Vacation 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.

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 tubAir conditioning

4.83 out of 5 average rating, 355 reviews

4.95 out of 5 average rating, 110 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.

Outdoor spacesHot tubAir conditioning

4.91 out of 5 average rating, 91 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 tubDecor

4.98 out of 5 average rating, 147 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!)

Hot tubOutdoor spacesCondition

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 tubOutdoor spacesCheckout

4.96 out of 5 average rating, 189 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

BathroomHot tubLayout

4.95 out of 5 average rating, 100 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

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, friends or couples. This stylish and serene home features 4 bedrooms, 2.5 bathrooms, a fully equipped kitchen, soaring ceilings, games room and movie room. Bring the outdoors in with oversized windows and over 1000 square feet of deck space overlooking the gorgeous pool (can be heated for a fee).

Hot tubBathroomPets

4.95 out of 5 average rating, 59 reviews

A spacious gourmet kitchen is equipped with white cabinetry and a large island featuring a light-colored countertop. Pendant lights hang above the island, and stainless steel appliances are visible in the background, complemented by a tile backsplash and modern fixtures throughout.

Home in Southold

Luxury by the Sea!!

Your search 👀 is over! Brand New 🔨 Construction. Charming, luxurious, private, comfortable Beach 🏖 House. This home is beautifully designed with too many architectural details to list. Property is fully furnished 🛋 with no detail spared . Open floor plan, spacious great room with gas fire place and flat screen, gourmet eat 🍝 in kitchen with large island is a wonderful place to entertain 🥂. Brand new washer/dryer, butlers pantry and mud room. Where the country meets the sea 🌊

Outdoor spacesBathroomBeach

4.93 out of 5 average rating, 272 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.

BathroomOutdoor spacesAmenities

4.82 out of 5 average rating, 50 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

Outdoor spacesBathroomWifi

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.

Outdoor spacesHot tubLocation

4.92 out of 5 average rating, 514 reviews

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 Greenport

Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)

100% Walking Score 1 block away from Village 3 blocks away from Beach. 1 block away from Shelter Island Ferry. Around the corner from Hampton Jitney & LIRR Newly renovated 2-Family Home! This is for rental of 1st floor apartment (only) plus cabana, plus outdoor jacuzzi. Close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place! Incredible location, safe, cozy.

BathroomOutdoor spacesSleep quality

Popular amenities for Southold hot tub rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a hot tub

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.

Hampton's Haven

Hot tubOutdoor spacesTV

4.93 out of 5 average rating, 167 reviews

Home in Shelter Island Heights

Surf Scoter Cottage Shelter Island

Outdoor spacesHot tubHospitality

4.92 out of 5 average rating, 100 reviews

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

Hot tubBathroomQuiet

4.8 out of 5 average rating, 40 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

Hot tubBathroomIndoor 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

Hot tubOutdoor spacesNearby

4.88 out of 5 average rating, 48 reviews

An open living area features high ceilings and large windows that bring in natural light. A sectional sofa in deep blue surrounds a vibrant orange rug, while an artwork adorns the wall. A dining area with a wooden table and chairs can be seen in the background.

Home in Baiting Hollow

North Fork True Beachfront Home

Hot tubBathroomQuiet

5.0 out of 5 average rating, 20 reviews

Home in Water Mill

Luxury Southampton Home/outdoor Sauna/hottub

BathroomHot tubBackyard

4.88 out of 5 average rating, 16 reviews

Home in Sag Harbor

Heated Pool and Spa in Sag Harbor w/ Tennis Access

BathroomOutdoor spacesFamily

Villa rentals with a hot tub

4.96 out of 5 average rating, 47 reviews

A modern farmhouse exterior is showcased, featuring a combination of wood and white siding. A spacious lawn is surrounded by natural stone landscaping, with a gravel driveway leading to the entrance. Lush greenery in the background enhances the serene setting.

Villa in East Hampton

Modern Farmhouse in East Hampton with beach access

Outdoor spacesHot tubAmenities

4.97 out of 5 average rating, 29 reviews

Villa in Hampton Bays

Hamptons Retreat | Pool, Hot Tub, Sleeps 10

Outdoor spacesHot tubIndoor spaces

4.95 out of 5 average rating, 100 reviews

Villa in East Hampton

Outdoor spacesHot tubIndoor spaces

4.91 out of 5 average rating, 91 reviews

Villa in Greenport

Year-Round Heated Pool Villa - 3 blocks from town

Outdoor spacesHot tubCondition

Other vacation rentals with a hot tub

Guesthouse in Southampton

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.

3 Bedroom Guest House in Southampton

BathroomOutdoor spacesBeach

4.96 out of 5 average rating, 23 reviews

Guest suite in East Hampton

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

BathroomHot tubValue

5.0 out of 5 average rating, 29 reviews

5.0 out of 5 average rating, 16 reviews

Cottage in Hampton Bays

Swim into Fall & Hot Tub through Winter!

Hot tubBathroomDecor

4.76 out of 5 average rating, 192 reviews

A spacious backyard is featured, surrounded by manicured landscaping. A fire pit made of stones and logs is centrally located on the gravel area. The cottage stands in the background, framed by lush trees and greenery, creating a serene outdoor environment.

Home in Springs

BlackBerry Private home with jacuzzi yearlong

BathroomHot tubNearby

5.0 out of 5 average rating, 20 reviews

Home in Hampton Bays

Hamptons Retreat • Hot Tub • Minutes to Beaches

Outdoor spacesHot tubCheck-in

Guesthouse in Shelter Island Heights

A serene saltwater pool is framed by lush greenery and blooming flowers, enhancing the outdoor space. A hot tub is positioned alongside, inviting relaxation. The guest house is visible in the background, surrounded by trees and well-maintained landscaping.

Bayfront 1BR/2BR detached guesthouse with pool

Hot tubOutdoor spacesCleanliness

4.97 out of 5 average rating, 79 reviews

4.97 out of 5 average rating, 59 reviews

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.

Home in Hampton Bays

Relax Villa ,Hot tub /New pool,7min from the beach

Outdoor spacesHot tubCheck-in