House - Rating 5 (17)

5 Jessamine Place | Sea Pines

$400.00 - $1,001.00 / night + taxes
Bedroom 4 bedrooms
Bathroom 4 bathrooms
Guests 13 guests
Pets Not Allowed Pets Not Allowed
Complimentary Concierge Services Included Complimentary Concierge Services Included
  • Address: 5 Jessamine Place
  • Location: Walk to Beach
  • Type: House
  • View: Landscape/Pool
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Bedding Bedding
User User User User
Bedroom 1
Sleeps: 4
1 King

Sleeper Sofa

Attached Full Bath

User User
Bedroom 2
Sleeps: 2
1 King

Attached Full Bath

User User
Bedroom 3
Sleeps: 2
1 Queen Bed

Attached Full Bath

User User User User User
Bedroom 4
Sleeps: 5
1 Bunk Bed set of Twins and 1 bunk with twin over full

Attached Full Bath

Description Description
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.

5 Jessamine Place is only a 10-minute walk to the best beach on Hilton Head Island!

This ranch-style cottage home is newly renovated and beautifully furnished. It offers four bedrooms and four bathrooms to comfortably host up to 13 guests. Nestled on a quiet street with a big yard and private heated pool plus spa, this home is perfect for outdoor activities with the whole family. It is sure to make for lifelong memories.

The massive great room has soaring ceilings and is beautifully lit with tons of natural sunlight. The living room features a cozy, plush couch with a large flat-screen TV for your entertainment. The kitchen is extremely spacious and offers plenty of countertop room with the marble island. It is also fully stocked, and brand new stainless steel appliances make for a chef's dream. The 2 dining tables offer enough seating for up to 12 people, and there are an additional 3 bar stools in the kitchen.

The master bedroom is located on the back side of the home, overlooking the pool. This spacious room offers a king-sized bed and queen sleeper sofa, along with a large flat-screen TV. Beautiful sliding barn doors open up to the master bathroom, consisting of a double vanity and large walk-in shower. The second bedroom also offers a king-sized bed and has its own private ensuite bathroom with a walk-in shower. The third bedroom has a queen-sized bed and an ensuite full bathroom. Through the third bedroom, you have a great office space equipped with a monitor. And the fourth bedroom consists of two bunk beds, one twin over full and the other twin over twin. It also has its own private, full bathroom.

Outside, your backyard oasis awaits. You will love spending your days in the newly updated private pool and spa, surrounded by lush landscaping all around. And there is plenty of seating for everyone outside on the brand new pool deck.

The backyard and the nearby beach with the finest sand on the island are sure to become your favorite places to spend those hot days.

Key Features:

- Proximity to the beach: 10 min walk

- The pool and spa can be heated for an additional charge, give us a call for heating rates and to make arrangements. Pool and spa 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.

- 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.

Amenities 50 Amenities
Amenities
  • Community Playground Community Playground
  • Complimentary Concierge Services Included Complimentary Concierge Services Included
  • Landscape View Landscape View
  • Vay K Life Vay K Life
Bathrooms
  • Bath Towels Bath Towels
  • Hair Dryer Hair Dryer
  • Travel sized toiletries (shower gel, shampoo, conditioner, soap) Travel sized toiletries (shower gel, shampoo, conditioner, soap)
Bedrooms
  • Bedding & Sheets Bedding & Sheets
  • Hangers Hangers
  • Pillows & Blankets Pillows & Blankets
Games & Entertainment
  • TV TV
Heating & Cooling
  • Air Conditioning Air Conditioning
  • Heating Heating
Housekeeping
  • Dryer Dryer
  • Iron Iron
  • Washing Machine Washing Machine
Indoor
  • No Pets Allowed No Pets Allowed
  • No Smoking No Smoking
Internet & Workspace
  • Designated Office Designated Office
  • Designated Work Space Designated Work Space
  • Desk Desk
  • Wifi Wifi
Kitchen & Dining
  • Bakeware Bakeware
  • Bowls, Plates, Mugs Bowls, Plates, Mugs
  • Cookware Cookware
  • Dinnerware Dinnerware
  • Dishwasher Dishwasher
  • Drip Coffee Maker Drip Coffee Maker
  • Forks, Spoons, Knives Forks, Spoons, Knives
  • Fridge Fridge
  • Glassware Glassware
  • Keurig Keurig
  • Microwave Microwave
  • Oven Oven
  • Paper Towels, etc. Paper Towels, etc.
  • Pots, Pans, Cutting Boards, Knives Pots, Pans, Cutting Boards, Knives
  • Stove Stove
Outdoor
  • Outdoor Grill Outdoor Grill
  • Private Grill Private Grill
Parking & Facilities
  • Garage Access Garage Access
Pool & Spa
  • Heatable Pool Heatable Pool
  • Private Pool Private Pool
  • Spa Spa
Property Features
  • Bunk Rooms Bunk Rooms
  • Monthly Stays Monthly Stays
  • Winter Monthly Stay Winter Monthly Stay
Safety
  • Clean with disinfectant Clean with disinfectant
  • Enhanced cleaning practices Enhanced cleaning practices
  • Keyless, no contact check-in and check-out Keyless, no contact check-in and check-out
  • Towels and bedding washed in water that’s at least 60 Towels and bedding washed in water that’s at least 60
Reviews Rating 5 (17) Reviews
Rating 5
Perfect rental home in Sea Pines!
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. from Reading - Posted: 3/16/2025
Thank you for the kind words Anne! We look forward to welcoming you back.
Island Time Hilton Head staff
Rating 5
Family-Friendly Home!!
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. from Franklin - Posted: 5/20/2024
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
Rating 5
Great house for family & kids
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.
Anonymous from Glenview - Posted: 5/20/2024
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 5
Hilton Head experience
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. from Union - Posted: 4/15/2024
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
Rating 5
Gem in Sea Pine
Well thought out home design. QR codes explaining everything was very helpful. This house checked all the boxes for us.
Joe G. from Independence - Posted: 3/24/2024
Thanks for the review, Joe. This house really is a gem, we hope to have you stay again next year!
Island Time Hilton Head staff
Rating 5
Perfect Vacation Home
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. from Reading - Posted: 3/17/2024
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 5
Perfect vacation home!
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. from Reading - Posted: 3/2/2024
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 5
Holiday Season Vacation
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. from Eagan - Posted: 1/2/2024
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 5
Perfect Family Escape
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. from Canton - Posted: 11/28/2023
Thank you for staying at 5 Jessamine Sue! We are happy you had the perfect family escape, and we hope to welcome you back to the island soon!
Island Time Hilton Head staff
Rating 5
Comfy family vacation home!
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. from Lawrenceville - Posted: 9/29/2023
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 5
5 Jessamine Place outstanding stay!
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. from Mineral - Posted: 9/27/2023
Thank you for staying with us Ralph. We hope to welcome you back soon!
Island Time Hilton Head staff
Rating 5
Family Beach Trip
We thought the Jessamine home was fantastic! It was very accommodating for ten adults and children, four of which were under 3 years old. The property was exactly as described with a few other great unexpected items, such as a wagon for the beach and a baby activity center. The interior and exterior of the house was clean, along with the pool. Island Time was also great to work with.
Meredith B. from Boise - Posted: 9/12/2023
Thank you for the kind words Meredith. We are so happy you had a fantastic family beach trip and hope to welcome you back on your next island adventure.
Island Time Hilton Head staff
Rating 5
GREAT STAY!
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.
Anonymous from CARMEL - Posted: 6/21/2023
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
Rating 5
Perfect Location, great for large families
Easy bike ride to South Beach & Harbor Town.
Easy walk to the beach, and Nice pool in the sun
Plenty of dishes, easy cooking in large kitchen & lots of towels!
Anonymous from Burr Ridge - Posted: 4/19/2023
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 5
Second Visit as Good as First
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. from Clemson - Posted: 9/29/2022
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
Rating 5
Nicely updated interior
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. from BLUFFTON - Posted: 6/29/2022
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
Rating 5
Excellent Renovation - Roomy House
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. from Clemson - 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
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Location +

Location
What to do nearby
Beach Club
Beach Club
0.92 miles

Unwind at the Beach Club, enjoying oceanfront dining, and a rooftop bar.
Harbour Town
Harbour Town
1.13 miles

Take a stroll past the Harbour Town Lighthouse onto the pier and watch the boats.
RBC Heritage
RBC Heritage
0.97 miles

Feel the thrill of the RBC Heritage at Harbour Town Golf Links.
Lighthouse
Lighthouse
0.98 miles

Climb the Lighthouse for panoramic views and explore the island's rich history.
Play Pickleball
Play Pickleball
1.42 miles

Join the excitement at South Beach Marina! After your match, relax and enjoy the view!
Atlantic Dunes
Atlantic Dunes
0.71 miles

Enjoy a memorable round at this beautifully constructed ocean course.
Heron Point Course
Heron Point Course
0.71 miles

Tackle the challenge of this golf course for a memorable golfing experience.
Golf Links
Golf Links
0.97 miles

Test your skills at the Golf Links, home to the RBC Heritage and one of the world's top courses.
Stan Smith Academy
Stan Smith Academy
1.13 miles

Join the Smith Sterns Academy to hone your skills with world-class coaching.
Forest Preserve
Forest Preserve
1.53 miles

Stroll through the Forest Preserve's trails, enjoying shady paths, wildlife, and scenic lakes.
Trail Rides
Trail Rides
1.53 miles

Enjoy a peaceful horseback ride through shaded trails and open fields, taking in nature’s beauty.
Pony Rides
Pony Rides
1.53 miles

Treat the little ones to a gentle pony ride, where they can enjoy a fun, safe adventure.
Animal Farm
Animal Farm
1.53 miles

Visit the animal farm to meet friendly goats, chickens, and more.
Water Activities
Water Activities


From jet skiing to paddle boarding and kayaking along scenic waterways.
Sea Pines Center
Sea Pines Center
0.67 miles

Explore Sea Pines shopping center for local crafts, dining, and relaxing spa services.
South Beach Marina
South Beach Marina
1.45 miles

Visit South Beach Marina for dining, shopping, and water sports all in one spot!
Salty Dog Cafe
Salty Dog Cafe
1.45 miles

Savor the world-famous Salty Dog Cafe, where delicious food and ice cream await!
Fitness Center
Fitness Center
0.67 miles

Stay active on vacation with the fitness center offering top equipment.
Bike Paths
Bike Paths


Embark on an active adventure with 15-mile network of leisure paths.
Stoney Baynard
Stoney Baynard
0.55 miles

Explore the rich history at Baynard Ruins and wonder the archaeological remains
Gregg Russell
Gregg Russell
0.98 miles

Experience the magic of live music under the Liberty Oak with interactive sing-alongs.
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How far is the beach?
- Posted: 08/24/2023

Answer:

The beach is a 10-minute walk away. To get to the beach, leave the house, turn right, and head back to the beginning of Jessamine. Cross Greenwood Drive and follow the bike/walking path left until you see the crosswalk and beach path crossing South Sea Pines Drive. Follow that path right to the beach.

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