Photo by Robbie Martin

Search Great Diamond Island Villa Rentals

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Browse Select Great Diamond Island Villas

Stillwater Lodge Limit 10 4 Bedroom Home by RedAwning

3.0 star property
Stillwater Lodge Limit 10 4 Bedroom Home by RedAwning
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Great Diamond Island
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Great Diamond Island

Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)

9.8 out of 10, Exceptional, (115)
"Very relaxing getaway."
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)

Gorgeous ocean-front home with stunning beach views

9.6 out of 10, Exceptional, (98)
"Great oceanfront location for a relaxing girls getaway. We enjoyed walking the beach and collecting shells. Great location to start from to see other cities in the area. Best part was watching the sunrise in the morning from the balcony. "
Gorgeous ocean-front home with stunning beach views

Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist

10.0 out of 10, Exceptional, (35)
"What a great place! Located in the arts district, this refurbished brownstone has every modern convenience within walking distance of restaurants and museums. Windows on both sides of the apartment provide street views, one active and bustling, one quiet with a view of Casco Bay and sunrises. And the rooftop patio is a dream - we loved being part of Portland history with an up close view of the florist's ad mural!"
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until December 4 with our Black Friday deals. Stay by December 15, 2025.