Holiday rentals with a hot tub in Water Mill

The image captures a spacious outdoor area featuring a large heated pool with a fountain and surrounding stone patio. Nearby, lounge chairs are arranged for relaxation, while a generous lawn stretches in the background, accompanied by a well-designed home nestled among trees.

4.78 out of 5 average rating, 145 reviews

Sprawling Hamptons Estate with Hot Tub & Amenities

Spacious & private Hamptons Oasis. High speed WiFi. Family friendly. Massive home on 1.4 acres hosts 15 guests across 6 bedrooms, 8 beds, 4 full baths plus crib & pack 'n play. Gorgeously decorated by Judy Posey Large heated gunite pool (42 x 20 feet) hot tub and sundeck. Fireplace, over-sized kitchen w/ 3 fridges, electric wood-fired grill, huge yard, firepit, bar/lounge, Golden Tee arcade™, bikes & kayaks. Just 2 miles from towns of East Hampton and Amagansett and several white sand beaches

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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, 350 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

Outdoor spacesHot tubView

4.96 out of 5 average rating, 109 reviews

A vibrant pool scene is captured, featuring a colorful unicorn float positioned on the water. Lush hydrangea blooms frame the area in shades of pink, complementing the surrounding greenery and the wooden fence that provides privacy.

Apartment in Southampton

Swimming pool wIth Fire Pit /Coffee Bar

Relax in this cozy loft filled with amenities that will create lasting memories. Recently renovated so fresh and clean. Located on a wooded lot. Large fenced in landscaped yard with hammocks and firepit. Heated pool seasonal. We are just minutes from the beach. Spend time in our 6 person jacuzzi. 10 min to Southampton village. 15 min to Sag Harbor. Centrally located. Fresh farm (home of Tate’s Cookies) around the corner with fresh meats and produce. A tasty restaurant near by and a deli too.

Outdoor spacesBathroomCheck-in

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, 146 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. (No AI used in these photos!)

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4.91 out of 5 average rating, 202 reviews

Home in Sag Harbor

Offseason Monthly, Utilities Included

Welcome to your Hamptons retreat. This bright single-level home sits in a quiet neighborhood just minutes from Main Street and the ocean. The private fenced yard overlooks a peaceful nature preserve and features a heated pool (June–Sept, heating available for a fee), hot tub, outdoor fireplace, and outdoor shower—perfect after a beach day. Family-friendly amenities include a sandbox, toys, crib, and highchair, with a separate safety fence surrounding the pool for added peace of mind.

Outdoor spacesBathroomSleep quality

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, 163 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.

Outdoor spacesBathroomKitchen

Luxe

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

4.99 out of 5 average rating, 68 reviews

SERENITY AT SHOREWOOD Pool is Open April 1 - November 1. Must be 25+ to book. 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.

Outdoor spacesHot tubLocation

An outdoor space featuring a saltwater pool with a jacuzzi positioned nearby. A patio area includes an umbrella and ample seating options. Lush green grass surrounds the pool, while two white decorative swan floats are visible on the water, enhancing the inviting atmosphere.

4.91 out of 5 average rating, 65 reviews

Hamptons Vacation Rental w/ Heated Pool & Jacuzzi!

Located in Hampton Bays just a 5 min drive to beaches, waterfront restaurants, wineries & golf courses. This vacation property offers an open concept single family home w/ 4 bedrooms, 5 baths, a spacious living room, an outdoor deck and patio with a table and chairs, pool, jacuzzi and a pool house! The pool is opened mid May - second week of October and can be heated at an additional cost. Located just 5 min away from Hampton Bays town and 5 min drive to one of our lovely beaches.

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Guesthouse in Southampton

A modern two-story building is viewed from the well-maintained lawn. The heated saltwater pool features clear water surrounded by lounge chairs under colorful umbrellas. Lush green trees provide a natural backdrop, creating a peaceful outdoor space for relaxation.

4.99 out of 5 average rating, 78 reviews

Southampton Modern Barn, Private Pool and Hot Tub

This magical getaway delivers peace and relaxation. Wake up to coffee on your private deck with bucolic views. Play in your heated, saltwater pool, and relax under the stars in your hot tub (open year round). During your stay, these amenities and more will be for your personal use. Stroll to the owner’s dock on Big Fresh Pond, for paddle boarding, kayaking and sunsets. You can also drive 8 minutes to Southampton Village for shopping, restaurants, art galleries and Ocean Beaches.

Hot tubOutdoor spacesFamily

4.83 out of 5 average rating, 220 reviews

The living area is characterized by high vaulted ceilings and large windows allowing natural light. A sofa with light cushions is centered around a wooden coffee table on a neutral rug. A decorative fireplace is framed with a modern mantle, adding warmth to the space.

Home in Southampton

Stylish & Chic w hot tub/ Near Beaches & Village

Stylish Hamptons retreat just minutes from Southampton Village and the area's best beaches. Enjoy a private backyard with a brand-new oversized deck, new outdoor shower, hot tub, fire pit, and sun lounge - perfect after a day at the beach. Cozy up by the indoor fireplace on cooler evenings. Next to Shinnecock Hills Golf Club, 15 minutes from Poxabogue, and close to Wölffer Estate, Duck Walk, Channing Daughters, Scallop Pond Preserve, and Elizabeth A. Morton Wildlife Refuge.

Outdoor spacesHot tubCheck-in

5.0 out of 5 average rating, 19 reviews

Home in Water Mill

Luxury Southampton Home/outdoor Sauna/hottub

This stunning 5-bedroom, 2-story Traditional home sits on just under an acre in Southampton, NY. It features a living room with a vaulted ceiling and fireplace, a gourmet kitchen with a dining area, a sunroom, and five bathrooms. The property includes a 2-car garage and a finished basement that offers a billiard room, media room, kitchenette, and bath. For summer gatherings, enjoy the 20' by 40' heated pool, expansive mahogany decking, and beautifully designed landscaping.

Hot tubOutdoor spacesKitchen

4.87 out of 5 average rating, 124 reviews

A spacious living area features exposed wooden beams and a cozy brick fireplace. Comfortable seating includes a brown sofa and recliner, with decorative pillows adding warmth. A glass coffee table stands on a colorful area rug, while large windows overlook the greenery outside.

Cabin in North Fork

Beach & Woods: Cozy Cabin, Hot tub, Peloton, Oh My

Welcome to nature's retreat, our secluded North Fork haven where 2+ acres of wild beauty and private beach access promise unparalleled relaxation. Delight in our hot tub's warmth under the stars, unwind on swings, or glide on bay waters with our kayak. With enchanting porch views, an invigorating outdoor shower, and nearby organic farms, our cabin is an idyllic escape. Experience the local charm with vineyard tours and return to a haven of comfort and adventure.

Outdoor spacesHot tubWi-Fi

Popular amenities for Water Mill hot tub accommodation

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a hot tub

4.99 out of 5 average rating, 211 reviews

A screened-in patio features a wooden ceiling and overhead fans, providing a comfortable space for relaxation. A navy blue sofa pairs with a coffee table, while tall chairs surround a dining table. Views of a spacious yard and trees are visible through the screens.

Home in Greenport

Greenport Village walking distance to all

BathroomOutdoor spacesView

4.93 out of 5 average rating, 271 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

Outdoor spacesHot tubFamily

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.

5.0 out of 5 average rating, 92 reviews

The Hamptons Surf Cottage!

BathroomHot tubIndoor spaces

A bright living area features wood-paneled ceilings and large windows with natural light filtering in. Two black sofas are arranged around a coffee table on a light-colored rug. A television is positioned on a wooden stand, while plants add a touch of greenery.

5.0 out of 5 average rating, 10 reviews

Relax & fun home

ComfortAmenitiesLocation

5.0 out of 5 average rating, 23 reviews

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.

Home in East Quogue

-:Cabin By The Sea:- -Salt Hot Tub- *Dog Friendly*

Hot tubOutdoor spacesHospitality

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.

5.0 out of 5 average rating, 8 reviews

Hamptons Waterview Cottage

Outdoor spacesAccuracyLocation

4.83 out of 5 average rating, 40 reviews

An outdoor area features a rectangular pool surrounded by stone patio. Comfortable seating is arranged near a fire pit, with a covered dining area visible. Lush greenery provides privacy, while a charming structure stands in the background, complete with a second-floor balcony.

Home in Southampton

Hamptons Luxury • Pool, Jacuzzi & Outdoor Kitchen

Hot tubOutdoor spacesAccuracy

5.0 out of 5 average rating, 20 reviews

Hamptons Retreat • Hot Tub • Minutes to Beaches

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Villa rentals with a hot tub

4.91 out of 5 average rating, 90 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 Greenport

Year-Round Heated Pool Villa - 3 blocks from town

Hot tubBathroomBiking

4.97 out of 5 average rating, 29 reviews

Villa in Hampton Bays

Hamptons Retreat | Pool, Hot Tub, Sleeps 10

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Villa in Shelter Island Heights

5.0 out of 5 average rating, 7 reviews

Superb Shelter Island 4 bed Designer with a Pool

BathroomOutdoor spacesFamily

4.95 out of 5 average rating, 98 reviews

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.

Villa in East Hampton

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Other holiday rentals with a spa

5.0 out of 5 average rating, 14 reviews

Cottage in Hampton Bays

Swim into Fall & Hot Tub through Winter!

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Guest suite in East Hampton

5.0 out of 5 average rating, 26 reviews

Peaceful Suite w/Pool, Hot tub, Private Entry.

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Holiday home in Shinnecock Hills

The kitchen features dark green cabinetry with natural wood countertops, complemented by a bright tiled backsplash. Stainless steel appliances, including a gas stove and a refrigerator, are present. The area is illuminated by natural light filtering through a window, with a brick wall adding texture.

4.76 out of 5 average rating, 41 reviews

Southampton Duplex with private Hotub + backyard

BathroomHot tubAccuracy

5.0 out of 5 average rating, 3 reviews

A spacious beachfront home is set against a bright blue sky, with lush greenery surrounding the property. A private dock extends into the calm water, while lounge chairs are positioned on the sandy shore, inviting outdoor relaxation and enjoyment of the scenic views.

Home in Water Mill

3BR/2BA: beachfront, pool, hot tub, outdoor dining

HospitalityFamilyLocation

Home in Westhampton Beach

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.

4.97 out of 5 average rating, 38 reviews

Magnificent Bayfront Retreat

BathroomHot tubDecor

The exterior of a spacious home is illuminated by soft twilight, showcasing a private pool with a smooth, blue surface. A shaded dining area beneath a pergola sits next to the inviting outdoor seating area, featuring a fire table. The wooden deck surrounds the house.

5.0 out of 5 average rating, 41 reviews

Hamptons Pool & Spa Retreat | Gym + 3.5 Acres

BathroomHot tubWi-Fi

Guest suite in Sag Harbor

A refreshing outdoor pool is surrounded by a paved area, featuring several potted plants and lounge chairs. Shade is provided by an umbrella next to the pool, while a wooden fence offers privacy. Sunlight illuminates the vibrant blue water.

5.0 out of 5 average rating, 28 reviews

1 Bedroom Apartment Sag Harbor with Pool/Hot Tub

Hot tubBathroomWalkability

An outdoor deck features a hot tub surrounded by a white railing, with a wooden dining set nearby. Soft lighting is strung overhead, creating a serene environment. The area is bordered by green foliage, and a barbecue grill is positioned on the deck.