Five Islands vacation rentals

We found 835 vacation rentals — enter your dates for availability

Discover a selection of 8 homes and other vacation rentals in Five Islands that are perfect for your trip. Vacation rentals provide the amenities you need and want for your stay with friends, family, or just your pet, such as WiFi and a pool. You'll be able to choose a rental that has what everyone needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Five Islands

Showing deals for:Nov 14 - Nov 21
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Find out more about Five Islands

Find out more about Five Islands

Why visit Five Islands

  1. Scenic coastal beauty: Experience breathtaking views of the ocean and picturesque islands that define Five Islands.
  2. Outdoor activities: Engage in hiking, kayaking, and exploring the stunning beaches and botanical gardens.
  3. Delicious seafood: Savor the local lobster delicacies that are a highlight of this charming fishing community.
  4. Welcoming atmosphere: Enjoy the friendly vibe and hospitality of the quaint village and its residents.
  5. Diverse accommodation options: Choose from cozy cottages to modern apartments for a comfortable stay.

Popular types of accommodation in Five Islands

Discover the charm of Five Islands with our selection of vacation rentals. Whether you're seeking a private vacation home, a cozy cottage, or a modern apartment, we have options to suit every traveller's needs. Explore our listings for Five Islands hotels and Maine vacation rentals, including the popular Coastline Inn. With transparency and savings, your perfect getaway awaits!

  • Houses: These spacious homes are the top choice for visitors to Five Islands, ideal for families or groups seeking comfort and privacy.
  • Cottages: Quaint and charming, cottages offer a delightful escape by the water, perfect for a cozy getaway.
  • Apartments: Conveniently located and well-equipped, apartments are a versatile option for those looking for a home-like experience.
  • Cabins: Embrace the great outdoors with rustic cabins, providing a peaceful retreat amidst nature.
  • Condos: Modern and stylish, condos offer a blend of comfort and amenities, perfect for a relaxing stay.**

Top attractions in Five Islands

Five Islands, Maine, is an ideal destination for outdoor enthusiasts and those seeking scenic beauty and adventure. Visitors can explore stunning beaches, picturesque islands, and charming botanical gardens. The area offers a rich blend of culture and outdoor experiences, making it perfect for travellers looking to immerse themselves in nature while enjoying the local attractions.

  1. Coastal Maine Botanical Gardens: Located 6.4km from Five Islands, this stunning botanical garden offers a serene escape with its beautiful landscapes, perfect for families and romantic strolls. Experience the vibrant flora and peaceful outdoor settings that reflect Maine's coastal charm.
  2. Boothbay Harbor Marina: Situated 8.0km away, this lively marina is ideal for adventure enthusiasts. Enjoy beach activities, boat rentals, and breathtaking views of the harbor, making it a perfect spot for outdoor fun.
  3. Reid State Park: Just 4.8km from Five Islands, this national park features rugged coastlines and scenic vistas. It's a fantastic destination for outdoor adventures like hiking, beach exploration, and wildlife watching.

Things to do recommended for couples

For a romantic getaway in Five Islands, consider a fun round at Dolphin Mini Golf, just 11.3km away, or enjoy the thrill of water sports at Paddleworks, 16.4km away. Embrace the adventure together while soaking in the beautiful coastal scenery.

Things to do recommended for families

During your family vacation in Five Islands, Maine, visit Pemaquid Point Lighthouse Park and Pemaquid Beach Park, both 16.1km away, for relaxation and stunning views. Fort Point, located 12.9km away, offers more recreational fun, perfect for creating lasting memories together.

Things to do recommended for groups

Groups visiting Five Islands can enjoy a delightful evening at the Carousel Music Theater for a mix of culture and entertainment, tee off at the scenic Boothbay Golf Course for some outdoor fun, and browse local produce at the Boothbay Farmers' Market for a taste of the community.

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

If you're planning a trip with a group, family, or pets, or if you're seeking extended stays, it's important to prioritize your filters wisely. 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 complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Five Islands with young kids: Travelling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with 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 families, a trip isn't truly fulfilling without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Five Islands: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Five Islands

Five Islands, Maine, is a charming coastal village perfect for outdoor enthusiasts and adventure seekers. Explore the picturesque scenery, indulge in the local lobster delicacies, and enjoy the friendly atmosphere of this quaint fishing community. Nearby, you can discover hidden gems and engage in recreational activities that highlight the natural beauty of the region. With its welcoming vibe and breathtaking views, Five Islands promises an unforgettable vacation experience.

  • Boothbay Harbor: Located a mere 8.0km from Five Islands, Boothbay Harbor is a picturesque coastal city renowned for its stunning outdoor experiences and scenic vistas. Visitors are drawn to its vibrant waterfront, where you can indulge in activities such as hiking, golfing, and exploring the many recreational areas. The nearby beaches and national parks offer ample opportunities for relaxation and adventure, making it an ideal destination for nature lovers. Don't miss a chance to explore the charming shops and eateries along the harbor, where fresh seafood is a highlight.
  • Phippsburg: Also situated 8.0km from Five Islands, Phippsburg is a serene coastal town that beautifully combines outdoor enjoyment with beachside relaxation. It's perfect for those looking to soak up the sun at its family-friendly beaches or engage in recreational activities like golfing or hiking. The local landscape features serene lakes and picturesque beaches, making it a great spot for a leisurely day outdoors. Visitors can enjoy the tranquil atmosphere while taking in scenic views that truly showcase Maine's natural beauty.
  • Boothbay: Just a short distance of 8.0km from Five Islands, Boothbay is another charming city that captivates travellers with its outdoor adventures and stunning scenery. Known for its hiking trails and recreational areas, Boothbay offers a fantastic blend of activities for those seeking adventure. Golf enthusiasts will appreciate the well-maintained courses, while the nearby national parks and lakes provide ample opportunities for exploration and relaxation. The local charm, combined with breathtaking views, makes Boothbay a must-visit on your Maine itinerary.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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

Booking with Vrbo is simple

Planning your next adventure and hoping to save some money? Being flexible with your travel dates can really pay off, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To help you find the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to support you every step of the way!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, keep your travel plans on track, or manage your existing bookings. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Choose a vacation rental for your Five Islands getaway

Experience the unique character of Five Islands with a stay in a vacation home rental. There's no shortage of things to see and do in the area.If you're looking for accommodations with space to entertain friends and family, Vrbo 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 attractions to visit in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Five Islands a fun place to get away. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • 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 looking for exciting outdoor activities or just want to spend some time taking in the scenery, Five Islands is a great place to spend some time outside. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Coastal Maine Botanical Gardens (4.2 mi / 6.7 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)
  • Waterfront Park (8 mi / 12.9 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 center. If you can't find a flight that works for your travel itinerary, 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 vacation rental accommodation in Five Islands?
According to our research, houses are considered the most popular vacation rental type in Five Islands. But as you'd expect, everyone's idea of an awesome trip can vary. Vrbo has vacation rentals of all shapes, sizes and budgets, and we'll help you find the perfect match.
How much does it cost to rent a vacation rental in Five Islands?
The average price for a vacation 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 cozy 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 vacation rentals in Five Islands?
Yes. There are. You can pick from five vacation rentals that allow pets in Five Islands. Lots of our pet-friendly vacation 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 vacation 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 vacation rental that fits your style with all the features you'll enjoy.
Are there large group vacation rentals in Five Islands?
Take your pick of five Vrbo vacation 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 vacationing with — and no one else.
Are there vacation 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 vacation 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 favorite option.
What are the top attractions for families in Five Islands?
Keeping the kids occupied during your Five Islands vacation is a snap with these awesome family-friendly attractions:

  • Georgetown Historical Society
  • Half Mile Beach
  • Reid State Park

Are there vacation 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 vacation homes with WiFi in Five Islands. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.
How old do you have to be to rent a vacation 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 vacation home before booking your escape.
How long can I rent a vacation rental in Five Islands for?
The length of time you can book a vacation 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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