Entire home

20 Tupelo: Charming Sea Pines Home, Private Pool, Free Bikes

Photo gallery for 20 Tupelo: Charming Sea Pines Home, Private Pool, Free Bikes

A beach with rows of blue umbrellas and beach chairs, a large building with a red roof in the background, and palm trees. - 20 Tupelo: Charming Sea Pines Home, Private Pool, Free Bikes (Hilton Head Island)
A rectangular swimming pool with a tiled deck, surrounded by a wooden fence and a house with a porch. - 20 Tupelo: Charming Sea Pines Home, Private Pool, Free Bikes (Hilton Head Island)
A spacious living room with a sofa, coffee table, and a striped rug. - 20 Tupelo: Charming Sea Pines Home, Private Pool, Free Bikes (Hilton Head Island)
A kitchen with white cabinets, a stainless steel refrigerator, and a bar area with wicker chairs. - 20 Tupelo: Charming Sea Pines Home, Private Pool, Free Bikes (Hilton Head Island)
A modern kitchen with white cabinets, a dishwasher, and a dining area with a wooden table and chairs. - 20 Tupelo: Charming Sea Pines Home, Private Pool, Free Bikes (Hilton Head Island)
20 Tupelo: Charming Sea Pines Home, Private Pool, Free Bikes provides laundry facilities and more. Guests can connect to free in-room WiFi.

Reviews

9.2 out of 10
Wonderful

Entire home

3 bedrooms2 bathroomsSleeps 8167 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Add dates for prices

About this property

20 Tupelo: Charming Sea Pines Home, Private Pool, Free Bikes

  • Proudly hosted by Island Rentals of Hilton Head, this newly renovated and tastefully furnished 3-bedroom home offers stunning golf course views and an unbeatable location within Sea Pines. Situated on peaceful Tupelo Street with minimal traffic, this retreat provides the perfect balance of tranquility and convenience—just a short bike ride from the nearest beach access. Inside, you’ll find an elegant open floor plan with a recently updated kitchen, spacious dining areas, and two inviting living spaces designed for both relaxation and entertainment.

    Comfortably sleeping up to eight guests, this home features a King bedroom, a Queen bedroom, and a third bedroom with two Full beds, plus a sleeper sofa for additional flexibility. Step outside to enjoy your private pool and spa, relax with picturesque golf course vistas, or fire up the gas grill for outdoor dining. Thoughtful amenities elevate your stay, including high-speed WiFi, four adult bicycles, four backpack beach chairs, and one hour of free tennis daily at South Beach Racquet Club.

    With complimentary linens, towels, and one Sea Pines car pass included, your vacation can begin the moment you arrive—simply pack your suitcase and beach towels. Offering comfort, style, and effortless convenience, this Tupelo Street haven is the perfect setting for your next Hilton Head Island getaway.

    • 1 Complimentary Car Pass for Sea Pines Included (Additional for purchase, 3 Car Maximum)
    • All Bed Linens and Towels Provided
    • 3 Bedrooms, 2 Baths
    • Sleeps 8: 1 King Bed, 1 Queen Bed, 2 Full Beds, Sleeper Sofa
    • Private Pool and Spa can be heated for an additional fee
    • Gas Grill for Outdoor Cooking
    • High Speed Wifi Internet
    • 1 Hour of Free Tennis Daily at South Beach Racquet Club
    • 4 Free Adult Bicycles from South Beach Cycles/ E-Bikes NOT permitted in Sea Pines
    • 4 Backpack Beach Chairs at the Home

    * All Reservations made for a duration of 1 month (28 Days) or longer are non refundable. Travel Insurance is highly recommended.

Property amenities

Pool/Spa

  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Limited on-site parking (max 1 space)

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Living room

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Gas grill
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near the sea

Things to do

  • Bicycles
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Horseback riding nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Bicycles
  • Property located in a resort
  • Unit size: 1,800 square feet

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  • Pool
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  • Washing machine
  • Dryer
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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

About the area

Located by the sea, this holiday home is in Sea Pines, a neighbourhood in Hilton Head Island. The area's natural beauty can be seen at Coligny Beach and Tybee Island Beach. Lawton Stables and Gregg Russell Harbour Town Playground are also worth visiting. Fishing offers a great chance to get out on the surrounding water, or you can seek out an adventure with ecotours and horse riding nearby. Visit our Hilton Head Island travel guide
View more Holiday homes in Hilton Head Island
Map
Hilton Head Island, SC

What's nearby

  • A serene lake surrounded by lush greenery and trees with Spanish moss hanging from the branches.
    Sea Pines Forest Preserve
    13 min walk - 1.2 km
  • A sign for Sea Pines with directions for Pass Holders and others.
    Atlantic Dunes by Davis Love III
    17 min walk - 1.4 km
  • A coastal landscape with a large body of water, sandy shores, and a cloudy sky.
    South Beach
    18 min walk - 1.5 km
  • Heron Point by Pete Dye
    17 min walk - 1.4 km
  • Lawton Stables
    17 min walk - 1.4 km

Getting around

  • Hilton Head Island, SC (HHH)
    23 min drive

Restaurants

  • The Quarterdeck
    6 min drive
  • Harbour Town Bakery & Cafe
    5 min drive
  • The Crazy Crab
    6 min drive
  • Reilley's Grill & Bar
    5 min drive
  • Loggerhead Landing
    4 min drive

Frequently asked questions

Does 20 Tupelo: Charming Sea Pines Home, Private Pool, Free Bikes have a pool?

Yes, this property has a pool.

Is 20 Tupelo: Charming Sea Pines Home, Private Pool, Free Bikes pet-friendly?

No, pets are not allowed at this property.

How much is parking at 20 Tupelo: Charming Sea Pines Home, Private Pool, Free Bikes?

On-site parking is available at the property.

What time is check-in at 20 Tupelo: Charming Sea Pines Home, Private Pool, Free Bikes?

Check-in begins at 4:00 PM.

What time is check-out at 20 Tupelo: Charming Sea Pines Home, Private Pool, Free Bikes?

Checkout is at 10:00 AM.

Where is 20 Tupelo: Charming Sea Pines Home, Private Pool, Free Bikes located?

Located in Sea Pines, this holiday home is within a 15-minute walk of Sea Pines Forest Preserve and Lawton Stables. Atlantic Dunes by Davis Love III and Heron Point by Pete Dye are also within 1 mile (2 km).

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20 Tupelo: Charming Sea Pines Home, Private Pool, Free Bikes Reviews

Reviews

Wonderful

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 55 out of 81 reviews
Rating 8 - Good. 17 out of 81 reviews
Rating 6 - Okay. 9 out of 81 reviews
Rating 4 - Poor. 0 out of 81 reviews
Rating 2 - Terrible. 0 out of 81 reviews

9.4

Cleanliness

9.8

Location

Reviews

From a partner site

10/10 Excellent

Great place!

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 the second time retiring to this property, and about to book a third. Great stay.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great views of golf course and the pool!

Terrific place to stay. All on one floor which is a bonus and the pool has easy access. Located near many amenities including the Sea Pines beach club and the wider bike trails. Wish we could have stayed longer!
Stayed 5 nights in Feb 2025
From a partner site

10/10 Excellent

Enjoyed this home!!!

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

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Serene Sea Pines Home

Nice for families, easy bike ride to the beach, heated pool (upon request), stocked kitchen with all utensils/pots/pans. Stocked with beach chairs, some kids beach toys, and pool noodles. Enjoyed the calmness of the neighborhood, golf course views, and ease of navigating HHI.
Stayed 5 nights in Mar 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Pool, Convenient & Quiet Location!

We enjoyed our stay and loved the pool. It was fun to watch golfers play the course during the day and there are lots of fun things to see and do in Sea Pines. The house was clean and spacious, easy to find, and very convenient to everything in Hilton Head. The management was very responsive via text when I had questions.
Stayed 3 nights in Jul 2024
From a partner site

8/10 Good

Heritage weekend

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: Overall we had a great experience, the living room furniture could use some updating - uncomfortable.
Stayed 4 nights in Apr 2024
From a partner site

10/10 Excellent

Golf Course Home

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 home was clean wit great views of the golf course. Everything was spotless and the pool was amazing. In quiet neighborhood that is quiet and lots of bike paths. Lots of space in the kitchen and ample kitchenware present. While you have to drive to the beach there is a neighboorhood shuttle that will take you there easily. I would absolutely stay in the home again.
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice house. Fun pool. Unfortunate bugs!

Overall the house was great! The pool was nice, not huge but big enough for our family of five to enjoy. The interior of the house was pretty clean. Comfortable beds. Plenty of space to spread out. Bathrooms were decent. The two coffee makers available need to be replaced. They did not work very well. Our biggest complaint was the palmetto bugs .. we killed at least six
Stayed 6 nights in Jul 2024
From a partner site

8/10 Good

Great stay despite the weather

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 relaxing week here. Rained ALOT and hubby was sick with a cold. But, the house made it worth the trip. Loved watching the golfers go by. So close, many waved to us. Hot tub us more like a circulating tub. Hot just no jet pressure like ours at home.
From a partner site

10/10 Excellent

House with great living space

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: A nice location, close to stable and close to hilton head ammenties. The house is very maintained with a great open living space and nice side room. The pool/hottub were great and well appreaciated by the kids.
Stayed 5 nights in Dec 2023
From a partner site

6/10 Okay

It was ok

Rating Details: The property manager was more than helpful. The vacation rental was very clean. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had a nice stay. A few hiccups with the hot tub not working and that was the reason we picked this home. A few unwelcome guests, cockroaches, but overall the house was clean and had plenty of room.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Private Location

Great location. Close to the beach, shopping and restaurants. Nice quiet private location with a pool.
Stayed 4 nights in Jun 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Loved our stay!

The pool and hot tub were wonderful! There was space in the house for everyone to have privacy after long days.
Stayed 7 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great House

Our family has a wonderful time. We all spent a lot of time in the pool and hot tub, and could easily bike anywhere in Sea Pines. We'd stay here again for sure!
Stayed 5 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great home!

Comfortable, spacious. great pool and hot tub! Easy to find and close to the beach! Great place to spend time with your family!
Stayed 7 nights in Feb 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Tupelo

It was a great spot for our family!
Stayed 6 nights in Sep 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family vacation

This was a great spot for our family of 4. Fully stocked kitchen, ample space with room for at least one more, a spacious and relaxing pool, bikes and beach chairs for 4. The golf course is right behind the property but plenty of privacy. Several hot spots including the beach, Harbour Town and Coligny plaza were all within bike riding distance.
Stayed 7 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect family vacation

This was the perfect spot for our family’s spring break! House was clean, kitchen well stocked and beds were comfortable. Was a bit cold for the beach during our stay but thanks to the heated pool we were still able to get lots of swimming time. Loved having the bikes available and the home is in a great location with easy access by bike or car to everything we needed!
Stayed 5 nights in Mar 2023
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Start to summer getaway

Our group of 4 (2 couples) had a great time staying in this Seapines home. It is in a great location to bike anywhere in Seapines and when staying put, we enjoyed watching the golfers, sitting near the pool (even though it was unusually cool for May!) and cooking in the well appointed kitchen.
Stayed 4 nights in May 2023
From a partner site

10/10 Excellent

Great Getaway!

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 home was clean and had everything we needed including bikes. The pool was great as well, and did not need to be heated while we were there at the end of June.
Verified review

6/10 Okay

Liked: Check-in, communication, location

Sea Pines rental

The interior of property was spotless, but exterior was a different story. Windows were so dirty you could barely see out. Furniture in living room is extremely uncomfortable. Rental agent was excellent and responded immediately as soon as we called.
Stayed 29 nights in Feb 2024
From a partner site

10/10 Excellent

Hilton Head 2022

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 rental was amazing for our 2nd year down to HHI. We would rent it again. The only things that need fixed or added really is extra blankets if need be, a drain stop for the bathtub and plungers in both bathrooms just in case you need it. The house sat in a quiet neighborhood with easy access to the beach 🏖 The kids loved the pool.
Stayed 7 nights in Jun 2022
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Ideal setting

We feel lucky to have found this great place to stay. It was so nice to be nestled into Sea Pines and on the golf course. The pool and hot tub were great, the updates to the kitchen and bathrooms were lovely. The only three cons would be that there aren’t convenient outlets to plug in chargers for phones in the bedrooms, the house needs ceiling fans in every bedroom because the ac had trouble keeping up in the July heat so we bought fans, and the little sun room gets HOT so when you’re using for guests, they can’t really be in there during the heat of the day. Since we used it for two of our kids, it worked out but adults would not be happy out there. We would rent again though! Great house!
Stayed 7 nights in Jul 2023
From a partner site

8/10 Good

A few upgrades & this is a TEN!

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was somewhat dissatisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We are so grateful that we were able to rent this home in Sea Pines for a "relocated quarantine home"! The pool, location to beach & view of golf course, bikes in the garage and open floor plan & lovely kitchen make this a STELLAR option for a family vacation. The 7 of us all concur.. this home was wonderful. The beds are another story: the master was bouncy, we could feel the springs, & too high from the ground. Our kids, all teenagers, had more bad nights of sleep than good as they finally faulted the beds w/o our prompting. The sofas are equally uncomfortable so the pool lounge chairs became napping places.
Verified review

6/10 Okay

Liked: Cleanliness, location, listing accuracy
Disliked: Check-in, communication
The house was great. The description was just as described. The pool was wonderful. The bikes were a big plus. Location was good. The communication with host/ property management was terrible. We never got the check in process email or VRBO text. We got to the gate and held up traffic while we tried to explain to the gate attendant that we had not received our pass. We were directed to pull over to the side. We called the number listed and it was after hours so we got voicemail. We left a message. They did finally call back and were not nice. We had to drive elsewhere to get a voucher to trade for our one pass. He gave us the house code and no other information. They never picked up the trash and I called the number listed on the fridge and they said they no longer had a contract. The trash was over flowing and wildlife had gotten into it and we had to pick it up. I called again and finally got Jay the property manager. He was very nice and got the trash picked up. We never got a checkout procedure. I messaged the host and they did not respond. We only got a response after we had left the property and were hours down the road. We did have a great trip and enjoyed the house and are glad that we went.
Stayed 7 nights in Jul 2025