Vacation rentals with a hot tub in Southold

4.78 out of 5 average rating, 145 reviews

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.

Home in East Hampton

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

Outdoor spacesHot tubCleanliness

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

BathroomHot tubParks

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 spacesBathroomGetting around

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

Pool heated to hot tub temperatures & open year round! This brand new construction house is perfect for large groups. Gather with friends and family in the double height ceiling open concept living room/dining room/kitchen area. Soak up the sun lounging by the pool. Take a super short walk to town to enjoy the incredible local shops, restaurants, and bars. Then end with a nightcap relaxing in the heated hot tub seating section of the pool. There's no better place to stay in Greenport Village.

BathroomHot tubComfort

4.98 out of 5 average rating, 145 reviews

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.

Home in East Hampton

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!)

Outdoor spacesBathroomQuiet

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.

BathroomOutdoor spacesLocation

4.97 out of 5 average rating, 163 reviews

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.

Home in East Hampton

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.

BathroomHot tubLaundry

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

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.

Hot tubBathroomLayout

4.83 out of 5 average rating, 48 reviews

A hot tub sits at the edge of a serene lake, surrounded by lush greenery and trees. The gentle ripples on the water reflect the sky, enhancing the tranquil setting. The peaceful landscape invites relaxation and offers a scenic view of nature.

Home in Southold

Southold Sea'renity

Kick back and enjoy the peaceful surroundings of this beautiful 3-bedroom, 2-bathroom house. Outdoor oasis with hot tub, BBQ, shower, brand new deck & kayaks. Steps away from a fishing lake & 6 houses away from Kenny's beach. This house has been completely remodeled & is perfectly located to fit your getaway needs. Master Bedroom- queen bed, full bath Bedroom 2&3- queen beds Pull out couch and some other extras. Towels, bed sheets, soap, toilet paper, and pillows are included

Hot tubBathroomComfort

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 spacesBathroomIndoor spaces

Home in Westhampton Beach

A contemporary ranch-style home is surrounded by lush greenery. The custom-shaped heated pool features a waterfall and is bordered by a stone patio with lounge chairs and umbrellas. A state-of-the-art hot tub is positioned nearby, enhancing the outdoor relaxation space.

4.93 out of 5 average rating, 165 reviews

Hampton's Haven

5 bedroom, 3.5 bath contemporary ranch style home, with custom shaped heated pool and meticulously maintained 7 seater hot tub. Expansive patio w/outdoor dining for 10 - close to beach, town and more! Our home has comfortable office space with gigabit wifi throughout! Fabulous game room with ping pong, 4 person air hockey, smart tv and board game lounge. Everything you'll need for a memorable gathering of friends or the perfect family vacation!

Outdoor spacesBathroomHospitality

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, 218 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.

Hot tubOutdoor spacesView

Popular amenities for Southold hot tub rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a hot tub

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

BathroomOutdoor spacesLocation

A large saltwater pool is framed by lush greenery and trees under a bright blue sky. Sunlight reflects off the water's surface, while a diving board extends into the pool, inviting relaxation and enjoyment.

4.75 out of 5 average rating, 12 reviews

Respite Ranch | Pool, Hot Tub & North Fork

Hot tubOutdoor spacesBeach

4.97 out of 5 average rating, 79 reviews

The exterior of a charming house is featured, showcasing warm orange siding with blue accents. A spacious deck with wooden railing and a grill is visible, surrounded by lush greenery. Large windows allow natural light into the interior, creating a welcoming atmosphere.

Home in Mattituck

Mattituck Dream House - Rental Opportunity

Outdoor spacesHot tubIndoor spaces

5.0 out of 5 average rating, 29 reviews

An outdoor dining area is set beneath a striped umbrella, surrounded by greenery. A wooden table with several chairs is positioned nearby, with a hammock visible in the distance. A heated saltwater pool glistens under the sun, complemented by lounge chairs along the poolside.

Home in Greenport

Delightful Cape House in Greenport

BathroomHot tubQuiet

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, 38 reviews

Greenport Saltbox | North Fork Wine Retreat

Outdoor spacesBathroomWifi

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!

Outdoor spacesHot tubQuiet

A light-filled living room features a working fireplace surrounded by a sleek white mantel. Comfortable seating options include two white sofas, a brown leather chair, and several blue poufs. Natural décor elements and artwork complement the space, creating a tranquil atmosphere.

4.98 out of 5 average rating, 48 reviews

Sprawling Modern Home Minutes from Beach

Hot tubOutdoor spacesBeach

5.0 out of 5 average rating, 19 reviews

Home in Water Mill

Luxury Southampton Home/outdoor Sauna/hottub

Outdoor spacesBathroomAmenities

Villa rentals with a hot tub

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

Hot tubBathroomBeach

4.97 out of 5 average rating, 29 reviews

Villa in Hampton Bays

Hamptons Retreat | Pool, Hot Tub, Sleeps 10

Hot tubBathroomPool

Villa in Shelter Island Heights

5.0 out of 5 average rating, 7 reviews

Superb Shelter Island 4 bed Designer with a Pool

Outdoor spacesHot tubGetting around

4.95 out of 5 average rating, 97 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

BathroomHot tubComfort

Other vacation rentals with a hot tub

Guest suite in East Hampton

5.0 out of 5 average rating, 26 reviews

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

BathroomHot tubTV

4.99 out of 5 average rating, 93 reviews

Home in East Quogue

Hamptons Oasis | Saltwater Pool, Hot Tub & Games

Hot tubOutdoor spacesPets

5.0 out of 5 average rating, 20 reviews

Hamptons Retreat • Hot Tub • Minutes to Beaches

Hot tubOutdoor spacesAmenities

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

Outdoor spacesBathroomKitchen

5.0 out of 5 average rating, 14 reviews

Cottage in Hampton Bays

Saltwater Pool + Hot Tub + Private Beach

Hot tubBathroomBeach

5.0 out of 5 average rating, 31 reviews

Home in Westhampton

Home in Westhampton - with Hot Tub

Outdoor spacesHot tubComfort

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

LocationComfortHospitality

A hot tub is filled with bubbles, illuminated by soft blue lighting. Two chairs are placed nearby, surrounded by potted plants and flowers, creating a relaxing outdoor atmosphere. The area is enclosed with a white fence, adding privacy and tranquility.