Holiday rentals with a pool in Greenport West

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Top-rated rentals with a pool in Greenport West

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Home in East Hampton

4.92 out of 5 average rating, 128 reviews

Heated pool, games room, near beach, kid-friendly

Contemporary 4-bed + 4 1/2 bath home sitting on a park-like acre of gardens. Swim in the large pool (open 04/19 - additional charge for heating - see below), relax in a hammock or bbq on the deck. Play ping-pong, darts, pool, shoot hoops, or take a 15 minute walk to the private (and empty) bay beach where you can use my paddle board. Or drive to the famous Atlantic beaches and visit picturesque Sag Harbor, Montauk. Reduced cleaning fee for small groups. RentReg 22-1590 Local taxes included

23 – 30 Oct

$7,808 AUD total

Guest favourite

Condo in Greenport

4.9 out of 5 average rating, 108 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat

20 – 27 Oct

$3,411 AUD total

Guest favourite

Guest suite in East Hampton

4.98 out of 5 average rating, 117 reviews

Hamptons Dream Suite

Hampton's Dream Suite- Is a guest suite in East Hampton, NY. From relaxing by the pool, to taking a day trip to Montauk, or visiting some of the best beaches in the Hamptons, the opportunities here are endless! It offers a bedroom with a Queen size Select Comfort bed, living room has two queen sofa beds and a full bathroom. It has a Kitchenette, Central AC/Heat with a 65" smart TV with surround sound and DVD, Blue ray and Xbox Games . There is also at TV and blue Ray player in the bedroom.

29 July – 5 Aug

$4,804 AUD total

Guest favourite

Cottage in Southampton

4.96 out of 5 average rating, 164 reviews

Secluded Southampton Cottage w/Pool & Spa

*Follow Us on Insta @SimmerCottage* This designer-decorated cozy cottage near Southampton Village & a short drive or bike to the beach has a stocked chef's kitchen, cozy living room with wood-burning stone fireplace, 2 SmartTVs, whimsical dining room, 3 bedrooms, one bath & charming sunroom w/reading nooks. The Cottage has central heating/air & is set on a gated 1/2 acre w/hot-tub, outdoor dining for 8 on a stone patio, outdoor string lights, fire pit, gardener's potting station & gas BBQ.

25 Jan – 1 Feb

$4,953 AUD total

Guest favourite

Guest suite in East Hampton

4.96 out of 5 average rating, 142 reviews

Be our guest! Peaceful private proximity to all.

Beautiful, bright, spacious king suite w fireplace, two bathrooms & private separate poolside entrance, in the country. We are just minutes to golf, hiking, biking, yoga, wineries and beaches. Play games, grill poolside or cozy up fireside w a good book or movie! The space is creatively designed with a nod to natural elements and luxe comfort. Sleep your very best on our super deluxe king sized bed w your choice of pillows. Complimentary coffee/tea/snacks and breakfast treats provided.

12 – 19 Sept

$4,678 AUD total

Guest favourite

Home in Sag Harbor

4.89 out of 5 average rating, 167 reviews

Kiddo Approved! Heated Pool/Hotub Renovated Home

Family friendly Sag Harbor one level beach house close to Main Street. Heated pool (for a fee), hot tub, enclosed grass yard, kids play area with sandbox and toys, crib, highchair, outdoor fireplace, outdoor shower, yard is fenced and gated with separate safety fence for pool area. Backs up to a nature preserve for privacy. Quiet Neighborhood. Short drive to the beach and Main Street. Pool open April 13th-Oct 1. Pool can be heated June-August (for a fee). Hot Tub open April- November.

15 – 22 Oct

$6,235 AUD total

Guest favourite

Home in East Hampton

4.97 out of 5 average rating, 116 reviews

Explore the Water & Woods at a Relaxing Retreat

Flick through records under soaring ceilings and hang out in the year-round hot tub at this East Hampton open-plan retreat. Unwind in the wooded backyard, take a dip in the pool or spa, detox in the sauna, grill on BBQ, relax in the movie-theatre seats to watch a film, then snuggle up to fireplace or firepit before drifting to sleep in super comfy beds. Minutes to village, beaches and hiking trails. Terrific for families & friends looking for a relaxing getaway.

15 – 22 Dec

$10,146 AUD total

Guest favourite

Condo in Greenport

4.92 out of 5 average rating, 125 reviews

Beautiful Waterview Condo on the North Fork of LI

Waterview luxury suite accommodates up to 6 guests with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York. This location is minutes from town as well as wineries and centrally located to the ferry which can take you to Shelter Island and the South Fork. The resort is well maintained with a pool , BBQ grills and private beach access as well as ample parking for guests.

19 – 26 Apr

$4,390 AUD total

Guest favourite

Home in Cutchogue

4.96 out of 5 average rating, 190 reviews

Private Oasis W/Stunning Vinyard And Pool Views

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

9 – 16 Mar

$9,595 AUD total

Guest favourite

Guest suite in East Hampton

4.89 out of 5 average rating, 222 reviews

Private Cozy Cottage with Pool / Private Beach

**POOL CLOSES SEPTEMBER 30TH** **POOL opens last week of May** This is a guest house for 1 or 2 adults. Its separate from the main house. Kids are allowed but must bring own sleeping arrangements. You do NOT have to do any chores before checking out. **PETS NOT ALLOWED** I hate to do this but someone ruined it for everyone. Max Occupancy: 4 Guests can only bring 1 vehicle since there is not enough room in the driveway

10 – 17 Oct

$2,929 AUD total

Guest favourite

Home in Sag Harbor

4.85 out of 5 average rating, 250 reviews

Exclusive Sag Harbor Compound

A private country compound in heart of Sag Harbor. House just gut renovated with all top of line (all Wolf and Subzero appliances). The main house is 3 bedrooms, 3.5 bath main house PLUS separate large guest cottage (with a King bed, bar fridge, and full bathroom). Gunite pool (i.e., salt chlorinated which makes it feels like clean freshwater). Walk to town, bay beach, public tennis courts, 1000 acre nature preserve.

2 – 9 Dec

$5,917 AUD total

Guest favourite

Home in Water Mill

4.91 out of 5 average rating, 110 reviews

Beach Barn w/ Sauna and Heated Pool - Dog Friendly

Dog friendly (upon request) Hampton Beach Barn with heated pool and infrared sauna. POOL OPEN - May 3, 2024 - October 28, 2024 This impressive house, nestled within a rustic, woodland plot, promises a tranquil stay. Eclectic modern decor is complemented by striking rustic touches, such as Dutch-style farm doors, exposed beams, and vintage wood-burning stove.

26 Nov – 3 Dec

$12,319 AUD total