Holiday rentals with a hot tub in Amagansett

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)

Family-friendly with pool, beach car, new hot tub

Huge, gunite pool with heater. Perfect spot for families or large groups. 5 bedrooms + 4 full baths. 2004 Land Rover included with parking permit—the only way to park at many exclusive Hamptons beaches! Outdoor shower, deck with BBQ & dining. 2 firepits. Kids' playscape. Fast Wi-Fi. Located in historic Springs area. Minutes from secluded beaches on Gerard point and private bay beaches and amenities at Clearwater Beach. Kayak and paddleboard available. No "share houses”. Rental number 17-522.

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.

Detached bungalow w/ private bath

Cozy, simple living, in separate guest house with use of amenities (shared with our family of 4). The bungalow/guesthouse features a Queen bed, its own private bathroom (shower), small kitchenette (countertop oven, micrwave, Keurig coffee maker & small fridge) and loveseat for relaxing. There is a dedicated separate outdoor seating area for 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.

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.

Sag Harbor Fringe East Hampton Pool, Hot Tub, Gym

Welcome to this all brand new 3000 sf beach house with flex 4/5 BR and 3 BA, situated on 3 acres at the end of a private cul-de-sac. Bonus room to 5th BR or flex live/work space. Gym equipment w/ Peloton bike. Heated pool from April to about Thanksgiving weather permitting, hot tub year round, fire table, large outdoor kitchen, outdoor commercial pyramid heaters, private fenced in. Village fringe property is 1.5 mi to Sag Harbor Village and about 2 mi to East Hampton Village

Luxury 4-bedroom in East Hampton [w/private beach]

Welcome to Camelot House East End, where Norman Rockwell meets the South of France. Your home away from home in the Hamptons is close to all the action, and yet, located in a tranquil paradise just steps away from a members-only beach. Camelot House is appropriate for individuals and families alike. The home is fully equipped with high end appliances and finishes, and yet, kid-friendly with a pool fence, stair gates, and a pack-n-play available for use.

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.

Luxe| Pool | GOLF Sim|HotTub|Movie|Arcade|firepit

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 or couples. This stylish and serene home features 4 bedrooms, 2.5 bathrooms, a fully equipped kitchen, soaring ceilings and an open floorplan. Bring the outdoors in with oversized windows and over 1000 square feet of deck space overlooking the gorgeous pool.