Photo by Rick Bucchino

Portland rentals with pool

We found 35 rentals with pool — enter your dates for availability

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to stay in a holiday rental with a pool in Portland?
Exactly where you stay, what time of year you travel and the length of your escape will influence the price of a holiday rental with a pool in Portland. Key in your travel details on Stayz, then select the best one for you and prepare to make a splash.
When is the best time to book a holiday rental with a pool in Portland?
If you want to visit Portland at one of its busiest times, plan your trip for September. This is when average temperatures range from 14ºC to 24ºC, and when most guests unwind in a holiday rental with a pool in this destination. Of course, there are other good times to travel to this corner of Connecticut, so do some research into which month or season works with your plans.
What holiday rentals with a pool in Portland have nice views?
Relaxation comes easy at Stayz's holiday rentals with a pool in Portland. Enjoy a leisurely swim or just take in the vistas. Filter your search by "Recommended" or "Guest rating" to find exceptional stays where you can soak up the stunning scenery as your cares drift away.
Are there holiday rentals with a private pool in Portland?
In Portland, you won't find any holiday rentals with a private pool, but we do have some fantastic stays we think you'll love. From standard amenities like separate bedrooms to premium perks like hot tubs, our accommodation come with a variety of features to cater to every preference and budget. And the best thing about our holiday rentals? You and whoever you're holidaying with will get the entire place all to yourselves.
What are the top things to do in Portland?
TPC River Highlands, Powder Ridge Mountain Park and Resort and Westfarms Mall are attractions that'll keep the whole family occupied in Portland. There's nothing like travel to get everyone together, so check out our holiday home rentals in this lively destination.
Why should I book my holiday rental with a pool with Stayz?
When you book a holiday rental with a pool with us, you'll enjoy more than the basic hotel experience — think a private space with a place to relax by the water. You're also covered by our Book with Confidence Guarantee. This means we're here to make sure everything goes smoothly throughout your entire trip. Have an unexpected change of plans? Check out our cancellation policies to see if you are eligible for a complete refund.