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Holiday homes in Southampton You’ll Love

Top-Rated Southampton Holiday homes for Every Budget and Style!

Looking for a holiday home in Southampton (Florida)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $50.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Southampton.

We found 38 Holiday-homes in Southampton and the surrounding area (within 20 miles)

Villa Gavin in Southampton, USA

Villa Gavin

Villa in Southampton, Florida , Montauk Highway
Villa Gavin is located in Southampton, just 20 miles from Splish Splash and 23 miles from Montauk Point Lighthouse.
  • Parking
  • Pets allowed
  • Family rooms
  • Indoor pool
  • Outdoor pool

Exceptional 1 Reviews 10.0

from $1.280.67 Show details »

Villa Perlman in Southampton, USA

Villa Perlman

Villa in Southampton, Florida , 25 Aqua Drive
Villa Perlman is located in Southampton, just 18 miles from Splish Splash and 26 miles from Montauk Point Lighthouse.
  • Parking
  • Pets allowed
  • Bar
  • Outdoor pool
  • Swimming pool

Exceptional 1 Reviews 10.0

from $2.199.64 Show details »

Villa Skylar in Southampton, USA

Villa Skylar

Villa in Southampton, Florida , 288 Montauk Highway
Featuring a garden, Villa Skylar provides accommodations in Southampton.
  • Parking
  • Pets allowed
  • Family rooms
  • Outdoor pool
  • Swimming pool

Exceptional 1 Reviews 10.0

from $2.391.83 Show details »

Villa Southampton Village in Southampton, USA

Villa Southampton Village

Villa in Southampton, Florida , Hill Street
Villa Southampton Village offers accommodations in Southampton, 1.9 miles from Cryder Beach and 21 miles from Splish Splash.
  • Parking
  • Pets allowed
  • Family rooms
  • Outdoor pool
  • Swimming Pool

no reviews

from $75.00 Show details »

Villa Lalam in Southampton, USA

Villa Lalam

Villa in Southampton, Florida , 2 Tuckahoe Rd
Providing a garden, Villa Lalam provides accommodations in Southampton.
  • Parking
  • Pets allowed
  • Bar
  • Family rooms
  • Outdoor pool

Exceptional 1 Reviews 10.0

from $60.00 Show details »

Villa Noyaan - Luxury with pool in Southampton, USA

Villa Noyaan - Luxury with pool

Villa in Southampton, Florida , 39 Pheasant Close South
1.5 miles from Little Plains Beach in Southampton, Villa Noyaan - Luxury with pool provides accommodations with access to a fitness center.
  • Parking
  • Pets allowed
  • Sauna
  • Fitness centre
  • Family rooms

Exceptional 1 Reviews 10.0

from $12.137.00 Show details »

Villa Revello - Luxury with pool in Southampton, USA

Villa Revello - Luxury with pool

Villa in Southampton, Florida , Saint Andrews Road
Offering a garden, Villa Revello - Luxury with pool provides accommodations in Southampton.
  • Parking
  • Pets allowed
  • Bar
  • Family rooms
  • Outdoor pool

no reviews

from $2.572.43 Show details »

Villa Qadus - Luxury with pool in Southampton, USA

Villa Qadus - Luxury with pool

Villa in Southampton, Florida , Halsey Farm Drive
Providing a garden, Villa Qadus - Luxury with pool features accommodations in Southampton.
  • Parking
  • Pets allowed
  • Bar
  • Fitness centre
  • Family rooms

no reviews

from $7.786.00 Show details »

Villa Flasses - Luxury with pool in Southampton, USA

Villa Flasses - Luxury with pool

Villa in Southampton, Florida , Spring Pond Lane
Featuring a casino, Villa Flasses - Luxury with pool offers accommodations in Southampton.
  • Parking
  • Pets allowed
  • Bar
  • Fitness centre
  • Breakfast in the room

Exceptional 1 Reviews 10.0

from $1.867.99 Show details »

Villa Emery in Water Mill, USA

Villa Emery

Villa in Water Mill near Southampton, Florida , 7 Ponds Road
Providing a garden, Villa Emery offers accommodations in Water Mill.
  • Parking
  • Pets allowed
  • Bar
  • Family rooms
  • Indoor pool

Exceptional 1 Reviews 10.0

from $98.00 Show details »

Villa Burak - Luxury with pool in Bridgehampton, USA

Villa Burak - Luxury with pool

Villa in Bridgehampton near Southampton, Florida , Silver Lane
Just 1.1 miles from Mecox Beach and 1.1 miles from Ocean Road Beach, Villa Burak - Luxury with pool features accommodations in Bridgehampton with a ba...
  • Parking
  • Pets allowed
  • Bar
  • Family rooms
  • Breakfast in the room

Exceptional 1 Reviews 10.0

from $211.00 Show details »

Villa Xmart - Luxury with pool in Water Mill, USA

Villa Xmart - Luxury with pool

Villa in Water Mill near Southampton, Florida , 14 Rose Hill Road
Offering a garden, Villa Xmart - Luxury with pool features accommodations in Water Mill.
  • Parking
  • Pets allowed
  • Bar
  • Family rooms
  • Outdoor pool

Exceptional 1 Reviews 10.0

from $4.132.19 Show details »

Villa Victoria - Cozy Hamptons Villa in Bridgehampton, USA

Villa Victoria - Cozy Hamptons Villa

Villa in Bridgehampton near Southampton, Florida , 81 Bridgefield Rd
Villa Victoria - Cozy Hamptons Villa offers accommodations in Bridgehampton, 15 miles from Montauk Point Lighthouse and 20 miles from Second House Mus...
  • Parking
  • Pets allowed
  • Family rooms
  • Outdoor pool
  • Swimming pool

Exceptional 2 Reviews 10.0

from $53.00 Show details »

Villa Zainip - Luxury with pool in Sag Harbor, USA

Villa Zainip - Luxury with pool

Villa in Sag Harbor near Southampton, Florida , 77 Northside Drive
Offering a garden, Villa Zainip - Luxury with pool provides accommodations in Sag Harbor.
  • Parking
  • Pets allowed
  • Bar
  • Sauna
  • Family rooms

Fabulous 1 Reviews 9.0

from $4.713.58 Show details »

lovely Southampton Estate on Shinnecock Bay in Hampton Bays, USA

lovely Southampton Estate on Shinnecock...

Holiday home in Hampton Bays near Southampton, Florida , 6 White Lane
16 miles from Splish Splash in Hampton Bays, lovely Southampton Estate on Shinnecock Bay provides accommodations with access to a fitness room.
  • Parking
  • Pets allowed
  • Fitness centre
  • Family rooms
  • Kids' outdoor play equipment

no reviews

from $72.00 Show details »

Hamptons 5 Bedroom Estate in Hampton Bays, USA

Hamptons 5 Bedroom Estate

Holiday home in Hampton Bays near Southampton, Florida , 6 White Lane
Hamptons 5 Bedroom Estate is located in Hampton Bays, just 16 miles from Splish Splash and 29 miles from Montauk Point Lighthouse.
  • Parking
  • Pets allowed
  • Swimming pool
  • Swimming Pool

no reviews

from $53.00 Show details »

Lovely Year Round Vacation Home in the Hamptons in Hampton Bays, USA

Lovely Year Round Vacation Home in the H...

Holiday home in Hampton Bays near Southampton, Florida , 6 White Lane
Lovely Year Round Vacation Home in the Hamptons is located in Hampton Bays, just 16 miles from Splish Splash and 29 miles from Montauk Point Lighthous...
  • Parking
  • Pets allowed
  • Bar
  • Sauna
  • Fitness centre

no reviews

from $50.00 Show details »

Bright and Airy in Hampton Bays in Hampton Bays, USA

Bright and Airy in Hampton Bays

Holiday home in Hampton Bays near Southampton, Florida , 44 Riverdale Drive
Bright and Airy in Hampton Bays is located in Hampton Bays, just 17 miles from Splish Splash and 29 miles from Montauk Point Lighthouse.
  • Parking
  • Pets allowed
  • Swimming Pool

no reviews

from $93.00 Show details »

Enormous Getaway Home w/private pool in Hampton Bays, USA

Enormous Getaway Home w/private pool

Holiday home in Hampton Bays near Southampton, Florida , 4 Lynn Avenue
Enormous Getaway Home w/private pool offers accommodations in Hampton Bays, 1.7 miles from Meschutt Beach and 16 miles from Splish Splash.
  • Parking
  • Swimming Pool

no reviews

from $74.00 Show details »

Hamptons Hideaway in Hampton Bays, USA

Hamptons Hideaway

Holiday home in Hampton Bays near Southampton, Florida
Hamptons Hideaway offers accommodations in Hampton Bays, 28 miles from Montauk Point Lighthouse.
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $99.00 Show details »

Hamptons Home Near Beaches with Pool and Water Views! in Southampton, USA

Hamptons Home Near Beaches with Pool and...

Holiday home in Southampton, Florida
Hamptons Home Near Beaches with Pool and Water Views! is located in Southampton, just 18 miles from Splish Splash and 25 miles from Montauk Point Ligh...
  • Parking
  • Bar
  • Spa and wellness centre
  • Outdoor pool
  • Swimming pool

no reviews

from $1.442.94 Show details »

Atterbury Estate in Southampton, USA

Atterbury Estate

Holiday home in Southampton, Florida
Atterbury Estate is located in Southampton, just 25 miles from Montauk Point Lighthouse and 30 miles from Second House Museum.
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Fabulous 1 Reviews 9.0

from $87.00 Show details »

Colonial Hampton Charm in Southampton, USA

Colonial Hampton Charm

Holiday home in Southampton, Florida
Colonial Hampton Charm is located in Southampton, just 24 miles from Montauk Point Lighthouse and 29 miles from Second House Museum.
  • Parking
  • Pets allowed
  • Fitness centre
  • Outdoor pool
  • Swimming pool

no reviews

from $87.00 Show details »

Southampton Beauty in Southampton, USA

Southampton Beauty

Holiday home in Southampton, Florida
Southampton Beauty is located in Southampton, just 24 miles from Montauk Point Lighthouse and 30 miles from Second House Museum.
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $95.00 Show details »

Holidays in the Hamptons! SH Gem mins from Town in Southampton, USA

Holidays in the Hamptons! SH Gem mins fr...

Holiday home in Southampton, Florida , 262 Montauk Highway
Offering a garden, Holidays in the Hamptons!
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $60.00 Show details »

Number of Holiday homes in Southampton 38
Number of guest ratings 1,122
Average price per night $976.00
Lowest price per night $50,00
Highest price per night $5.714,35

Top 10 Cheapest Holiday-homes in Southampton

Discover the Cheapest Holiday-homes in Southampton – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Southampton

Check out the Most Booked Holiday-homes in Southampton – Based on Guest Popularity.

Holiday homes in Southampton (Florida), comfortable and familiar

Staying in a holiday or vacation home in Southampton can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Southampton for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Southampton should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com