Holiday rentals with a hot tub in Montauk

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

Hot tubOutdoor spacesBiking

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, 349 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 tubWi-Fi

4.95 out of 5 average rating, 210 reviews

A spacious pool area is framed by well-maintained greenery and flowering plants. Two large umbrellas provide shade over lounge chairs beside a sparkling pool, with expansive coastal views and a serene landscape of grasses and trees beyond.

Cottage in Guilford

Luxury cottage by the sea with hot tub and pool

We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

Outdoor spacesHot tubIndoor spaces

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

Welcome to the beautiful 5-bed, 3-bath Harbor House, located just a short walk from Gardiners Bay beaches. Enjoy open-concept living, fully equipped kitchen, comfy beds, gunite pool, private patio with gas grill & outdoor dining, hot tub, & fully fenced backyard. Walk/bike to harbor, rent kayaks, use our paddleboards, or explore nearby restaurants and shops. Whether you’re looking for a romantic getaway for 2 or a family vacation, our home is the perfect retreat for your next Hamptons adventure!

BathroomOutdoor spacesPool

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 w/Hot tub 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 spacesDecor

5.0 out of 5 average rating, 260 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 spacesBathroomIndoor spaces

4.98 out of 5 average rating, 144 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!)

BathroomHot tubKitchen

4.91 out of 5 average rating, 201 reviews

Home in Sag Harbor

Barefoot Bliss | Quiet Family Retreat Heated Pool

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.

BathroomHot tubAmenities

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 tubValue

4.96 out of 5 average rating, 184 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

Hot tubBathroomHeating

4.99 out of 5 average rating, 109 reviews

Home in Branford

Steps to Beach • Hot Tub • Game Room • Water Views

Beautiful coastal beach house directly across from a private beach and tennis club with complimentary guest access. Backing up to a serene marsh with stunning views, this home offers a peaceful, upscale setting perfect for families and groups. Relax in the hot tub with outdoor TV, fire pit, and kayaks. Inside features 4 bedrooms, a workspace, and a new game room with a 100” TV, pool table, shuffleboard, and darts. Minutes from Branford’s town center, dining, and waterfront attractions.

Outdoor spacesBathroomCheck-in

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, 67 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.

BathroomOutdoor spacesBackyard

Popular amenities for Montauk hot tub accommodation

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a hot tub

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

BathroomHot tubValue

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

Outdoor spacesHot tubDecor

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 spacesBiking

5.0 out of 5 average rating, 17 reviews

Home in Montauk

Montauk Modern Home

Outdoor spacesHot tubWalkability

4.91 out of 5 average rating, 90 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

Outdoor spacesBathroomCondition

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

BathroomOutdoor spacesComfort

5.0 out of 5 average rating, 20 reviews

An aerial view showcases the expansive property featuring a spacious house and a long salt-water pool surrounded by greenery. Multiple trees and landscaped areas provide natural separation. The layout demonstrates ample outdoor space for activities.

Home in Montauk

Chic Farm House with a Lakeview

Outdoor spacesHot tubAccuracy

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 tubAccuracy

Villa rentals with a hot tub

4.91 out of 5 average rating, 89 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 tubOutdoor spacesLocation

4.96 out of 5 average rating, 28 reviews

Villa in Hampton Bays

Hamptons Retreat | Pool, Hot Tub, Sleeps 10

Outdoor spacesBathroomBackyard

Villa in Shelter Island Heights

5.0 out of 5 average rating, 7 reviews

Superb Shelter Island 4 bed Designer with a Pool

Hot tubOutdoor spacesComfort

4.9 out of 5 average rating, 40 reviews

The exterior of the house is framed by lush greenery, with a wrap-around deck highlighted by large windows. The warm glow from the interior lights contrasts with the natural surroundings, while the fieldstone chimney adds an element of rustic charm. A pathway leads towards the entrance.

Villa in Guilford

TREETOPS! An upscale, unique 5 bdrm home with POOL

Outdoor spacesHot tubHiking

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

4.92 out of 5 average rating, 13 reviews

A clear view of the outdoor pool highlights a serene setting with two large umbrellas shading lounge chairs. Green lawn and bushes surround the pool, with a backdrop of coastal landscape and gentle waters visible in the distance.

Villa in Guilford

Private Luxury Waterfront Home

Hot tubOutdoor spacesView

Other holiday rentals with a spa

Guest suite in East Hampton

5.0 out of 5 average rating, 25 reviews

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

Hot tubBathroomTV

4.93 out of 5 average rating, 46 reviews

An expansive hallway features arched doorways and rustic wooden beams overhead. Potted plants add greenery, while large windows dressed with floral curtains allow natural light to illuminate the stone floor. Comfy seating arrangements are positioned along the walls, creating inviting spaces for relaxation.

Condo in Montauk

1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!

Hot tubOutdoor spacesHospitality

5.0 out of 5 average rating, 4 reviews

A spacious dining area features a large wooden island with a herringbone pattern. Black woven chairs surround the island, and large windows reveal views of the beach and ocean, bathed in soft afternoon light. A comfortable seating area is partially visible in the background.

Condo in Montauk

Amazing Waterfront VIEWS!

Hot tubComfortNearby

5.0 out of 5 average rating, 21 reviews

Cottage in Bridgehampton

New Bridgehampton Sag Harbor Hamptons Cottage

Hot tubOutdoor spacesAccuracy

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 spacesNearbyAccess

5.0 out of 5 average rating, 20 reviews

Hamptons Retreat • Hot Tub • Minutes to Beaches

Outdoor spacesHot tubIndoor spaces

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.

4.96 out of 5 average rating, 57 reviews

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

Outdoor spacesHot tubWalkability