Southampton Rentals, Southampton Summer Vacation Rentals, Rent Southampton Homes & Properties
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 | $115,000April through Labor Day 2026 $19,000April through May 2026 $8,000April 1-30th 2026 $42,500August 1st to Labor Day 2026 $42,500August 1-31st 2026 $85,000July 1st thru Labor Day 2026 $42,500July 1-31st 2026 $70,000June-July 2026 $48,000June 1-30th 2026 $105,000May through Labor Day 2026 $12,000May 1-31st 2026 $90,000Memorial Day to Labor Day 2026 $8,000November 1-30th 2026 $12,000October 1-31st 2026 $15,000September 1-30th 2026 $175,000Year round 2026 | Southampton Summer Rental 4BR w Pool, Jeep Wrangler & Beach Pass 21 Kennedy Dr |
 | $40,000August 1st to Labor Day 2026 $40,000August 1-31st 2026 $75,000July 1st thru Labor Day 2026 $35,000July 1-31st 2026 $95,000Memorial Day to Labor Day 2026 $6,500April 1-30th 2026 $6,500January 1-31st 2026 $6,500March 1-31st 2026 $6,500November 1-30th 2026 $6,500October 1-31st 2026 | 5 BR 2½ 2600 sq ft Single Family Rental |
 | $40,000April through May 2026 $20,000April 1-30th 2026 $60,000August 1st to Labor Day 2026 $12,000January 1-31st 2026 $12,000March 1-31st 2026 $25,000May 1-31st 2026 $12,000November 1-30th 2026 $12,000October 1-31st 2026 $20,000September 1-30th 2026 $225,000Year round 2026 | 6 BR 5½ 4000 sq ft Single Family Rental |
 | $40,000August 1-31st 2026 $35,000July 1-31st 2026 | 3 BR 2½ 2500 sq ft Single Family Rental |
 | $25,000September 1-30th 2026 | Ideal Quogue Village rental situated on the prestigious Dune Road 76 Dune Rd |
 | $30,000April 1-30th 2026 $25,000January 1-31st 2026 $375,000July 1st thru Labor Day 2026 $150,000June 1-30th 2026 $25,000March 1-31st 2026 $40,000May 1-31st 2026 $425,000Memorial Day to Labor Day 2026 $25,000November 1-30th 2026 $25,000October 1-31st 2026 | 5 BR 7½ 5300 sq ft Single Family Rental |
 | $17,500September 1-30th 2026 | 4 BR 4 3074 sq ft Single Family Rental |
 | $30,000January 1-31st 2026 $30,000March 1-31st 2026 $30,000November 1-30th 2026 $40,000October 1-31st 2026 $175,000August 1st to Labor Day 2026 | 6 BR 7½ 5312 sq ft Single Family Rental |
 | $18,000August 1-31st $18,000August 1st to Labor Day | Beautiful Home in The Bucolic Hamlet of Remsenburg 20 Basket Neck Ln |
 | $125,000August 1st to Labor Day 2026 $100,000July 1-31st 2026 $50,000June 1-30th 2026 $250,000Memorial Day to Labor Day 2026 $50,000September 1-30th 2026 | 6 BR 5½ 5600 sq ft Single Family Rental |
 | $20,000July 1st thru Labor Day 2026 $25,000Memorial Day to Labor Day 2026 $5,000September 1-30th 2026 | Village Apartment 89 Jobs Ln Apt 4 |
 | $20,000June 1-30th $25,000Short term | 3 BR 1.5 1200 sq ft Single Family Rental |
 | $185,000August 1st to Labor Day 2026 $350,000July 1st thru Labor Day 2026 $175,000July 1-31st 2026 $235,000June-July 2026 $70,000June 1-30th 2026 $400,000Memorial Day to Labor Day 2026 $40,000April 1-30th 2026 $25,000January 1-31st 2026 $25,000March 1-31st 2026 $50,000May 1-31st 2026 $25,000November 1-30th 2026 $25,000October 1-31st 2026 $45,000September 1-30th 2026 | 6 BR 6½ 6000 sq ft Single Family Rental |
 | $10,000November 1-30th 2026 $10,000October 1-31st 2026 $25,000September 1-30th 2026 $75,000July 1-31st 2026 $100,000June-July 2026 $35,000June 1-30th 2026 | Perfection on Shinnecock Bay 46 Atterbury Rd |
 | $28,000August 1st to Labor Day 2026 $45,000July 1st thru Labor Day 2026 $24,000July 1-31st 2026 $60,000Memorial Day to Labor Day 2026 $9,800October 1-31st 2026 $9,800September 1-30th 2026 | 4 BR 3½ 3400 sq ft Single Family Rental |
 | $115,000Memorial Day to Labor Day 2026 $25,000June 1-30th 2026 $45,000July 1-31st 2026 $50,000August 1-31st 2026 $55,000August 1st to Labor Day 2026 $95,000July 1st thru Labor Day 2026 | Sag Harbor Waterfront Home 27 Clearview Dr |
 | $20,000August 1st to Labor Day 2026 $37,000July 1st thru Labor Day 2026 $20,000July 1-31st 2026 | 4 BR 3 2000 sq ft Single Family Rental |
 | $15,000April 1-30th 2026 $55,000August 1st to Labor Day 2026 $50,000August 1-31st 2026 $12,000January 1-31st 2026 $100,000July 1st thru Labor Day 2026 $50,000July 1-31st 2026 $75,000June-July 2026 $30,000June 1-30th 2026 $12,000March 1-31st 2026 $20,000May 1-31st 2026 $125,000Memorial Day to Labor Day 2026 $12,000November 1-30th 2026 $12,000October 1-31st 2026 $22,000September 1-30th 2026 $30,000Winter 2026 $225,000Year round 2026 | Southampton Village 4 Bedroom 5 Juniper Ln |
 | $70,000April through Labor Day 2026 $20,000August 1st to Labor Day 2026 $38,000July 1st thru Labor Day 2026 $18,000July 1-31st 2026 $30,000June-July 2026 $20,000June 1-30th 2026 $60,000May through Labor Day 2026 $50,000Memorial Day to Labor Day 2026 $5,000November 1-30th 2026 $6,000October 1-31st 2026 $12,000September 1-30th 2026 $90,000Year round 2026 | Beautiful 4 Bedroom in Sag Harbor Sag HarborWebID# 1087353 4 BR 3 2000 sq ft Single Family Rental |
 | 4 BR 4.5 4695 sq ft Single Family Single Family | |
 | $45,000August 1-31st | 4 BR 4 4000 sq ft Single Family Rental |
 | $195,000August 1-31st $195,000August 1st to Labor Day | 4 BR 4.5 3700 sq ft Single Family Rental |
 | $125,000August 1-31st | Unique opportunity in the heart of Westhampton Beach 86 Jessup Ln |
 | $10,000September 1-30th 2026 | 4 BR 3 1602 sq ft Single Family Rental |
 | $75,000July 1-31st $75,000August 1-31st | 1 of a kind rental in Southampton SouthamptonWebID# 1736525 6 BR 5 4500 sq ft Single Family Rental |
 | $275,000August 1st to Labor Day | Stunning Estate:Luxury Living Just Minutes from the Ocean! 108 Fairfield Pond Ln |
 | $75,000July 1st thru Labor Day $96,000Year round $15,000September 1-30th | Southampton Summer or Year Round Rental Close to Village & Beach 16 Kings Ln |
 | $70,000July 1-31st | Refined Restoration in Southampton Village - 6 Bed With Pool 305 North Main St |
 | $85,000August 1-31st $25,000September 1-30th $85,000July 1-31st $190,000July 1st thru Labor Day $290,000Year round | 7 BR 6 4500 sq ft Single Family Single Family |
 | $210,000April through Labor Day $30,000April through May $15,000April 1-30th $215,000May through Labor Day $17,500May 1-31st $205,000Memorial Day to Labor Day $215,000Extended season $115,000June-July $115,000June 1-30th $175,000July 1-31st $110,000August 1st to Labor Day $100,000August 1-31st $20,000September 1-30th $15,000October 1-31st $13,500November 1-30th $13,500December 1-31st $220,000Year round $12,500January 1-31st $12,500February 1-28th $13,500March 1-31st $15,000April 1-30th $115,000June 1-30th $175,000July 1-31st | FURNISHED 5 BR 6 4800 sq ft House House |
 | $105,000August 1-31st $110,000August 1st to Labor Day $22,500September 1-30th $20,000October 1-31st $13,500November 1-30th $13,500December 1-31st $12,500January 1-31st $12,500February 1-28th $12,500March 1-31st $15,000April 1-30th $17,500May 1-31st $35,000June 1-30th $95,000July 1-31st $205,000Memorial Day to Labor Day $215,000Extended season $220,000Year round $215,000April through Labor Day $30,000April through May $210,000May through Labor Day | Sagaponack 4BD/4BA. 1.2mi to beach w/ Pool House 5 Ranch Ct, Sagponack, NY 11962 |
 | $40,000September 1-30th $150,000August 1st to Labor Day | Recently Built Modern Barn 44 Lee Ave |
 | South of Hwy Watermill 5 Br Gunite Pool Near Ocean 294 Rose Hill Rd Unit 294 | |
 | $20,000Short term $79,000August 1-31st $55,000July 1-31st $37,000September 1-30th | Southampton Village Rental 20 Little Plains Rd |
 | $100,000July 1-31st $110,000August 1-31st | One of a Kind in Heart of Horse&Wine Country with Pool and Tennis 1366 Scuttle Hole Rd |
 | $279,900Year round $179,900May through Labor Day $169,900July 1st thru Labor Day $189,900April through Labor Day $25,000October 1-31st $25,000November 1-30th $25,000December 1-31st $60,000Winter $12,000Short term | 5 BR 4 4000 sq ft Residential Rental |
| 495 found | ||
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