Five Islands holiday lettings

We found 804 holiday rentals — enter your dates for availability

Discover a selection of 8 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:10 Oct - 17 Oct

Why visit Five Islands

  • Scenic Coastal Exploration: Discover the breathtaking beauty of Five Islands and its surrounding areas, perfect for outdoor adventures.
  • Charming Marina Vibes: Enjoy the picturesque marina, ideal for leisurely strolls and soaking in the coastal atmosphere.
  • Botanical Serenity: Visit the delightful botanical garden, offering a tranquil escape amidst vibrant flora.
  • Local Culinary Delights: Savor fresh seafood at the renowned Islands Lobster Co, a must-try for food enthusiasts.
  • Welcoming Community: Experience the friendly locals and rich cultural charm that enhance your holiday experience.

Popular types of accommodation in Five Islands

If you're wondering about the best accommodation options in Five Islands, look no further. Our most sought-after choices include Houses, charming Cottages, and comfortable Apartments. Whether you're searching for Five Islands hotels or delightful vacation rentals, we provide transparent information to help you make the right choice. Don't miss out on the local experience, including the renowned Islands Lobster Co in Maine, as you enjoy a memorable stay in one of our lovely vacation homes.

  • Houses: The top choice for visitors in Five Islands, offering spacious and comfortable accommodation ideal for families or groups.
  • Cottages: A delightful option, these quaint lodgings provide a picturesque and homely atmosphere for a relaxing getaway.
  • Apartments: Perfect for those seeking convenience, apartments offer modern amenities and easy access to local attractions.
  • Cabins: For a rustic experience, cabins immerse you in nature, perfect for a peaceful retreat.
  • Condos: These stylish properties combine comfort and luxury, ideal for a pampered stay.**

Top attractions near Five Islands

Five Islands, Maine, is a picturesque destination ideal for outdoor and adventure holidays. Visitors can explore stunning islands, a charming marina, and a delightful botanical garden. The area offers a blend of beach activities, cultural experiences, and ample opportunities for outdoor pursuits. Don't miss the attractions around Georgetown as you indulge in the natural beauty and local charm that Five Islands has to offer.

  • Coastal Maine Botanical Gardens: Nestled 2.5km from Five Islands, these stunning gardens offer a romantic and family-friendly atmosphere, featuring beautifully curated landscapes and vibrant floral displays, ideal for leisurely strolls amidst nature.
  • Boothbay Harbor Marina: Located 3.1km away, this lively marina provides adventurous opportunities, including boating and seaside activities, while showcasing the charm of Maine's coastal lifestyle with picturesque views.
  • Reid State Park: Just 1.9km from Five Islands, this national park boasts breathtaking scenery, with sandy beaches and rugged coastline, perfect for outdoor enthusiasts seeking adventure and stunning natural landscapes.

Things to do recommended for couples

For a delightful couple's getaway in Five Islands, Maine, enjoy a round at Dolphin Mini Golf, just 4.3km away, for some light-hearted competition. For an adventurous twist, head to Paddleworks, 8.7km away, where you can partake in exhilarating water sports amidst stunning outdoor scenery.

Things to do recommended for families

Your family will delight in the scenic beauty of Pemaquid Point Lighthouse Park and Pemaquid Beach Park, both providing relaxing atmospheres just 6.2km from Five Islands. Fort Point, located 5.0km away, offers further opportunities for enjoyment and exploration amid nature's charm.

Things to do recommended for groups

Groups visiting Five Islands can enjoy a delightful evening at the Carousel Music Theater for a taste of local culture, hit the Boothbay Golf Course for some outdoor sports, and explore the Boothbay Farmers' Market for a vibrant local shopping experience.

Booking with Vrbo is simple

Are you aiming to save on your upcoming journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you could enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Where to stay near Five Islands

Five Islands, nestled in the heart of Midcoast Maine, offers an idyllic escape for those seeking outdoor adventure and stunning scenery. With its charming coastal vibes, visitors can enjoy relaxing excursions and friendly locals. Explore the picturesque towns nearby, where recreation and natural beauty abound. Whether you're wandering the Southern Maine coastline or indulging in local delights, your vacation here promises a delightful blend of relaxation and adventure.

  • Boothbay Harbor: Nestled a mere 3.1km from Five Islands, Boothbay Harbor is a charming coastal city renowned for its stunning outdoor adventures and breathtaking scenery. Visitors flock here for activities such as hiking along picturesque trails and enjoying the local recreational areas. The vicinity is adorned with beautiful beaches and national parks, making it an ideal spot for nature enthusiasts. Golf aficionados can also indulge in a round at the nearby golf courses, ensuring a delightful experience amidst the stunning backdrop of coastal Maine.
  • Georgetown: Just 1.9km from Five Islands, Georgetown is a delightful city that captivates visitors with its enchanting beaches and serene lakes. Perfect for those seeking outdoor activities, Georgetown offers plenty of recreational areas and educational opportunities. Families will appreciate the inviting family beaches, providing a great environment for relaxation and fun in the sun. The natural beauty and tranquil atmosphere make Georgetown a must-visit for those looking to immerse themselves in Maine's scenic coastal landscape.
  • Phippsburg: Located 3.1km from Five Islands, Phippsburg is a picturesque city that combines outdoor adventures with stunning beach vistas. This gem is ideal for those who revel in outdoor pursuits, including golf and recreational activities. The beautiful local beaches and serene lakes provide a perfect setting for a day of relaxation or family fun. With its captivating scenery and welcoming community, Phippsburg is a fantastic destination for tourists eager to explore the natural wonders of Maine.

Best time to go to Five Islands

If you're planning a trip to Five Islands, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from July to September, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.5°F (-3.6°C)Light RainMostly SunnyLowSlightly Low
February26.2°F (-3.2°C)Light RainMostly CloudyAverageSlightly Low
March32.9°F (0.5°C)Light RainMostly SunnyAverageSlightly Low
April43.0°F (6.1°C)Light RainMostly CloudyAverageAverage
May52.9°F (11.6°C)Light RainMostly SunnyAverageAverage
June60.8°F (16.0°C)Light RainMostly SunnyAverageSlightly High
July67.8°F (19.9°C)Light RainMostly SunnyHighSlightly High
August67.5°F (19.7°C)Light RainMostly SunnyHighSlightly High
September61.3°F (16.3°C)Light RainMostly SunnyHighAverage
October51.4°F (10.8°C)Light RainMostly SunnyAverageAverage
November40.5°F (4.7°C)Light RainMostly SunnyLowAverage
December32.2°F (0.1°C)Light RainMostly SunnyLowAverage

What do I need to keep in mind when booking a vacation in 'Five Islands

If you're travelling with a group, family, or pets, or if you're seeking longer stays, it's essential to use the appropriate filters to prioritise your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Five Islands with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Five Islands with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, while also seeking out suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Five Islands: For many, a family holiday wouldn’t feel complete without their furry companion by their side. If you can relate to this, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortably at home.
  • Planning for a long term stay visiting Five Islands: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. You might also want to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Vrbo Trips: Planning as easy as it gets

Vrbo's clever Trip Board offers you a dedicated space to plan new adventures, pick up from where you last paused, or manage your existing arrangements. You can easily find properties you have previously saved or booked under the sections for Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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:

  • Maine State Aquarium (3.7 mi / 6 km)
  • Boothbay Golf Course (5.5 mi / 8.8 km)
  • Paddleworks (14 mi / 22.6 km)
  • Land's End Gift Shop (16.2 mi / 26.1 km)
  • Pemaquid Craft Co-op (11.1 mi / 17.8 km)
  • Brunswick Golf Course (15.4 mi / 24.9 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)
  • Grimes Cove Beach (5.8 mi / 9.3 km)
  • Popham Beach (6.1 mi / 9.9 km)
  • Hunnewell Beach (7.1 mi / 11.3 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.

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