Hilton Head Snowbird Rentals

More to Enjoy This Winter 

Escape the cold and embrace the mild temperatures, scenic shorelines, and laid-back lifestyle of Hilton Head Island. Whether you're searching for a cozy 1-bedroom villa by the beach or a spacious 7-bedroom retreat to host family and friends, our Hilton Head monthly rentals provide the perfect place to call home for the season. Enjoy access to top island attractions, from championship golf courses and picturesque bike trails to waterfront dining and boutique shopping. Whether you prefer outdoor adventure or a peaceful place to relax and unwind, our winter rentals cater to every type of traveler.


A Home Away from Home 

Our Hilton Head winter rentals offer spacious floorplans, natural light-filled interiors, and tasteful furnishings, ensuring a comfortable and stylish extended stay. 

  • Spacious, Open-Concept Living – Many rentals feature large windows, vaulted ceilings, and inviting living areas designed for comfort. 
  • Fully Equipped Kitchens – Prepare your favorite meals with ease in a modern, well-stocked kitchen or explore Hilton Head’s fantastic restaurant scene. 
  • Modern Conveniences – Enjoy Wi-Fi, large flat-screen TVs, and cozy living spaces for entertainment and relaxation. 
  • Comfortable Bedrooms – Plush mattresses and spacious bedrooms provide the perfect retreat after a day of exploring the island.

Upgrade Your Winter Stay 

Looking for something extra? Customize your winter escape with luxury amenities tailored to your lifestyle. 

  • Oceanfront Views – Wake up to the sound of the waves and unparalleled coastal scenery. 
  • Pet-Friendly Rentals – Bring your four-legged friend along for the adventure! 
  • Outdoor Showers & Heated Pools – Enjoy the ultimate comfort and convenience throughout your stay.


Properties Available 115 properties available
2 BEDS, 2 BATHSHigh-end villa located in Palmetto DunesFully equipped kitchen w/ high end appliancesSuitable for families, golf groups, and weekend getawaysXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to the jewel of the island, 924 Inverness! This stunning vacation home is located in the prime location of Hilton Head wi
Villa - Inverness 924, Palmetto Dunes
Condos/Villas Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
2 BEDS, 2 BATHSBuilding Construction from Sep 2024 - May 2025, subject to changeTastefully decorated villa with elegant ambiancePrivate decks with stunning ocean viewsDirect oceanfront access to wide sandy beaches and gentle surfXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to your luxurious vacation home in Hilton Head I
Villa - Sea Cloisters 307, Folly Field
Condos/Villas
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
2 BEDS, 2 BATHSBuilding Construction from Sep 2024 - May 2025, subject to changeLocated in the picturesque Folly Field areaSpacious and inviting interiorPrivate deck with ocean viewsXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to your dream vacation home in Hilton Head Island! Located in the picturesque Folly Field area,
Villa - Sea Cloisters 312, Folly Field
Condos/Villas
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
3 BEDS, 2 BATHSBuilding Construction from Sep 2024 - May 2025, subject to changeVilla w/ tasteful coastal decorSpacious living and dining areasPerfect for a relaxing and peaceful getawayShort walk to a beautiful beachXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to your own piece of paradise at Sea Cloisters! This th
Villa - Sea Cloisters 101, Folly Field
Condos/Villas
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
2 BEDS, 1 BATHOpen and airy villa with a short walk to the beachStunning furnishings and contemporary designInviting back patio for relaxationLarge, shaded swimming pool for cooling off and relaxationXplorie - 2 Free Adult Bikes (Valid for stays between 3 -21 nights)Welcome to this beautiful beach-oriented villa in Hilton Head Island! Recently reno
Villa - Stones Throw 4, Folly Field
Condos/Villas Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 baths , 1 Half
Guests 7 guests
2 BEDS, 2 BATHSCozy villa with a private balcony overlooking a pondOpen living space with comfortable furnishingsSteps from the beach and bike path in Palmetto DunesConcishare (Includes access to luxury concierge service)Xplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to your beautiful vacation home in Palmetto Dunes o
Villa - Barrington Park 706, Palmetto Dunes
Condos/Villas
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
2 BEDS, 2 BATHSBuilding Construction from Sep 2024 - May 2025, subject to changeTastefully designed with a coastal ambianceMaster suite with king bed, private bath, and balcony accessAccess to expansive and private oceanfront poolWide sandy beaches and gentle surfXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to our beauti
Villa - Sea Cloisters 108, Folly Field
Condos/Villas
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
2 BEDS, 2 BATHSOceanfront villa perfect for a beach getawaySpacious living area with natural lightingAccess to complex pool and hot tubClose to miles of bike paths and golf coursesXplorie - 2 Free Adult Bikes (Valid for 3-21 night stays)Escape to luxury at Hampton Place, Palmetto Dunes' newest oceanfront gem. Nestled in one of North America'
Villa - Hampton Place 6303, Palmetto Dunes
Palmetto Dunes Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
2 BEDS, 2 BATHSStunning vacation villa in Palmetto DunesSpacious living space with comfortable seatingPrivate balconies in both bedroomsJust steps away from the beachXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to 3230 Villamare, a stunning vacation home located in the beautiful Palmetto Dunes community of Hilton Head Is
Villa - Villamare 3230, Palmetto Dunes
Condos/Villas
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
3 BEDS, 2 BATHSBuilding Construction from Sep 2024 - May 2025, subject to changeTotal Interior Remodel Scheduled for Oct 2024 - April 2025, Be the first to rent in 2025!First-floor location for easy accessHigh-speed wireless internetSteps away from the pool and private beachXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to
Villa - Sea Cloisters 113, Folly Field
Condos/Villas
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
2 Beds, 2 BathsBuilding Construction from Sep 2024 - April 2025, subject to changeFifth floor villa located in Palmetto DunesBreathtaking ocean views from the living room and balconyKitchen with a raised countertop barConcishare (Includes access to luxury concierge service)Xplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights) Welco
Villa - Windsor Place II 2513, Palmetto Dunes
Condos/Villas
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 guests
3BDS, 2BTHSPet friendly, secluded family homeNewly renovated interior with comfortable furnishingsPeaceful and serene lagoon views from deckClose access to complex pool and beachXplorie - 2 Adults (Valid for 3 - 21 night stays)Welcome to your newly remodeled oasis at 57 Night Heron, nestled just inside the exclusive Sea Pines gated community. This
Home - 57 Night Heron, Sea Pines
Homes Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests

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