- USA
- Maine
- Boothbay Harbor
- Five Islands
- Cottage Rentals
Five Islands Cottage Rentals & Holiday Homes
Find the best cottages in Five Islands - We found 41 exact matches
- Air Conditioner
- TV
- Balcony/Terrace
- Parking
- Pet Friendly
- View
- Air Conditioner
- Parking
- TV
- Parking
- Pet Friendly
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Parking
- Pet Friendly
- View
- Parking
- TV
- View
- Air Conditioner
- Parking
- TV
- Parking
- TV
- Balcony/Terrace
- Parking
- TV
- Balcony/Terrace
- TV
- Balcony/Terrace
- Security/Safety
- Parking
- Pet Friendly
- View
- Parking
- Pet Friendly
- TV
- Parking
- View
- Ocean View
- Parking
- TV
- Accessibility
- Air Conditioner
- Parking
- View
- Parking
- Pet Friendly
- TV
- Parking
- TV
- Balcony/Terrace
- Parking
- TV
- Balcony/Terrace
- Parking
- Pet Friendly
- TV
- Parking
- Pet Friendly
- TV
- Parking
- Pet Friendly
- TV
- Parking
- Balcony/Terrace
- Security/Safety
About Five Islands Cottage Rentals on The Beaches Estates
Searching for cottages to rent near Five Islands? The Beaches Estates features more than 41 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Five Islands have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. The Beaches Estates’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Five Islands.
Are you planning to travel to the lakeside, beach, or mountain area? The Beaches Estates’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.
The Beaches Estates boasts of 41 holiday cottages and places to stay in Five Islands. The site provides unique Airbnb, VRBO, The Beaches Estates-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.
Frequently Asked Questions About Five Islands Cottage Rentals
What are the top rated Cottage 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 Cottage Rentals in Five Islands:
- Seawood Sunset Cottage: Southport Island
- The Ticket Office - Just the ticket for a Private & Romantic Getaway!
- Charming Waterfront Cottage with Private Dock
- Romley House | Deck & New Luxe Kitchen | Near Boothbay Harbor
- Waterfront Cottage With An Awesome View Of Capital And Burnt Island
- Charming 3-bedroom cottage in Southport with water views and close to Boothbay.
- Coastal Island Retreat - Privacy and Convenience. Boat rental available.
- Classic Maine Cottage with Screen Porch
- Adorable guest house with kitchenette, gas grill, free WiFi & great location
- Quiet Waterfront Cottage on coven
How much does it cost to rent a cottage in Five Islands?
The average cost for a cottage rental in Five Islands is $544 per night. Thebeachestates has a wide list of great cottages near Five Islands that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in Five Islands that allow pets?
Yes, here are the top cottage rentals in Five Islands that allow you to bring your pet:
- A Cozy Retreat on Southport Island
- Charming cottage near the beach with balcony, deck, grill, fireplace - dogs OK
- 3 one-bedroom fully equipped cottages with free WIFI/weekly rental
- Enjoyable 1-bedroom rustic cottage in Southport.
See all pet-friendly vacation rentals in Five Islands on Thebeachestates
Do you have any rental cottages in Five Islands that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in Five Islands to find one that works for you.
Are there quality cottages in Five Islands that have indoor swimming pools?
As of 2026, the data from Thebeachestates shows that there are Over 41 private swimming pools or cottages with indoor pools in the Five Islands area along with other great amenities.