owl House - Your Coastal Retreat in East Boothbay!

  • 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

Choose a holiday rental for your Five Islands getaway

Learn about the unique charm of Five Islands with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Five Islands

Do you want to discover things to do in the area? Venture out of your holiday home and check out everything that Five Islands has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Brunswick Golf Course (15.4 mi / 24.9 km)
  • Maine State Aquarium (3.7 mi / 6 km)
  • Boothbay Golf Course (5.5 mi / 8.8 km)
  • Pemaquid Craft Co-op (11.1 mi / 17.8 km)
  • Ash Cove Pottery (15.8 mi / 25.5 km)

Exploring the natural features in Five Islands

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Five Islands is a great spot to appreciate mother nature. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Coastal Maine Botanical Gardens (4.2 mi / 6.7 km)
  • Barrett Park (4.9 mi / 8 km)
  • Cabbage Island (5.4 mi / 8.7 km)
  • Linekin Bay (5.4 mi / 8.7 km)
  • Grimes Cove Beach (5.8 mi / 9.3 km)
  • Popham Beach (6.1 mi / 9.9 km)

How to get to and around Five Islands

Fly into Wiscasset, ME (ISS), the closest airport, located 9.7 mi (15.5 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Augusta, ME (AUG-Augusta State), which is 34.4 mi (55.3 km) away.

Frequently asked questions

What is the best area to stay in Five Islands when booking a holiday rental?
When looking for the best area to stay in Five Islands, Maine, you might consider the charming neighbourhood of Southport Island. This picturesque area is known for its stunning coastal views and laid-back atmosphere, making it an ideal spot for a relaxing holiday. Southport Island offers a range of holiday rentals, from quaint cottages to spacious homes, providing a delightful experience for visitors.One of the top attractions in Southport is the iconic Southport Island Lighthouse, which offers breathtaking views of the surrounding waters and is a great spot for photography enthusiasts. Additionally, the nearby Boothbay Harbor is just a short drive away, where you can explore its bustling waterfront, indulge in fresh seafood, or take a scenic boat tour to admire the natural beauty of the coastline.
When is the best time to visit Five Islands for a holiday rental?
September is the most popular time to visit Five Islands, Maine, as it perfectly captures the essence of late summer and early autumn. This month offers a wonderful blend of warm days and cooler evenings, making it ideal for outdoor activities such as kayaking, hiking, and exploring the picturesque coastline. Visitors can enjoy the stunning views of the Atlantic Ocean, with temperatures typically ranging from 10 to 20 degrees Celsius, ensuring a comfortable experience for those keen on sightseeing or simply relaxing by the shore.The peak travel season in Five Islands runs from July to September, attracting travellers who flock to the area for its charming villages, fresh seafood, and beautiful landscapes. September, in particular, provides a slightly quieter atmosphere compared to the bustling summer months while still offering plenty of activities and opportunities to bond with fellow travellers.For those seeking more economical options, November presents a fantastic opportunity to visit. The crisp autumn air and serene environment make it a wonderful time for peaceful walks and enjoying the natural beauty of the region. While some attractions may be closed for the season, the tranquillity of Five Islands during this time can be quite refreshing.Ultimately, your choice of when to visit Five Islands will depend on whether you wish to revel in the lively summer scene or embrace the calm and beauty of autumn.
What are the top attractions in Five Islands?
In Five Islands, Maine, visitors can enjoy a range of picturesque attractions that showcase the area's coastal charm. The Five Islands Lobster Co. offers a quintessential Maine experience with fresh seafood and stunning views of the Damariscotta River, making it a popular spot for both locals and tourists.Nearby, the scenic Five Islands Beach provides a lovely setting for beachgoers to relax and take in the beautiful surroundings. The area is also known for its charming fishing wharves and quaint shops, where visitors can find unique local crafts and souvenirs. For those interested in outdoor activities, the nearby conservation areas and trails offer opportunities for hiking and exploring the stunning coastal landscapes.
Are all fees included in the Five Islands holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Five Islands holiday homes with parking?
Stayz offers a wide selection of holiday homes in Five Islands with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Five Islands holiday homes?
You can find great discounts on holiday homes in Five Islands on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Five Islands holiday home booking on Stayz?
To find Five Islands holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Five Islands?
A long-stay holiday home in Five Islands is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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.
How early should I book a Five Islands holiday home?
Book your Five Islands holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Five Islands?
Prices for holiday homes in Five Islands vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Five Islands to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ 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.
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.
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.

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