Vacation rentals with a hot tub in Wainscott

The living area features a cozy fireplace with modern seating options positioned around a stylish coffee table. A large overhead light fixture adds a unique touch, while greenery and decorative elements enhance the space's tranquility. Large windows allow natural light to fill the room.

5 out of 5 average rating, 21 reviews

Walkable Designer Home in East Hampton Village!

WALK TO THE VILLAGE, BIKE TO THE BEACH from this Original East Hampton Village House! Chef Kitchen, marble countertops and High-End Appliances. Living and Dining Area w/ French Doors leading to patio and HEATED SALTWATER POOL. 3 bedrooms, 2.5 baths. Sonos sound inside and out. 2nd patio off kitchen with grill and fire pit. WALKABLE TO ALL VILLAGE SHOPS & EATS—Prada, Brunello Cucinelli, Louis Vuitton, CHANEL & more! House Keeping & Bartending Available. Inquire for Monthly & Off-Season Rental!

5 out of 5 average rating, 239 reviews

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 The Hamptons

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)

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, 147 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.

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 out for a spin, then relax in a stylishly modern, luxurious setting.

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.

4.92 out of 5 average rating, 492 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).

A spacious outdoor area features a heated gunite pool surrounded by sun loungers and greenery. The villa is visible in the background, showcasing large windows and a blend of natural materials. Shade is provided by overhanging trees scattered around the property.

4.98 out of 5 average rating, 47 reviews

Incredible 9+ Bed Watermill Home Wellness Retreat

Luxury 9000 SF Southampton villa with a heated gunite pool, hot tub, steam shower & sauna, 9-bedroom, 8.5-bathroom, nestled on a quiet cul-de-sac in Watermill. Bright with large windows, e-shades in bedrooms, indoor/outdoor sound system, W/D on every floor (3 sets). Formal dining/living area, chefs' kitchen, TV room, movie room, gym, outdoor kitchen, arcade, pool table, air hockey and foosball. Please read our disclosures & house manual. Not a party house and no events permitted.

Guesthouse in The Hamptons

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, 338 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.

4.94 out of 5 average rating, 253 reviews

The open living area features a custom slate pool table with a vibrant arrangement of billiard balls. A modern kitchen is visible in the background, including sleek cabinetry and a refrigerator. A tasteful seating area includes a fireplace and a large wall-mounted television.

Home in Shirley

By NYC & Hamptons - Hot Tub, Pool Table, Speakeasy

Welcome to Coast to Coast - the perfect getaway from NYC! You may have heard about our new little secret - but you’ll have to come see it for yourself to believe it! Step back into prohibition era Long Island in our hidden speakeasy! Right by Smith Point Beach, we provide accommodations that go above and beyond- this is not your average AirBnB! Soak up the sun at one of LI's top beaches, then enjoy complimentary Netflix, Hulu, cable and more while you shoot pool or play games.

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, 122 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.

Place to stay in The Hamptons

4.96 out of 5 average rating, 141 reviews

Walk-To-The-Beach House In The Dunes

(Weekly in season! Please inquire before booking!) This south-of-the highway artist residence is just three minutes by foot to the ocean. Up to 4 bedrooms + a queen sleeping loft, 2 full en site indoor bathrooms, one half off common room, 3 massive outdoor bathrooms, new central AC, multi-zone hi-fi, x2 two-person soaking hottubs. Fireplace, propane and charcoal grills, fiberoptic internet at blazing 500mbps! Only 6 mins to Montauk or Amagansett. Short walk to jitney stop.

A crystal-clear swimming pool is surrounded by a landscaped garden featuring lush greenery and blooming flowers. Natural stone patio borders the pool, offering space for lounging and relaxation in a private setting nestled among trees.

4.98 out of 5 average rating, 136 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.

A well-designed outdoor area features a pristine pool with colorful floats, bordered by a spacious deck. Lounge chairs, adorned in striped blue and white, provide comfortable seating under large umbrellas. The house is illuminated, showcasing a welcoming atmosphere amidst lush greenery.

4.98 out of 5 average rating, 66 reviews

Insta: @staywithhamptonsmama PINKWOOD PLAYHOUSE is the perfect spot for your Hamptons stay, offering elevated design and relaxed luxury with laid back beach vibes. Perfect for families or couples. This stylish and serene home features 4 bedrooms, 2.5 bathrooms, a fully equipped kitchen, soaring ceilings and an open floorplan. Bring the outdoors in with oversized windows and over 1000 square feet of deck space overlooking the gorgeous pool.

Popular amenities for Wainscott hot tub rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a hot tub

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.

4.97 out of 5 average rating, 210 reviews

Private Oasis W/Stunning Vinyard and Pool Views

5 out of 5 average rating, 9 reviews

Chic Hamptons Retreat | Fireplace, Hot Tub, Beach

5 out of 5 average rating, 13 reviews

A serene coastal sunset is captured over the water, with vibrant sunflowers framing the foreground. The sun dips into the horizon, casting warm hues across the sky and reflecting on the tranquil ocean waves, while lush greenery lines the scenic coastline.

Home in Shoreham

Beach home waterfront LI amazing view 3/3 bed bath

A bright living area features a comfortable white sofa and two accent chairs. A coffee table sits in front, accompanied by a floral centerpiece. Natural light filters through a window, and a wall-mounted TV is positioned across from the seating. Steps lead to the kitchen area.

5 out of 5 average rating, 48 reviews

The Hamptons Surf Cottage!

A spacious deck surrounds a large pool, complemented by red umbrellas and lounge chairs. Lush greenery and blooming hydrangeas create a serene backdrop. A cozy seating area is visible under a shaded structure, enhancing the outdoor relaxation space.

4.95 out of 5 average rating, 84 reviews

Family Friendly Springs Beach House

A modern two-story home stands illuminated at dusk, showcasing a welcoming porch with wooden steps. The facade features a combination of white metal and black trim. Lush landscaping with lighted pathways guides visitors toward the entrance, enhancing the exterior's contemporary appeal.

5 out of 5 average rating, 25 reviews

Hamptons Modern Retreat NEW CONS

A charming cottage-style home is set amid lush greenery, featuring a covered porch with white railings. A gravel pathway leads to the entrance, surrounded by manicured shrubs and a well-kept lawn. The exterior is finished with natural wood siding and a sloped gray roof.

5 out of 5 average rating, 6 reviews

Hamptons Waterview Cottage

4.96 out of 5 average rating, 158 reviews

Home in Mastic

Paradise Citadel hottub, Htd pool, sauna, golf.

Villa rentals with a hot tub

5 out of 5 average rating, 5 reviews

An outdoor heated pool is surrounded by lush greenery, featuring built-in loungers along the pool's edge. A spill-over pool spa adds tranquility, while several white poolside loungers offer ample space for relaxation under the sun.

Villa in North Fork

Villa Emilio -pool/beach retreat

4.98 out of 5 average rating, 47 reviews

Incredible 9+ Bed Watermill Home Wellness Retreat

4.89 out of 5 average rating, 72 reviews

A modern outdoor space features a rectangular pool with crystal clear water, framed by a wooden deck. Comfortable seating arrangements, including two chairs with cushions and a dining table set for six, are complemented by an umbrella for shade.

Villa in North Fork

Year-Round Heated Pool Villa - 3 blocks from town

4.98 out of 5 average rating, 66 reviews

Other vacation rentals with a hot tub

4.91 out of 5 average rating, 70 reviews

A rectangular heated pool is framed by a grassy area and surrounded by a black safety fence. Two lounge chairs are positioned on the pool deck, offering a place to relax. In the background, an outdoor dining area is visible beyond the pool, shaded by trees.

Farm stay in North Fork

North Fork Wine Country Retreat

An outdoor seating area features a spacious wooden deck overlooking the ocean. Comfortable furnishings include a dining table with chairs, and lounge seating with decorative cushions under shaded umbrellas. The serene water view complements the minimalist design of the space, surrounded by greenery.

4.9 out of 5 average rating, 21 reviews

Chic Beach House Waterfront, Vineyards, Hot Tub

4.92 out of 5 average rating, 39 reviews

An expansive hallway features arched doorways and rustic wooden beams overhead. Potted plants add greenery, while large windows dressed with floral curtains allow natural light to illuminate the stone floor. Comfy seating arrangements are positioned along the walls, creating inviting spaces for relaxation.

Condo in The Hamptons

1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!

Guesthouse in The Hamptons

A serene outdoor space showcases a heated saltwater pool framed by neatly trimmed hedges. Comfortable lounge chairs are arranged beside the water, while a large umbrella provides shade. A two-story house is visible in the background, surrounded by greenery.

4.92 out of 5 average rating, 13 reviews

3 Bedroom Guest House in Southampton

The exterior of the home is surrounded by lush greenery, featuring a spacious yard. A cozy fire pit area is set with several chairs. A hot tub sits on a wooden deck beside large glass doors that lead into the house.

4.79 out of 5 average rating, 33 reviews

The Saltbox Greenport

4.92 out of 5 average rating, 12 reviews

A spacious living area displays a large sectional couch adorned with assorted cushions. A wooden dining table is surrounded by black chairs. Natural light filters through multiple windows, highlighting the cozy atmosphere, while decorative baskets add an organic touch.

Bungalow in The Hamptons

Stylish East Hampton Surf Cabin: Hot Tub & Office

A cozy outdoor space is illuminated by string lights, highlighting comfortable seating arranged around a central fire pit. Soft hues from a nearby hot tub create a tranquil atmosphere among greenery, enhancing the inviting yard setting during the evening hours.

5 out of 5 average rating, 14 reviews

-:Cabin By The Sea:- -Salt Hot Tub- *pet friendly*

A bright and airy living space features a cozy beige sofa facing large windows with water views. A staircase leads to the upper level, and natural light illuminates the open layout. Light-colored furniture and decorative accents create a relaxing coastal ambiance.