
Vacation rentals with a pool in Sag Harbor
Find and book unique homes with a pool on Airbnb
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 1,810 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 40 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!
Top-rated rentals with a pool in Sag Harbor
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Serene w/ large pool ~1 block to waterfront dining
Serene, chic Hamptons oasis! Located 1 block to waterfront dining + 8 mins to Main St. A perfect escape for any time of year! During summer, swim all day + walk 1 block to waterfront dining for dinner, drinks, coffee on the sea! During fall/winter, enjoy the firepit, indoor wood burning fireplace, 80' streaming TV + large fully stocked Chef's kitchen! The home is nestled in nature and serenity, perched back on a large piece of private property. Perfect for a serene escape to relax and unwind!

Beachglass Barn Gated prvt pool King suite 2 bths
Clean beautiful bright King suite w/cozy Fireplace 2 ensuite Bths & prvt separate Poolside Entrance. Pool is all yours Closes9/15 We are just mins to beaches, shopping, golf, hiking, biking, yoga, eateries and wineries. Solo travelers r secure here! 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 best on our super deluxe king sized bed w/your choice of pillows. Enjoy coffee/tea/treats

Modern House close to the beach
This modern home has all the amenities and comfort you would expect. You are 5 minutes from Southampton Village, 5 minutes from Flying Point Beach by car. Spacious back yard with beautiful patio furniture which gives onto beautiful pond. Fully equipped kitchen with Wolf stove. Lots of sun on this property. Quiet back patio area with barbecue and patio furniture. Fireplace available in the winter months. We use cotton linen and towels. Pool open in May. Pool heating is an additional cost.

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 lighted deck and huge yard. The house features two wood-burning fireplaces in the living room and den and an outdoor fire-pit. RR# 26-891

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.

Designer's Own, w Pool, 5 min. to Ocean & Village
Our 4BR airy home in a prime Hamptons location--Water Mill South--offers comfort, luxury, and tranquility, all while being just 5 min. away from ocean beaches, restaurants in Bridgehampton Village, and the area's best fields and farm stands. Impeccably renovated, comfortable, family-oriented traditional shingle house is in a quiet, established neighborhood perfect for walks or bike rides. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking

Oasis backyard, Pool, Gym, and Sunroom!
Oasis pool and landscaping makes it feel like your on a private island. Sunroom with smart TV over looking oasis back yard. Decks in the back yard with lounge chairs and 2 patio dining tables. Front deck with lounge chairs. Outdoor gym located in the corner of the yard. Paddle boards, boogie boards, beach chairs, and beach towels provided. Walk to EHP Resort (SiSi Restaurant), and Harbor Bistro featured on Delicious Destinations. Paddle Diva paddle board/kayak rentals also nearby.

Private & Pristine with Pool and Kid’s Playard
INSTANT BOOK/ dates are current. Private and Pristine 3 bed / 2 bath home in the heart of East Hampton set on 1.3 acres. Home features a chef's kitchen, in-ground gated pool, and pure privacy and relaxation. Close proximity to East Hampton Village (5 mins) and East Hampton, Amangansett and Bay Beaches (7mins), Montauk (20 mins), Sag Harbor (15 mins). Kids adore the huge playground! Entire property fenced-in to ensure the safety of kids! Heated Pool open: Memorial Day - Sept 30.

East Hampton Oasis - Pool and Hot Tub
Nestled at the end of a private road in the Springs section of East Hampton, this classic Hamptons home will keep you and your friends/family entertained. Living room with sonos sound system, kitchen, 3 bedrooms, 2 bathrooms, outdoor living area with lounge chairs, a bbq, bar, pool and hot tub. All 3 bedrooms have AC. Towels and linens provided. Washer/dryer available. CLOSE TO BEACH AND EH VILLAGE. The pool is open May 5 through October 5. The hot tub remains open year round.

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR
Beautiful basement apartment partially in-ground, with many windows and private entrance is located in Sag Harbor , 3 minutes from village and Heavens Bech by car or 15 minutes walking distance . The apartment has king size bed and comfortable sofa in the living room . In the kitchen you can find coffe maker , toaster , microwave, dishwasher, small fridge , hot plate for light cooking . Tv , WiFi , Airconditoining , access to pool from May till end of the September .

Southamp Waterview, DogsFREE! Kayaks, Ping-Pong
Beachy casual feel-good home easily located at the entrance to The Hamptons. Lovely views of Bay, Nightly Sunsets & birds! Launch our Kayaks at street's tiny beach flowing from Cold Spring Pond into Bay. Or cuddle by the fireplace and play our many available games. We provide soft sheets & towels for the showers and & beach...priding ourselves on your comfort! Our Private-Pool is heatable & plant-surrounded with Outdoor Shower.

Pool Central Private Bridgehampton Home
Longer stay and reduced rate please email 169bridgehamptoncottage@gmail.com. NOTE* Rest assured, as always, even more so now, our housekeeper is aware to put in the extra tedious clean needed for a happy healthy stay! 7 minute drive to Hampton classic or less 20 min bike ride. Restaurants, studio 89 gym, on same rd. Ocean+bay 5-10 min drive. Bike to 1 ocean Yoga/winery. Halfway to Sag Harbor+Bridgehampton. There is pet fee.
Popular amenities for Sag Harbor rentals with a pool
House rentals with a pool

4 BD w/ Heated Pool in E Hampton, Fully Furnished

Secluded Farmhouse - Studio Apartment Style Unit

Contemporary East Hampton 4 Bedroom, Pool

Sag Harbor Charming Forest Home

Quintessential Summer Classic

Sunny, walk to beach, large pool

4 Bedroom Sag Harbor Home w/ Pool & Tennis Access

Hamptons Home w/ Salt Water Pool
Condo rentals with a pool

Beautiful Waterview Condo on the North Fork of LI

Waterfront Escape | Private Beach, Pool & Views

Beautiful condo on Long Islands Northfork

Sound Front Condominium

Greenport Getaway at Cliffside Condos

Beachside Waterview 2Br Condo w/ Pool in Greenport

Waterfront Condo C-204 at The Cliffside Resort

A Unique Piece of Paradise, Water Front pool
Home rentals with a private pool

Explore the Water & Woods at a Relaxing Retreat
East Hampton Villa | Heated Saltwater Pool & Beach
Enchanting Home with Large Decks and Heated Pool
Saltbox with Separate Poolhouse in Northwest Woods
Perfect Getaway at Sunny Modern Shampton LakeHouse
When is the best time to visit Sag Harbor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €920 | €856 | €890 | €643 | €857 | €1,051 | €1,286 | €1,371 | €896 | €710 | €760 | €912 |
| 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 |
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