Peaks Island vacation rentals

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Top-rated vacation rentals in Peaks Island

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Portland

4.86 out of 5 average rating, 170 reviews

Booking Now: Year-Round Peaceful Island Getaway

*Quiet and Peaceful *Easy Portland Access *Sparkling Bathroom Remote Downeast island experience just two hours from Boston ... Renovated home in the tranquil Tolman Heights section of Peaks (the island’s highest point) offers a modern kitchen and sparkling new bathroom. Sleeps 6-plus comfortably in bedrooms all equipped with ceiling fans. Spacious home is a short stroll to the Back Shore, with its dramatic views of Casco Bay and the open ocean. Great biking, hiking, swimming, and kayaking.

Guest favorite

A collection of magazines is displayed on a wooden surface. Titles include local interests and lifestyle themes, showcasing vibrant covers with imagery related to nature and cuisine. The arrangement features a slight overlap, creating a casual yet organized presentation.

Guest suite in Falmouth

4.94 out of 5 average rating, 247 reviews

Pristine Waterfront Studio Apt. Retreat

Studio apt. on the water where Casco Bay meets the Presumpscot River. Downtown Portland 2 minutes away. Perfect to... *Relax & enjoy the sunset & water views from decks *Head into Portland-Bon Appetite 2018 Restaurant City of the Year & "The Best Lobster Roles in Maine" *CNN named Portland as "one of the best towns to visit in 2024" *Drive up the coast, explore the beautiful beaches, lighthouses, quaint towns *Adventure inland for amazing hikes & mountainous views *Awesome music scene!

Top guest favorite

Yurt in Chebeague Island

4.98 out of 5 average rating, 135 reviews

Yurt on Chebeague Island

Imagine staying in a yurt in the woods of Chebeague Island, nestled peacefully in a private clearing in the woods. Explore island beaches and hidden trails. This yurt is “glampy” inside with leather chairs and a substantial log bed. The yurt has a rusticator kitchen with all of the basics for cooking, small fridge, stovetop, sink. Water. Outdoor fire pit. WiFi . Check ferry options on Casco Bay Lines or Chebeague Transportation. Host will provide transport to/from ferry to the yurt.

Top guest favorite

A modern kitchen area is illuminated by natural light streaming through a skylight and a large window. A stainless steel sink is positioned under the window, complemented by wooden counters and open shelving. A single orange chair adds a pop of color, enhancing the minimalist design.

Apartment in Portland

4.98 out of 5 average rating, 151 reviews

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.

Top guest favorite

An open-concept space is shown, featuring a modern kitchen with stainless steel appliances and a dining area with a table set for six. Large windows provide natural light and city views, while exposed wooden beams and sleek furnishings enhance the contemporary design.

Condo in Portland

4.97 out of 5 average rating, 206 reviews

Waterfront Two Master Suite Penthouse with Rooftop

2023 City of Portland Registration #20185280-ST Penthouse suite w/modern amenities, exposed beams and brick, poplar walls. Rooftop deck w/views of harbor and city. Separate master suites with custom showers and one with soaking tub. Gas-fired Jotul stove in living room. Washer/dryer in unit. Easy elevator access. Spacious kitchen with granite countertops and wine cooler. Please note: animals (including assistance animals) not allowed due to owner's health.

Top guest favorite

Home in Bridgton

5 out of 5 average rating, 103 reviews

Wren Cabin + Wood fired Sauna

We built the Wren Cabin to be a serene space filled with light and art and with lots of cozy details. Lofted ceilings, a spiral staircase and large open concept with lofted bedroom. The cabin also has a gorgeous wood-fired sauna for those colder days. Wren cabin has a large wraparound deck for relaxing and an outdoor fire pit, as well as shared access to Adams Pond. The space is modern Scandinavian, light and aery, and filled with thoughtful details.

Top guest favorite

A charming storefront presents a colorful display with a large red sculpture and a vibrant flower garden. The shop window is adorned with playful designs and bright signage, while striped awnings provide shade over the entrance. Nearby buildings complement the quaint, inviting atmosphere.

Guest suite in South Portland

5 out of 5 average rating, 251 reviews

Bright Guest Studio Near Lighthouses and Beach

This bright guest studio is steps from the Greenbelt Walkway. Walk (within 10 mins) to two lighthouses, Willard beach, Bug Light Park, Scratch Bakery, Willard Scoops ice cream and a variety of restaurants. Portland is an 8 minute drive or 20 minute bike over the bridge. The space is minimal, bright and airy with windows surrounding, an elevated bed with comfy queen mattress, fully equipped kitchen, washer/dryer, and cozy couch for lounging.

Guest favorite

A bathroom doorway opens into a compact space featuring a white toilet and a small sink. Light blue walls create a soothing contrast with the warm wood flooring. A mirror and a few shelves are mounted above the sink, providing functional storage.

Guest suite in Portland

4.92 out of 5 average rating, 282 reviews

Gorgeous Studio 2 Blocks from Eastern Prom!

Located in Portland's trendy East End and within walking distance to the Old Port and Downtown, this beautiful studio is only 2 blocks from the Eastern Promenade and Casco Bay! You will have the Unit entirely to yourself with its own entrance, air conditioning, kitchenette, queen sized bed and an additional pull out single. Easily walk to all of the cool breweries, great restaurants, coffee shops, and night life! Welcome to Portland!

Superhost

A charming beach cottage is nestled in a park-like setting along a quiet road. The ocean is visible in the background, framed by bare trees. The cloudy sky reflects soft shades of blue, while coastal rocks and waves can be seen nearby.

Cottage in Portland

4.85 out of 5 average rating, 148 reviews

Artist's Retreat

A 1900's beach cottage on Peaks Island, a 5 minute walk from the ferry, but nestled off the road in a park like, peaceful setting. Hear the waves at night from the backyard, walk 5 minutes to Sandy Beach for swimming and to Picnic Point, with its view of Cushing Island and Whitehead Pass. Experience the beauty of Peaks -- but take a 17 minute ferry ride into downtown Portland for award winning restaurants. The best of both worlds!

Top guest favorite

The cozy cabin is illuminated by soft outdoor lights, enhancing its charming facade. The front porch features a seating area, with potted flowers adding a touch of nature. The surrounding grassy area includes stone steps leading towards the entrance, promoting a welcoming atmosphere.

Tiny home in Portland

4.96 out of 5 average rating, 479 reviews

The Garden Cabin Tiny Home

Curious about tiny homes? Love dogs, gardens, pine trees, campfires, and birds? Hate cleaning fees? Our private 128 sqft cozy cabin is for you! On the spectrum between camping and a hotel room, it's a chill place to call home while visiting Portland. Enjoy our garden while sipping a beverage from your own deck or around the campfire. Heat and A/C when needed. Please, no smokers, kids under 13, or guest pets. STHR-000718-2018

Guest favorite

A light green door is positioned prominently against a softly painted wall. A small, wall-mounted shelf displays decorative items. Nearby, a wooden dining table with two chairs is illuminated by natural light filtering through a window with light, sheer curtains.

Guest suite in South Portland

4.92 out of 5 average rating, 255 reviews

Top of the Hill So Po In Law

Lovely In law apartment in desirable Meeting House Hill area of South Portland .We were recently the hottest real estate market in the country .Conveniently located , 10 minutes to Portland , and on the doorstep of local beaches, State parks , restaurants ,unique boutique shops ,amazing bakeries and coffee , lunch and antiquing .All you need for a home away from home . Your going to love this neighborhood !

Guest favorite

The cabin is surrounded by a winter landscape, showcasing a dark exterior with large windows. Snow covers the ground and roofs, with evergreen trees in the background. A wooden door with a wreath adds a welcoming touch, while a small seating area is visible near the front.

Cabin in Kennebunk

4.97 out of 5 average rating, 139 reviews

HotTub/5min to K-port, Pet friendly, @anchorunwind

Follow us on IG @anchorunwind. Escape to a hidden gem nestled in the heart of the Kennebunkport area, where modern comfort meets nature's serenity. Our cabin offers an unforgettable vacation experience. ✭"...A must stay location. The host’s were very helpful and genuine..." ✭"...We’ve travelled all around the world and this is in our top 3 Airbnbs we’ve stayed in."