Holiday rentals with a pool in Fort Pond

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Top-rated rentals with a pool in Fort Pond

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

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Guest favourite
A cozy bedroom features a queen bed with a light blue quilt and a green loveseat nearby. Natural light enters through sliding glass doors, revealing a serene outdoor space. A decorative plant and framed artwork add a touch of interest to the room.
Guesthouse in East Hampton
4.82 out of 5 average rating, 339 reviews

Detached bungalow w/ private bath

Cozy, simple living, in separate guest house w/ use of amenities (shared with our family of 4) including sauna & hot tub. The bungalow/guesthouse features a Queen bed, its own private bathroom (shower), small kitchenette (countertop oven, Keurig coffee maker & small fridge) and loveseat for relaxing. There is a dedicated separate outdoor seating area for 2 guests. 2 Adult guests ONLY, no children due to size of guesthouse and proximity to the pool. Please NO pets allowed since owners have pets

Top Guest favourite
Home in East Hampton
4.9 out of 5 average rating, 113 reviews

1 block to waterfront~chic + serene Hamptons oasis

Escape to your serene, chic, Hamptons getaway, set on a private half-acre property located just 1 block to the water! Swim in your pool all day + night, BBQ + spark up the firepit under the starry sky. Cook in your Chef's kitchen, rinse off in the outdoor shower, enjoy indoor or outdoor dining areas. Stream on your 80' TV. Walk just 1 block to the best waterfront dining, cocktails + cafe. Enjoy magnificent sunsets @ the marina. You'll be 5 minutes to Main St, shopping, beaches + so much more!

Top Guest favourite
An enclosed outdoor living space features a wooden deck overlooking a heated pool. Furnished with a large round table and comfortable seating, natural light floods through the screens, creating an airy atmosphere. Elegant trees and lounge chairs visible outside enhance the serene environment.
Home in Sagaponack
4.94 out of 5 average rating, 322 reviews

Amazing Home close to Everything -

Elegantly designed home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches, Wolffer Vineyard, and the vibrant Bridgehampton/Sag Harbor villages. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Familiarize yourself with our disclosures, guidelines, and house rules. We maintain a strict no events, no parties, and no smoking policy — our home and property grounds are smoke-free.

Guest favourite
A serene pool area is surrounded by lush greenery and colorful hydrangea flowers. Lounge chairs offer relaxation under large umbrellas, while the inviting pool reflects the clear blue sky. A charming home stands in the background, adding to the peaceful setting.
Home in Southampton
4.92 out of 5 average rating, 122 reviews

Southampton Charmer, 5 bedrooms w pool - Location

This 5-bedroom home boasts en-suite baths and elegant furnishings. The gourmet kitchen features marble countertops and stainless steel appliances, leading to a dining area. The lower level includes a spacious seating area and a game room with toys. The second floor houses a master suite with stunning views and three additional en-suite bedrooms. Located minutes from the village center, with restaurants, shops, and beaches nearby. A heated pool invites you to relax and enjoy the comfort of home.

Top Guest favourite
A light blue house features a welcoming front porch with bright blue chairs. The well-maintained lawn is surrounded by a white picket fence and shaded by a leafy tree. A gravel driveway leads to the garage, creating an inviting outdoor space.
Cottage in Montauk
4.93 out of 5 average rating, 167 reviews

Montauk Cottage Escape

EH Town Rental Registry: 23-483 Escape to Montauk’s Quiet Side- Enjoy the peaceful beauty of Montauk in the off-season from this updated, spacious, comfortable home - close to town, beaches, and scenic trails. Between cozy nights in and crisp coastal walks, this is the perfect retreat for a weekend getaway or a work-from-home reset. Reliable Wi-Fi and a fully equipped kitchen make it easy to settle in for a few days—or weeks. Dogs are welcome with prior approval (Additional pet fee applies.)

Top Guest favourite
Two wooden Adirondack chairs are positioned on a spacious sun deck, overlooking expansive views of lush greenery and the waterfront. The bright blue sky complements the serene atmosphere, creating an inviting space for relaxation and enjoyment of the natural surroundings.
Condo in Montauk
5 out of 5 average rating, 246 reviews

Montauk Waterfront Condo w/ Sunset Views

Modern 1 Bedroom Condo in gated community (Rough Riders) with sunset views from beautiful deck. The community has multiple tennis courts, pool, jacuzzi, and sauna (pool / sauna / jacuzzi only open Late May - early October). The property is great for walks along the boardwalk and many guests enjoy swimming off the pier. The unit is less than a 5 minute car / Uber ride to town and a short 5-10 minute walk to Navy Beach and Duryea's. Strong wifi in unit, Smart TV ( Netflix, etc, - no cable)

Superhost
A modern home is set on a spacious green lawn, featuring a combination of wood and metal siding. Large windows allow natural light to fill the interior. A stone pathway leads to the entrance, framed by lush landscaping and trees, enhancing the outdoor tranquility.
Home in East Hampton
4.89 out of 5 average rating, 116 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

Peace and serenity in East Hampton and minutes from the Village. This exquisite modern home features high-end finishes such as Sub-Zero and Wolf appliances, quartzite waterfall kitchen island and counters, marble tiled bathrooms, designer mid-century decor and separately zoned air conditioning. The heated saltwater pool is surrounded by a bluestone patio, Ipe deck and huge yard. The house also features two wood-burning fireplaces in the living room and den and an outdoor fire-pit. RR# 24-656

Top Guest favourite
The living area features two rattan chairs facing a coffee table, surrounded by vibrant wall art. A cozy sofa and plants add life to the space. Natural light streams through large windows, creating a bright and inviting atmosphere.
Home in Montauk
4.99 out of 5 average rating, 104 reviews

3 BR/Pool. Walk to Beach & Town!

Welcome to Good Tauk – a cheerful, retro-inspired 3BR, 2BA cottage tucked in the heart of Montauk and walkable to town and the beach. Thoughtfully renovated and full of personality, it’s perfect for families or longer stays. The vibe is fun, relaxed, and unmistakably Montauk. Outside, unwind in your private backyard with a pool, grill, and dining patio—ideal for lazy afternoons and sunset dinners. Just minutes from the beach, town, and everything that makes Montauk magical.

Superhost
A view from the balcony overlooks the pool area, featuring a clear blue pool surrounded by lounge chairs. Colorful umbrellas provide shade for several tables, while the surrounding buildings reflect a simple, two-story design.
Condo in Montauk
4.8 out of 5 average rating, 241 reviews

Montauk Royal Atlantic Beach Resort North

My place is at Royal Atlantic Beach Resort North. The beach is across the street and can be seen from my front door. The Suite is within walking distance to town with great restaurants, live music and dancing, mini-golf, paddle boarding and sailing. You can walk the cliffs at Shadmoore State Park where you’ll see the famous hoodoos. It’s good for couples, solo adventurers, business travelers and families. No pets allowed. No smoking. Cable TV has 100 channels.

Guest favourite
An expansive view of the ocean stretches across the horizon, framed by wooden sliding doors. Gentle waves wash onto a sandy beach, with greenery in the foreground. A potted plant rests on the railing, adding a natural touch to the serene scene.
Apartment in Montauk
4.88 out of 5 average rating, 128 reviews

Recharge at our Renovated ocean front unit

Looking for a relaxing weekend to recharge on the beach? Then this newly renovated, bohemian-chic, apartment is perfect for you. Imagine waking up every morning to beautiful unobstructed ocean views and ending your night with a drink in hand watching the sunset. If you’re lucky, you might see some whales or dolphins breaching in the water right off our private beach. We would love to host you for your Montauk beach getaway.

Guest favourite
A spacious green lawn extends towards the ocean, with gentle waves visible in the distance. A multi-story building with defined balconies is situated to the left, surrounded by well-maintained bushes and trees, contributing to a serene coastal atmosphere.
Condo in Montauk
4.83 out of 5 average rating, 101 reviews

Beautiful Condo on the Ocean Bluffs

Located just outside of town on Old Montauk Highway that runs along the ocean. Just a 10 minute walk to town, enjoy a private beach, beautiful grounds and stunning pool. Located at the Atlantic Bluffs Club, one of the nicest private condo facilities in Montauk, you get to enjoy the peace and tranquility of Montauk yet you’re just a short walk to the village with its restaurants, shops and nightlife.

Guest favourite
A spacious backyard features a heated swimming pool surrounded by a sun deck, adorned with loungers. Lush greenery and trees provide a natural backdrop to the inviting setting, while a charming house is visible in the distance.
Home in East Hampton
4.88 out of 5 average rating, 130 reviews

4 BD w/ Heated Pool in E Hampton, Fully Furnished

Rent a beautiful and spacious 4 bedroom/3 bathroom property in East Hampton with a heated swimming pool in the backyard. This three level house with large kitchen, central A/C, BBQ in the backyard, and a garage is the perfect place to entertain guests or to relax and escape in East Hampton.

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