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:25 Dec - 1 Jan

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

Driftwood Beachfront Luxury Home Magnificent Ocean Views

Phippsburg

8% off
S$11,236
for 7 nights, 1 home
S$1,605 per night
includes taxes & fees
Driftwood Beachfront Luxury Home Magnificent Ocean Views
Upstairs balcony entry third bedroom
Mossy Glen Lodge - entire lodge is your private secluded hideaway
Stairs from second and third bedroom
Christmas look at Mossy Glenn Lodge
Exceptional
(23 reviews)

Mossy Glen Lodge 'Log Cabin' with a tiny brook and hammock

Boothbay

12% off
S$2,935
for 7 nights, 1 room
S$419 per night
includes taxes & fees
Mossy Glen Lodge 'Log Cabin' with a tiny brook and hammock
Dining
Property grounds
Interior
Interior
Exceptional
(61 reviews)

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

Trevett

8% off
S$2,729
for 7 nights, 1 home
S$390 per night
includes taxes & fees
Waterfront Cottage on Cove with Private Dock, Kayaks & Fire Pit
Exterior detail
Exterior
Private kitchen
Room
Exceptional
(10 reviews)

Quiet waterfront serenity awaits!

Georgetown

8% off
S$4,647
for 7 nights, 1 home
S$664 per night
includes taxes & fees
Quiet waterfront serenity awaits!
Living room.
Aerial view of condo on the left side.
Living room to kitchen.
Outdoor dining
Exceptional
(9 reviews)

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

Boothbay Harbor

8% off
S$4,126
for 7 nights, 1 apartment
S$589 per night
includes taxes & fees
Beautiful Condo on Ocean Cove - Easy walk to harbor-side town
Living area
Exterior
Back deck and screen porch
Screen porch
Exceptional
(9 reviews)

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

East Boothbay

8% off
S$3,696
for 7 nights, 1 home
S$528 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 most popular type of holiday rental accommodation in Five Islands?
According to our research, houses are considered the most popular holiday rental type in Five Islands. But as you'd expect, everyone's idea of an awesome trip can vary. Vrbo has holiday rentals of all shapes, sizes and budgets, and we'll help you find the perfect match.
How much does it cost to rent a holiday rental in Five Islands?
The average price for a holiday home in Five Islands is based on a number of factors, like property type, length of stay and time of year. Whether you'd like a sprawling villa with lots of bedrooms or a cosy condo for just you and your sweetheart, just add your dates of travel to view stays with unbeatable value.
How much does it cost to rent a beach house in Five Islands?
Prices for beach houses in Five Islands vary depending on the size and style of the property and when you plan to travel. Simply enter your dates of travel into Vrbo and how many guests to view your rental options and prices. From there you can use our filter tool to narrow down your search by nearby activities, ratings, amenities and more.
Are there pet-friendly holiday rentals in Five Islands?
Yes. There are. You can pick from five holiday rentals that allow pets in Five Islands. Lots of our pet-friendly holiday rentals even have an outdoor area for your furry friend to run around in, special dog beds, complimentary treats and proximity to parks. Apply the "Pets allowed" filter to find your pawfect holiday home on Vrbo.
What are popular rental amenities in Five Islands?
A garden, a barbecue grill and an ocean view are the most popular rental amenities in Five Islands. Whether you're heading away as a party of one, with your spouse or a group of family members, Vrbo will help you find a holiday rental that fits your style with all the features you'll enjoy.
Are there large group holiday rentals in Five Islands?
Take your pick of five Vrbo holiday homes in Five Islands that can host a group of five or more people. You'll enjoy all the privacy and room you need to spend time with the people you're holidaying with — and no one else.
Are there holiday rentals in Five Islands that welcome kids?
Gather the whole crew for an epic adventure in Five Islands at one of our five family-friendly holiday homes. Lots of these stays provide amenities that are perfect for getaways with the kids, like full kitchens, extra bedrooms and private pools. Just click on the "Properties good for families" filter box and choose your favourite option.
What are the top attractions for families in Five Islands?
Keeping the kids occupied during your Five Islands holiday is a snap with these awesome family-friendly attractions:
  • Georgetown Historical Society
  • Half Mile Beach
  • Reid State Park
Are there holiday rentals with WiFi in Five Islands?
Whether you want to keep up with the latest news, check emails or surf social networks, there are two holiday homes with WiFi in Five Islands. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.
How old do you have to be to rent a holiday rental in Five Islands?
The minimum age is generally 16, 18 or 21. It can change between properties on Vrbo, so look at the rules of your chosen Five Islands holiday home before booking your escape.
How long can I rent a holiday rental in Five Islands for?
The length of time you can book a holiday rental in Five Islands differs according to the property. Just enter your desired dates to view a list of options offering extended stays. With tons of amenities such as kitchens and air conditioning, as well as some offering weekly or monthly discounts, you're sure to find a terrific place to call your home away from home in Five Islands.