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$376-1344 (rate range) For Rent Daily 5 Jessamine Place Hilton Head Island, South Carolina 29928   Bedrooms 4 Baths 4 Sleeps 13 Sq Ft 2793 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). 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 4 brand new 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.

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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
• 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
• Desk
• Wifi
• Free Wifi
• Office
• Computer Monitor
• Desk Chair
• Coffee Maker
• Dishes & Utensils
• Dishwasher
• Kitchen
• Microwave
• Oven
• Refrigerator
• Stove
• Toaster
• Dining Table
• beachcombing
• bird watching
• eco tourism
• horseback riding
• outlet shopping
• paddle boating
• photography
• scenic drives
• sight seeing
• walking
• Beach
• Resort
• Deck / Patio
• Golf
• Lawn / Garden
• Outdoor Grill
• Tennis
• Hot Tub
• 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
• wind-surfing
• children welcome
• non smoking only
• pets not allowed
• Long-term Renters Welcome
• Minimum Age Limit for Renters
• flexible
• recommended
• Dining Area
• Concierge
• 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
• Designated work space
• Complimentary Concierge Services
• Symphony Orchestra
• Beach
• Private Pool
• Heatable Pool
• Spa
• Heatable Pool & Spa
• BBQ Grill
• Gas Grill
• Near Beach
• 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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Ad No. 27374. This ad has been viewed 17 times.
Visitor Reviews (21) Write a Review! "Great Family Getaway 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. " Jul 28, 2025 - Ryan D., Lake Forest, IL "Thoma Family Vacation 2025 Overall we had a great week. Very nice accommodations along with plenty of room for all 10 of us adults. Everything was very comfortable. About a 15min walk to the beach just as the listing said. " Jul 22, 2025 - , Russellville, KY "This was a Nice Home but Never Again with Island Time Management While the house was lovely we will not rent again from this management company. We were quite frustrated when the spa would not work so we reached out to the property manager. Future renters, be warned, if you do not pay for pool heat the spa heat will not turn on. We did not want or need the pool heated, it was June and very hot outside. My husband and I were really looking forward to using the spa in the evenings once the sun went down. The houses we rent on HHI all have pools with an attached spa and there has never been a charge to turn on the spa bubbles and heat with other rental companies, especially in the summer. We will not rent from this company again because the manager we spoke to was rude and condescending. There is room for improvement in the descriptive listing of the home. They should call out that the spa will not turn on unless pool heat is paid for as we felt miss informed. Also, the sheets were pilled and not washed with fabric softener. We literarily went to HomeGoods and bought cotton sheets to use while staying here. Our experience was that this management firm will nickel and dime you and cuts corners on amenities like quality sheets and extras like beach towels. Had they not been rude on the phone and offered an apology and or a solution I would have never written a negative review about our experience. I work with the general public and alway approach things in a kind manner and was not met with that type of service when I called. We did have a couple of maintenance things go wrong with the home that I mentioned to them and they didn't even give us warning that they were sending maintenance to fix things. Also, when we checked in we were told to go to the wrong beach access. Again, when all of these things were brought to the attention of the property manager she was an absolute jerk to us. Her personality and the lack of professionalism she exhibited really rained on our stay. Customer service was lost on her." Jul 09, 2025 - Lauren B., Valencia, PA "5 Jessamine Well done, just wish the thermostat could be set a little lower than 70 degrees. " Jul 09, 2025 - Sharon F., Canton, OH "Great House The house was spacious, clean, good location, heated pool was great for our entire family, and the front yard was perfect for our kids!" Apr 29, 2025 - , Marietta, GA "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!" Mar 19, 2025 - Anne C., Reading, PA "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. " May 21, 2024 - , Glenview, IL "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!!" May 21, 2024 - Jen S., Franklin, TN "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." Apr 15, 2024 - Jared P., Union, KY "Beautiful property and ideal location Staying at 5 Jessamine Pl. was a wonderful time for everyone- 4 adults and 2 children. House was well stocked and very comfortable furniture. We even rebooked for next year! Had a maintenance issue with the hot tub but was taken care of-sadly, on last day, but otherwise an ideal rental property. I highly recommend using Island Time Realty. They are professional, friendly and very helpful. You will love staying at 5 Jessamine Pl!" Apr 08, 2024 - Kathy C., Brunswick, OH "Gem in Sea Pine Well thought out home design. QR codes explaining everything was very helpful. This house checked all the boxes for us." Mar 28, 2024 - Joe G., Independence, MN "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." Jan 04, 2024 - Dale F., Eagan, MN "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. " Nov 28, 2023 - Sue I., Canton, GA "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." Oct 02, 2023 - Barbara E., Lawrenceville, NJ "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. " Sep 28, 2023 - Ralph T., Mineral, VA "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. " Sep 13, 2023 - Meredith B., Boise, ID "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." Jun 21, 2023 - , CARMEL, IN "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!" Apr 24, 2023 - , Burr Ridge, IL "Nice property. Misleading location. The house as rennovated is very nice. Fantastic natural light. The kitchen/great room and master bed/bath are wonderful. Our disappointment was the location is not as advertised and included rental fees in the price. This is not a "5 min walk to beach" house. The management property added fees for beach equipment and "app" that were significant percentage and added little value to our experience. It would be better to reduce or eliminate these fees for a better value. I would maybe stay here again, but would look at other property management offerings in the future." Jul 06, 2022 - , Cincinnati, OH "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!!" Jun 29, 2022 - Donna R., BLUFFTON, SC "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!" May 03, 2022 - Brooke W., Clemson, SC
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