Vacation rentals with a hot tub in Sagaponack

The heated saltwater pool is surrounded by lush greenery, creating a serene atmosphere. Colorful pool floats in the shape of a flamingo and palm leaves rest on the surface. A hammock is visible nearby, inviting relaxation under the dappled sunlight.

4.97 out of 5 average rating, 32 reviews

Chic & Spacious Designer Home, Heated Pool/Spa

RowHouse_EH, Ideally located just down the block from East Hampton's best waterfront restaurants, this chic beach house is designed as a year-round getaway. This 3 bedroom & 2.5 bath home combines sunny interiors & dreamy outdoor living spaces with thoughtful amenities & privacy on a 1-acre lot. Heated saltwater pool & spa, designer chef’s kitchen with Viking appliances. Walk to dinner on the water, take the four bikes or kayak out for a spin, then relax in a stylishly modern, luxurious setting.

4.96 out of 5 average rating, 93 reviews

An open-concept living space features a modern dining area with a wooden table set for six, complemented by sleek metallic chairs. A comfortable sectional sofa is positioned across from a wall-mounted television, with a fireplace and green outdoor views visible through large windows.

Cottage in Bridgehampton

Calf Creek Cottage (Water Mill/Bridgehampton)

Enjoy the peaceful seclusion of this charming, updated 3 bedroom, 2 bath cottage located on a private, acre-sized flag-lot south of the highway right on the border of Water Mill and Bridgehampton. Each bedroom (1 king, 2 queen) features ample closet space and new smart TVs . The new, fully-stocked kitchen, propane BBQ, outdoor dining table for 8, outdoor shower and spa with lounge furniture, and wood burning fireplace make it the perfect getaway for either summer or the winter season. Pets OK.

4.96 out of 5 average rating, 196 reviews

A charming cottage is framed by lush greenery and well-maintained landscaping. The light-colored exterior features large windows and a welcoming green door. A stone walkway leads to the entrance, while a gravel driveway curves around, enhancing the natural setting.

Cottage in Southampton

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.

Top guest favorite

A spacious backyard features a large heated saltwater pool surrounded by greenery. The house's two levels create a relaxed atmosphere with multiple outdoor seating areas. Sun loungers and umbrellas are arranged beside the pool, providing options for shade and relaxation.

Home in Sag Harbor

4.97 out of 5 average rating, 32 reviews

Beautiful Sag Harbor BEACH House

My neighbor is building a house, I’ve lowered the price to reflect any construction noise. Walk to the most magical beach in the Hamptons! House is beautifully designer decorated. Mint Condition, everything you could want in a great Hamptons, Sag Harbor Home! Finished, super comfortable Basement Heated Salt Water Pool and Spa, w/ auto pool cover. Outdoor Shower, Fire Pit, Ping Pong Super Clean Fully stocked Washer/Dryer on Main level and upstairs Fully enclosed fenced in Backyard

A contemporary house exterior features a combination of wood and metal finishes, set against a backdrop of lush greenery. Large glass windows provide ample natural light, and a pathway of stepping stones leads through a manicured lawn, enhancing the inviting atmosphere.

4.97 out of 5 average rating, 143 reviews

East Hampton (walking distance to village)

Relax by the hot tub and fire pit with local wines or walk to the village for shopping and dining. House is just a few blocks from Serafina and the famous Nick and Toni’s. Complimentary cruiser bikes included to get around town. IGA supermarket is around the corner and gas grill is on site and ready to use. The house is also walking distance to the train station if your coming from Manhattan. The second bedroom features a Murphy Bed that folds out of the wall and over the couch pictured.

Top guest favorite

A spacious living area features a dark leather sofa adorned with colorful throw pillows, complimented by a patterned area rug. A ceiling fan is positioned above, and natural light streams through multiple windows. An adjoining dining area with a black table and chairs is visible.

Home in North Fork

4.92 out of 5 average rating, 486 reviews

Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)

Ranked #1 AirBNB. Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Guesthouse in East Hampton

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.

4.82 out of 5 average rating, 327 reviews

Detached bungalow w/ private bath

Cozy, simple living, in separate guest house with use of amenities (shared with our family of 4). The bungalow/guesthouse features a Queen bed, its own private bathroom (shower), small kitchenette (countertop oven, micrwave, Keurig coffee maker & small fridge) and loveseat for relaxing. There is a dedicated separate outdoor seating area for 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.

A wooden structure with multiple windows is set among lush greenery. The deck surrounds a newly built pool, offering a serene outdoor space. The pool's clear water reflects the surrounding trees and the vibrant blue sky.

4.88 out of 5 average rating, 26 reviews

4 BR/3BA Quiet Pool Home

We welcome you to our family home, up to 5 guests, pets are welcome with additional pet fee. Nice new pool and surrounding deck with outdoor sitting area, chairs, umbrella, and charcoal grill. 1 gbps internet for movies streaming on disney plus, prime video, or for your work. 5-8 minutes to town and the beaches. Plenty of nice restaurants and great local shopping. We don't allow other guests on property that is not mentioned in advance. No gatherings and no parties. Thank You.

An outdoor area features a rectangular pool surrounded by a wooden deck. Lounge chairs are positioned along the pool's edge, and a shaded seating area is located nearby under an umbrella. Lush trees provide privacy and a natural backdrop.

4.84 out of 5 average rating, 112 reviews

East Hampton Oasis - Pool and Hot Tub

Nestled at the end of a private road in the Springs section of East Hampton, this classic Hamptons home will keep you and your friends/family entertained. Living room with sonos sound system, kitchen, 3 bedrooms, 2 bathrooms, outdoor living area with lounge chairs, a bbq, bar, pool and hot tub. All 3 bedrooms have AC. Towels and linens provided. Washer/dryer available. CLOSE TO BEACH AND EH VILLAGE. The pool is open May 5 through October 5. The hot tub remains open year round.

Top guest favorite

A serene outdoor area showcases a saltwater pool with a spa, surrounded by well-maintained landscaping featuring vibrant yellow flowers. Lush green fields extend into the distance, framed by a clear sky with scattered clouds.

Home in North Fork

4.97 out of 5 average rating, 207 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.

4.97 out of 5 average rating, 36 reviews

An aerial view of the Mid Century Modern home is showcased, surrounded by lush greenery. The spacious yard features a heated pool, deck chairs, and a large checkered game board. A shaded seating area is positioned nearby, offering a perfect gathering spot amidst the natural landscape.

Villa in East Hampton

SERENITY AT SHOREWOOD Luxurious Newly Renovated Mid Century Modern Home in East Hampton with Beach Car! Peaceful and stylish with three bedrooms, 3 1/2 baths, spectacular great room, huge deck, heated pool and more, less than four miles to the heart of East Hampton Village, world renowned for its restaurants, shopping and ocean beaches. A designer-curated architectural gem! Kick back and relax in this calm, stylish space.

A modern kitchen and dining area feature an open layout with sleek cabinetry and stainless steel appliances. Four high-backed bar stools are positioned at the kitchen island. Large windows provide natural light, and outdoor patio space is visible through the glass doors.