Holiday rentals with a pool in Bridgehampton

Modern Southampton Cottage | Heated Pool & Peloton

Modern Hamptons cottage with mid-century modern interior, our 3 bedroom/ 2 bathroom cottage is set on manicured grounds and perfectly equipped for your stay. Heated gunite pool (summer months only) with retractable cover, Peloton bike and Central Air throughout. Newly renovated kitchen with high end appliances, large outdoor deck perfect for entertaining with new Weber grill. Private driveway accommodates 4 cars. 4 adult bicycles. 8 min ride to Southampton village. 15 min to Coopers Beach.

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

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)

Relax with friends / family at this home in a magical setting overlooking Lily pond Completely private but 5 mins to Sag Harbor downtown / restaurants / Havens beach, and 10 mins to Bridgehampton. Location, location! And Views! - 3 Beds and 2.5 baths + pool house - Pool house with twin sofa bed + full bath - 50ft heated Gunite pool (125/d extra to heat) - Outdoor deck overlooking pond - Amazing views! - Fire pit with Adirondack chairs Unique house to unwind while being close to the action

Southampton Charmer, 5 bedrooms w pool - Location

This 5-bedroom home boasts en-suite baths and elegant furnishings. The gourmet kitchen features marble countertops and stainless steel appliances, leading to a dining area. The lower level includes a spacious seating area and a game room with toys. The second floor houses a master suite with stunning views and three additional en-suite bedrooms. Located minutes from the village center, with restaurants, shops, and beaches nearby. A heated pool invites you to relax and enjoy the comfort of home.

Private oasis~1 block to water, 5 mins to Main St.

Escape to your chic, serene, Hamptons oasis! Perched back on a large piece of private property, located just steps to the water. During Summer, swim in your large pool, BBQ + spark up the firepit under the starry sky. Stroll just 1 block to waterfront dining for dinner, cocktails + the most magnificent sunsets in the area. Curl up at the wood burning fireplace, 80' TV + cook in the Chef's kitchen. You'll be 1 block to the water, 5-8 minutes to many beaches, Main Street, shopping + much more!

Modern farmhouse w/ pool, beach, horses and winery

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

Explore the Water & Woods at a Relaxing Retreat

No AI used in these photos! 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.

Stunning 3 bed 2 bath home W Pool

Nestled on a serene an acre off a tranquil lane, this contemporary, designer-updated residence provides an idyllic Hamptons retreat. With 3 delightful bedrooms, 2 sleek bathrooms, and a seasonal heated pool amidst mature landscaping, you're promised a calming respite. We kindly ask that you familiarize yourself with the detailed disclosures, & guidelines. We maintain a strict policy against events, parties, and smoking. our home and property grouds are smoke-free.

Private central cozy king suite 2 baths fireplace

Beautiful, bright, spacious King suite w fireplace, two en-suite bathrooms & private separate poolside entrance. We are just minutes to beaches, boating, golf, hiking, biking, yoga and wineries. Play games, grill or cozy up fireside w a good book or movie. The space is creatively designed with a nod to natural elements and luxe comfort. Sleep your very best on our super deluxe king sized bed w/your choice of pillows. Complimentary coffee/tea/treats

Luxury Hamptons Home with Heated Saltwater Pool

Get away from it all in this meticulously renovated Westhampton Beach home. Pull up to the cottage in the heart of Westhampton Beach, a place that delivers all the Hamptons have to offer, all while being within a two hour drive of NYC. No detail was overlooked in the renovation of this cottage… the beauty is only matched by the comfort and function. With the open floor plan, sunny kitchen, furnished open air patio, you won’t want to leave.

Cheerful East Hampton home with Pool

Situated off of a quiet lane on one and a half-acres of land, this amazing residence offers a peaceful and quiet Hamptons getaway. The home consists of 4 wonderful bedrooms, 3.5 modern bathrooms, a heated pool & mature landscaping. Additionally, please read my disclosures and "rules". Not a party house. No Events, parties & No smoking will be permitted. The house is beautiful, tranquil and very comfortable. THANK YOU!

Classic Southampton Village Home w/ Pool

Newly renovated Southampton village home with great light, offering the best of indoor-outdoor living. A beautiful backyard with a pool surrounded by lush privet hedges for privacy. Perfectly situated in the heart of the village, one block from restaurants, shopping, and one mile from the ocean beaches. Perfect with space to spread out, play or work remotely! Ask about special rates for long-term summer rental!