Holiday houses in Little Diamond Island

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Charming Cottage house, 2 bedrooms & Jacuzzi tub

Unwind with your family at this charming cottage, where comfort meets convenience. This vibrant, newly renovated home boasts a warm, colorful interior with a cozy patio overlooking a pond. Fully furnished, it includes all utilities and offers free parking on-site. Nestled in a quiet neighborhood yet steps away from downtown, this sunny cottage offers both privacy and access to city attractions. Enjoy a peaceful retreat close to the heart of the city—perfect for a relaxing, hassle-free stay.

Ocean View Cottage on Peaks Island

Welcome to Ocean View Cottage! Just a short walk from the ferry dock, yet feels off the beaten path. Only minutes away from the best beach, as well as all the restaurants, shops and the island grocery store. Guests are provided with bikes, beach chairs and beach toys making it easy to experience Peaks Island living. Pet and family friendly with a Packnplay onsite. Ocean View Cottage is a fully stocked home setup for you enjoy and relax during your island getaway. License #STHR-007357-2025

Luxury One Bedroom Loft in Portland’s Old Port

Immerse yourself in the culture of the Old Port at your luxury loft. A top choice for travelers, The Docent's Collection was most recently awarded Condé Nast Readers' Choice (2025) and Tripadvisor Travelers' Choice (2025). Enjoy this spacious open-concept floor plan featuring a full-sized kitchen and bedrooms with soft luxurious linens and cozy pillows for your comfort. Admire the tapestry of a curated collection of local artists and enjoy five-star service from our local hospitality team.

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

The Copper Fox Treehouse

Named the 10th most spectacular tree house in the world by the BBC Featured in the book: Modern Tree Houses by Taschen Airbnb's Most wishlisted property in Maine in 2025! Come experience the whimsy and craftsmanship of this red fox head shaped treehouse for yourself. The magic of this wild adventure awaits you in the treetops... Come to relax, explore and make lasting memories your family and friends will talk about for years. Follow our journey on IG at @thecopperfoxtreehouse

Luxury Retreat In Back Cove | 10 Min to Downtown

Bike to downtown just 2 miles away. Ideal for a couple or family looking for a restorative getaway in a quiet, locals neighborhood. The architect owner designed and built this light-filled spacious eco-suite to meet the needs of the most discerning guest with luxurious accommodations. Organic and down-topped king mattress, linen bedding, spacious marble rain shower, deep soaking tub, fenced in backyard with deck, hammock, and pool - everything you need for a memorable Maine vacation!

Peaks Island Master Bedroom Suite

Enjoy your stay at this conveniently located, light-filled, modern, chic living space--only a 4-minute walk from ferry, great sunsets, close to market and restaurants with a private entrance and deck. Walking distance to the best island beaches. Located on a quiet, dead end road off the main street. The space is found at the rear of one of Peaks Island's most beautiful, original Cape homes. Guests can enjoy a comfy queen size bed, organic cotton sheets, and a pull-out sofa bed.

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

Mermaid's Chair | Private Beach | Hot Tub

*Hot tub not available after October 27- April This is a rare one. A classic 1939 Maine camp sitting directly on Casco Bay with a private dock, sweeping water views, and a saltwater hot tub, all on a quiet private road. Properties like this don't come around often, and once you're here, you'll understand why. The dock puts you right on the water, with one slip available for guests. Wolf's Neck State Park and Wolf's Neck Farm are a short walk away, and Downtown Freeport.

Downtown Penthouse Suite - Stunning Harbor Views

CO2024-01992 Private 1850's Old Port Penthouse w/Breathtaking Views and Complimentary Parking Nearby. Gorgeous contemporary suite full of light located right across from the working waterfront. Lobster and seafood off the boat is 100 meters from your front door. Watch ferries and smell the salt air from your private deck. Welcome to Portland! Please note: animals (including assistance animals) not allowed due to owner's health.

Peaceful Beach Getaway

Located steps away from the beautiful Willard Beach, this modern dwelling insures a peaceful getaway. Take a walk up the street for freshly baked bagels and mouth watering pastries, or down the Greenbelt Walkway for a lovely lighthouse excursion. Drive 10 minutes into Portland for a night-out on the town, and return to your newly-renovated one-bedroom suite for a restful night on a glorious king bed.