5 Jessamine Place

Excellent stay.

Jeramie S. - Posted: 8/8/2026

Thank you for the excellent review Jeramie! We're so glad that you enjoyed your stay at 5 Jessamine Place. We appreciate you choosing Island Time and hope to welcome you back to Hilton Head soon.

Island Time Hilton Head staff

Great play. Really enjoyed our stay.

James - Posted: 8/1/2026

Nice spacious open floor plan and laid out well for an Airbnb

Christina - Posted: 6/6/2026

Thank you for the wonderful review Christina! We’re so glad you enjoyed the spacious open floor plan and thoughtful layout of the home. We hope to welcome you back to Hilton Head again soon.

Island Time Hilton Head staff

Beautiful home, comfortable beds, excellent communication from host and rental company!

Laurie - Posted: 1/4/2026

Thank you for the wonderful review Laurie! We’re so glad that you found the home beautiful, the beds comfortable, and our communication excellent. We look forward to welcoming you back to Hilton Head soon!

Island Time Hilton Head staff

Place was fantastic. Perfect for large family. Loved the main living area. Was large, open, and convenient for our family to be together. Pool, patio, hot tub was really nice. Having the added touch of being able to rent bikes ahead of time and waiting at the house for when we arrived, was awesome. Kudos to property mgmt

Keith - Posted: 9/21/2025

Thank you for the amazing review Keith! We're so glad 5 Jessamine Place was a great fit for your large family, especially the spacious main living area. Happy to hear you enjoyed the pool, patio, and hot tub, and that the pre-arranged bike rentals made arrival easy. Thanks for the shout-out to 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 very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Second summer in a row that 8 of us (two families) have enjoyed this property. House is on a quiet court yet you have easy bike access to the beach, Salty Dog Cafe & Harbour Town. Open concept kitchen / family room is great for hanging out. Kids loved the pool & the adults enjoyed the spa.

Ryan - Posted: 7/27/2025

Thank you for the amazing review Ryan! We're so glad your group returned to 5 Jessamine for a second summer and enjoyed the home’s layout and location. It’s great to hear the kids loved the pool and the adults got to relax in the spa. We hope to welcome you back again next year!

Island Time Hilton Head staff

Second summer in a row that 8 of us (two families) have enjoyed this property. House is on a quiet court yet you have easy bike access to the beach, Salty Dog Cafe & Harbour Town. Open concept kitchen / family room is great for hanging out. Kids loved the pool & the adults enjoyed the spa.

Ryan Dau - Posted: 7/27/2025

Overall it was a very nice property and very roomy for all 10 of us adults.

David - Posted: 7/21/2025

Thank you for your review, David! We're glad the property comfortably accommodated your group and hope to welcome you all back to Hilton Head again soon.

Island Time Hilton Head staff

We loved this home. It was everything we wanted. We stayed for two weeks and wanted a home that felt relaxing and very "beach-like," but also a home that we could settle into and enjoy family meals. The amenities were great, and we loved the pool!!

Erin - Posted: 7/8/2025

Thank you, Erin, for your wonderful review! We’re glad the home provided the relaxing, beachy atmosphere you were looking for and that you enjoyed the amenities and pool during your two-week stay. It was our pleasure to host you and your family, and we’d be happy to welcome you back anytime.

Island Time Hilton Head staff

This was a WONDERFUL place to stay and just perfect for our family of 9. We felt very taken care of by Island Time and the whole process was smooth. We can't wait to come back!

Hayden - Posted: 6/7/2025

Thank you for your wonderful review, Hayden! We're pleased to hear that our place was perfect for your family and that you felt well taken care of. We look forward to welcoming you back on your next visit!

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: Well done, just wish the thermostat could be set a little lower than 70 degrees.

Sharon - Posted: 6/1/2025

Well done, just wish the thermostat could be set a little lower than 70 degrees.

Sharon Fitch - Posted: 6/1/2025

The house was spacious, clean, good location, heated pool was great for our entire family, and the front yard was perfect for our kids!

George Lipsey - Posted: 4/22/2025

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: The house was spacious, clean, good location, heated pool was great for our entire family, and the front yard was perfect for our kids!

Ralph L. - Posted: 4/22/2025

Thank you for the great review! We’re so glad the house, pool, and yard worked well for your family. We hope to welcome you back soon!

Island Time Hilton Head staff

We enjoyed our time at this beautifully appointed home! It accommodated our family perfectly! The master bedroom was just what we needed! The location is very peaceful! Would definitely rent again! We had one minor issue and Island Time responded immediately! They were so easy to work with!

Anne Cheri - Posted: 3/16/2025

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 enjoyed our time at this beautifully appointed home! It accommodated our family perfectly! The master bedroom was just what we needed! The location is very peaceful! Would definitely rent again! We had one minor issue and Island Time responded immediately! They were so easy to work with!

Anne C. - Posted: 3/16/2025

Thank you for the kind words Anne! We look forward to welcoming you back.

Island Time Hilton Head staff

Home perfect for our group of 8. Nice open kitchen, living room and games area. Lots of games to choose from and extra spices in pantry. Only thing missing was a fly swatter. Three large bedrooms with private baths and we made good use of the 4 bunk beds, too and 4th bathroom. Loved the pool and splurged for the heated hot tub…great to rent bikes (at least 2) to ride on the beach and on the bike paths. Easy walk to beach access; not so easy with over 75 old because it’s still about 1/2 mile walk and there’s no dropoff point. Loved night at Harbor Town, lunch at Salty Dog and trying out the different golf courses in the area. We’d definitely recommend it!

Verified traveler - Posted: 9/7/2024

Clean property and spacious enough to hold my immediate and extended family. Short walk to beach access without having to deal with all that sand. Ideal rental property. Pool was a much appreciated amenity.

Peter H. - Posted: 8/15/2024

Thank you for your review, Peter. We appreciate your feedback. We are glad you enjoyed your getaway with us.

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: Really enjoyed our stay at 5 Jessamine Place. Property was clean, well maintained and the kitchen was fully equipped with everything we needed. The pool and spa were big hits. The Sea Pines location was also great for getting to the beach (.5 mile), Harbour Town & Salty Dog. We recommend renting bikes to make it easier to get to all of those locations. Island time provided a bunch of useful information and was easy to get a hold of whenever we had questions. Only frustration about the property was no beach towels and only 3 beach chairs. Island time was upfront about a lack of both, however we have found those items to be standard at previous homes we've rented on the island.

Ryan D. - Posted: 8/6/2024

Thank you for staying with us, and thank you for your feedback. Have a great day!

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 house overall, good space for adults and young children. Location to beach was great and close to the trails to walk and or bike around sea pines. Rooms were spacious enough for all and the pool in the backyard is a huge plus.

Melissa A. - Posted: 5/21/2024

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 very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Wonderful week in this newly updated property. We loved having an open floor plan for everyone to be together but doing different things simultaneously. We paid the extra fee for the pool and spa to be heated, which was well worth it. Would definitely stay here again!!

Jen S. - Posted: 5/21/2024

Thank you for staying with Island Time! We're thrilled to hear that you had a wonderful week in our newly updated property. It's great to know that you enjoyed the open floor plan and the heated pool and spa. We can't wait to welcome you back for another fantastic stay!

Island Time Hilton Head staff

The house and surrounding area is perfect! We had 8 adults and 5 kids and it fit us perfectly. The only issue was the spa pool. It’s very hard to know how to get it heated because there are zero instructions. With the cost to heat, detailed instructions should be included. There are buttons to press, but the numbers are all worn off. I asked for help but was never given instructions. Luckily I found help on YouTube and then it worked perfectly!!

Beth L. - Posted: 5/14/2024

Thank you for staying with us. The pool deck was recently expanded with additional seating and a non-slip texture was applied. The spa controller numbers were over-sprayed accidentally in the process. The labels on the spa controller have been replaced and instructions have been added for spa use. We appreciate the feedback and hope you stay with us again.

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: I would highly recommend this property. It was on a quiet street and a bike ride away from the beach club, Harbour town and Salty dog. This house was perfect for our family.

Jared P. - Posted: 4/16/2024

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

Island Time Hilton Head staff

Great spot

Joe G. - Posted: 3/26/2024

Thanks for taking the time to leave us a review, Joe. We hope to welcome 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 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 5 Jessamine, it was very well equipped! At one point we had 8 people including our two great grandchildren and the house satisfied everyone’s needs! Loved the location! The staff at Island Rental was great to work with! Would love to go back!

Anne C. - Posted: 3/18/2024

Thank you so much for the kind words. We are so happy that you enjoyed your stay. We hope to have you back again sometime 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: Home was very well equipped! We had 8 people for a week and the house easily accommodated everyone! We were there in February and only our crazy great grandchildren used the pool and loved it! Island time was very helpful and easy to work with! Hope to return!

Anne C. - Posted: 3/3/2024

Thank you for staying with us Anne! We are happy you had a great vacation and look forward to welcoming you back.

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: Awesome place for our family for our first visit to Hilton Head. One thing for improvement would be additional dish towels and hot pads for kitchen.

Dale F. - Posted: 1/3/2024

Thank you for spending the holiday with us, Dale. We appreciate your recommendation and will place additonal dish towels and hot pads in the kitchens. We hope to welcome you back.

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: 5 Jessamine Place was the perfect fit for our kids and grandkids. The homes one story layout and flat yard worked out well for us. The management company was very helpful. We would be very likely to stay again.

Sue I. - Posted: 11/29/2023

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 comfy home! Updated, clean and roomy. The pool was very nice, grandkids loved it and it was a plus to relax in while they were napping! Night swimming was great, too! The furniture was comfy, more than enough seating for meals and the second fridge came in handy for beverages. I would definitely rent again.

Barbara E. - Posted: 9/30/2023

Thank you so much for the kind words, Barbara, we are so happy that you enjoyed your stay. We hope to have you back again sometime soon!

Island Time Hilton Head staff

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: 5 Jessamine Place was outstanding, and we really enjoyed the stay! The location of the property was excellent, and we enjoyed biking to the beach and to other places as well. The property was well maintained and met our expectations. I would highly recommend this lovely property and location.

ralph T. - Posted: 9/28/2023

Thank you for staying with us Ralph. We hope to welcome you back soon!

Island Time Hilton Head staff

All in all we had a great experience at the Jessamine house. Island Time (Haleigh) was very responsive, the neighborhood/street was beautiful and well kept, and the listing accurately describes what to expect when entering the house. It was spacious, clean, and accommodating. We were also pleasantly surprised by the walk to the beach access. It was even easier than I envisioned. We did find a wagon out back that we utilized, as well.

Meredith B. - Posted: 9/13/2023

First time in Hilton head. Amazing location, convenient and exactly as advertised.

douglas w. - Posted: 8/1/2023

We have been coming to HHI for years and this was our favorite place to stay with the family. Greay house for entertaining and relaxing! We will return to this property.

Madeline H. - Posted: 7/15/2023

Rating Details: 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 including my 3 children stayed at this property and it was perfect for us. We will look to stay here again. Check-in and check-out was very easy, the home is beautiful and well maintained, getting to the beach was easy, and our kids loved using the pool everyday. Would recommend this to anyone.

Ronald N. - Posted: 6/22/2023

Thank you for staying with us Ronald. We are happy you and your family and a great stay. We hope to welcome you back to the Island soon!

Island Time Hilton Head staff

The property was just as described and was perfect for our group which was 3 adult couples. We had a few issues with the pool/spa heat prior to our check in and the management staff went above and beyond to make sure everything worked and even came out after checking in to follow up and show us how to operate it. Already looking forward to our next stay.

Jon C. - Posted: 5/9/2023

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: Easy bike ride to South Beach & Harbor Town.Easy walk to the beach, and Nice pool in the sunPlenty of dishes, easy cooking in large kitchen & lots of towels!

Janet W. - Posted: 4/20/2023

Thank you for staying with us Janet! We are happy to hear you had a great vacation. We can't wait to welcome you back to the island.

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: This is a wonderful house and is well acquitted with everything you need for a great stay at Hilton Head. It is great for large groups and there is plenty of places to sleep. Would only suggest a love seat or some comfy chairs for to add to the living room. We had a large group on a rainy day and needed more comfy seating.

Brooke W. - Posted: 9/30/2022

Thank you for staying with us Brooke! We are happy to hear you had a great time with us. We will pass on your recommendation of comfy seating to the homeowners. We hope to welcome you back soon.

Island Time Hilton Head staff

We had a great time and everything went as smooth as possible in terms of securing the rental, checking in, renting beach gear, property manager was wonderful in helping us find the quickest route to the beach. House was perfect in terms of space and cleanliness. My only “complaint” is that the walk to the beach was a solid 15 minutes, which I don’t think was made clear in the description. It’s not a quick walk. That being said, it didn’t put a damper on the things, it’s just a lot to coordinate with such a big group that ranged from elderly guests to very young kids and lugging all the “stuff.” Would def recommend this place though!! Also very conveniently located near tons of shops, activities, restaurants, etc.

AnnMarie M. - Posted: 8/31/2022

Thank you for staying with us AnnMarie! We are happy to hear you had a great time with us! We hope to welcome you back to the island.

Island Time Hilton Head staff

This property was perfect for our family of nine—six adults and three children! The layout was wonderful with the bedrooms (all with en-suite bathrooms) just off of the great room. The pool/spa area was great with plenty of seating space for us all. We can’t say enough about the property management team, Island Time. From the original booking to check in to check out, things could not have gone any smoother. The attention to detail is unsurpassed. When we arrived, the house was spotless, the beds were all made up, and the towels were nicely presented on each bed. In addition, we were provided with sundries (washer/ dishwasher pods, shampoo/conditioner/lotion, etc. )to get us through about three days—so helpful. They were very responsive to our questions while we were there. All in all, we had a great experience.

George and Roberta M. - Posted: 8/14/2022

Thank you for staying with us George! Thank you for the kind words. We are so happy to hear you had a fantastic vacation. We can't wait to welcome you back.

Island Time Hilton Head staff

It was good. I especially appreciated the calls from Island Getaway asking if we needed anything and kept in touch throughout the process. Brenda from Island Getaway was the best communicator. She is excellent in serving the clients. However, I will never book with VBRO again. They have never refunded my money from booking back in March 16 and canceling on March 24 for June 25 date. I’ve called several times and never got a response back Sorry VBRO you lost a good customer and many along the way as I share my experience.

Charles - Posted: 7/2/2022

Thank you for staying with us Charles. We apologize for the experience of VRBO. We hope to welcome you back through 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: This is a great rental property. Worked perfectly for our 3 family get together. The inside is fully updated and kitchen was well stocked. The outside still needs work. The landscaping is a work in progress. 2 things the management co. didn't know was there are two coffee makers, one regular one Kuerig and the carport is now a full two-car garage. The outdoor shower was a bonus for kids coming back from the beach. Because it in a new rental it doesn't have some of the fun extras rentals often have like books or games. Easy walk to the beach, close to everything in Sea Pines. Enjoy!!

Donna R. - Posted: 6/30/2022

Thank you for staying with us Donna. We are happy to hear you enjoyed your stay. We look forward to welcoming you back.

Island Time Hilton Head staff

The house is currently being remodeled and is very beautiful. The photos online are not accurate. We had a fabulous time and the following comments are meant to be constructive. There is not enough seating in the main family area. One sectional but the house sleeps 13. We had 8 adults and 2 toddlers and the seating wasn’t adequate. Also no side tables for placing drinks etc. The kitchen should be better equipped for large groups. The bathroom that serves the main area smelled like sulfur. And there is only 1 can for trash which isn’t enough when you have that many people. Overall the house is great. Great location!!

Tracie D. - Posted: 6/3/2022

Thank you for staying with us Tracie. We do appreciate the feedback as it helps us continue to improve. We are happy you enjoyed your stay. 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: This home was a beautiful renovation of an older home. It has been well done and is well outfitted for a stay. With 7 beds and a pull out sofa - there is plenty of room to share and be comfortable. There is even a mini office off one of the bedrooms that we ended up using for another bedroom with a blow up mattress. It allowed nine friends to each have their own bed and worked well for a girls getaway weekend. Would definitely stay here again!

Brooke W. - Posted: 5/3/2022

Thanks for taking the time to leave us a review, Brooke. We appreciate your feedback. We are glad you enjoyed your getaway with us. We look forward to seeing you again!

Island Time Hilton Head staff