Vacation rentals with a pool in Remsenburg-Speonk

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Top-rated rentals with a pool in Remsenburg-Speonk

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Apartment in Deer Park

4.95 out of 5 average rating, 115 reviews

Best Studio-Private Entrance+Parking-Close To All

Make yourself at home! This Deer Park Den is your perfect suburban hideaway in the heart of Long Island, close to everything and right in the middle of all the fun. Walking distance to lots of great restaurants that give you plenty of great options for ordering in or dining out. Other local destinations include: - Tanger outlets (1 Mile) - Heartland Golf Park (1.5 Miles) - Edgewood Oak Brush Plains Preserve (0.5 Mile) - Robert Moses state park (12 Miles) - Sunken Meadow state park (12 miles)

Aug 17 – 24

G$33,941 GYD per night

Guest favorite

Cottage in Southampton

4.96 out of 5 average rating, 164 reviews

Secluded Southampton Cottage w/Pool & Spa

*Follow Us on Insta @SimmerCottage* This designer-decorated cozy cottage near Southampton Village & a short drive or bike to the beach has a stocked chef's kitchen, cozy living room with wood-burning stone fireplace, 2 SmartTVs, whimsical dining room, 3 bedrooms, one bath & charming sunroom w/reading nooks. The Cottage has central heating/air & is set on a gated 1/2 acre w/hot-tub, outdoor dining for 8 on a stone patio, outdoor string lights, fire pit, gardener's potting station & gas BBQ.

Oct 9 – 16

G$102,853 GYD per night

Guest favorite

Home in Mastic Beach

4.93 out of 5 average rating, 107 reviews

Gorgeous Waterfront and Indoor Pool Family Oasis!

Breathtaking Waterfront home with 37 foot heated indoor pool. 3 Bedrooms plus a 800 Sq/Ft master bedroom with wood burning fireplace. WiFi, 3rd floor entertainment room with 120 inch screen movie projector, karaoke, fooseball, pool table. Wraparound terrace, sunroom, 45ft dock with launching ramp, putting green, sand trap, outdoor kitchen, bar & stone patio with tables & BBQ grills & fire pit. Ability to catch abundant fish & blue crabs right from the dock. Picture tells a thousand words.

Jan 21 – 28

G$234,127 GYD per night

Guest favorite

Home in Hampton Bays

4.94 out of 5 average rating, 111 reviews

Beautiful Hampton’s Home Pool/Tennis/HotTub/Sauna

Beautiful Hampton home down a long secluded driveway on 1.3 acres of land. Our one level luxurious home offers a heated inground pool, hot tub, full size tennis court and sauna. Our modern open floor concept contains six bedrooms and four baths all newly renovated with an enclosed sunroom. Close to Tiana Bays and 10 minute drive to Ponquogue Beach. Hampton Bays is the closest of the Hamptons which makes it the easiest to get to - less than 2 hours from Manhattan; escape to serenity.

Mar 27 – Apr 3

G$204,373 GYD per night

Guest favorite

Home in Manorville

4.99 out of 5 average rating, 201 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

Ultimate house with 4 Bds, 3 Baths, finished basement with entertainment area and gym. Minutes from the Hamptons and North Fork. Everything for your rest in any weather and season. Yamaha piano, Japanese massage chair, karaoke, drum set, electric guitars, ping pong, fossball and pool tables,board games. Fully landscaped backyard with flowering plants, outdoor lights. 2 BBQ areas, Gazebo with fireplace and projector. Easy access to beaches, restaurants, farms, vineyards and shopping.

Oct 18 – 25

G$119,972 GYD per night

Guest favorite

Home in Hampton Bays

4.98 out of 5 average rating, 112 reviews

Beach House Feel - newly renovated backyard Oasis

You will love this sunny, completely renovated three bedroom ranch. It's beautifully decorated with beach and nautical themes throughout the house. You can cook or barbeque at home on your private deck or go out and enjoy the many award winning restaurants in the area. Come home from the beach or shopping and lounge by the pool. At night, gather around the fire pit while making smores or just admiring the stars. This house is perfect for families, couples, or a girls/guys getaway.

Oct 25 – Nov 1

G$111,195 GYD per night

Guest favorite

Home in Westhampton

5.0 out of 5 average rating, 5 reviews

1940’s waterfront renovated bungalow

Come stay at this centrally located hamptons chic property. The whole group will enjoy easy access to many beaches, downtown Westhampton Beach and many NoFo wineries. Westhampton Beach is 6 minutes from the house and filled with many amazing restaurants and shops to explore. Explore all of the Hamptons and Northfork from this beautiful 4 bed and 3.5 bath home with inground pool. (Open MDW- mid September) *** No smoking or drugs on property. ***No pets

Jan 7 – 14

G$170,234 GYD per night

Guest favorite

Home in Westhampton Beach

4.93 out of 5 average rating, 134 reviews

Hampton's Haven

5 bedroom, 3.5 bath contemporary ranch style home, with custom shaped heated pool and meticulously maintained 7 seater hot tub. Expansive patio w/outdoor dining for 10 - close to beach, town and more! Our home has comfortable office space with gigabit wifi throughout! Fabulous game room with ping pong, 4 person air hockey, smart tv and board game lounge. Everything you'll need for a memorable gathering of friends or the perfect family vacation!

Oct 30 – Nov 6

G$161,018 GYD per night

Guest favorite

Home in Cutchogue

4.96 out of 5 average rating, 190 reviews

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.

Mar 7 – 14

G$173,097 GYD per night

Guest favorite

Guesthouse in Brookhaven

4.97 out of 5 average rating, 216 reviews

The Unhampton

This Brookhaven Hamlet detached space (totally separate) is for people who love nature and preserved quiet spaces. Fire Island is a ferry ride away, Manhattan is one hour by train and the Hamptons are a 25 minute ride.15 minutes from the restaurants and coffee shops in Patchogue and just a couple of minutes from Bellport Village. Centrally located and truly peaceful!

Feb 20 – 27

G$34,066 GYD per night

Guest favorite

Guesthouse in Westhampton

4.95 out of 5 average rating, 19 reviews

The “Birdy” Guest house

Take it easy at this peaceful guesthouse near Westhampton Beach village, Country Club, wine country (North folk), Moriches Bay and Westhampton Beaches. An amazing location for birding and kayaking. Ideal place for a couple looking to escape the city, attend a wedding, or explore wine country for a weekend to get some fresh air and experience nature.

Sep 20 – 27

G$68,478 GYD per night

Guest favorite

Loft in Southampton

4.89 out of 5 average rating, 145 reviews

Getaway cottage privet and quiet

Cottage is on the property with the owner but it is completely separate from our own home. We are in a lovely quiet neighborhood. We are friendly with animals we have our own dog as well. 5 Minute drive to the bay and 10-minute drive to the ocean. Baby crib can be additionally installed. Pool is shared with my family on property

Dec 3 – 10

G$82,413 GYD per night