Cottage vacation rentals in Hilton Head Island

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Popular amenities for Hilton Head Island cottage rentals

Cottage rentals with a pool

Guest favorite
Cottage in Saint Helena Island
4.82 out of 5 average rating, 28 reviews

707 Ocean Cottage breathtaking views!

LisaRating, 5 stars5 months ago
Pam was a wonderful host,-great communication! Was comfortable place with beautiful ocean views! Clean place and nice touches for Disney Polynesian decor —- We really liked exploring around Fripp Island with golf cart , beautiful island!!
Superhost
Cottage in Tybee Island
4.94 out of 5 average rating, 17 reviews

VintageTybee Beachhouse/Pool/Pets/EVchg/Free2 Park

LeslieRating, 5 stars1 month ago
Our family loved our stay! The house was full of so much charm - the screened-in porch in front was perfect for coffee in the morning, the patio was peaceful and relaxing! Our kids loved the pool and the sauna and hot tub were an added bonus. We had so much fun exploring the island on a golf cart, Tybee has great beaches and restaurants! We spent one day exploring Savannah, too. Lauren was super responsive and helpful and we hope to come back soon!
Top guest favorite
Cottage in Savannah
4.95 out of 5 average rating, 232 reviews

Moss Lake Cottage

JacquelineRating, 5 stars4 days ago
Lori's place provided us with a peaceful place to rest. The cottage was well equipped with everything a guest might need. Evidence of Lori's thoughtful hospitality in every corner. Grocery stores were minutes away. We were able to prepare meals at the cottage which kept us from having to eat out so much. We chose this location because of it's centrality. Tybee Island about 15 minutes away and Savannah the same distance. We enjoyed the best of both.
Top guest favorite
Cottage in Habersham
5 out of 5 average rating, 28 reviews

Low Country Cottage in Beautiful Habersham

MelissaRating, 5 stars1 week ago
We stayed here over Easter while visiting friends in the neighborhood. Beautiful home, lots of great amenities, walkable neighborhood with lovely scenery. We had our two children, ages 6 and 11, and this house fit all of our needs. The hosts were extremely gracious and communication was top notch. We visited the pool two days and also attended Easter church service. Highly recommend and would definitely stay here again!
Superhost
Cottage in Saint Helena Island
4.85 out of 5 average rating, 82 reviews

Saltwater Zen - A Fripp Island Oceanfront Retreat

GailRating, 5 stars2 weeks ago
Beautiful view and comfortable place to stay. Pool is right next door. Make sure you pick up any food prior to getting to Fripp Island. The closest store is on Lady Island where there are 3 great grocery stores. Wish the beach was closer to the cottage but knew it was not before we got there. Hunting Island State Park is close by with a lovely beach that is easily accessible. The beach at Fripp Island is beautiful too but you need to walk quite a way to get to the water. Sand dunes are between the boardwalk and beach. This was not a real issue for us but may be for some beach lovers.
Cottage in MidTown
4.81 out of 5 average rating, 31 reviews

Adorable Dog Friendly Cottage, Heated Pool Access

PatrickRating, 5 stars3 weeks ago
A fantastic 2 bedroom apartment just a 10 minute walk away from Forsyth Park and the historic district. The accommodations were great and the apartment was perfect for our 2 night stay in Savannah. Would stay here again when visiting Savannah.
Guest favorite
Cottage in Fripp Island
4.95 out of 5 average rating, 22 reviews

Fripp Haven Cottage w/Cart & Golf Course Views

KimRating, 5 stars9 months ago
Wonderful stay on Fripp Island. Renee was super responsive and helpful and the home was exactly what we needed.
Guest favorite
Cottage in Hilton Head Island
4.89 out of 5 average rating, 46 reviews

Hilton Head Beach Getaway, 2 Bedroom beach house

CarieRating, 5 stars1 week ago
We absolutely loved our stay here with our 4 year old and 6 year old. The cottage was even cuter in person and felt both tucked away and connected to everything. The walk to the beach was easy (especially with the provided bikes) and we were able to easily get around Sea Pines by bike. (We rented from Sea Pines which made it super easy.) The kitchen was well stocked and we loved meals on the screened in porch. The pool was lovely on hot afternoons! Highly recommend for an easy stay in Hilton Head.

Cottage rentals with a hot tub

Top guest favorite
Cottage in Tybee Island
4.98 out of 5 average rating, 132 reviews

Couples Retreat FREE Golf Cart/Bikes/Kayaks + Dock

LisaRating, 5 stars1 day ago
We decided to check out Tybee Island on our drive back to Maryland from Florida this year. It was a perfect weekend respite to break up the long drive. The cottage is just as pictured -cozy, rustic and delightfully charming. I loved all of the whimsical touches throughout (particularly the champagne bell!) The king bed and living area chairs were very comfortable but the best spot was out on the screened dock porch-lounging on the swinging bed-cool in the shade and by the constant breezes. While the tide swings didn't cooperate for use of the kayaks, we did enjoy biking all over the island and the use of the golf cart to explore. The outdoor shower was also a big win! I highly recommend this spot for some R&R!
Guest favorite
Cottage in South Historic District
5 out of 5 average rating, 17 reviews

DT Area + Hot Tubs+ Pets allowed + Next to Forsyth

BobbieRating, 5 stars2 weeks ago
We had a great experience. It worked well for our two families and it had a private space in the back. The host was very responsive and responded immediately.
Cottage in Hardeeville
4.8 out of 5 average rating, 5 reviews

2 Bedroom Tiny Home

GretchenRating, 5 stars2 weeks ago
What a hidden gem! We absolutely loved our short weekend stay in one of the tiny houses! Private yet homey feeling. This park was great with the pool, hot tub, gaming options and the surroundings were so serene. Staff were super friendly and helpful. Check in and check out was super smooth. We are already looking to book another stay soon! Highly recommend!
Guest favorite
Cottage in Tybee Island
5 out of 5 average rating, 11 reviews

Tybee Couples Retreat/Pool/Hot Tub/Golf Cart/Bikes

VickyRating, 5 stars2 months ago
Loved staying at Missy’s place on Tybee Island. Especially loved the enclosed porch with TV and 2 swinging couches. Missy provided everything we could possibly need in her cozy adorably decorated place. The hot tub was great! She even provided a golf cart so we were able to explore most of the beautiful Tybee island without paying parking fees. Missy gave us recommendations for restaurants. The Crab Shack was a fun place to eat with great food and some alligators and birds to see. Definitely recommend Missy’s Salty Mermaid Couples retreat and hope to visit again one day. Missy truly is the hostess with the mostest.
Guest favorite
Cottage in Tybee Island
4.98 out of 5 average rating, 142 reviews

Honeymooners Anniversary Small families Retreat

Jessica & TiffanyRating, 5 stars2 weeks ago
Wonderful house with thoughtful touches. We loved the proximity to the beach and used a golf cart to get everywhere we needed to go. My MIL slept on the sofa bed and said it was comfortable which is not easy to find! The pool and spa were perfect especially because it was still a little chilly. Thank you for a great stay! 10/10 recommend!
Guest favorite
Cottage in South Historic District
4.88 out of 5 average rating, 130 reviews

Historic District + Hot Tub + Games + Forsyth Park

QuindaijahRating, 5 stars1 month ago
nice cottage , hot tub , very nice bathroom , it is a shared backyard but it's nice to enjoy
Top guest favorite
Cottage in Tybee Island
5 out of 5 average rating, 46 reviews

TIKI Couples Retreat, FREE Golf Cart/Bikes/Hot Tub

MonkeiaRating, 5 stars2 days ago
Missy’s cottage was incredible—the perfect peaceful escape. It’s beautifully set up with so many thoughtful amenities that you truly don’t need to leave the property to enjoy your stay. I highly recommend booking a getaway here and can’t wait to return!
Guest favorite
Cottage in Tybee Island
4.94 out of 5 average rating, 140 reviews

Salty Mermaid: Private Pool/Hot Tub, Walk to Beach

RichardRating, 5 stars1 month ago
This place was terrific! Even better than the pictures. Clean and tastefully decorated. Kitchen was great as were the bedrooms and outside amenities. Would highly recommend and look forward to coming back!

Pet-friendly cottage rentals

Guest favorite
Cottage in North Historic District
4.94 out of 5 average rating, 127 reviews

Cozy | Historic 1790 Guest House Steps to River St

GusRating, 5 stars1 week ago
This is an awesome place to stay in Savannah. Short walk to many coffee shops, courtyards, and restaurants. Maybe a 15 minute walk from awesome places like Forsyth Park, Market Street, and the Cathedral of St. John the Baptist. Such a cool and historic building with great amenities. Hosts were awesome and responsive and gave excellent recommendations. Especially awesome given the price!
Top guest favorite
Cottage in Savannah
5 out of 5 average rating, 140 reviews

Screened Patio, Fenced Yard, & Pet Friendly!

Mary JaneRating, 5 stars2 weeks ago
Molly is a great host. From start to finish, she was always responsive and very proactive. She gave us the address and recommendations for both Savannah and Tybee. The house was spotless and everything we needed was there. Our dog loved the backyard..so private and Peaceful. Beds were very comfy. The house is in a great location to access downtown Savannah as well as Tybee Island. We loved Savannah We would stay here again. Thank you Molly!!
Top guest favorite
Cottage in Saint Helena Island
5 out of 5 average rating, 230 reviews

Harbor River Cottage

SherryRating, 5 stars2 days ago
This was our 2nd stay and will definitely stay again. Peaceful and quiet in a beautiful coastal setting with a vast array of plants and flowers. Sue and her husband are wonderful hosts. Everything you need is in the kitchen. Enjoyed our coffee in the screened in porch where we could watch our dog in the fenced in portion of the yard.
Superhost
Cottage in Beaufort
4.85 out of 5 average rating, 85 reviews

Sweet Pine Cottage

BhavnaRating, 5 stars1 month ago
We were in town for a marine's graduation and this home was absolutely perfect for our family. The backyard was amazing for our dog and Kristyn was extremely communicative. Thank you for an amazing stay!
Guest favorite
Cottage in Hardeeville
4.94 out of 5 average rating, 482 reviews

Tranquil Savannah River Cottage w/ Views+Breakfast

StaciRating, 5 stars4 days ago
All i can say is if you are viewing this listing, BOOK IT!!!. The pictures are great and even better in person. It takes you back to nature. The place is clean, well kept, and the perfect getaway from the city. I did not want to leave. I will be booking again.
Guest favorite
Cottage in Beaufort
4.97 out of 5 average rating, 123 reviews

Bright Dreamy Cottage w/ Fenced Yard & Beach Pass

MarieRating, 5 stars4 weeks ago
Fabulous stay and extremely responsive host! Lots of conversation with the host beforehand that made everything so simple. Would highly recommend. Thank you, Alyssa & Justin
Guest favorite
Cottage in Tybee Island
4.92 out of 5 average rating, 437 reviews

Dreamsicle Cottage (1.5 blocks to the beach)

ScottRating, 5 stars1 week ago
Thanks again Matthew. Would recommend to anyone!
Top guest favorite
Cottage in Beaufort
4.97 out of 5 average rating, 69 reviews

Ladybug Cottage

Mary JoAnnRating, 5 stars5 days ago
What a great place to stay with your dogs! The place was immaculate & nicely decorated. The kitchen was well appointed & had everything we needed. Katie was accommodating. She let us get in early which was important. We had our dogs & it was very hot outside. Loved the location. It was a beautiful walk into town. We were able to bring our dogs, shop, eat & relax in downtown Beaufort. Would love to stay again!

Quick stats about cottage rentals in Hilton Head Island

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ367 before taxes and fees

  • Total number of reviews

    1.4K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

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