Search
Close this search box.

Portland Maine Vacation RENTALS

Find the Perfect Place to Stay

Home > Stay > Vacation Rentals > Portland ME Vacation Rentals

Book the Perfect Portland Maine Vacation Rental

As Maine’s largest city, Portland is one of Maine’s busiest tourist destinations known for its coastal location, historic Old Port shopping district, diverse culinary scene, its captivating commercial waterfront, and the nearby islands of Casco Bay. The Portland area offers numerous vacation rental homes and properties with a variety of amenities and services for travelers looking for quality accommodations. You can find information about some of the more popular vacation rental homes and properties in the Portland, Maine, area listed below for your convenience.

TOP PORTLAND MAINE AREA VACATION RENTALS
Luxury Penthouse | Modern Design | Old Port Downtown

FEATURED AD (T3)

Luxury Penthouse | Modern Design | Old Port Downtown

Portland, ME

Stay in luxury at this modern penthouse in Downtown Portland, just steps away from Portland’s historic Old Port  and Portland Peaks Island Ferry Station. This newly renovated two-level apartment features 2 bedrooms, a gourmet kitchen, and stylish high-end furniture. Ideal for exploring Portland’s vibrant scene, the penthouse is close to top restaurants, breweries, and waterfront attractions. Amenities include free WiFi, a 55″ Roku TV, air conditioning, and an open-concept layout with a professional workspace. Enjoy the convenience of nearby public parking and easy access to the city’s best spots. Note: Window units installed seasonally; unit is not baby proofed. Weekly and monthly stays welcome in this smoke-free property. Suitable for 5 guests.

2 Bedrooms; 1 Bath; Sleeps 5
Starting from $788/night

Portland Vacation Rental with Spectacular Views

FEATURED AD (T3)

Portland Vacation Rental with Spectacular Views

Portland, ME

Discover the charm of Portland from this captivating East End apartment, offering a blend of stunning water and city views. Ideal for couples or small families, this retreat features a master bedroom with a new, comfortable queen bed and a spacious living area with a convertible futon. Situated in Portland’s hip ‘little Brooklyn’, you’re steps away from the beautiful Eastern Promenade, East End Beach, and Portland’s vibrant Old Port. Relish serene mornings and enchanting evenings on your private roof deck, overlooking the harbor. With convenient off-street parking, exploring Portland’s wonders becomes effortlessly enjoyable. Experience Portland’s vibrant culture from this serene yet centrally located retreat.

2 Bedrooms; 1 Bath; Sleeps 5
Starting from $586/night

Old Port Vacation Rental

Superb Spacious Condo in the Heart of Portland's Old Port

Stay in the heart of Portland’s historic Old Port District in this spacious walk-up loft apartment, ideal for families, groups, or business travelers. This stunning condo features 3 bedrooms, each with an en-suite bathroom, a fully equipped kitchen, and a living area adorned with vaulted ceilings, original wood beams, and exposed brick. Luxurious linens and modern decor provide comfort for up to 8 guests. Although there’s no dedicated parking, on-street parking is available, along with a nearby garage. Enjoy the close proximity to top restaurants, boutiques, and vibrant nightlife, all while soaking in the maritime charm of Casco Bay. Note: Potential for noise and a 5% cancellation fee applies. This smoke-free property includes amenities like WiFi, a TV, washing machine, A/C, and heating.

3 Bedrooms; 3 Baths; Sleeps 8
Starting from $1,075/night

TOP PORTLAND MAINE AREA VACATION RENTALS
Lovely Cape Elizabeth Family Vacation Home

Lovely Cape Elizabeth Family Vacation Home

Cape Elizabeth, ME

Enjoy a serene stay in this lovely Cape Elizabeth family home, spanning 3,700 sq ft and located just 5 miles from Portland and beautiful Maine beaches. This cottage-style home features a bright, open floor plan in a tranquil residential neighborhood, adjacent to wooded trails and near the Rachel Carson wildlife preserve. The house boasts 5 bedrooms, including a master suite with a king bed and a unique 700 sq ft ‘boat room’ ideal for kids or extra living space. Amenities include central air conditioning, a gourmet kitchen, a fenced backyard with a blue stone terrace, a front porch, and easy access to beaches and Portland’s vibrant dining and microbrew scene. With a fully-equipped kitchen, spacious living areas, and a private office, it’s perfect for family vacations or group getaways, comfortably sleeping 8 guests. 

5 Bedrooms; 3 Baths; Sleeps 8
Starting from $895/night

Upscale Large 3 Bedroom Vacation Rental in Portland

Upscale Large 3 Bedroom Vacation Rental in Portland

Portland, ME

Discover Portland’s charm from this upscale 3-bedroom vacation rental home, boasting a designer-inspired, vibrant interior with an open floor plan and a comfortable, inviting atmosphere. Located within walking distance to Portland’s eclectic restaurants, coffee shops, waterfront, and Old Port, you can park your car and explore the city on foot. The property features a modern kitchen, cozy living spaces, two bathrooms, a patio, air conditioning, and free WiFi. Perfect for up to 8 guests, it’s a smoke-free environment without pets, ensuring a pleasant stay for everyone. Enjoy the convenience of local meal delivery and the ease of exploring Portland’s city center from this stylish vacation rental  retreat.

3 Bedrooms; 2 Baths; Sleeps 8
Starting from $1,210/night

Best Vacation Rental Home in Portland Maine for the Money

Best Vacation Rental Home in Portland for the Money

Portland, ME

Experience the heart of Portland’s West End in this charming vacation rental property, offering a tranquil neighborhood vibe with the excitement of downtown just blocks away. This pet-friendly home features 3 cozy bedrooms, 2 bathrooms with a washer/dryer, and a spacious, open-concept ground floor with a large kitchen, living, and dining area. This vacation rental home offers hardwood floors and tile flooring, a fenced patio, barbecue grill, free WiFi, and two off-street parking spots. Perfect for up to 6 guests, the property is nicely equipped with air conditioning, a smart TV, and a fully stocked kitchen. Enjoy Portland’s nightlife, dining, and bars within easy walking distance from this welcoming and conveniently located vacation rental home in Portland, Maine.

3 Bedrooms; 2 Baths; Sleeps 6
Starting from $536/night

Superb Spacious Condo in the Heart of Portland's Old Port

Superb Spacious Condo in the Heart of Portland's Old Port

Portland, ME

Stay in the heart of Portland’s historic Old Port District in this spacious walk-up loft apartment, ideal for families, groups, or business travelers. This stunning condo features 3 bedrooms, each with an en-suite bathroom, a fully equipped kitchen, and a living area adorned with vaulted ceilings, original wood beams, and exposed brick. Luxurious linens and modern decor provide comfort for up to 8 guests. Although there’s no dedicated parking, on-street parking is available, along with a nearby garage. Enjoy the close proximity to top restaurants, boutiques, and vibrant nightlife, all while soaking in the maritime charm of Casco Bay. Note: Potential for noise and a 5% cancellation fee applies. This smoke-free property includes amenities like WiFi, a TV, washing machine, A/C, and heating.

3 Bedrooms; 3 Baths; Sleeps 8
Starting from $1,075/night

Luxury Penthouse | Modern Design | Old Port Downtown

Luxury Penthouse | Modern Design | Old Port Downtown

Portland, ME

Stay in luxury at this modern penthouse in Downtown Portland, just steps away from Portland’s historic Old Port  and Portland Peaks Island Ferry Station. This newly renovated two-level apartment features 2 bedrooms, a gourmet kitchen, and stylish high-end furniture. Ideal for exploring Portland’s vibrant scene, the penthouse is close to top restaurants, breweries, and waterfront attractions. Amenities include free WiFi, a 55″ Roku TV, air conditioning, and an open-concept layout with a professional workspace. Enjoy the convenience of nearby public parking and easy access to the city’s best spots. Note: Window units installed seasonally; unit is not baby proofed. Weekly and monthly stays welcome in this smoke-free property. Suitable for 5 guests.

2 Bedrooms; 1 Bath; Sleeps 5
Starting from $788/night

Spacious Portland Home: Walk to Downtown Portland

Spacious Portland Home: Walk to Downtown Portland

Portland, ME

Enjoy a spacious stay in this charming Portland cottage, ideally located in the East Bayside neighborhood, close to the beach. This smoke-free property offers 3 bedrooms, 2.5 bathrooms, and a fully equipped kitchen with modern appliances. Guests can benefit from free WiFi, offsite parking, and convenient access to a private beach and marina. The cottage also features a comfortable living room, TV, books, and barbecue grills. Nearby attractions include Casco Bay Lines Ferry Terminal and the Children’s Museum and Theatre of Maine. It’s a perfect spot for families or groups, offering direct beach access, a laptop workspace, and essential amenities like air conditioning, a ceiling fan, and heating. Note: This property is not pet-friendly. 

3 Bedrooms; 3 Baths; Sleeps 8
Starting from $1,257/night

Beautiful Combo Home Located in Downtown Portland

Beautiful Combo Home Located in Downtown Portland

Portland, ME

Discover the “Pearl of Portland,” a unique downtown property offering two separate living spaces, ideal for families or friends seeking both togetherness and privacy. This beautiful combo home, just half a mile from the Old Port, features two contemporary kitchens, cozy living rooms with a gas fireplace, cable TV, and Netflix streaming. It’s perfectly located near local eateries, shops, Casco Bay Lines, Merrill Auditorium, and Portland Observatory. Enjoy the nearby East End Beach, only a mile away. The home has separate entrances for each unit (Cumberland Charm and A Foodie’s Delight), free WiFi, two sofa beds, and parking for two vehicles. Note: an upstairs tenant lives full-time in the property. This non-smoking accommodation is air-conditioned, heated, and comfortably sleeps up to 8 guests, offering a unique blend of urban convenience and a coastal Maine experience.

2 Bedrooms; 2 Baths; Sleeps 8
Starting from $513/night

Portland Vacation Rental with Spectacular Views

Portland Vacation Rental with Spectacular Views

Portland, ME

Discover the charm of Portland from this captivating East End vacation rental unit, offering a mesmerizing blend of stunning water and city views. Ideal for couples or small families, this retreat features a cozy master bedroom with a new, comfortable queen bed and a spacious living area with a convertible futon. Situated in Portland’s hip ‘little Brooklyn’ neighborhood, you’re steps away from the beautiful Eastern Promenade, East End Beach, and Portland’s vibrant Old Port. Relish serene mornings and enchanting evenings on your private roof deck, overlooking the bustling harbor. With convenient off-street and free street parking, exploring Portland’s wonders becomes effortlessly enjoyable. Adhere to simple house rules, including quiet hours (from 10pm-7am), and pet rules if bringing furry friends. Experience Portland’s vibrant culture from this serene yet centrally located vacation rental retreat.

2 Bedrooms; 1 Bath; Sleeps 5
Starting from $586/night

Wonderful Portland Waterfront Vacation Rental Home

Wonderful Portland Waterfront Vacation Rental Home

Portland, ME

Escape to this charming waterfront home in Portland, Maine, offering breathtaking views and direct access to the water. Ideal for kayaking, fishing, and birdwatching, this 1915 cottage-style residence is just 3 minutes from downtown Portland’s Old Port, with its array of restaurants, galleries, and microbreweries. The home features a pool table, HD TV, and WiFi. Boasting 2 bedrooms, a living room, a billiard room, and 2 full baths, the property is well-equipped with a modern kitchen and hardwood flooring. Start your day with coffee on the master bedroom’s deck and enjoy evenings on the main deck or by the fire pit. This unique home, one of the few waterfront properties in Portland, provides off-street parking and is pet-friendly, welcoming one dog. It’s perfect for those seeking a serene yet convenient waterfront location, ensuring a memorable stay of relaxation and exploration.

2 Bedrooms; 2 Baths; Sleeps 4
Starting from $565/night

TRAVEL MAINE BLOG

Discover the best of Maine with our travel blog highlighting special travel tips, sightseeing suggestions and regional interest stories to make the most of your Maine vacation trip. We bring you insigthful articles about unique places, kid-friendly activities, and regional entertainment that will help in planning your trip to Maine.

Scroll to Top