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$379-1272 (rate range) For Rent Daily 2 Tupelo Drive Hilton Head Island, South Carolina 29928   Bedrooms 4 Baths 4.5 Sleeps 12 Sq Ft 2600 Pets No   Waterfront Water View Water frontage	Contact Owner/Manager/AgentX Arrive    Depart   Adults     - Select -123456789101112131415161718192021222324252627282930 Children  - Select -123456789101112131415161718192021222324252627282930 Name  Email  Phone  Question/Comment:  Receive Special Offers via email
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Description

Welcome to this distinctive vacation property managed locally by (Property Management). Thoughtfully refreshed and beautifully appointed, this 4-bedroom, 4.5-bath home in the heart of Sea Pines Plantation offers inviting coastal comfort with multiple gathering spaces, serene golf-course views, and a renovated pool deck perfect for relaxing days in the sun. A brand-new driveway and newly updated front steps create a warm and polished arrival experience. Stepping inside, you enter the first of two living and dining areas. This welcoming space features soft natural light, comfortable seating, a dining table for six, and recently added blinds and sconces that bring a fresh, stylish glow to the room. It’s an ideal spot for quiet mornings, board games, or enjoying a peaceful moment before the day begins. Just off this entry space, and positioned to the right, is the home’s main living and entertaining area. Here, the atmosphere opens up beautifully, with a spacious sectional, soaring ceilings, and brand-new ceiling fans that circulate the gentle ocean breeze. Large windows frame calming views of the surrounding landscape, creating an effortless connection between indoor comfort and the natural beauty outside. The adjacent dining area flows seamlessly into a bright, updated kitchen with generous counter space, bar seating, and a built-in desk perfect for planning island adventures or catching up on vacation emails. The first floor also includes three well-appointed bedrooms. Bedroom 1 offers two full-size beds, while the Bedroomn 2 and Bedroom 3 both feature a king bed and a soothing, relaxed aesthetic. Each room includes a newly renovated ensuite bathroom, with one offering a tub and shower combination and the others showcasing modern walk-in showers with updated tile and fixtures. Upstairs, the top floor has been thoughtfully renovated into a charming, flexible sleeping retreat. With a queen bed, two twin beds, and its own refreshed bathroom, this level is perfect for children, teens, or anyone seeking a cozy, tucked-away escape. Outdoor living is at the heart of this home. The renovated pool deck invites you to spend long afternoons swimming, lounging, or soaking up the sunshine. A covered deck overlooking the 3rd hole of Heron Point provides a breezy spot for evening cocktails, outdoor dining, or simply enjoying the sounds of the Lowcountry. Exploring Sea Pines is effortless, with the beach just a seven-minute bike ride away along scenic tree-lined trails. A nearby Sea Pines Trolley stop offers convenient, seasonal access to the Beach Club, ensuring that the very best of the area is always within easy reach. Blending fresh updates, inviting living spaces, and an exceptional location, this home offers a relaxed and memorable Hilton Head getaway. If you'd like, I can make it even warmer, more luxurious, more detailed, or more concise. Key Features: • Proximity to the beach: 7 minute bike ride • The pool can be heated for an additional charge, give us a call for heating rates and to make arrangements. Pool heat must be scheduled at 14 days prior to arrival. Additional fees apply for last minute requests prior to arrival or after arriving at the property. If the weather drops below 60 degrees, the pool may not be capable of being heated and or reaching optimal temperature. • Pool Dimension: 16X24 • Pets are not allowed • Sea Pines Resort Amenities Rent price includes: Rental Rate, Hospitality Program, Beach Gear Credit, Booking Processing Fees, and Departure Clean. Your Luxury Concierge is included with no additional cost.

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• king
• shower
• toilet
• bay/sound
• churches
• cinemas
• festivals
• forests
• library
• live theater
• marina
• museums
• playground
• recreation center
• restaurants
• ruins
• synagogues
• Dining
• Game Room
• Ping Pong Table
• Satellite / Cable
• Television
• Smart TV
• Air Conditioning
• Clothes Dryer
• Garage
• Hair Dryer
• Heating
• Internet
• Iron & Board
• Linens Provided
• Living Room
• Parking
• Towels Provided
• Washing Machine
• Shampoo & conditioner
• Wifi
• Free Wifi
• Desk Chair
• Coffee Maker
• Dishes & Utensils
• Dishwasher
• Ice Maker
• Kitchen
• Microwave
• Oven
• Refrigerator
• Stove
• Toaster
• Dining Table
• Kitchen Island
• beachcombing
• bird watching
• eco tourism
• horseback riding
• outlet shopping
• paddle boating
• photography
• scenic drives
• sight seeing
• walking
• Beach
• Golf Course View
• Balcony
• Deck / Patio
• Outdoor Grill
• Heated Pool
• Private Pool
• basketball court
• cycling
• deepsea fishing
• fishing
• freshwater fishing
• golf
• hiking
• jet skiing
• paragliding
• sailing
• sound/bay fishing
• surf fishing
• surfing
• swimming
• tennis
• water skiing
• water tubing
• children welcome
• non smoking only
• pets not allowed
• Minimum Age Limit for Renters
• flexible
• recommended
• Dining Area
• Adventure
• Away From It All
• Budget
• Family
• Historic
• Romantic
• Spa
• Sports & Activities
• Tourist Attractions
• Outdoor lighting
• Smoke detectors
• Carbon monoxide detector
• Fire extinguisher
• First aid kit
• Enhanced cleaning practices
• Clean with disinfectant
• No-contact check-in and check-out
• High touch surfaces cleaned with disinfectant
• Towels and bedding washed in water that's at least 60sC/140sF
• SafeHome (VRMA & VRHP)
• Full Kitchen
• Refrigerator
• Coffee Maker
• Microwave
• Toaster
• Cookware
• Bakeware
• Bowls Plates Mugs
• Dinnerware
• Pots Pans Cutting boards Knives
• Glassware
• Starter Kitchen Amenities
• Keurig
• Ice Maker
• Central Air
• Air Conditioning
• Washer & Dryer
• Ironing Board
• Hangers
• Pillows and Blankets
• Bedding and Sheets
• Bunk Rooms
• Nearby ATM
• Nearby Post Office
• Nearby Internet Cafe
• Nearby FedEx
• Nearby Bank
• Nearby Medical Services
• Nearby Grocery
• Outlet Shopping
• Movie Theatres
• Golf Course
• Keyless
• Internet
• Linens Provided
• Starter Bathroom Amenities
• Beach Gear / Bikes & Activities
• Winter Monthly Rentals
• Complimentary Concierge Services
• Symphony Orchestra
• Beach
• Private Pool
• Heatable Pool
• Deck
• BBQ Grill
• Gas Grill
• Near Beach
• Fairway Collection
• Cable TV
• Monthly Stays
• Streaming TV's

Check-In	Check-Out
16:00	10:00

Pets Not Allowed
CANCELLATION POLICY

Villas:
• Before 31 days of arrival date we will refund the initial payment after the forfeiture of the booking processing fee plus tax and the Credit Card fee plus tax if applicable.
• Inside 30 days of arrival date all payments are nonrefundable
• The Booking Processing Fee plus tax and Credit Card fee plus tax are non-refundable.

Homes:
• Before 61 days of arrival date we will refund the initial payment after the forfeiture of the booking processing fee plus tax and the Credit Card fee plus tax if applicable.
• Between 60 and 31 days prior forfeiture of 50% of the total booking charges.
• Inside 30 days of arrival date all payments are nonrefundable
• The Booking Processing Fee plus tax and Credit Card fee plus tax are non-refundable.

Long Stay Reservations – reservations for 28 days or more.
• Before 91 Days of arrival date we will refund the initial payment after the forfeiture of the booking processing fee plus tax and the Credit Card fee plus tax if applicable.
• Inside 60 days of arrival date all payments are nonrefundable
• The Booking Processing Fee plus tax and Credit Card fee plus tax are non-refundable.

Trip Preservation –We recommend purchasing travel insurance to protect your investment. If Guest has purchased travel insurance, any or all trip reimbursement will be subject to the policy terms and conditions. The travel insurance agreement is between Guest and the Policy Provider. Island Time Hilton Head is not the policy provider, Rental Guardian Insurance Services is the holder.
• If selected, the travel insurance premium is charged at the time of selection and is nonrefundable.

Early Departures and No Shows - No refunds for early departures or no-shows. If you have purchased travel insurance, any or all trip reimbursement will be subject to the policy terms and conditions.

Storms - There are no refunds given for cancelation or interruption of your stay due to an event of inclement weather including: a tropical storm, tropical depression, hurricane, or named storm, and all payments will be forfeited. If Guest has purchased travel insurance, any or all trip reimbursement is between you and the insurance company and will be subject to the policy terms and conditions.

Cancellation Refund Schedule –The Cancellation Policy is binding at the time of booking; as outlined in Reservation Confirmation, failure to complete the rental agreement does not exclude Guest from responsibilities of the Cancellation Policy.

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Visitor Reviews (16) Write a Review! "Memory Week Excellent week - we dideverything we hoped for - beach, biking, golf, pool, putt putt, dining out. The house was exceptional - clean, well stocked, pool, great location!" Jun 04, 2025 - Michael L., Charlotte, NC "Sea Pines Haven We had a great stay in this home! It was very clean when we arrived. The spaces were well-appointed, cozy, and comfortable. The pool, deck, and backyard area were very nice. The updates to the home were beautifully done. The kitchen was stocked with everything necessary for cooking. The property manager was super responsive and gracious. He let us know that the backyard grill area was under renovation and not quite complete (which looks to be wonderful for future guests). When we texted to let him know the pool was getting to the point of needing to be treated, he had someone at the house within 30 minutes! Great service! The golf course views were great, and the proximity to the beach and bikes paths in Sea Pines made this a great location overall. Adults and kids alike loved our time in this home. Our only feedback would be that it was a little strange not to have doors on the bathrooms in the two main bedrooms, and it was awkward that the glass windows in the master shower provided no privacy for anyone taller than a child. This would be simple enough to rectify by frosting the glass. Neither of these things would prohibit us from renting this home again, but they may be helpful to note. Overall, this was a fantastic vacation home for two families to share! " Apr 10, 2025 - , Minneapolis, MN "Great Spring Break vacation with family! We had a wonderful stay at 2 Tupelo in Sea Pines. The house was very nice and kitchen well equipped. Family had a great time and there was plenty of room for everyone. We heated the pool and although temperatures were cool it was tolerable to swim with the kids. We would definitely recommend this home rental again. " Apr 10, 2025 - , Cincinnati, OH "Perfect Stay with Island Time We loved Island Time's hospitality and thoughtfulness that helped create a perfect experience! We also loved this home. Everything was super clean. Home was well stocked with essentials. The great room was perfect for our large family. Nice pool area, and we all enjoyed playing ping pong. The master shower with dual rainfall shower heads and a spray hose was amazing. When our adult son accidently broke the internet wire somehow, Island Time was out to fix it immediately and couldn't have been more polite! From booking to checkout, everyone went above and beyond our expectations. We have booked with other rental companies on the island, and never had such a seamless experience before. We will only use Island Time moving forward... can't recommend them highly enough! " Feb 10, 2025 - , Ridgeland, SC "Excellent Family Get Away! My family and I enjoyed a pre-Christmas get away and thoroughly enjoyed our stay at 2 Tupelo Drive. The home was very comfortable for our family of five. " Dec 30, 2024 - , Cumming, GA "2 Tupelo road review We were very happy with the overall stay The location was great The house and pool area were everything we wanted and needed The staff was in contact to make sure we had everything we needed A few of the issues we had The fourth bedroom on the top floor had some problems The main bed had bumps and lumps in the mattress The electric outlets did not work The door fell off the track every time you opened or closed it and there was a hole in the wall where it hit when it fell off We couldn’t find some of the light switches And you should let future renters know if all the things available in the house such as Games Swimming things Swim towels Beach gear Having the starter things and the option of food delivered for our arrival was great Overall we were very happy and would come back although we like to try different properties" Oct 09, 2024 - Scott P., Pittsburgh, PA "Wonderful property Very pleased with this house. Fully stocked kitchen along with a generous sized pool. We enjoyed the 2 living rooms and the nice balcony overlooking the pool. Rental company was very responsive. We would book again!" Jul 16, 2024 - Margie H., Columbus, OH "Family Vacation with little ones Great property and location! This was our 7th trip to HHI and one of our favorite houses to stay in. Our family loved the layout of this house. We had 3 adults, 3 late teens and 3 little children all together for a family vacation and there was plenty of room for everyone. Every room is decorated high quality, and the house is kept clean. Everyone loved the deck and pool area and the kids really appreciated all the pool toys! We are a little hesitant on the location because the house sits on the corner of Greenwood and Tupelo but there was never an issue with road noise. We will be back! " Jun 19, 2024 - , Dublin, OH "Sea Pines Vacation Home My family and I had a wonderful time at 2 Tupelo Rd. The home was clean and fully stocked with all of the essentials. Even though the house is located on the corner off of a well traveled road noise wasn’t much of a concern. The team at Island Time was very responsive to all inquiries that I had and I would definitely choose them again to help procure our vacation home in the future on Hilton head Island. " May 13, 2024 - Everett M., Atlanta, GA "A beautiful property! Would highly recommend!" Mar 08, 2024 - Ralph M., Richmond, KY "Wonderful house for a great week with the family The house worked perfect for our family. We loved the pool and deck area. Every room is decorated high quality, and the house is kept clean. We would highly recommend it. " Aug 23, 2023 - , Wellington, FL "Gorgeous Sea Pines House This house is just amazing. Beautifully decorated and very spacious. It had everything we needed for our days at the beach- chairs, bocce ball, strike ball. Wish I had known- wouldn't have brought ours. Tons of family games, Roku TVs in every room, large swimming pool! On the corner of Greenwood and Tupelo so a lot of road noise but wasn't terrible. Hit all of our favorite haunts- Truffles, Salty Dog, and Crazy Crab in Sea Pines. Be sure to check out Pirate's Island Adventure Golf. We had a blast! We definitely loved our stay and look forward to returning and renting through Island Time Hilton Head again. " Apr 25, 2022 - Sarah G., Cincinnati, OH "Great home, beautifully decorated! We stayed 5 weeks and thoroughly enjoyed our time there! Island Time was wonderful to work with, and responded quickly anytime I called. The property manager was great as well!" Mar 02, 2022 - , Richmond, KY "Great vacation! Perfect house for a big group. This was our first stay in Hilton Head, and we had a great family vacation. The weather wasn't great, but we still stayed busy. We were a group of 12 with 2 babies who needed to nap. The layout of the house keeps the bedrooms very quiet. As many people as we had, the house never felt crowded. It is in great condition, clean and well equipped. A/C in the first floor bedrooms may need an update - it did stay humid in those, but not terrible. The pool was amazing! It got pretty deep for a residential pool - about 7' - but the kids loved it. Parents, too. A great house at a fair price." Aug 10, 2021 - David L., Frederick, MD "Beautiful Property Everything was top not. Well appointed. Except refrigerator didn’t get cold. " Aug 10, 2021 - Glen B., Wilmington , OH "Great house and great pool in Sea Pines! This is the first time we stayed in this house but we always stay in Sea Pines. The house was recently renovated and is great for one family or multiple. We like to be at the beach or pool all day and be low key at night. This house was perfect. It had an area for games, ping pong and a large sectional where we could all hang out. The deck and pool made it great to be outside. It’s a little farther from the beach than we normally stay but the design of the house was enough to overcome the distance. We would defiantly stay again!" Jul 14, 2021 - , Woodstock, GA
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