Holiday rentals with a hot tub in Northwest Harbor

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

Hot tubOutdoor spacesBackyard

4.83 out of 5 average rating, 355 reviews

Home in Shelter Island Heights

Surf Scoter Cottage Shelter Island

New heated gunnite Pool & pea gravel driveway. 4BR renovated mid-century ranch with a breezy nautical theme. Central A/C. Giant back deck: Propane & Charcoal BBQ, Jacuzzi, Hammock & glorious Outdoor Shower. Private front & back yards. Fab mirrored bar, sleek kitchen, double-sink master bath+full 2nd bath. Impressive vinyl collect & 4 speaker Bluetooth stereo, Piano, chill basement media room + ping pong & foosball! washer/dryer. 4 bikes, beach chairs, cooler & umbrella. $100 /dog sorry no cats

Outdoor spacesHot tubBackyard

4.92 out of 5 average rating, 100 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 tubAccess

5.0 out of 5 average rating, 261 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 Montauk

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)

Outdoor spacesBathroomAmenities

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, 148 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!)

BathroomOutdoor spacesBeach

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.

BathroomHot tubValue

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 tubSleep quality

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 tubOutdoor spacesBeach

A wooden structure with multiple windows is set among lush greenery. The deck surrounds a newly built pool, offering a serene outdoor space. The pool's clear water reflects the surrounding trees and the vibrant blue sky.

4.9 out of 5 average rating, 30 reviews

4 BR/3BA Quiet Pool Home

We welcome you to our family home, up to 5 guests, pets are welcome with additional pet fee. Nice new pool and surrounding deck with outdoor sitting area, chairs, umbrella, and charcoal grill. 1 gbps internet for movies streaming on disney plus, prime video, or for your work. 5-8 minutes to town and the beaches. Plenty of nice restaurants and great local shopping. We don't allow other guests on property that is not mentioned in advance. No gatherings and no parties. Thank You.

BathroomOutdoor spacesCheckout

The exterior of the home features a modern facade with natural wood siding and a green lawn surrounding a heated pool. Two umbrellas provide shade for patio seating, while large windows allow for ample natural light. Trees frame the backdrop for a serene atmosphere.

4.98 out of 5 average rating, 42 reviews

Chic East Hampton 7 Bedroom, 7 Bath, heated Pool

Elegantly designed 7 Bedroom / 7 Bath home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches and the vibrant Easthampton Village. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Kindly familiarize yourself with our disclosures, guidelines, and house rules. We maintain a strict no events, no parties, and no smoking policy — our home and property are smoke-free.

BathroomOutdoor spacesHospitality

4.88 out of 5 average rating, 16 reviews

Home in Sag Harbor

Heated Pool and Spa in Sag Harbor w/ Tennis Access

Private Sag Harbor retreat just minutes from the Village, Beach & bay. This 4 bedroom, 2 bath home features a Brand New heated saltwater Gunite pool and built-in spa, spacious yard, outdoor dining. Inside are 2 living room areas, with a pullout couch and bright sunroom, 2 king bedrooms, 1 queen and 1 full, plus a fully equipped kitchen and dining for up to 10. Perfect for families and friends looking for a relaxing Hamptons getaway. Inquire below: IG @ Tal.Adla.Hamptons

Outdoor spacesBathroomNearby

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

This beautiful expanded newly renovated 4 bedroom, 2 bathroom cottage is nestled on manicure landscaped property. Enjoy the boxwood garden & have a relaxing time roasting marshmallows by the fire pit & enjoying the outdoor jacuzzi year-round (available for an extra fee) while listening to the calming sounds of nature. This property has an oversized back yard with plenty of space to enjoy. The location makes your stay easy and convenient to navigate the east end.

Outdoor spacesBathroomBeach

Popular amenities for Northwest Harbor hot tub accommodation

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday 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

BathroomHot tubHeating

4.93 out of 5 average rating, 167 reviews

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

Hot tubOutdoor spacesGetting around

4.91 out of 5 average rating, 92 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

BathroomOutdoor spacesSleep quality

5.0 out of 5 average rating, 45 reviews

A spacious backyard is featured, with a circular stone fire pit surrounded by several colorful Adirondack chairs. Lush green grass extends towards a charming white house in the background, bordered by trees under a clear blue sky.

Home in Southold

Private Waterfront Access + Hot Tub + Scenic Yard

Hot tubBathroomAccuracy

4.95 out of 5 average rating, 44 reviews

A spacious backyard is bordered by lush greenery and has a view of the tranquil water. Two surfboards are propped against the house, and a set of bright pink chairs surrounds a dining table. Pathways made of stones lead to the water's edge.

Home in Shelter Island

Waterfront shelter island gem

BathroomOutdoor spacesFamily

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

BathroomOutdoor spacesCheckout

4.84 out of 5 average rating, 67 reviews

A serene backyard features a heated salt-water pool with stone tile surrounding it. Lounge chairs are positioned beside a shaded cabana and an umbrella. Lush greenery offers a sense of privacy, enhancing the tranquil atmosphere of the outdoor space.

Home in Springs

Salt Pool 4BR Sanctuary w ~Private Beach Access

Hot tubOutdoor spacesBarbecue

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!!

BathroomOutdoor spacesWalkability

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 tubCondition

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

BathroomHot tubKitchen

4.97 out of 5 average rating, 29 reviews

Villa in Hampton Bays

Hamptons Retreat | Pool, Hot Tub, Sleeps 10

BathroomOutdoor spacesPool

4.95 out of 5 average rating, 100 reviews

Villa in East Hampton

Hot tubBathroomHospitality

Other holiday rentals with a spa

5.0 out of 5 average rating, 26 reviews

Cottage in Bridgehampton

Cozy Bridgehampton Cottage w/Hot Tub & Fire Pit

Hot tubOutdoor spacesAccuracy

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

Hot tubBathroomHospitality

4.96 out of 5 average rating, 23 reviews

5.0 out of 5 average rating, 16 reviews

Cottage in Hampton Bays

Swim into Fall & Hot Tub through Winter!

Hot tubBathroomFamily

5.0 out of 5 average rating, 12 reviews

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.

Home in Hampton Bays

Relax & fun home

Indoor spacesHospitalityBarbecue

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

BathroomOutdoor spacesBackyard

4.97 out of 5 average rating, 79 reviews

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.

1 Bedroom Apartment Sag Harbor with Pool/Hot Tub

Outdoor spacesHot tubCheck-in

5.0 out of 5 average rating, 29 reviews

4.91 out of 5 average rating, 67 reviews

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.

Home in Hampton Bays

Hamptons Vacation Rental w/ Heated Pool & Jacuzzi!

BathroomOutdoor spacesLayout