Best Vacation Homes in Five Islands
Cottage
10.0(32 Reviews)
2 Bedrooms
2 Baths
8 Guests
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
R8,469/Night
7 Nights - R59,294
House
9.5(2 Reviews)
1 Bedroom
2 Baths
8 Guests
2098.96 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
Child Friendly
R9,047/Night
7 Nights - R63,332
R3,175/Night
7 Nights - R22,231
Cottage
10.0(20 Reviews)
1 Bedroom
1 Bath
4 Guests
Oceanfront- Fireplace/Heating
Ocean View- Balcony/Terrace
R3,879/Night
7 Nights - R27,159
House
8.0(1 Review)
1 Bedroom
1 Bath
6 Guests
1905.21 ft²
Private Beach- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R9,248/Night
7 Nights - R64,733
Cottage
10.0(10 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
Parking
R2,874/Night
7 Nights - R20,122
House
10.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R5,458/Night
7 Nights - R38,200
House
10.0(1 Review)
2 Bedrooms
1 Bath
6 Guests
- Pet Friendly
- Kitchen
Internet- Child Friendly
R9,176/Night
7 Nights - R64,238
Five Islands Luxury Rentals
House
4 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
View
R64,367/Night
7 Nights - R450,573
House
9.4(6 Reviews)
6 Bedrooms
5 Baths
18 Guests
7000 ft²
- Oceanfront
Spa- Fireplace/Heating
- Ocean View
R43,986/Night
7 Nights - R307,908
House
1 Bedroom
5 Baths
18 Guests
6996.54 ft²
- Fireplace/Heating
- Balcony/Terrace
- Child Friendly
Wheelchair Accessible
R38,810/Night
7 Nights - R271,669
House
4 Bedrooms
2 Baths
8 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Internet
R25,198/Night
7 Nights - R176,383
Cottage
10.0(6 Reviews)
5 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R23,352/Night
7 Nights - R163,463
House
10.0(3 Reviews)
6 Bedrooms
3 Baths
14 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R22,804/Night
7 Nights - R159,623
House
10.0(4 Reviews)
4 Bedrooms
3 Baths
8 Guests
3500 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R20,165/Night
7 Nights - R141,149
House
10.0(5 Reviews)
4 Bedrooms
3 Baths
8 Guests
Hot Tub- Spa
- Fireplace/Heating
- Ocean View
R17,563/Night
7 Nights - R122,939
Five Islands Pet Friendly Vacation Rentals
House
9.6(19 Reviews)
2 Bedrooms
2 Baths
8 Guests
3587 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R9,095/Night
7 Nights - R63,661
House
7.0(1 Review)
1 Bedroom
2 Baths
8 Guests
3584.38 ft²
- Balcony/Terrace
- Pet Friendly
- Child Friendly
Restaurant
R9,377/Night
7 Nights - R65,639
Cottage
9.4(20 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R7,021/Night
7 Nights - R49,143
House
1 Bedroom
2 Baths
6 Guests
1227.09 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Child Friendly
R7,696/Night
7 Nights - R53,872
Cottage
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R7,259/Night
7 Nights - R50,807
House
10.0(14 Reviews)
4 Bedrooms
3 Baths
13 Guests
2200 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R15,573/Night
7 Nights - R109,014
House
9.8(31 Reviews)
3 Bedrooms
2 Baths
10 Guests
1600 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R6,886/Night
7 Nights - R48,203
Cottage
9.6(27 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R3,144/Night
7 Nights - R22,000
Five Islands Large Vacation Homes
New
House
10.0(1 Review)
6 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
Air Conditioner- Internet
- Child Friendly
R7,275/Night
7 Nights - R50,922
House
9.6(8 Reviews)
5 Bedrooms
1 Bath
9 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R10,521/Night
7 Nights - R73,648
Other
10.0(25 Reviews)
5 Bedrooms
3 Baths
10 Guests
2500 ft²
- Fireplace/Heating
Pool- Balcony/Terrace
- Kitchen
R13,864/Night
7 Nights - R97,049
House
9.8(42 Reviews)
3 Bedrooms
2 Baths
11 Guests
1875 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R9,318/Night
7 Nights - R65,227
House
9.8(38 Reviews)
5 Bedrooms
2 Baths
10 Guests
1722 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R2,954/Night
7 Nights - R20,682
House
10.0(3 Reviews)
4 Bedrooms
2 Baths
12 Guests
2600 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R9,520/Night
7 Nights - R66,644
House
10.0(2 Reviews)
5 Bedrooms
3 Baths
8 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R15,887/Night
7 Nights - R111,205
House
10.0(1 Review)
5 Bedrooms
2 Baths
8 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R9,169/Night
7 Nights - R64,189
Why Choose Rent By Owner for your Five Islands Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Five Islands
When should you plan your Vacation Rentals stay?
Choosing the ideal time to vacation in this scenic area can enhance your experience, as seasons influence the weather and local activities, helping you select the perfect period to enjoy the region’s natural beauty and tranquility.
Peak Season Highlights
June - August
During these summer months, the region experiences its warmest weather, making it ideal for outdoor activities and enjoying the stunning coastal scenery.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
September - October
Early fall brings mild temperatures and vibrant foliage, creating a picturesque setting that attracts those seeking a peaceful retreat and scenic views.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Off-Season Highlights
November - February
The winter months are quieter, with cooler temperatures and fewer visitors, offering a serene environment perfect for relaxing in cozy vacation rentals.
Average Temperature Daytime: 35°F to 45°F - Nighttime: 20°F to 30°F
March - May
Spring ushers in milder weather and blooming landscapes, providing a refreshing escape before the busy summer season begins.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 30°F to 40°F
Weekly Weather Forecast for Five Islands
How to Book Your Five Islands Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Five Islands
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy access to private or shared outdoor seating areas where you can relax and take in the scenic views of the region's coastlines.
- Take advantage of outdoor picnic tables and barbecue grills, perfect for al fresco dining during your stay in this coastal destination.
- Benefit from well-maintained gardens or landscaped yards that enhance the natural beauty of the area.
- Make use of shaded patios or verandas ideal for enjoying morning coffee or sunset evenings by the water.
- Request outdoor fire pits or fireplaces to gather around as you share stories and enjoy the crisp sea air.
- Discover accessible outdoor parking areas designed to accommodate visitors exploring here by car.
- Utilize boat docks or waterfront access points, providing convenient options for those looking to indulge in boating or fishing activities.
Top Attractions Around Five Islands
What attractions are nearby?
While staying here, you can enjoy a variety of outdoor activities such as exploring scenic coastal walks, kayaking along the shoreline, or visiting local parks to unwind and take in the natural beauty that surrounds this destination.
Family Activities
- Exploring the Five Islands Lobster Fleet: You can witness the region’s renowned lobster fishing industry firsthand with a boat tour or visit local working docks to see traditional fishing practices in action.
- Visiting Reid State Park: Relax on pristine beaches, enjoy picnicking areas, and explore scenic walking trails suitable for family outings in this popular coastal park.
- Discovering Boothbay Railway Village: Step back in time with train rides, historic exhibits, and interactive activities designed to entertain children and connect you with the area’s rich history.
- Engaging in Water Activities at the Coastal Waters: Kayaking, paddleboarding, and sailing are perfect ways to experience the region's calm waters and create memorable family adventures here.
Adult Activities
- Sea Kayaking Adventures: Explore the tranquil waters surrounding this coastal area by sea kayak, offering you a peaceful way to discover hidden coves and scenic shoreline views.
- Bird Watching Tours: Enjoy observing diverse bird species in their natural habitat along the region’s lush coastlines and salt marshes, perfect for nature enthusiasts seeking serenity.
- Historic Lighthouse Visits: Tour iconic lighthouses that have guided mariners here for generations, providing a glimpse into maritime history and spectacular ocean vistas.
- Charter Fishing Excursions: Embark on a fishing trip with local experts, where you can try your luck catching fresh seafood against the stunning backdrop of the Maine coast.
Five Islands Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Activities in Advance: Take advantage of the area’s scenic surroundings by researching local waterfront activities and outdoor adventures to make the most of your stay.
- Choose a Well-Located Vacation Rental: Select a property that offers easy access to the region's charming coastal sights and tranquil beaches for a convenient and relaxing experience.
- Explore Local Cuisine and Markets: Sample fresh seafood and regional specialties at nearby markets and eateries to immerse yourself in the authentic flavors of this destination.
- Practice Responsible Tourism: Respect the natural environment and local community to ensure your visit remains sustainable and enjoyable for future travelers here.
Transportation Options
- Car Rentals: Renting a vehicle offers you flexibility and convenience for exploring the scenic coastline and nearby attractions of this region.
- Public Transit: Local buses provide an affordable and eco-friendly way to navigate around the area without the need for a personal vehicle.
- Private Transfers: Chauffeur services and private shuttles offer a comfortable, reliable option for quick access to your vacation rental in Five Islands or surrounding spots.
- Biking and Water Transport: Biking along designated trails and utilizing water taxis give you a unique perspective of the area's natural beauty and coastal charm.
Local Customs Options
- Seafood Celebrations: Locals here take pride in their maritime heritage, often celebrating with traditional seafood festivals that showcase fresh catches from the region.
- Respect for the Environment: Preservation of the area's natural beauty is deeply rooted in community customs, encouraging visitors to practice responsible tourism and conservation.
- Sailing Traditions: The region has a rich history of sailing, and you’ll find that boat handling and seamanship are important aspects of local culture.
- Community Gatherings: Small-town events and gatherings are common here, fostering a welcoming atmosphere that highlights the region’s friendly and close-knit community spirit.
Frequently Asked Questions About Five Islands?
1. What are the top vacation rentals in Five Islands?
There are a lot of options in Five Islands. If you plan on staying in the Five Islands area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Five Islands:
- Beautiful Cottage On Water, Near Beach, Pet Friendly!
- Wiggleswick Cottage; Dogs Welcome Certified! Summer availability! No pet fees
- Enjoy the stunning views while relaxing on the deck at East Ledge Cottage
- Oceanfront home with private deep water dock on Harmon Harbor, Georgetown, ME
- Water's Edge - Waterfront Cottage on Southport - Wrap-Around Porch!
- Unique, romantic, motorless floating island w/4 hp skiff
- Romance and Adventure on the High Seas! The Charles Andrew with Motorized Skiff
- Saltwater farmhouse on 2+ acres of waterfront with private dock
- Welcoming vacation home offers a private setting on the water's edge
- Decker Cove Southport Paradise with Central Air Conditioning
2. Which vacation homes in Five Islands are best for families?
If you are looking for a family-friendly vacation home in Five Islands, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Five Islands:
3. How many Rentbyowner vacation rentals are available in Five Islands?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 123 in the Five Islands area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Five Islands.
4. What is the cancellation policy for booking vacation rentals in Five Islands, Maine?
Cancellation policies vary by property, so it’s important to review the specific terms listed in your chosen rental. You can find detailed cancellation and refund policies in the listing or contact the owner directly for clarification.
5. How do I confirm my reservation and what do I need to check before booking?
To confirm your booking, ensure that all details, including dates, number of guests, and special requests, are accurate. Review the property's description and amenities, and reach out to the owner if you have any questions before completing the reservation.
6. Are there any house rules or restrictions I should be aware of during my stay?
Yes, each vacation rental typically has its own set of house rules regarding noise, pets, smoking, and occupancy limits. These are outlined in the listing, and you should read them carefully before booking or contacting the owner for further details.
7. What amenities are usually included with vacation rentals here?
Most properties offer essential amenities such as Wi-Fi, kitchen facilities, linens, and parking. Specific amenities vary per rental, so review the listing to ensure it meets your needs and contact the owner for any additional inquiries.
8. What should I do if I encounter issues during my stay in a vacation rental in this area?
If you experience problems during your stay, contact the property owner or manager promptly. For unresolved concerns, you may also refer to the support contact provided by your booking platform to ensure a smooth resolution.
Five Islands Top Rated Vacation Rentals
Hotel
7.8(25 Reviews)
12 Baths
374.05 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R4,515/Night
7 Nights - R31,608
Cottage
10.0(54 Reviews)
2 Bedrooms
1 Bath
4 Guests
950 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
R3,296/Night
7 Nights - R23,072
House
4 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Pool
- Ocean View
Lake View
R6,928/Night
7 Nights - R48,500
