Holiday rentals near Truman's Beach
We found 581 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals near Truman's Beach that can be your home away from home. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the amenities that you expect for your stay, which might include parking and a pool. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Truman's Beach
Showing deals for:15 May - 22 May
Image gallery for New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!

10 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
Southold
8% off
Price is AU$16,424
for 7 nights, 1 home
AU$2,346 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Find the best place to stay - Truman's Beach

Spacious 6-bedroom house, PRIVATE BEACH with AC/HEAT, WiFi in charming Old Lyme
Sleeps 16 · 6 bedrooms · 2+ bathrooms
10 out of 10
exceptional
(3 reviews)
Top rated rentals - Truman's Beach

Magical oasis on Shelter island
10 out of 10
exceptional
(28 reviews)
We stayed at Edward and Tracy’s oasis in Shelter island for a month. Words cannot express the magic of this house and property. We created lifelong memories, taking advantage of the amazing view, lawn and dock.
We came during C-19 to shelter in place and escape NYC and there couldn’t have been a more perfect place with ample workstations, super fast wifi, a kitchen with all the gadgets for your at-home chef dreams and tranquility in the beautifully made up bedrooms that felt like you were in a boutique hotel! Edward and Tracy really made us feel safe, making sure we had ample supplies and ensuring the house was fully sanitized before we stayed.
There is so much to do at the property that you don't ever need to leave including swimming off the dock, lovely picnics on the lawn at sun set, grilling on the patio, taking a bath that overlooks the water and meditating on the dock. This was perfect for us to shelter in place in shelter island :) Although we never really needed to leave we do highly recommend the lobster and oysters from Commander Cody after going for hikes in the nature preserve a mile away…!
We couldn’t recommend their home more, we feel very grateful for Edward and Tracy opening up their house and they were an absolute pleasure in all of our communications and all. We cannot wait to go back. Thank you Edward and Tracy!
Negar A.
Stayed May 2020
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
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