Southampton vacation rentals

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Best Southampton vacation rentals

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$149 - $707$707 - $1,265$1,265 - $1,823$1,823 - $2,381$2,381+ per night

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Most recommended vacation rentals in Southampton

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Bermuda Connections Guest House - Southampton - Patio
Bermuda Connections Guest House
Southampton, Bermuda
8.6Very good(147)
Parking
Free Wi-Fi
Pool
$246+
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Brand New, modern, light, delightful small apartment packed with luxuries - Southampton - Bedroom
Brand New, modern, light, delightful small apartment packed with luxuries
Southampton, Bermuda
8.5Very good(14)
$206+
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Spacious Beachfront and Private Resort living - Southampton - Patio
Spacious Beachfront and Private Resort living
Southampton, Bermuda
9.8Wonderful(60)
Free Wi-Fi
$335+
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Charming , Comfortable Cottage Near Amenities - Southampton - Living room
Charming , Comfortable Cottage Near Amenities
Southampton, Bermuda
9.9Wonderful(36)
Free Wi-Fi
$253+
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Palmsprings Accommodations - 1 Bedroom Apt., Near Horseshoe Bay - Southampton - Beach
Palmsprings Accommodations - 1 Bedroom Apt., Near Horseshoe Bay
Southampton, Bermuda
9.7Wonderful(9)
Free Wi-Fi
$228+
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Location! Location! Half Price Sale @ 100 Nightly, October 1 - 17 And 27- Nov 1 - Southampton - Beach
Location! Location! Half Price Sale @ 100 Nightly, October 1 - 17 And 27- Nov 1
Southampton, Bermuda
9.9Wonderful(25)
Free Wi-Fi
$253+
Check availability
Clairfont, Jobson's Cove / Warwick Long Bay/ Horseshoe Beach - Apartment 7 - Southampton - Bedroom
Clairfont, Jobson's Cove / Warwick Long Bay/ Horseshoe Beach - Apartment 7
Southampton, Bermuda
9.5Wonderful(4)
$288+
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Large studio apartment w/ views. Close to beaches - Southampton - Beach
Large studio apartment w/ views. Close to beaches
Southampton, Bermuda
10Wonderful(23)
Free Wi-Fi
$243+
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Private studio cottage with pool near beaches - Southampton - Kitchen
Private studio cottage with pool near beaches
Southampton, Bermuda
8.5Very good(4)
$295+
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A Charming Bermuda Gem - Southampton - Balcony
A Charming Bermuda Gem
Southampton, Bermuda
10Wonderful(26)
Free Wi-Fi
$350+
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Palmsprings Accommodations - 3 Bedroom Cottage Near Horseshoe Bay - Southampton - Balcony
Palmsprings Accommodations - 3 Bedroom Cottage Near Horseshoe Bay
Southampton, Bermuda
10Wonderful(9)
Free Wi-Fi
$482+
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Stunning Views Of Horseshoe Bay Beach. Enjoy The Sounds Of The Lapping Waves! - Southampton - Kitchen
Stunning Views Of Horseshoe Bay Beach. Enjoy The Sounds Of The Lapping Waves!
Southampton, Bermuda
9.9Wonderful(35)
Free Wi-Fi
$1,851+
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Lovely Garden Setting, Close to Sail GP Site, PGA Port Royal,2 min walk to Beach - Southampton - Kitchen
Lovely Garden Setting, Close to Sail GP Site, PGA Port Royal,2 min walk to Beach
Southampton, Bermuda
9.8Wonderful(37)
Free Wi-Fi
$406+
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Palmsprings Accommodations - 2 Bedroom Apt., Near Horseshoe Bay - Southampton - Kitchen
Palmsprings Accommodations - 2 Bedroom Apt., Near Horseshoe Bay
Southampton, Bermuda
9.0Wonderful(2)
Free Wi-Fi
$354+
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'panatola' Studio With Breathtaking Views - Close To Beach - Southampton - Bedroom
'panatola' Studio With Breathtaking Views - Close To Beach
Southampton, Bermuda
10Wonderful(10)
$256+
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Southern Views - Southampton
Southern Views
Southampton, Bermuda
10Wonderful(43)
$1,505+
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Booking Insights

KAYAK’s insights for vacation rentals in Southampton

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Southampton with confidence.

Which month has the cheapest vacation rental rates in Southampton?

Vacation rentals are cheapest in Southampton in January, with average rates of $486. In comparison, July is the most expensive month, with prices at $1,811.

What is the cheapest day of the week to book a vacation rental in Southampton?

Wednesday offers the lowest rates in Southampton, with an average nightly price of $751. The highest prices are found on Thursday, with average rates at $1,309.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

January
July
$979
$1,015
Cheapest month to stay with an average 51% drop in price.
Most expensive month to stay with an average 84% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Southampton vacation rental deals

  • Vacation rentals in Southampton are around 41% cheaper than hotels on average. Search here to compare prices for all accommodation types in Southampton.
  • The best vacation rental properties in Southampton are Southern Views (10.0, 43 reviews), Large studio apartment w/ views. Close to beaches (10.0, 23), and A Charming Bermuda Gem (10.0, 26), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Southampton, you should consider visiting during the low season. The cheapest vacation homes in Southampton can be found in January and December.
  • The cheapest night for renting a vacation home in Southampton is Wednesday. In contrast, the most expensive is Thursday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Southampton for 4 days.

FAQs when booking a vacation home in Southampton

  • How much is a Rental rental for a week in Southampton?

    The average price for a weekly Southampton Rental rental found by KAYAK users in the last 2 weeks is $7,344. Though this can obviously vary depending on the time of year of your stay and when you make the booking.

  • How much is a Rental rental for a month in Southampton?

    The average price for a monthly Southampton Rental rental found by KAYAK users in the last 2 weeks is $32,321.

Where to stay in Southampton?

Our map will help you find the perfect place to stay in Southampton by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Southampton

Hotels near airports in Southampton

Hotels near Hamilton L.F Wade Intl Airport

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