
Vacation rentals with a pool in Sag Harbor
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Sag Harbor
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Modern East Hampton Home w/ Heated Saltwater Pool
Peace and serenity in East Hampton and minutes from the Village. This exquisite modern home features high-end finishes such as Sub-Zero and Wolf appliances, quartzite waterfall kitchen island and counters, marble tiled bathrooms, designer mid-century decor and separately zoned air conditioning. The heated saltwater pool is surrounded by a bluestone patio, Ipe deck and huge yard. The house also features two wood-burning fireplaces in the living room and den and an outdoor fire-pit. RR# 24-656

East Hampton Village Fringe, Renovated with Pool
This remarkable East Hampton home, nestled along a quiet cul-de-sac, is just moments from shopping, restaurants, and ocean beaches. The residence features an abundance of natural light, crisp neutral color tones, and tall, pitched ceilings that enhance the sense of space. The calming, heated pool provides a perfect retreat for relaxation. Please review our disclosures and house manual to ensure this home meets your needs and expectations. We want to make sure it’s the perfect fit for you.

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.

Stunning Hamptons Waterfront Escape w/ Sunset View
Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views from our spacious deck. Vaulted ceilings and large windows flood the space with natural light. Brand new Weber Grill (2025). We have completed renovations of 3 bathrooms, 2 kitchens, and the entire pool house over the last 18 months. Our home is <10 minutes drive to the beach, groceries, and restaurants! Note our pool and dock are closed and will open Memorial Day Weekend (late May 2026).

Stunning luxury Retreat I Wineries & Fall Farm Fun
Chic & Luxurious North Fork Farmhouse Retreat Set on a private 1-acre lot, this stylish farmhouse offers a pool, lounge areas, and refreshing ocean breezes. Just 1.5 hours from NYC, you’ll be minutes from beaches, wineries, farm stands, hiking, and golf. Inside, enjoy modern interiors, a full kitchen, and fast Wi-Fi. Perfect for families, couples, or friends, this retreat is ideal for a peaceful escape, remote work, or exploring wine country near the Hamptons and North Fork.

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.

Spacious East Hampton Getaway with Pool
This bright and comfortable 3 bedroom, 2 bath Scandinavian home awaits! Located just a 5 minute drive Sag Harbor and 10 minutes to the heart of East Hampton to enjoy beaches, shopping, restaurants and bars. The light hardwood floors create a crisp feel that you have to witness. The first floor's two guest beds open out to a lovely eat-in kitchen with dining and living rooms featuring a wood-burning fireplace and pool to check every box for year-round fun.

B our guest! King bed 2 bths Fireplace convenient
Beautiful, bright, spacious King suite w fireplace, two 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/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

Peaceful Retreat in Immaculate Architect’s House
This "like new" contemporary home features 4 bedrooms, 3.5 baths, open living spaces, soaring ceilings, abundant natural light, and a modern kitchen. Nestled in tranquil West Tiana Shores, minutes from bay & ocean beaches, and charming Hampton villages (Southampton, Westhampton, Quogue). The living room directly faces your private pool, cedar deck, and lush garden—a perfect getaway for vibrant summers and relaxing winters

Exclusive Sag Harbor Compound
A private country compound in heart of Sag Harbor. House just gut renovated with all top of line (all Wolf and Subzero appliances). The main house is 3 bedrooms, 3.5 bath main house PLUS separate large guest cottage (with a King bed, bar fridge, and full bathroom). Gunite pool (i.e., salt chlorinated which makes it feels like clean freshwater). Walk to town, bay beach, public tennis courts, 1000 acre nature preserve.

Beach Barn w/ Heated Pool & Sauna - Dog Friendly
Dog friendly (upon request) Hampton Beach Barn with pool and infrared sauna. POOL OPEN - May 15th - October 20, 2025 US GOLF OPEN 2026 - 6 miles from Shinnecock Hills Golf Club This impressive house, nestled within a rustic, woodland plot, promises a tranquil stay. Eclectic modern decor is complemented by striking rustic touches, such as Dutch-style farm doors, exposed beams, and vintage wood-burning stove.

Dream Home with a wonderful heated pool in SH
Situated on a half-acre of land, this designer, updated, modern residence offers a peaceful and quiet Hamptons getaway. 4 wonderful bedrooms 3 modern bathrooms and a solar heated pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking –
Popular amenities for Sag Harbor rentals with a pool
House rentals with a pool

Spectacular Southampton Retreat!

Sag Harbor Gem! Private and close to it all.

Stylish+Cozy Hamptons Winter Getaway-5min to Beach

Stunning Central E. Hampton Home w/ gunite pool.

Hampton Oasis with private Tennis, Pool, Theater

Classic Southampton Village Home w/ Pool

Sunny, walk to beach, large pool

Secluded Luxury: New Gunite Pool, Walk to Bay
Condo rentals with a pool

Beautiful condo on Long Islands Northfork

Waterfront Elevated Bungalow - Spectacular Views

Beautiful Waterview Condo on the North Fork of LI

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

A Unique Piece of Paradise, Water Front pool

Waterfront Autumn Escape in Wine Country: 2BR

Beachside Waterview 2Br Condo w/ Pool in Greenport

Beautiful 2 Bedroom 2 Bathroom Pool-Side Condo
Home rentals with a private pool

East Hampton Ranch with Access to Clearwater Private Beach

Explore the Water & Woods at a Relaxing Retreat
Enchanting Home with Large Decks and Heated Pool

Southampton Quiet Private Home/Pool 6min to Villag
Perfect Holiday Getaway with Gourmet Kitchen
Saltbox with Separate Poolhouse in Northwest Woods
When is the best time to visit Sag Harbor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 860 | € 860 | € 860 | € 843 | € 980 | € 1,061 | € 1,217 | € 1,348 | € 1,011 | € 774 | € 770 | € 846 |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 15°C | 21°C | 24°C | 23°C | 19°C | 13°C | 8°C | 3°C |
Quick stats about vacation rentals with a pool in Sag Harbor

Total vacation rentals
Explore 120 vacation rentals in Sag Harbor

Nightly prices starting at
Sag Harbor vacation rentals start at € 77 per night before taxes and fees

Verified guest reviews
Over 1,990 verified reviews to help you choose

Family-friendly vacation rentals
110 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wi-Fi availability
120 of Sag Harbor vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Sag Harbor rentals

4.9 Average rating
Sag Harbor stays are highly rated by guests—averaging 4.9 out of 5!
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