Summer Rentals · Hamptons, New York · Luke Cawley SERHANT.

Hamptons Rental Homes
Your Summer Awaits

From Memorial Day to Labor Day — and beyond. Luke Cawley matches renters with exceptional Hamptons homes and helps owners maximize their seasonal rental income across every community on the South Fork.

Find Your Summer Rental View Rental Rates
$80K
Avg. Summer Season Rental
$300K
Peak Oceanfront Weekly
June–Sept
Peak Season Window
16+
Hamptons Communities
Hamptons Rentals

Find Your Perfect
Hamptons Summer Home

The Hamptons summer rental market is one of the most sought-after in the world. From modest three-bedroom cottages in Hampton Bays to oceanfront estates on Meadow Lane available for $300,000 per week, Luke Cawley connects renters with the right property at the right price — and owners with the most qualified tenants.

The peak rental season runs Memorial Day through Labor Day. The most desirable properties — particularly oceanfront and village-adjacent homes — are typically booked by January for the following summer. If you are seeking a premium Hamptons rental, start your search early and work with an agent who knows what's available before it hits the market.

Luke's Rental Service
Access to exclusive and unlisted rental inventory
Full rental contract and lease preparation
Owner rental listing and marketing services
Tenant qualification and screening
Guidance on rental permit requirements (Southampton & East Hampton)
Year-round market — fall, winter, and spring rentals available
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Entry / Seasonal
$10K–$35K/week
Memorial Day – Labor Day
Hampton Bays, Springs, Flanders, Remsenburg. Three to five bedroom homes, pools, and community access. Ideal for families and groups seeking Hamptons proximity with accessible rates.
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Mid-Tier Luxury
$35K–$80K/week
Peak Season
Sag Harbor, Bridgehampton, Amagansett, Water Mill. Five to seven bedroom homes with pools, media rooms, and village proximity. The core of the Hamptons summer rental market.
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Ultra-Luxury
$80K–$300K+/week
Peak Season
Ocean Village, East Hampton Village, Sagaponack oceanfront. Seven-plus bedroom estates with direct ocean access, staff quarters, tennis, pool, and unmatched amenities. Book by January.
Community-by-Community

Hamptons Rental Rates
by Community

Southampton Village
$25K–$150K/week
Village estates and oceanfront homes on Gin Lane and Meadow Lane. The most in-demand summer rental community in the Hamptons.
East Hampton Village
$30K–$200K/week
Further Lane, Lily Pond, and Georgica oceanfront estates. The prestige address of the Hamptons rental market.
Bridgehampton
$18K–$80K/week
Farm-view and ocean-proximity estates. Luke's home market — exceptional properties at competitive rates between the two villages.
Sagaponack
$25K–$300K+/week
The most exclusive ocean-facing community. True oceanfront here commands the highest rates in the entire Hamptons market.
Amagansett
$15K–$75K/week
Beloved beach town with exceptional ocean access. Loyal repeat renter base. Books early every year.
Sag Harbor / Springs
$10K–$45K/week
Bayfront retreats and year-round community charm. Outstanding value for renters who want a genuine Hamptons experience.
Renters & Owners

Whether You're Looking
to Rent or to List

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Finding a Hamptons Rental
Luke's rental search service gives you access to properties that never appear on public platforms. Unlisted inventory, word-of-mouth opportunities, and properties available through the SERHANT. agent network — all curated to match your specific requirements.
  • Budget-matched curation across all Hamptons communities
  • Access to unlisted and exclusive rental inventory
  • Lease preparation and tenant-side representation
  • Direct owner relationships — no corporate middlemen
  • Year-round availability including fall and shoulder season
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Listing Your Hamptons Home
Turning your Hamptons property into a rental income machine requires skilled marketing and the right tenant. Luke helps homeowners maximize seasonal rental income with strategic pricing, professional marketing, and rigorous tenant screening.
  • Rental permit guidance for Southampton and East Hampton
  • Strategic weekly pricing to maximize seasonal revenue
  • Tenant qualification and financial screening
  • Lease drafting and legal compliance
  • Off-season rental opportunities to extend income year-round
Common Questions

Hamptons Rentals
FAQ

When should I start looking for a Hamptons summer rental?
Yesterday. The best Hamptons rental properties — particularly oceanfront and village-adjacent homes — are typically booked by December or January for the following summer season. For a July 4th rental, start no later than October. Working with Luke gives you access to unlisted inventory that the public never sees.
Do I need a rental permit to rent my Hamptons home?
Yes. Both Southampton Town and East Hampton Town require rental permits for short-term rentals. The permit process includes a property inspection and fee. Luke guides owners through the full permit process — failure to obtain a permit can result in significant fines.
What is the difference between renting and buying in the Hamptons?
Renting provides flexibility and the ability to experience different communities before committing to a purchase. Many Hamptons buyers start as renters and find their preferred community through seasonal experience. Luke helps renters who decide to buy make the transition smoothly — with the advantage of having lived in the market.
How much can I earn renting my Hamptons home?
Peak season Hamptons rentals (Memorial Day through Labor Day) generate substantial income. A modest three-bedroom in Sag Harbor might rent for $10,000–$15,000/week. An oceanfront estate can generate $100,000–$300,000 or more per week. Many owners cover 100% of their annual carrying costs with 10–12 weeks of peak rental income.

Hamptons Rental Homes — Your Complete Guide

The Hamptons rental market is one of the most dynamic and competitive seasonal rental markets in the United States. From Memorial Day through Labor Day, the South Fork of Long Island transforms into one of the most sought-after summer destinations in the world — and demand for quality rental homes consistently exceeds available supply across every price tier and community.

Hamptons summer rentals span an enormous range. Hampton Bays and Springs offer accessible seasonal rentals from $10,000 to $25,000 per week, while the oceanfront estates of Sagaponack and East Hampton Village command $100,000 to $300,000 or more per week at peak season. Between these poles lies the heart of the Hamptons rental market: well-appointed three to five bedroom homes in Bridgehampton, Amagansett, Sag Harbor, Water Mill, and Southampton Village from $18,000 to $80,000 per week.

For homeowners considering renting their Hamptons property, the income potential is extraordinary. A well-priced, well-maintained Hamptons home can generate enough seasonal rental revenue to cover 100% of annual carrying costs — mortgage, taxes, insurance, and maintenance — leaving the property essentially self-financing between owner visits. Luke Cawley guides Hamptons homeowners through the full rental process: permit acquisition, strategic pricing, tenant qualification, and lease documentation.

For renters, Luke's access to unlisted and off-market Hamptons rental inventory is the most important advantage in a market where the best properties are claimed months before the season begins. Contact Luke Cawley today to discuss your Hamptons rental search or to learn how to maximize the income potential of your Hamptons property.

Find Your Hamptons
Summer Home

Luke Cawley matches renters with exceptional Hamptons homes — including unlisted inventory that never hits the public market. Start your search today.

Start Your Rental Search
Rental Inquiry

Tell Luke What
You're Looking For

Whether you're seeking a summer rental or looking to list your Hamptons home, Luke is ready to help. All inquiries are handled promptly and confidentially.

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OfficeSERHANT. · Bridgehampton, NY 11932
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Phone(631) 555-0100
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Emailluke.cawley@serhant.com
Hamptons Rental Inquiry
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