Holiday rentals with a pool in Remsenburg - Speonk

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Remsenburg - Speonk

Total holiday rentals
Explore 40 holiday rentals in Remsenburg - Speonk
Nightly prices starting at
Remsenburg - Speonk holiday rentals start at €129 per night before taxes and fees
Verified guest reviews
Over 420 verified reviews to help you choose
Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 10 rentals that welcome pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 of Remsenburg - Speonk holiday rentals include wifi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Remsenburg - Speonk rentals
4.8 Average rating
Remsenburg - Speonk stays are highly rated by guests – averaging 4.8 out of 5!

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 favourite

Home in Springs

Serene + private ~ 1 block to waterfront dining

Enjoy zen living at this serene, chic, Hamptons oasis! Ideally located 1 block to waterfront dining, 8 minutes to beaches + 9 minutes to Main St! Relax poolside w/ tons of greenery + nature views. Spark up the BBQ + firepit under the starry sky. Listen to the crickets + spot a deer on the property. Curl up to the wood burning fireplace, cook in your Chef's kitchen + stream on your 80' TV Enjoy coffee on the sea + dinner w the best sunsets just 1 block away. A perfect escape + place to unwind!

4.91 out of 5 average rating, 141 reviews

Top guest favourite

A heated saltwater pool is surrounded by a spacious green lawn and lounge chairs, with a tree-lined white fence in the background. The house features a charming design with large windows and a wide patio area, suitable for outdoor dining and relaxation.

Home in Hampton Bays

Stylish+Modern Cape w/Saltwater Pool-5min to Beach

Stylish+Modern Cape Beach House nestled in Hampton Bays South of the highway, 5 min drive to beaches. Heated Saltwater Pool. 4 Bedrooms+Crib room & Office. 2 Bathrooms. Outdoor deck w/family dining+BBQ. Fully-fenced, tree-lined back yard w/ beautiful sunsets. Upstairs King bedroom w/ensuite bthrm + Twin bedroom directly off master. Main floor has another King bedroom+Twin bedroom, master bath, lounge+kitchen w/huge sit-around island. TV Den. Central AC. 15 min walk/ 2 min drive to shops+train.

4.97 out of 5 average rating, 154 reviews

Top guest favourite

A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.

Home in Mattituck

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.

4.93 out of 5 average rating, 134 reviews

Guest favourite

A calm waterfront scene features a vibrant sailboat gliding across the bay, surrounded by green marshland. A wooden dock leads into the water, with several colorful chairs positioned for relaxation. Soft hills and houses line the distant shore under a gentle mist.

Home in Mastic Beach

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.

4.92 out of 5 average rating, 142 reviews

Top guest favourite

A contemporary home with large windows overlooks a serene pool area. Lush greenery surrounds the property, providing a natural backdrop. Sun loungers are positioned beside the pool on spacious stone decking, inviting relaxation and outdoor enjoyment.

Home in Westhampton Beach

Hamptons Oasis: pool, grill, lush landscape

Kick back and relax in this calm, stylish, contemporary masterpiece. 4 beds, 3 baths, eco pool, and expansive outdoor living space. Architecturally impressive structure surrounded by lush landscape and tastefully decorated. The outdoor space includes a pool, a new outdoor grill, a fire pit, pool lounge chairs, a dining table under a wisteria pergola and an outdoor sofa area big enough to fit your entire party. Fully equipped kitchen. Short drive to the beach and to downtown Westhampton.

4.94 out of 5 average rating, 143 reviews

Guest favourite

Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

🛏 6 Bedrooms, 9 beds & 3 Full Baths 🏊‍♂️ Heated Pool & Relaxing Hot Tub 4-person Sauna 🏀 Half Basketball Court & 🏐 Volleyball Area 🏌️‍♂️ Private Golf Putting Green 🔥 Cozy Firepit & Outdoor Lounge Area 🛝 Swing Set & Kid-Friendly Yard 🍽 Fully Stocked Kitchen & Spacious Dining 🌐 High-Speed Wi-Fi & Smart TVs 10 min to Smith Point Beach & Boardwalk 15–20 min to Long Island Wine Country Nearby hiking at Wertheim Wildlife Refuge Short drive to Tanger Outlets & restaurants

4.96 out of 5 average rating, 184 reviews

Top guest favourite

A landscaped outdoor area features a stone fire pit surrounded by bright blue chairs on a gravel surface. Lush greenery and tall trees provide privacy, while a spacious pool bordered by lounge chairs is situated in the background.

Home in East Quogue

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.

4.99 out of 5 average rating, 151 reviews

Guest favourite

A serene scene features a well-kept pool surrounded by lounge chairs, reflecting the colors of the sunset. The main house and pool house are visible, each with large windows and inviting outdoor spaces. Lush greenery outlines the property, enhancing the tranquil setting.

Home in Hampton Bays

Stunning Hamptons Waterfront Escape w/ Sunset View

Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views and sunset 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! Our pool will close on September 15th, 2026 and will reopen May 29, 2027.

4.87 out of 5 average rating, 137 reviews

Guest favourite

Home in East Quogue

Est.1840 Farmhouse | Heated Pool & by Bay

Pull up Friday and the 200-year-old farmhouse settles you — wide front porch set up for morning coffee, heated pool glowing out back, and that specific exhale that only happens when you've actually left the city behind. Goldberg's Bagels is a short walk. The bay is around the corner. The neighborhood is quiet — and the Jitney drops you right here. Come for the Hamptons. Stay because of the house. Your group has been trying to plan this trip. You just found the place.

4.94 out of 5 average rating, 100 reviews

Guest favourite

A spacious backyard is showcased with a large saltwater pool, featuring a floating inflatable and sun loungers arranged along the edge. The house stands in the background, framed by trees and an inviting grassy area, enclosed by a black fence.

Home in Hampton Bays

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach

Unwind in Hamptons Bliss! A coastal oasis awaits at this exquisite vacation house. Immerse yourself in luxury, from the elegant interiors to the serene outdoor retreat including a massive fenced-in salt water heated pool (Memorial Day to Labor Day) that will leave you in awe. Indulge in beachside bliss, upscale shopping, and culinary delights. Create memories that will linger long after the sun sets over the horizon. Your dream Hamptons getaway starts here!

4.94 out of 5 average rating, 116 reviews

Top guest favourite

A contemporary ranch-style home is surrounded by lush greenery. The custom-shaped heated pool features a waterfall and is bordered by a stone patio with lounge chairs and umbrellas. A state-of-the-art hot tub is positioned nearby, enhancing the outdoor relaxation space.

Home in Westhampton Beach

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!

4.93 out of 5 average rating, 165 reviews

Top guest favourite

A serene outdoor area showcases a saltwater pool with a spa, surrounded by well-maintained landscaping featuring vibrant yellow flowers. Lush green fields extend into the distance, framed by a clear sky with scattered clouds.

Home in North Fork

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.

4.97 out of 5 average rating, 218 reviews