2 Tupelo Drive

Awesome house! From the open kitchen to the attic room and spectacular pool, we really enjoyed it! Island Time was in constant contact with us to make sure our stay was without trouble. Thank you and we will definitely be back!

Xiong V. - Posted: 7/9/2026

Thank you for the incredible review Xiong! We’re thrilled to hear you enjoyed the home’s open kitchen, unique attic room, spectacular pool, and all the special touches that made your stay so memorable. Your kind words about our Island Time team mean so much to us, and we’re delighted we could help make your vacation worry-free. We can’t wait to welcome you back to Hilton Head again soon.

Island Time Hilton Head staff

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: we visited with our entire family (6 adults and 5 children) - first time in Sea Pines - we all loved the bike paths; rode everywhere - close to Lawton Stables, much to the delight of the grandchildren - explored the natural preserve area and saw all sorts of creatures - took the trolley to the Sea Pines Beach Club - swam in the pool; walked on the golf cart paths after hours - cooked on the outdoor grill - house was well apportioned and we did not want for anything - everyone had their own bed - kitchen was large and well equipped - plenty of room to spread out and enjoy ourselves - would definitely recommend this home for future rentals

Jim B. - Posted: 6/23/2026

Thank you for the wonderful review Jim! We’re delighted to hear your entire family had such a memorable first visit to Sea Pines and enjoyed everything from the bike paths and Lawton Stables to the Nature Preserve, Beach Club, and time spent together at the home. It’s wonderful to know the spacious layout, well-equipped kitchen, and outdoor living areas made your stay so comfortable for everyone. We truly appreciate your recommendation and hope to welcome you back to Hilton Head again soon.

Island Time Hilton Head staff

Great family friendly, large home. Plenty of room for 3 families (6 adults, 5 kids). Each room has its own en suite bathroom plus one extra bathroom. Comfy beds with lots of pillows! Spacious pool (shallow and deep end so bring floaties for little ones). Great view of golf hole. Appreciate extra safety for kids like locks on top of doors. Kitchen very well stocked with cookware! Some drawbacks / things to be aware of: deck a little rickety and gets very hot in the afternoon so have kiddos wear shoes. First house off the busy road so a little noisy, house had bikes (at least 4 but maybe 6? Can’t recall), cooler, beach chairs so don’t HAVE to rent those. Not walking distance to beach but quick drive and we were able to get parking both days we went before 10 am. Only provided one parking pass. Would have hoped to have at least 2 free given the house accommodates many people.

Holly - Posted: 6/14/2026

Thank you for the wonderful review! We are so happy to hear that the home was a great fit for your group and that you enjoyed the spacious layout, private en-suite bathrooms, comfortable beds, pool, golf course views, and well-stocked kitchen. We also appreciate all of your helpful feedback, and we will be sure to share your comments with our team. We hope to welcome you back to Hilton Head again soon!

Island Time Hilton Head staff

Easy to rent from and great communication about rental

Nancy Morrow - Posted: 4/21/2026

We loved the house! Worked perfectly for our 6 adults and 5 kids. Having stayed at HHI numerous times we were familiar with the house location. Would definitely stay again, if another full family vacation gets scheduled.

Theresa - Posted: 7/9/2025

Thank you for your review, Theresa. We're glad the house was a great fit for your group and that you enjoyed the location. We’d be happy to welcome you back for another family vacation anytime!

Island Time Hilton Head staff

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!

Michael List - Posted: 6/1/2025

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: 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!

Michael - Posted: 6/1/2025

We have a group of 8 women and have been going on an annual trip for 20 years. This was the best house! Great location, lots of bed, lots of bathrooms, great kitchen, and great location.

Lori - Posted: 5/1/2025

Thank you for your review, Lori! We are thrilled to hear that your annual trip was a success and that our house met all your needs. We hope to welcome you and your group back for many more years to come!

Island Time Hilton Head staff

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: 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!

Gretchen D. - Posted: 4/7/2025

Thank you for the wonderful review! We’re so glad you had a great time and enjoyed the home, pool, and service. We appreciate your feedback about the bathroom privacy and will definitely consider it for future improvements. We’d love to host you again!

Island Time Hilton Head staff

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!

Gretchen Dolan - Posted: 4/7/2025

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.

Rita Hoppins - Posted: 4/3/2025

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: 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.

Rita H. - Posted: 4/3/2025

Loved staying in the house. All went perfectly. Had a few hiccups with getting access but management was quick to reply and get it resolved.

Scott W. - Posted: 2/19/2025

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!

Telie White - Posted: 2/9/2025

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: 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!

Telie W. - Posted: 2/9/2025

Love it! Thank you for your review, Telie, we are so glad to hear you have such a positive experience with our team and enjoyed your stay! We look forward to welcoming you back on your next visit to Hilton Head.

Island Time Hilton Head staff

2 Tupelo was a great place for our family to gather after Christmas! The living space was enough for some to work from home while others relaxed watching tv. Great layout for living and sleeping spaces!

Shannon C. - Posted: 1/5/2025

Thank you for your review, Shannon. We are so glad to hear that you had a great stay.

Island Time Hilton Head staff

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.

Aaron Smith - Posted: 12/28/2024

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: 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.

Aaron S. - Posted: 12/28/2024

Thank you for your review, Aaron. We are glad to hear you enjoyed your stay with Island Time.

Island Time Hilton Head staff

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: 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!

Margie H. - Posted: 7/16/2024

Thank you, Margie, we truly appreciate you taking time out of your day to post this and look forward to your return!

Island Time Hilton Head staff

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: 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!

Wendi H. - Posted: 6/18/2024

Love it! Thank you, Wendi we are so happy, that you enjoyed your visit and look forward to having you back on the Island again very soon!

Island Time Hilton Head staff

Great

Mary - Posted: 6/16/2024

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The house fit our families needs wonderfully!! House was clean and well appointed. The kids (and adults) loved the pool - especially after a day at the beach. Island Time was great to work with - very responsive!All in all a great week for us.

Mike L. - Posted: 5/27/2024

Thank you for staying with us Mike. We are happy to hear you enjoyed your family getaway. We hope to welcome you back to the island soon.

Island Time Hilton Head staff

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: 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.

A guest from Atlanta, GA - Posted: 5/13/2024

Thanks for the review, Everett. This house really is a gem, we hope to have you stay again next year!

Island Time Hilton Head staff

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Would highly recommend!

Beverly M. - Posted: 3/4/2024

Thanks for the review, Beverly. This house really is a gem, and we hope to have you stay again next year!

Island Time Hilton Head staff

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: 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.

Matt W. - Posted: 8/23/2023

Thanks so much for your stay with Island Time. We look forward to welcoming you back on your next trip to Hilton Head.

Island Time Hilton Head staff

Great place right in Sea Pines. Pool was incredible, overall house is in great shape and well appointed for those who plan on cooking and entertaining. Would stay here again.

Patrick G. - Posted: 7/16/2023

We loved everything! The pool was such a blessing. Plenty of living space for 6 adults (3 couples) and 4 kids under 5. Would definitely go back!

Christina N. - Posted: 5/24/2023

We had such a wonderful time staying in at Sea Pines! The house was perfect for our two families. The kids shared the bunk beds and had their own bathroom which was perfect for showering them after the beach. The house was clean and had everything you could think of. plenty of towel, linens, and cleaning products. The kitchen is updated with smart appliances and well stocked with anything you need for cooking and entertaining. The living room was cozy we super comfortable couches. As parents of toddlers, we appreciated the stash of children's toys and games. The kids were excited to play with something new. The upstairs bedrooms were spacious and the bathrooms were very nice with showers. We loved hanging out on the back porch and eating dinner out there. The location is perfect too. Also it was a quick drive or bike ride to the beach. We loved the small town feel and being able to bike everywhere! We biked to the beach, Harbortown, the Lighthouse, and other various shops. The beach was clean and family friendly. Sea Pines is very clean and environmentally friendly. This was our first vacation to Hilton Head Island and we can't wait to go back. It truly was a wonderful vacation. We highly recommend this rental!

Matthew B - Posted: 11/25/2022

Great experience

Matt C. - Posted: 9/12/2022

Thanks so much for your stay with Island Time. We look forward to welcoming you back on your next trip to Hilton Head.

Island Time Hilton Head staff

The property was just as advertised in the pictures, a lot of times the pictures were clearly taken several years ago. This one is in great shape, clean, fantastic pool and golf course view, and well stocked with all the dishes/new appliances/amenities you would need. Very very happy with this stay!

Nicholas P. - Posted: 9/9/2022

Thanks so much for your stay with Island Time Nicholas. We look forward to welcoming you back on your next trip to Hilton Head.

Island Time Hilton Head staff

This house is filled with everything you could need for a comfortable week at the beach. A little far from the beach club but very close to the trolley shuttle and the private pool made up for the distance. The lack of door on the primary suite did make tracking with babies an unexpected challenge but overall the house was designed with families in mind.

Jenni G. - Posted: 6/30/2022

Thank you for staying with us Jenni! We are happy you and your family had a great time. We can't wait to welcome you back!

Island Time Hilton Head staff

We had a great time! The house was in a great location and our grandsons loved their attic room! The family room was perfect for gathering when we weren’t enjoying the pool! Highly recommend.

Mary D. - Posted: 4/11/2022

Thanks so much for your stay with Island Time. We look forward to welcoming you back on your next trip to Hilton Head.

Island Time Hilton Head staff

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: 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.

Sarah G. - Posted: 3/29/2022

Sarah, thank you for such a kind review. We are very happy to hear this home worked out great your vacation! Thank you for choosing Island Time, we hope to welcome you back soon.

Island Time Hilton Head staff

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: 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!

Ralph M. - Posted: 2/28/2022

Beverly, we are so happy to hear you enjoyed your time and had a great experience with our team. We hope to welcome you back to Hilton Head soon!

Island Time Hilton Head staff

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: 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.

David L. - Posted: 8/9/2021

Thanks for the review, David. We are thrilled that you enjoyed your stay with us. We have addressed the A/C and is good to go. We hope to have you back to Sea Pines again soon!

Island Time Hilton Head staff

Only issue with property was refrigerator never got food and beverages cold. Everything else was top notch.

Glen B. - Posted: 7/26/2021

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: 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!

Kris M. - Posted: 7/12/2021

So happy you enjoyed your stay with us. We look forward to welcoming you back on your next trip to Hilton Head.

Island Time Hilton Head staff