Holiday rentals with a pool in Portland

4.95 out of 5 average rating, 617 reviews

Loft in Falmouth

Loft Apartment on Tree-Lined Street in Falmouth

Staying in this huge second floor loft (32'x25’), you will find a quiet oasis in the treetops. The 16' ceilings and stylish decor provide sanctuary after a busy day of sight seeing. We offer a queen bed and two twins. You are surprisingly close to Portland's restaurants and shops, well located for day trips up and down the Maine coast. Start the day with a self-brewed local coffee. Relax at the end of the day streaming your favorite entertainment on a 55" 4K-HD TV paired with a Sony sound bar. Soak in the secluded backyard HOT TUB, OPEN YEAR ROUND, with a pool available in the summer. The loft is bright and airy given its 16 foot cathedral ceilings, four sky lights and five large windows. Each window has room darkening blinds and full curtains that can darken the room for an afternoon nap. It is accessed through a private entrance up a wide stairwell in the stand alone garage. An In-Suite thermostat allows you to control a comfortable room temperature. The newly renovated space is equipped with queen bed and a twin trundle bed, which pulls out a second twin bed (sleeps two). The beds are fitted with 100% cotton sheets. The living room lounge area has a 55" 4K Ultra UHD flat screen TV equipped with a Roku streaming device. Spectrum TV streaming app provides the broadcast networks, as well as ESPN, TNT, AMC, Bravo and others. Bring your log-in ID to access your favorites programming, such as NETFLIX, HBO-Go, HULU and SlingTV. A Blu-ray/DVD player is available upon request. (There are 3 redbox locations within 2 miles.) The full bath has a shower stall (no tub). Plush towels and premium soap, shampoo and conditioner are provided. Enjoy use of backyard hot tub year round and in ground pool during summer season. Children are welcome. The loft is stocked with books and board games. There is a baby gate available. We are happy to assist you in making plans to see the area. Please ask us if you need recommendations to things to do during your stay. While you will have your own private space and free standing four walls, we will generally be nearby and available. The setting of this property is a long and winding street with large, open lots and eye-catching homes. Stroll to the mouth of the Presumpscot River, which empties into Casco Bay. Dine and shop in the heart of the Old Port, only 14 minutes away. There are no bus lines close to the house. One could manage navigating the area via Uber if not driving a car. The loft has an efficiency kitchen with toaster oven, mini fridge, coffee maker, electric tea kettle, two burner hot-plate, pans, utensils, plates and silverware. We keep the loft stocked with Wicked Joe Sumatra blend. Wicked Joe is a local family-owned company committed to producing exceptional coffees using sustainable business practices from crop to cup. Additional large beach towels provided for hot tub and pool use. We can connect you with local area shops for surf board, stand-up paddle board and bike rentals. We have plenty of ideas on restaurants, shops and points of interest which we are happy to share. Local area magazines and tourist information available in the loft.

Apartment in Cape Elizabeth

4.87 out of 5 average rating, 553 reviews

Portland & Beach & Lighthouses! Romantic! Lovely

Location! You get the BEACH + Portland in minutes! HUGE BEDRM Romantic canopy bed w/ lux linens Chaise lounge couch turns into twin bed TV Giant mirror for weddings etc 35’ Great Rm w/ TV Kitchen *quality pots etc New Q Sofa Bed Priv entrance Beachy Light filled tall ceilings Spacious for 2-can fit 5 pond/bridge firepit 2 decks+patio Teak Furniture Open views New bthrm A/C Parking No stairs/Garden Level All in Cape: Crescent Beach 2 Lights State Pk Portland Headlight Prtlnd 8 min! 210780

4.83 out of 5 average rating, 144 reviews

Home in Kennebunk

Kennebunk/Kennebunkport Beach House w/Pool!

Perfect home for hosting and entertaining! Private in-ground pool, 600+ sq. ft. sprawling deck, large yard, and close proximity to beaches, restaurants, and shopping. Brand new renovations throughout! Amenities and features include: Newly renovated top to bottom 2 beautiful kitchens w/ granite, stainless steel appliances In-ground pool and 600 sq. ft. wrap-around deck Spacious 2 acre yard One mile from the beach Walking distance to Kennebunk Lower Village/Kennebunkport Dock Square Pet friendly!

4.95 out of 5 average rating, 127 reviews

Home in North Deering

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Your crew 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 eateries and breweries. 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, no loud partying after 10 pm. City of Portland License #: STHR-004465-2022

5 out of 5 average rating, 67 reviews

Apartment in Back Cove

Luxe Eco Studio near Back Cove

2 miles from downtown, perfect for a couple or family looking for a restorative getaway. The owners, architect and landscaper, spent the last three years designing and building this light-filled spacious suite to meet the needs of the most discerning guest. Settle in with luxurious accommodations. Organic and down-topped king mattress, linen bedding, spacious marble rain shower, deep water soaking tub and heated slate floors are just a few amenities that will ensure a memorable Maine vacation!

5 out of 5 average rating, 14 reviews

Home in Scarborough

Dreamy Indoor Pool/Hot tub/Sauna Near Beaches

Experience the luxury of your own solar-powered, eco-friendly spa getaway in Maine! Enjoy a private spa in a four-season sunroom, featuring a heated indoor fitness pool and hot tub. Boost your immune system with hydrotherapy, then step outside to a sauna and fire pit -a truly indulgent retreat. Plus, we’re just minutes from beaches, lighthouses, and Portland’s Old Port! Enjoy complimentary access to beautiful local beaches and parks with our included beach pass—yours to use during your stay!

4.98 out of 5 average rating, 254 reviews

Apartment in Rosemont

Maine Hacienda w/hot tub & seasonal pool

Our renovated suite at the foot of Deering Highlands is a 10 minute drive to downtown Portland. A cozy, quiet, modern space with a maritime edge. A short walk to Woodford’s corner and Forest Ave - home to many restaurants & coffee shops. The space includes a seasonal pool and year-round hot tub. Ideal for singles, couples or couples with one or two small children. A maximum of three adults can be accommodated. The hot tub is available all year. The pool is open early June to late September.

4.9 out of 5 average rating, 307 reviews

Home in Harrison

Riverfront Luxury in the woods, Million $ Views.

Secluded A-frame nestled along Crooked River, breathtaking views and world-class fly fishing beckon. Swim in the river or explore scenic hiking trails right from your doorstep. Inside, savor modern comforts including central AC. Just minutes from pristine lakes, primo golf courses, and thrilling ski slopes, this charming private oasis offers an ideal mix of tranquil relaxation and outdoor adventure. Book your unforgettable getaway today and immerse yourself in this one-of-a-kind retreat!

4.94 out of 5 average rating, 148 reviews

Cottage in Wells

Cozy Cottage with Ocean Views, Wells Maine

Ocean breezes, panoramic views of the Atlantic, comfortable cottage to relax & enjoy your time in Maine, what more could you ask for on a getaway?! This cozy cottage for 6 boasts near panoramic views of the Rachel Carlson preserve and the Atlantic Ocean. Tastefully decorated and newly updated, our cottage offers AC/heat, ceiling fans, fully equipped kitchen with dishwasher, outdoor gas grill, cable TV in all rooms, WiFi, cabled phone, skylights, in unit W/D & a large screened in porch.

4.82 out of 5 average rating, 110 reviews

Home in Deering Center

There's No Place Like Home

Our home is filled with cozy spaces to relax and unwind. From the outside deck and pool to the quaint private bedrooms! This family friendly BnB provides a kitchen, dining room and two living areas for a vacation haven . This home has the feel of a true BnB, yet the entire space is dedicated to our guests. We are on site in our in-law quarters, so are close at hand for questions and help if needed. Our home is located in a convenient, quiet and safe neighborhood with off street parking.

4.99 out of 5 average rating, 296 reviews

Apartment in Rosemont

Tower Suite w/ Hot Tub, W/D, Pool & Parking

This newly renovated, gorgeous, spacious suite, located on the 3rd floor of our 1865 mansion, is just 10 mins to downtown and the airport. Relax by the firepit or soak in our hot tub and enjoy our gardens. We are owner-operated. The suite includes a newly renovated bath with rain shower and radiant floor heating; W/D; lounge and kitchenette w/ work table; and a large bedroom. Our half-acre yard provides ample space for privacy. Level 2 EV station is available #allarewelcome

4.76 out of 5 average rating, 134 reviews

Generic Two Bedroom - Stair access only

Our two-bedroom units are located on the first, second or third floor in our all-stair property. All of our two-bedroom units have two bedrooms, with a varying number of beds, two bathrooms, full kitchen, living room, dining room and patio/balcony. They have a washer and dryer too! All kitchens come equipped with standard dishes, baking and cooking supplies, as well as full size appliances! Best for larger families to spread out! Room requests are accepted but not guaranteed.

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Popular amenities for Portland rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 34 reviews

Love OOB! NEW 3 BR, 2.5 BA Maine Home

TrishRating, 5 stars6 days ago

we can't say enough about lovely our stay was at this beautiful house in OOB. the house is so clean and bright. its within walking distance to restaurants and stores. its right across from the heated pool. it really is such a gem!

4.98 out of 5 average rating, 82 reviews

Faith Lane with community pool

JamesRating, 5 stars6 days ago

Jason's place was great. My wife and I have three young children, and were traveling with my parents and brother. The house still felt big, and we all felt right at home. The upstairs bedrooms and bathroom are very large, and the house was clean and had very little stuff at little kid eye level, which we appreciated. The main living area has a large open space where we could play cards and our baby could crawl around, and the streets outside were rather quiet outside. Overall, would stay again and totally recommend!

4.9 out of 5 average rating, 10 reviews

Oceanfront Cottage 1

LoganRating, 5 stars2 months ago

We had a wonderful time! Going during off season was very peaceful and quiet will definitely book again in the future!

5 out of 5 average rating, 19 reviews

Home in Mechanic Falls

Lovely home with hot tub and pool

AngelicaRating, 5 stars8 months ago

Beautiful Airbnb! Everything in the Airbnb was very well thought out. The host was super nice and always quick to respond. My only regret was not spending more time here!

5 out of 5 average rating, 40 reviews

Our Beach House Getaway

JenniferRating, 5 stars9 months ago

It was exactly as the pictures on the website. I reached out to Linda prior to leaving. She was very responsive answered all my questions. Great memories made with the family this week. Would definitely come back again. The ease of getting in and out of old Orchard Beach was great. Was only a 3-4 min drive to the beach. The pool there was a huge hit with the grandkids as the ocean in Maine is never really that warm.

5 out of 5 average rating, 51 reviews

Home in Wells

2BR, Sea & Relax w/ Wells Reserve View

SamiraRating, 5 stars3 weeks ago

Jordanna’s place was beautiful and cozy! Perfect for a small family or girls trip up to 3 people. Place was spotless, lots to do in the area and will close proximity to Ogunquit and Kennebunkport. Would go back anytime!

5 out of 5 average rating, 9 reviews

Home in Arundel

Maritime Meadows – Charming Resort-Style Home!

JaneRating, 5 stars2 weeks ago

A beautiful home in a quiet neighborhood with everything you could need. Located a short distance from the beaches, towns, shopping and restaurants. We were here the last week of May when the crowds were not too bad. The weather was perfect—60’s and 70’s. The hosts are extremely responsive. Would definitely stay here again.

5 out of 5 average rating, 63 reviews

Home in Ogunquit

Ogunquit Village 5 BDR, Heated Pool, Walk to Beach

ChristineRating, 5 stars6 days ago

We absolutely loved our stay at The Lazy Lobster! A beautiful home, clean, large & perfect for a big group. Andrew was wonderful. He was always responsive & helpful! Plus the location was fantastic. We walked to breakfast, shops, the beach, dinner & bars everyday with no issues. We will definitely be coming back!

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Condo rentals with a pool

4.74 out of 5 average rating, 19 reviews

Condo in Ogunquit

Lovely 1 Bedroom condo with amazing ocean view

FrankRating, 5 stars10 months ago

Marko was outstanding with responses and caring about our stay. The location is perfect.. walking distance to everything! And the VIEW was more beautiful than the photos!

4.97 out of 5 average rating, 30 reviews

Cozy Beach Condo in Wells - Hot Tub & Pool!

EmilyRating, 5 stars2 weeks ago

Kathleen’s Ogunquit Airbnb is perfect! She has thought of everything you may need and more. Kathleen was responsive when needed and communicated helpful details throughout our stay. The location is fantastic and made exploring the Maine coastline very convenient. Thank you, Kathleen!!!

4.67 out of 5 average rating, 3 reviews

Condo in Ogunquit

Footbridge Escape A Comfy Condo w/ Pool, the Beac

JimRating, 5 stars20 months ago

Great location -- perfect for a "work away from home" week or an autumn visit -- hosts four adults super comfortably, location is great. Third year in a row and we always come back to here!

4.98 out of 5 average rating, 46 reviews

Condo in Ogunquit

Pretty Boutique Studio, Pools, Walk to Everything!

MollyRating, 5 stars7 months ago

This was a great place to stay! My husband and I were very happy. Highly recommend!!

4.91 out of 5 average rating, 92 reviews

Starfish Condo Wells Beach

WendyRating, 5 stars1 month ago

This was a great find and enjoyed our 3 week there - We got to meet a few neighbors, and they were very nice as well - Very close to restaurants and Wells Beach - WIFI worked great as I work from home and the tip about leaving the second car at the Wells Transportation Center helped a lot ! Danielle was great with communication and rules - We would stay here again

4.69 out of 5 average rating, 32 reviews

2 Bdrm condo with a pool 1/2 mile from beach

JessicaRating, 5 stars7 months ago

Kate & Kate’s place was fantastic. The location was perfect for both enjoying the beach and fall weather, and also doing some shopping nearby. There are restaurants very close by as well. It was very clean, the beds are extremely comfortable, and the little things really stood out here- many towels, washer and dryer, all the things you need for your stay are provided and so appreciated. Excellent place to stay!!

4.71 out of 5 average rating, 7 reviews

Awesome get away spot in Wells!

ManuelaRating, 5 stars8 months ago

Lovely cottage with EVERYTHING you need (e.g, kitchen & bath items are very well stocked with many options - condiments, coffee/tea, hair dryer, towels, health & beauty products - you name it!)! The location is close to lovely attractions and eateries. We visited Lobster Pt. Lighthouse and took a cliff walk - beautiful views! Ogunquit beach is also close by. Highly recommend Hobbs Harborside Restaurant - great seafood! Diane was a very accommodating and responsive host! It was the perfect location for our weekend getaway.