
Holiday rentals in South Portland
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Top-rated holiday rentals in South Portland
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in South Portland
Guest favourite

Home in Scarborough
4.93 out of 5 average rating, 59 reviewsGorgeous 4 BR home with HOT TUB
ShellyRating, 5 stars2 weeks ago
Gregory's place was great for our 2 night getaway. Hot tub was amazing and private from neighbors. Bathrooms and kitchens were well stocked. I will definitely go back for another getaway
Guest favourite

Home in Limerick
4.93 out of 5 average rating, 122 reviewsLakefront Getaway
MarieRating, 5 stars2 weeks ago
We LOVED our weekend on Arrowhead Lake! Great house for families. We have three teenagers and loved having separate spaces for everyone, as well as places we could all gather together, inside or out! There was something for everyone! Perfectly set up for those who love to cook, fish, kayak, walk or just read a book outside! Nearby we enjoyed the farm stands, our first attempt at disc golf, my son's first catch of a small mouth bass and shopping at the Limerick Grocery Store (very well stocked!). We hope to return again soon!! Elizabeth was a wonderful and attentive host!
Top guest favourite

Home in Gray
4.97 out of 5 average rating, 63 reviewscozy 3 bedroom ranch with deck and screen porch
MichaelRating, 5 stars4 months ago
The house is lovely and, if it’s not new, it sure feels that way. In a very quiet area with tons of outdoor space yet just a mile or two from more main roads. Had a lovely white Christmas/Hanukkah with fresh snow on the 24th. Diana was a great host, always answering questions promptly and rolling with some last minute travel issues. Would love to stay here in warmer months to take advantage of the outdoors and the lovely sun porch.
Top guest favourite

Home in Lebanon
4.96 out of 5 average rating, 255 reviewsTranquility, Relaxation, Family, Romance
LauraRating, 5 stars4 days ago
Kathy's place a wonderful spot to settle in. We were pleasantly surprised at how clean and fresh her place was. Having a place out back for the dog to run around was an extra bonus!
Top guest favourite

Home in Bath
5 out of 5 average rating, 101 reviewsWaterfront Farmhouse with Modern Flair!
Tony & KellyRating, 5 stars2 months ago
The home was very welcoming and accommodating for our family of 5. The views were spectacular at sunrise, sunset and during the snowstorm. Bald Eagles and hawks would land in the trees right in front of the house. Also, there was a skating pond down the street my family love to visit almost each evening. There was an alarm going off as soon as we arrived, Debbi was incredibly fast responding and sending someone to check it out clear it up. On the plus someone came and plowed the driveway after the snowstorm it was great. She left a basket of local food and my family ate it up. We are so thankful for our relaxing week and would love to return.
Top guest favourite

Home in Old Orchard Beach
4.98 out of 5 average rating, 89 reviewsWoods Lane Golf and Beach Vacation
MarjorieRating, 5 stars7 months ago
Our group of 5 adults were so pleased we chose to stay at Jason’s house in Old Orchard Beach. We first looked at places in Portland, but Jason’s spacious house offered a quieter setting, with parking and more amenities, at a better price. Comfortable beds, immaculate throughout. Very thoughtfully appointed, with nightstands on both sides of the beds, and superior blackout blinds in the bedrooms. And we ended up spending less time in Old Port, because we enjoyed exploring the towns south of Portland: Old Orchard Beach, Saco, Biddeford, and we found good restaurants (including Holy Donuts!) nearby. We had no issues: we contacted Jason to confirmed our arrival/departure and he responded within minutes. We highly recommend!
Guest favourite

Home in Shapleigh
4.96 out of 5 average rating, 146 reviewsSecluded Lakehouse/2 private docks*Hottub*big yard
CarlyRating, 5 stars1 month ago
We had a wonderful stay at this home for a mother daughter weekend end of March. Great location for each of us coming from different states in New England. The home was very clean, each of us commented on how comfortable the beds were, also loved the good quality linens. The huge dining table was unique for a rental and was awesome for sharing meals and doing arts & crafts. Lots of space and seating in the living room as well. Highly recommend staying here!
Top guest favourite

Flat in Old Orchard Beach
5 out of 5 average rating, 50 reviewsHorizon View Hideaway with Deck
ReneeRating, 5 stars7 months ago
The house is beautiful and very comfortable. We had everything we needed. The host was very friendly and responsive. We would definitely stay there again.
Quick stats about holiday rentals in South Portland
Total rentals
550 properties
Total number of reviews
65K reviews
Family-friendly rentals
260 properties are a good fit for families
Pet-friendly rentals
170 properties allow pets
Rentals with dedicated workspaces
300 properties have a dedicated workspace
Wifi availability
540 properties include access to wifi
Destinations to explore
- Pet-friendly rentals South Portland
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- Ogunquit Beach
- Wells Beach
- Sebago Lake
- Scarborough Beach
- York Harbor Beach
- Ogunquit Playhouse
- Long Beach
- Surfside Beach
- Fox Ridge Golf Club
- Popham Beach State Park
- Brunswick Golf Club
- Long Sands Beach
- Purity Spring Resort
- East End Beach
- King Pine Ski Area
- Wentworth by the Sea Country Club
- Palace Playland
- Pemaquid Point Lighthouse
- Pemaquid Beach
- Crescent Beach
- Mothers Beach
- Laudholm Beach
- Dunegrass Golf Club
- Ferry Beach