Pet-friendly holiday rentals in Portland

Large Historic 7 Bedroom home with Pool & Hot Tub

Very Unique, large historial home in beautiful Falmouth, Maine. Originally built in 1725, this nearly Three-Hundred-Year old Federal-style farmhouse still retains some original features. In the early 1900's, this home served as a bootleg hard cider mill, and more recently, an oriental rug business. Great place for families with kids to stay while enjoying coastal Maine and Portland. Less than a mile from Portland and 4 miles from the historic Old Port district. (Hot tub open year-round)!

Outdoor spaces · Walkability · Checkout

Amazing Bay View Home with Hot Tub

This enchanting 2-bedroom home is a coastal dream come true! Luxurious and well-appointed, Casco Bay House sleeps up to six, provides a five-star stay, offers all of the comforts of home AND a relaxing hot tub spa. With stunning views of the water, the house also has easy access to dining, shopping, and sightseeing in Portland's lively Old Port district (just 5 minutes away). Whether you seek quiet tranquility or want to hit the town, this waterside house is the perfect home away from home!

Walkability · Outdoor spaces · TV

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

You will be close to everything when you stay at this centrally-located place with a pool and spacious yard! Enjoy the home and it is a quick 10 minute uber to downtown Portland to the most popular shops and restaurants. This home is located perfectly to explore greater Portland from beautiful parks/trials to the shopping outlets not far away. This is a family neighborhood and out of respect for my neighbor’s, quiet hours after 10 pm. No parties. City of Portland License #: STHR-004465-2022

Pets · Walkability · Wi-Fi

Old Port Artist Loft • Free Parking • Spacious 3BR

Upscale 3-bedroom apartment in Portland’s Old Port, offering style, space, and comfort just steps from the city’s top restaurants, shops, breweries, and the waterfront. Designed with bold art and modern furnishings, this home includes a fully equipped kitchen, high-speed Wi-Fi, and rare free on-site parking. Perfect for families, friends, or couples seeking a luxury stay in the heart of Portland’s vibrant food, culture, and coastal charm. Seasonal rates reflect premium location and amenities.

Outdoor spaces · Walkability · Wi-Fi

OOB Oasis: 6BR Home w/ Private Pool Near Beach

Welcome to our stunning home and your private oasis in Old Orchard Beach! Just 5 minutes from the ocean, this expansive custom-built home offers 3 suites (each with its own private bath), a gourmet kitchen with high-end appliances, a sprawling open floor plan, and ample parking for large groups. Step outside to enjoy a large fenced backyard, spacious deck with BBQ grill, new hot tub and sparkling in-ground pool; perfect for summer fun, fall gatherings, or relaxing after a day at the beach.

Outdoor spaces · Walkability · Quiet

Luxurious Two Bedroom Loft Adorned with Local Art

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.

Pets · Walkability · TV

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!

Outdoor spaces · Pets · Location

Higgins Beach *New* Beach Home & Private Offices

Custom designed contemporary at the beach. Perfect for a relaxing getaway, visiting family and friends or working remotely. Chef's kitchen w/ high end appliances, granite countertops, enclosed porch grill area. 3 bedrooms and 2 private offices Huge windows and amazing views from all of the rooms highlight the natural beauty of high tides, sun rises and sun sets. Wonderful beachfront walks and beautiful surroundings inside and out. Easy proximity to Portland's Old Port.

Pets · Walkability · Wi-Fi

Bright and cozy Munjoy Hill neighborhood apartment

Bright and cozy apartment in Portland's Munjoy Hill neighborhood with private backyard deck. Short walk (like a minute!) to neighborhood bagels, coffee, breweries, beach, playgrounds, restaurants and 15 minute walk to the Old Port & Downtown. Ample/free street parking available. Our family of four lives upstairs, our home is surrounded by flower gardens and located on the Portland Trail system. We welcome all folks of all backgrounds to our home and neighborhood!

Outdoor spaces · Walkability · Access

3 bedroom house in the heart of Portland

New urban 2000 sq ft home in Portland's vibrant up and coming East End/ Munjoy Hill neighborhood. Mid-century style decor. Open concept kitchen/dining/ living area, 3 spacious bedrooms plus a quiet office/study. 2 balconies with views west to Back Cove. 2 car garage and plenty of free off street parking. There are restaurants and bars with great food and live music close by. There is a convenience store around the corner for any last minute needs.

Walkability · Pets · Value

Back Cove Retreat | 3BR w/ Patio & 2-Car Parking

Historic charm meets modern comfort in Portland’s Back Cove. This renovated first-floor 3BR/2BA offers space, style, and parking for two cars — a rare Portland perk. Walk to the Back Cove trail, local coffee shops, restaurants, dog park, and sports fields. Or just a 5-minute drive to the Old Port and the bustling downtown waterfront area. The perfect home base for your Portland stay.

Outdoor spaces · Walkability · Indoor spaces

Safe, Quiet, Friendly area

Situated in a wonderful, friendly, family neighborhood. Walking distance to restaurants, coffee shops, shopping, parks & trails. 10 minutes from The Old Port & Arts Districts and many other local attractions. Less than 2 miles from Thompsons Point concert and food truck venue! The unit is a Large (1200 square ft) and comfy 2 bedroom apartment located on the 2nd floor.

Outdoor spaces · Walkability · Decor