Holiday rentals with a hot tub in Southold

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, 351 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 tubBarbecue

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.

BathroomOutdoor spacesCheck-in

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.

BathroomOutdoor spacesKitchen

4.98 out of 5 average rating, 146 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 spacesBathroomWalkability

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.

Hot tubBathroomCleanliness

4.96 out of 5 average rating, 185 reviews

Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

🛏 6 Bedrooms, 9 beds & 3 Full Baths 🏊‍♂️ Heated Pool & Relaxing Hot Tub 4-person Sauna 🏀 Half Basketball Court & 🏐 Volleyball Area 🏌️‍♂️ Private Golf Putting Green 🔥 Cozy Firepit & Outdoor Lounge Area 🛝 Swing Set & Kid-Friendly Yard 🍽 Fully Stocked Kitchen & Spacious Dining 🌐 High-Speed Wi-Fi & Smart TVs 10 min to Smith Point Beach & Boardwalk 15–20 min to Long Island Wine Country Nearby hiking at Wertheim Wildlife Refuge Short drive to Tanger Outlets & restaurants

Outdoor spacesHot tubKitchen

Superhost

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

4.93 out of 5 average rating, 272 reviews

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 tubBathroomParking

4.82 out of 5 average rating, 49 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

BathroomOutdoor spacesBarbecue

4.79 out of 5 average rating, 39 reviews

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.

Home in North Fork

Greenport Saltbox | North Fork Wine Retreat

This impeccably restored historic Saltbox blends timeless character with modern comfort. Stylish and chic with an updated kitchen, baths, open living spaces, and fireplaces, guests walk on original 19th-century floors while enjoying thoughtfully curated design. The Saltbox Greenport is a luxury North Fork vacation rental minutes from Greenport Village, Long Island wineries, and beaches, perfect for wine country weekends, beach escapes, and North Fork getaways from NYC.

BathroomHot tubAmenities

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.

BathroomHot tubCleanliness

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 spacesHot tubCheck-in

4.97 out of 5 average rating, 218 reviews

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

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.

BathroomHot tubAccess

Popular amenities for Southold hot tub accommodation

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a hot tub

Superhost

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

4.83 out of 5 average rating, 221 reviews

Stylish & Chic w hot tub/ Near Beaches & Village

Hot tubOutdoor spacesBeach

4.98 out of 5 average rating, 80 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

BathroomOutdoor spacesBeach

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

BathroomOutdoor spacesAmenities

5.0 out of 5 average rating, 18 reviews

Home in Mattituck

North Fork Getaway Southold Compliant Property

Outdoor spacesHot tubHospitality

5.0 out of 5 average rating, 57 reviews

An aerial view of a backyard features a spacious wood deck surrounding a gunite pool. Comfortable lounge chairs are positioned near the pool, alongside a shaded area with an umbrella. The natural greenery provides a serene backdrop to the outdoor dining area.

Home in Springs

Secluded Luxury: New Gunite Pool, Walk to Bay

BathroomOutdoor spacesHospitality

4.98 out of 5 average rating, 49 reviews

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.

Home in North Fork

Sprawling Modern Home Minutes from Beach

Hot tubBathroomView

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!

BathroomHot tubNearby

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 spacesBeach

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

BathroomOutdoor spacesDecor

4.97 out of 5 average rating, 29 reviews

Villa in Hampton Bays

Hamptons Retreat | Pool, Hot Tub, Sleeps 10

BathroomOutdoor spacesSleep quality

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

Hot tubOutdoor spacesBackyard

Other holiday rentals with a spa

Guest suite in East Hampton

5.0 out of 5 average rating, 27 reviews

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

Hot tubBathroomValue

5.0 out of 5 average rating, 22 reviews

Cottage in Bridgehampton

New Bridgehampton Sag Harbor Hamptons Cottage

Hot tubOutdoor spacesBackyard

5.0 out of 5 average rating, 20 reviews

Hamptons Retreat • Hot Tub • Minutes to Beaches

Hot tubOutdoor spacesNearby

4.91 out of 5 average rating, 91 reviews

A serene outdoor space features a newly installed heated pool surrounded by a patio. The area is complemented by comfortable lounge chairs and lush greenery, providing a tranquil setting for relaxation. A wooden fence offers privacy, while manicured shrubs frame the pool.

Home in Springs

Bright & Modern E Hampton Getaway w/ Pool & Spa

Hot tubOutdoor spacesHospitality

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

CleanlinessComfortHospitality

5.0 out of 5 average rating, 14 reviews

Cottage in Hampton Bays

Swim into Fall & Hot Tub through Winter!

Hot tubBathroomCleanliness

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.