Vacation rentals with a pool in Sag Harbor

Find and book unique homes with a pool on Airbnb

When results are available, navigate with up and down arrow keys or explore by touch or swipe gestures.
0 of 0 items showing
1 of 3 pages

Popular amenities for Sag Harbor rentals with a pool

House rentals with a pool

Superhost

Home in Hampton Bays

4.77 out of 5 average rating, 97 reviews

Jacuzzi & pool. Fenced in property.

HannahRating, 5 stars1 month ago
We loved our stay at AJ’s home. It was beautiful and spacious. The movie theater was our favorite place to hide out and watch movies/play games. We will definitely think about returning in the warmer months to use the pool! AJ himself was very responsive, kind, and helpful. You can tell he cares about his guests. Couldn’t recommend this home more!
Guest favorite

Home in East Hampton

4.97 out of 5 average rating, 31 reviews

Pretty East Hampton Village Fringe - Hansom Hills

JonathanRating, 5 stars3 months ago
Cindy is a great host! Her place is peaceful and decorated with quirky art and historical trinkets. The only issue we had was that the pool pump and heater automatically turns off in the evening, and there was no way to turn it on
Guest favorite

Home in East Hampton

4.89 out of 5 average rating, 18 reviews

4 BR/3BA Quiet Pool Home

MicheleRating, 5 stars2 months ago
Stayed for a family wedding and loved the accommodations! Close to family, restaurants, wineries and beaches. Dog friendly which was a huge plus. Would love to stay again.
Superhost

Home in East Hampton

4.88 out of 5 average rating, 109 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

BrittanyRating, 5 stars3 months ago
The house is beautiful, looks like photos. Stephen is a great host! Overall great stay, could not recommend more!
Superhost

Home in East Hampton

4.74 out of 5 average rating, 89 reviews

Clean Home Pool Cent-Loc. Quiet Reserve Pet Friend

AntoineRating, 5 stars3 months ago
Mike is a great host with helpful recommendations and plenty of advice. The house is amazing. Well located, calm, clean and so convenient. The pool is huge and very deep. Everything is perfect. Felt like at home. We will be back
Guest favorite

Home in East Hampton

4.91 out of 5 average rating, 43 reviews

Bright Modern Home With Stunning Yard & Pool

JamesRating, 5 stars3 months ago
Tabitha's place was spotless, very comfortably set up and a great setup for my family. 5 minutes by Uber to all the restaurants and activities. Will definitely look to rent this house again!
Superhost

Home in East Hampton

4.82 out of 5 average rating, 91 reviews

East Hampton Oasis - Pool and Hot Tub

DavidRating, 5 stars2 months ago
Tim was a great host! My brother came into town earlier than expected and Tim let him put his luggage in the back of the house until check in. During the first day of our stay, our toilet wasnt functioning correctly and Tim had a plumber within the hour after I told him about the issue. Also, my niece left her jacket in the house after we checked out and I asked Tim if he could ship the jacket and I would pay for shipping. Tim not only shipped the jacket but he insisted on paying for the shipping and sent me the tracking info. If I am in the Hamptons again, I would definitely stay at Tim's again! It's a shame that it was off season and the pool was closed because it looked like it could be a lot of fun! I highly recommend this Airbnb if your planning on staying in East Hampton!
Guest favorite

Home in Southampton

4.94 out of 5 average rating, 52 reviews

Amazing Home in SH with private Pool

HyojungRating, 5 stars4 months ago
Thanks to Giuseppe we can have meaningful time in there. It couldn't be better!

Condo rentals with a pool

Condo in North Fork

4.93 out of 5 average rating, 15 reviews

Cliffside Resort Poolside Condo A204

JoyRating, 5 stars5 months ago
Everything was just perfect! Just what I expected. Expect the best when you book here. They're worth every penny. Will return again.
Guest favorite

Condo in North Fork

4.83 out of 5 average rating, 102 reviews

Beautiful condo on Long Islands Northfolk

RobinRating, 5 starstoday
Absolutely lovely place to stay. Thanks so much!
Superhost

Condo in North Fork

4.83 out of 5 average rating, 125 reviews

Seaside Escape w Pool, Private Beach + Patio

ShirleyRating, 5 stars1 month ago
Lovely stay in greenport! Short drive from major north fork activities. Can imagine its even better during the busy season!
Superhost

Condo in Hampton Bays

4.78 out of 5 average rating, 23 reviews

Waterfront Elevated Bungalow - Spectacular Views

SteveRating, 5 stars51 months ago
If we don't give a good review, can we keep this to ourselves?! Patti was a perfect host; the views were fantastic, whether from the outdoor porch or inside through the French doors looking out on the water. Access to the small beach and pool were excellent and we were close to several good restaurants (many of which Patti suggested, including some on the water) for take-out during the pandemic. Wifi was great and everything was very clean and as advertised. We generally fly for vacations and long weekends but had to stay closer to home this year and this was a perfect choice.
Guest favorite

Condo in North Fork

4.89 out of 5 average rating, 148 reviews

Beautiful Waterview Condo on the North Fork of LI

AnnaRating, 5 stars3 weeks ago
Such a beautiful condo by the water! Too bad we stayed in November, we would have enjoyed the terrace way more! Mia was so responsive and helpful with my questions prior to the weekend at her place.
Superhost

Condo in Bridgehampton

4.88 out of 5 average rating, 17 reviews

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

StaceyRating, 5 stars3 months ago
Had a wonderful stay with my family. Clean, comfortable, great location. Good communication. Had a little trouble with the front door first day but someone was available quickly to help. A+
Guest favorite

Condo in North Fork

5 out of 5 average rating, 107 reviews

"Breathtaking Waterfront Water's Edge view"

KaitlinRating, 5 stars3 months ago
Overall relaxing stay and trip to Greenport. Sherri is very communicative and her instructions and listing is clear and accurate. The condo is well decorated and clean and has everything you need for a nice weekend. One thing to note- we were aware check in is between 3 and 5 pm based on the listing (wound up being around 4) but it would be nice for it to be earlier. Still 5 stars though!

Home rentals with a private pool

Home in East Hampton

4.73 out of 5 average rating, 15 reviews

Historical Estate Home with Backyard Pool

GeoffreyRating, 5 stars4 months ago
The appointments were rich and exquisite. By far the nicest of a dozen places we’ve tried. The master bedroom was a suite of bathing, dressing, sitting and sleeping quarters and there were three more bedrooms with private baths. The two basement bedrooms were serviceable and spacious.
Guest favorite

Home in East Hampton

4.98 out of 5 average rating, 128 reviews

Explore the Water & Woods at a Relaxing Retreat

JulianaRating, 5 stars3 months ago
We had an amazing time staying at this house! It was in a great location, well-stocked with everything we needed, and the host was incredibly responsive. The check-in process was seamless, making our stay even more enjoyable. My family and I had a wonderful experience, and we would definitely book again!
Guest favorite

Home in Southampton

5 out of 5 average rating, 81 reviews

Best of Country and Beach Living

DavidRating, 5 stars3 months ago
My family had a great stay. Mary Ann was sweet and helpful. Very comfortable home with tons of amenities that we enjoyed. The kids really liked helping to feed the chickens and all the natural wild life at the property. Highly recommend for family or groups.
Guest favorite

Home in East Hampton

4.82 out of 5 average rating, 45 reviews

Enchanting Home with Large Decks and Heated Pool

LynnRating, 5 stars2 months ago
Beautiful home worked perfect for our wedding visit. Loved sitting on the deck! Beautiful landscaping and very private! We were very confortable and able to relax between events and visit. Donna wad very flexible and allowed us to enter early so a dew of our family members could do s little remote eork. I hope to rent here again in the future! As a special surprise we saw the northern lights from the deck one night!!
Guest favorite

Home in Southampton

4.93 out of 5 average rating, 61 reviews

Southampton Quiet Private Home/Pool 6min to Villag

SoniRating, 5 stars3 months ago
Monica was a lovely host! The place is peaceful, beautiful and very relaxing. Enjoyed the last bit of summer with the heated pool.
Guest favorite

Home in Southampton

4.95 out of 5 average rating, 20 reviews

Perfect Getaway at Sunny Modern Shampton Lake House

ScottRating, 5 stars2 months ago
One could not ask for a better hosts than Christina and Phil - they are extremely communitive, proactive and helpful. Their house is beautiful - gourmet kitchen, in-ceiling speakers throughout the house, nice deck, pool and a picturesque location. The master bedroom has access to the back deck and a great shower. We had all three bedrooms full and everyone enjoyed their stay. We did not take advantage of the kitchen, but if we come back to the Hamptons we would stay here for longer and cook some meals. We are art collectors, so definitely appreciated the works Christina & Phil have amassed. The one thing I would bring to the attention of future renters is that you definitely know you are in somebody else's home - this is the first time we have unpacked only to find that every drawer was full, so we had to place stuff on top of the dresser or on the few open shelves in the closet. That said - totally worth it and would definitely recommend this Airbnb. Hope to be back soon!

Home in East Hampton

5 out of 5 average rating, 13 reviews

Saltbox with Separate Poolhouse in Northwest Woods

KatieRating, 5 stars29 months ago
Mike’s place made for the perfect Hamptons vacation. The location was the perfect starting point for day trips to Montauk and the harbors and we enjoyed the short walk to the beach daily… but there really is no need to leave this amazing property. Our family cannot stop raving about the amazing outdoor setup that we took full advantage of every day. Mike was very responsive and provided a detailed guide for the house and excellent recommendations for the area. We would 100% book again when we’re in the area and would recommend this place to anyone looking for an amazing Hamptons experience.

Quick stats about vacation rentals with a pool in Sag Harbor

  • Total rentals

    120 properties

  • Nightly prices starting at

    $90 before taxes and fees

  • Total number of reviews

    1.8K reviews

  • Family-friendly rentals

    110 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

Destinations to explore