A white house with a steep roof, two dormer windows, and a chimney, surrounded by a manicured lawn, hedge, and white picket fence with a gate and a lamp post in front.

Short Term Rental Management in The Hamptons Long Island & Catskills Hudson Valley area

More income. Less hassle. Expert management for homeowners, condos, and co-ops.

Get Started
Bright living room with white sofas, armchairs, a wooden coffee table, large windows with views of a green backyard, and exposed wooden beams on the ceiling.
A snowy landscape with a wooden house, snow-covered car, tall pine trees, and a mountain in the background.

Local. Boutique. Proven.

Deep Local Knowledge
We live and work here. From Westhampton to Montauk, and throughout the Catskills and Hudson Valley, we understand what guests want and what homeowners need.

Multi-Channel Marketing
Not just Airbnb. We manage listings across Airbnb, VRBO, Booking.com, TripAdvisor, and more.

Full-Service Management
From guest support to housekeeping, maintenance, and pricing — we handle it all, so you don’t have to.

Flexible Agreements
No long-term contracts. Just long-term value.

Why Olander & Sons is Different

Our services

  • Channel Management

    We market your property across the world’s most trusted booking platforms to maximize exposure and revenue.

  • Guest Communications & Support

    24/7 guest messaging, check-in coordination, and emergency support — all handled professionally in-house.

  • Maintenance & Operations

    From routine upkeep to urgent repairs, our team ensures your property is always guest-ready.

  • Dynamic Pricing

    We monitor market demand and adjust rates daily to maximize your earnings while keeping occupancy high.

  • Housekeeping

    Reliable, detail-oriented cleaning teams keep your home spotless and ready for every guest.

  • Asset Management Services

    We protect and maintain your property as if it were our own, with transparency and regular reporting.

View from a balcony overlooking a beach, with sand, dunes, and ocean, and neighboring beachside buildings.

More Than Just Homes

Our expertise goes beyond single-family homes. We’ve successfully managed co-op and condo rental programs, and we know how powerful they can be. By managing entire property pools, we:

Provide seamless booking across dozens of units.

Oversee dedicated housekeeping and maintenance teams.

Handle both individual owner rentals and building-wide rental programs.

Caitlin's five-star review from Lindenhurst, New York, describing a house perfect for family vacation, with a pool and yard for kids to run around.
Text review about a historic house stay near a pool and farmhouse in New York.
Screenshot of a review by Janine from Hoboken, New Jersey, dated June 2024, describing her positive experience at a vacation rental with a pool and backyard, mentioning the house's proximity to town and the beach, parking space, and her boyfriend's proposal in the backyard.

Guest Testimonials

What Our Guests Are Saying About Us

Review by Jen for a stay in August 2024, praising the hostess C and describing the home as charming, spacious, modern, with a backyard, and excellent hospitality.
Screenshot of a five-star review from Nathaniel about his stay in Great Neck, New York, praising the home's decor, amenities, host responsiveness, and early check-in.
A review from a guest named Christopher describing a cottage in New York, with details about the home, kitchen, garden, pool, and hosts.
Screenshot of an Airbnb review by Michael, from New York, New York, dated July 2024, praising the home and amenities.
Review describing a stay at a house with a garden and pool in the Hamptons, praising the location and hosts.

Where we work

South Fork, Long Island — from Westhampton to Montauk

including Quogue, Hampton Bays, Southampton, Water Mill, Bridgehampton, Sagaponack, Sag Harbor, Wainscott, East Hampton, Amagansett, and Montauk.

Catskills & Hudson Valley

including Woodstock, Hunter, Jewett, Windham, Tannersville, Phoenicia, Beacon, Cold Spring and Rhinebeck.

Side-by-side images of nature: the left shows a beach with a grassy foreground, sand, and calm ocean waters under a partly cloudy sky; the right shows a mountainous landscape with green trees, a lake, and a distant mountain at sunset.

Ready to Get Started?

Whether you’re a homeowner, co-op, or condo board, Olander & Sons makes short-term rental management simple and profitable.