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Vacation rentals in Peaks Island

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Top-rated vacation rentals in Peaks Island

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

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Top guest favorite
A serene vista showcases the city skyline reflected in calm waters, framed by lush green grass and trees. The scene captures a tranquil moment, inviting viewers to appreciate the natural beauty and urban blend surrounding the space.
Home in Portland

Top Deck - Portland Property with Views!

Views, Views, Views! 2 huge decks overlooking water and city skyline. This home is adjacent to Payson’s Park – Portland’s largest park. 5-7 min ride to downtown Portland and the Old Port’s fabulous bars and restaurants. The main floor has bedroom with bath, kitchen, and living room. The upstairs has a large bedroom with bath, open room that can be used as 2nd living room or a 3rd/4th bedroom space. Sleeps 10-12. Off street parking 6-8. Large yard. Portland License #STHR-002587-2020

FamilyValueBackyard

4.92 out of 5 average rating, 304 reviews
Top guest favorite
Cottage in Portland

4br2ba House+parking@PeacefulOasis on Munjoy Hill

This standalone 1500sf 3-story cottage is set in an ideal location, close to the Eastern Prom, cafes, award-winning restaurants, breweries and the Old Port. -Main floor: well-equipped kitchen + open concept living/dining room -Upper floor: 3BR (1 queen, 1 full, 1 twin) + bath -Garden level: 1BR/1 bath (queen) with private entrance - Off-street parking for 1 car This charming home @ A Peaceful Oasis offers plenty of space, privacy & comfort, making it the perfect home base for your stay.

ValueLocationQuiet

4.97 out of 5 average rating, 301 reviews
Guest favorite
Home in Naples

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!

LocationFamilyNearby

4.97 out of 5 average rating, 197 reviews
Top guest favorite
Treehouse in Pownal

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

ValueFamilyGrill

4.99 out of 5 average rating, 192 reviews
Top guest favorite
A bright hallway leads into the living space, featuring light wood flooring and white walls. A dining area is seen to the left with a small table and chair, while decorative elements, including potted plants and books, add character to the space.
Apartment in Peaks Island

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.

LocationFamilyWalkability

4.99 out of 5 average rating, 229 reviews
Top guest favorite
The exterior of the A-frame cabin is showcased, featuring a unique wooden facade and metal roof. Sunlight streams through tall triangular windows, illuminating the surrounding wooded area. A gravel path leads to the entryway, enhancing the cabin's connection to nature.
Cabin in Freeport

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!

LocationValueAccuracy

5.0 out of 5 average rating, 152 reviews
Guest favorite
Home in Peaks Island

Year-Round: Peaceful and Quiet 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. STHR-007313-2025

FamilyValueGrill

4.87 out of 5 average rating, 185 reviews
Top guest favorite
A modern lounge area is highlighted by large skylights, allowing abundant natural light to fill the space. A sleek, white sectional is complemented by colorful accent pillows and a patterned area rug. Exposed brick walls add an element of rustic charm, with scenic views of the harbor visible through the glass.
Apartment in Downtown Portland

Old Port Penthouse Suite - Amazing Harbor Views

CO2024-01992 Private Old Port Penthouse w/Breathtaking Views + Your Own Cupola. Quiet + Secure. 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 the ferries to the islands from the cupola. Smell the salt air from your private deck. Welcome to Portland! Please note: animals (including assistance animals) not allowed due to owner's health.

LocationValueCheck-in

4.97 out of 5 average rating, 327 reviews
Guest favorite
A charming beach cottage stands in a serene setting, featuring a weathered wooden exterior with red-trimmed windows. A yellow door welcomes guests, while a wooden staircase leads to the entrance. Lush greenery and colorful flowers surround the home, indicating a well-tended garden.
Cottage in Peaks Island

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!

LocationValueAir conditioning

4.84 out of 5 average rating, 164 reviews
Top guest favorite
A spacious sleeping area features natural wood paneling and a high ceiling. A comfortable bed is dressed in light blue and white linens, accompanied by two decorative pillows. A wooden cabinet and a bedside lamp add functional elements, while a window allows soft light to fill the room.
Barn in Portland

Garrison Cove Studio

Rare, Portland waterfront studio located in the heart of the historic Stroudwater neighborhood, awaits one or two guests looking for an urban hideaway. The studio occupies a 150 year old post and beam barn situated on the banks of the Stroudwater and Fore Rivers. Enjoy morning coffee on the river swing, meditate to the soothing sound of the nearby waterfall or linger over your favorite beverage in one of our comfy Adirondacks.

LocationFamilyLong stay

5.0 out of 5 average rating, 491 reviews
Top guest favorite
A well-maintained cottage is positioned beside a tranquil body of water, surrounded by lush greenery. A spacious lawn is visible in the foreground, showcasing an outdoor seating area with a patio umbrella. The scenic view of the water complements the serene setting.
Home in Harpswell

Waterfront Cottage On Basin Cove - Amazing Sunsets

Bright, airy cottage right on Basin Cove,a tidal cove in Harpswell Maine. Cool breezes with pristine views, especially for the sunsets over the cove. At the end of Harpswell Neck, so it feels like you're far away, but still only an hour from Portland, 1/2 hour from Freeport & 15 minutes from Brunswick. Use it as your hub to explore Midcoast Maine or hunker down and enjoy the screened in porch after a swim in the cove.

ValueFamilyParking

4.98 out of 5 average rating, 240 reviews
Guest favorite
A scenic view of the ocean framed by green trees and a grassy area. A distant lighthouse is visible on the horizon, while the sky is partly cloudy, creating a peaceful atmosphere. The landscape includes several large rocks scattered across the lawn.
Home in Peaks Island

Stunning Ocean Views From This Peaks Island Home

Completely remodeled classic Peaks Island home with stunning Atlantic Ocean white water views. Welcome to the newly renovated Valhalla on Peaks. This classic home underwent a complete renovation for your family's enjoyment. From the minute you step onto the property, your senses will be overwhelmed by the views, ocean breeze, salty smell, and the property's nostalgic feel.

FamilyLocationComfort

4.9 out of 5 average rating, 123 reviews

Popular amenities for Peaks Island vacation rentals

Free parking on premisesGymBBQ grillLaptop-friendly workspaceWifi

Peaks Island house rentals

Guest favorite
A charming coastal home is showcased with light-colored siding and a bright blue front door. Surrounding greenery includes tall trees and manicured shrubs. The property is set back from a grassy area, adding to its inviting curb appeal.
Home in Falmouth

Amazing Bay View Home with Hot Tub

ValueFamilyComfort

4.9 out of 5 average rating, 328 reviews
Top guest favorite
A welcoming living area is furnished with two dark sofas adorned with vibrant orange cushions. A rustic coffee table is centered on a colorful area rug, while large windows allow natural light to fill the space, highlighting the wall art above.
Home in Portland

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

ValueLocationCondition

4.97 out of 5 average rating, 174 reviews
Top guest favorite
An open living area is highlighted by large windows that frame scenic views of the marsh. A modern gas fireplace serves as a focal point, while a light-colored sofa and a small table with a plant create a welcoming ambiance. Bar seating for four extends to the kitchen.
Home in Higgins Beach

Higgins Beach *New* Beach Home & Private Offices

FamilyValueIndoor spaces

5.0 out of 5 average rating, 115 reviews
Top guest favorite
An inviting living area features a comfortable sofa facing a large television mounted on the wall. A rustic trunk serves as a coffee table on a patterned area rug. Natural light enters through double doors with sheer curtains, adding warmth to the space.
Home in Portland

East End Unit

FamilyValueHospitality

4.94 out of 5 average rating, 187 reviews
Guest favorite
Home in Westbrook

Cozy Maine Cottage • Near Jetport & Coast

LocationValueBreakfast

4.89 out of 5 average rating, 641 reviews
Top guest favorite
An open-concept living area features warm wooden flooring and mid-century style decor. A vibrant orange sofa is positioned opposite a dining table with wooden chairs. Natural light floods in through large windows, and a set of stairs leads to the upper level.
Home in Portland

3 bedroom house in the heart of Portland

ValueFamilyBackyard

4.98 out of 5 average rating, 411 reviews
Top guest favorite
A spacious living area features a large sectional sofa adorned with patterned throw pillows. A wooden coffee table sits nearby, complementing the light wood flooring. Natural light fills the room through large windows, with a mounted television and decorative wall art enhancing the modern aesthetic.
Home in Old Orchard Beach

Luxury Home w/HOT TUB & Fire Pit

ValueFamilyAir conditioning

4.96 out of 5 average rating, 232 reviews
Guest favorite
A sunlit sunroom features three woven chairs adorned with soft cushions in varying shades of blue. A low wooden table with a vintage checkers board is situated in the center. Sheer white curtains gently drape around the windows, allowing natural light to enter.
Home in Falmouth

Beautiful +Nostalgic + Coastal Maine Cottage

ValueFamilyQuiet

4.85 out of 5 average rating, 230 reviews

Peaks Island cottage rentals

Top guest favorite
The exterior of a post and beam cottage is shown, featuring a light wood facade and a brown shingled upper section. Two black Adirondack chairs are placed on a wooden deck, accompanied by potted plants. Large windows offer a view of the forested surroundings under a partly cloudy sky.
Cottage in Pownal

Dreamy Post&Beam Hideaway Near Portland & Freeport

FamilyValueBathroom

4.99 out of 5 average rating, 477 reviews
Top guest favorite
An inviting entryway is presented under a large, sloping roof supported by exposed wooden beams. Comfortable seating is arranged on the porch, with decorative pumpkins placed on the ground. Pathways made of stones lead to the entrance, surrounded by a tranquil natural setting.
Cottage in Biddeford

Secluded Coastal Home & Cottage 3 Minutes to Beach

FamilyLocationEV charging

5.0 out of 5 average rating, 105 reviews
Guest favorite
Cottage in Harpswell

Quaint & Peaceful Designer's Oceanfront Cottage

ValueLocationBathroom

4.87 out of 5 average rating, 239 reviews
Guest favorite
A tranquil view of the ocean is visible from a spacious wooden deck, featuring several white Adirondack chairs. The calm water reflects the clear blue sky and surrounding greenery, while distant islands can be seen along the horizon.
Cottage in Harpswell

Classic Maine Cottage - dock, sauna & kayaks

FamilyValueAir conditioning

4.89 out of 5 average rating, 180 reviews
Top guest favorite
A cozy cottage is surrounded by lush trees and greenery. Two blue chairs are placed outside near the entrance, with a small table between them. A gas grill is positioned nearby, creating a welcoming space for outdoor relaxation and dining.
Cottage in Scarborough

Bright, clean, private cottage near Higgins Beach!

FamilyValueBackyard

4.97 out of 5 average rating, 274 reviews
Top guest favorite
Cottage in Yarmouth

Buoys on Bates | Couples' Cottage near Portland

FamilyLocationLaundry

4.96 out of 5 average rating, 179 reviews
Superhost
Cottage in Cape Elizabeth

Beach, Parks, Trails, Tranquil, Quiet, Peaceful

ValueLocationKitchen

4.86 out of 5 average rating, 162 reviews
Guest favorite
A scenic view of a tranquil lake is captured, with a boat dock extending into the water. A boat is anchored near the dock, surrounded by lush greenery. A picnic table sits on sandy ground nearby, inviting relaxation by the lakeside.
Cottage in Gray

Edgewater Retreat - Lakefront w/Sauna & EV Charger

FamilyLocationNearby

4.82 out of 5 average rating, 119 reviews

Other great vacation rentals in Peaks Island

Top guest favorite
A wooden dock extends toward calm water, with a gentle sloping pathway leading down from the boathouse. The clear water reveals stones at the bottom, while green trees frame the picturesque lakeside view.
Guesthouse in New Gloucester

On the water Boathouse!

FamilyLocationGrill

4.9 out of 5 average rating, 175 reviews
Top guest favorite
A panoramic view of lush green land, featuring an array of colorful flowers. The coastline is visible in the distance, with water reflecting the clear blue sky. A shaded area with trees complements the vibrant plants, creating a serene outdoor environment.
Apartment in Cape Elizabeth

Crescent Beach Gardens

ValueLocationCheckout

4.99 out of 5 average rating, 136 reviews
Top guest favorite
An open dining area features a round wooden table surrounded by blue chairs. A comfortable living room area is visible, with a gray sofa and art on the walls. Large windows allow natural light to brighten the space, enhancing the modern design.
Apartment in Portland

Harborview - Curated East End Escape w/ Parking

LocationFamilyGetting around

4.99 out of 5 average rating, 153 reviews
Top guest favorite
The exterior of the cottage is showcased, featuring a spacious deck with partial railings and two blue chairs. Lush green landscaping borders the property, complemented by a grassy area. A sloped pathway leads up to the cottage, which is set among trees and other structures.
Home in Peaks Island

Ocean View Cottage on Peaks Island

FamilyLocationAccuracy

5.0 out of 5 average rating, 80 reviews
Top guest favorite
Apartment in Peaks Island

Beach Front, Waterfront, Ferry Beach

LocationFamilyIndoor spaces

5.0 out of 5 average rating, 48 reviews
Top guest favorite
A spacious living area showcases a light-colored sofa paired with a wood coffee table, surrounded by hardwood flooring. Natural light floods in through the windows, highlighting the open layout that connects to the kitchen area featuring wooden cabinets and modern appliances.
Cottage in Peaks Island

Classic Peaks Island Cottage - 5 min walk to Ferry

LocationValueAmenities

5.0 out of 5 average rating, 74 reviews
Top guest favorite
A modern cottage is positioned on a gently sloping landscape, showcasing large windows that maximize natural light. Surrounding gardens display vibrant flowering plants, creating a tranquil outdoor setting. The cottage features a charming architectural design with a blend of vertical and horizontal siding.
Home in Peaks Island

"The Cottage" on Peaks Island

LocationFamilyBackyard

4.9 out of 5 average rating, 99 reviews
Guest favorite
An outdoor deck features a black table surrounded by six matching chairs. A small centerpiece of flowers adorns the table. Comfortable seating is visible in the background, with expansive views of Casco Bay beyond. Bright blue skies complement the inviting space.
Apartment in Peaks Island

Peaks Island Casco Bay View Condo w/ Beach Access

FamilyLocationCondition

5.0 out of 5 average rating, 13 reviews

Frequently Asked Questions

  • Where is Peaks Island located?

    Peaks Island is situated just off the coast of Portland, Maine, within Casco Bay. It is part of the city of Portland and has a shoreline neighborhood surrounded by the bay's maritime setting.

  • When is the best time to visit Peaks Island?

    Late spring through early fall is often recommended for visiting Peaks Island, when temperatures are milder and outdoor spaces are more accessible. Winter months bring quieter scenery, cooler air, and increased rainfall.

  • What are some things to do near Peaks Island?

    Peaks Island has scenic beaches, cycling paths, and nature trails, along with galleries and local restaurants. Visitors can explore its art studios, attend performances at community venues, or discover historic sites around the island.

  • How is the weather near Peaks Island?

    Peaks Island has cool winters, with temperatures ranging from 16–38°F (-9–4°C), and mild summers between 55–80°F (13–26°C). Rain is frequent in spring and fall, so packing layers and a waterproof jacket is often suggested.

Destinations to explore