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.
114 properties available
2 BEDS, 2 BATHSBuilding Construction from Sep 2024 - May 2025, subject to changeDirect oceanfront second floor villa with sunrise viewsMaster bedroom with king bed and private bathroomOcean views from dining room, living room, and master bedroomXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to our absolutely cute and comfo
2 BEDS, 2 BATHSBuilding Construction from Sep 2024 - May 2025, subject to change1st floor villa with convenient beach and pool accessMaster suite with king-size bed and ocean viewsHigh-speed wireless internetXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nightsWelcome to our lovely 1st floor villa in the exclusive gated complex of Sea Cl
2 BEDS, 2 BATHSBuilding Construction from Sep 2024 - May 2025, subject to changeStylishly furnished villaSpacious interior exudes elegance and sophisticationExpansive and private oceanfront poolXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to Villa 309, a recently renovated and updated vacation home in Hilton Head Is
3 BEDS / 3 BATHSWaterfront villa located in Palmetto DunesSpacious bedrooms with comfortable beddingPrivate deck with views of 11-mile lagoonWalking distance to the beachXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights) Welcome to our stunning waterfront villa in Palmetto Dunes, Hilton Head! This spacious villa is the perfect v
2 BEDS, 2 BATHSPet -friendly villa in Palmetto DunesRenovated kitchen w/ stainless steel appliancesPrivate patio that features comfortable patio furnitureAccess to complex pool and tennis courtsXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to our newly remodeled Palmetto Dunes vacation home, a 2 bedroom, 2 bathroom villa
3 BEDS, 2BATHSPet friendly villa close to bike paths and natural trailsSpacious living area with comfortable furnishingsSteps from the beach and bike pathXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Escape to Hilton Head Island and experience the perfect family vacation or weekend getaway in this true three bedroom vacation home
2 BEDS, 2 BATHSPet friendly villa perfect for a relaxing getawaySpacious living area with comfortable furnishingsPrivate patio with grillEasy access to bike paths, fishing, and natureXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to your perfect vacation destination at 597 Queens Grant, a 2-bedroom villa located in Palmett
1 BED, 1.5 BATHStunning villa perfect for a beach getawaySpacious open living space with comfortable furnishingsSpacious balcony with breathtaking ocean viewsWalking distance to the beachXplorie - 2 Free Adult Bikes (Valid for 3-21 night stays)Welcome to the luxurious one bedroom Barrington Villa, located on the third floor with stunning oceanfront
3 BEDS, 3 BATHSBuilding Construction from Sep 2024 - May 2025, subject to changeCozy and inviting living area perfect for relaxationPrivate deck breathtaking views of the oceanLocated in the heart of Hilton Head IslandXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to your luxurious vacation home in Hilton Head Island,
3 BDS / 2 BATHSDog friendly home with golf course viewsFully equipped kitchen perfect for home mealsSpacious private deck perfect to relax and unwindXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Introducing 51 Wood Duck! This beautiful one level home overlooks the 14th Club Course Fairway. With the impressive fully st
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
3 BEDS, 2.5 BATHSSpacious pet friendly unit in Palmetto DunesUpdated kitchen and cottage-style furnishingsPrivate deck perfect for relaxationShort walk to the beachXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Escape to the beautiful Hilton Head Island and experience the perfect vacation in this spacious and charming 3-bedroom vi
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