Vacation rentals in Skidaway Island

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Popular amenities for Skidaway Island vacation rentals

Stay near Skidaway Island's top sights

Wormsloe Historic Site155 locals recommend
Pin Point Heritage Museum23 locals recommend
Driftaway Cafe22 locals recommend
Sandfly Barbeque20 locals recommend
Walmart Supercenter17 locals recommend
Pearl's Saltwater Grille15 locals recommend

Other great vacation rentals in Skidaway Island

Guest favorite
Condo in Hilton Head Island
4.75 out of 5 average rating, 138 reviews

Salty Sand-Close to the pool, steps to the beach!

AliceRating, 5 stars1 month ago
This was a great stay for our family vacation, close to everything, beach was perfect. Just right for what we needed! ☀️ 🌊
Guest favorite
Condo in Hilton Head Island
4.97 out of 5 average rating, 30 reviews

The Spa at Port Royal Sound 3237

SaraRating, 5 stars1 week ago
Paul’s place was the perfect retreat for our family of five. I appreciated the privacy and 24/7 gated security. Paul’s place had everything we needed for our stay, and Paul communicated with me right along the way. The amenities at the spa were great, and I enjoyed reading and drinking my coffee on the balcony. We recommend!
Superhost
Home in Savannah
4.75 out of 5 average rating, 136 reviews

Family huddle!

DavidRating, 5 stars2 weeks ago
A very nice home, the pictures don’t do it justice it looks much nicer in person and the location is great with easy way to get to downtown Savannah in less then 30min.
Guest favorite
Apartment in Hilton Head Island
4.95 out of 5 average rating, 21 reviews

Best family vacation ever!

ChristopherRating, 5 stars4 weeks ago
Loved our time here. The location was a short walk to the beach. Rented bikes all week and had access to tons of bike paths. It was great to have the pool steps from the back door.
Superhost
Condo in Hilton Head Island
4.86 out of 5 average rating, 56 reviews

Need a break from ordinary? Relaxing quite Resort

TammyRating, 5 stars1 month ago
This condo is exactly as listed, quiet and relaxing. It is definitely our home away from home! Love coming here and enjoying everything the condo and Hilton Head Island have to offer. Dennis is a very responsive host and the condo is kept up and very clean, comfortable. Looking forward to our next visit already!!
Superhost
Condo in South Beach
4.75 out of 5 average rating, 4 reviews

Stunning Water View Villa Near Beach, Hilton Head

PaulRating, 5 stars24 months ago
We had a wonderful long weekend stay, I would highly recommend this apartment to anyone looking for the perfect place to enjoy Hiilton Head. The amenities were all within a short walk and the fishing was an even shorter walk. I can't wait to come back again.
Superhost
Home in Hilton Head Island
5 out of 5 average rating, 3 reviews

Singleton beach-off season bookings

RuthRating, 5 stars11 months ago
We loved the home it was lovely. In my opinion the distance to the beach was an inconvenience. It’s a good walk for families with little kids or older retired adults. The golf cart was not accessible on one of the days and we didn’t get any communication about the situation until we were already at the beach. Driving was an option but even then the distance was long for my parents who are 80+. We still made memories and had a good time. The house was beautiful and very clean. Big enough for everyone to have their own space. My grandchildren loved the bunk beds 3-4 years of age. The hostess was wonderful. She was willing to help if needed.
Guest favorite
Home in Hilton Head Island
4.9 out of 5 average rating, 51 reviews

Amazing Location & Value Family-Golf-Tennis Trips!

BradRating, 5 stars3 days ago
We gathered at Sea Pines on Hilton Head to celebrate our Dads 80th birthday & Tom’s house couldn’t have been better! The location was a short walk to Harbor Town GC Lighthouse/Shops & restaurants! We’ll definitely be back. Thanks!

Quick stats about vacation rentals in Skidaway Island

  • Total rentals

    70 properties

  • Nightly prices starting at

    $50 before taxes and fees

  • Total number of reviews

    3.6K reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

Frequently Asked Questions

  • Where should I stay in Skidaway Island?

    Make yourself at home in Skidaway Island by choosing from our most frequently booked neighborhoods. We have over 320 vacation rentals in Southside, over 540 vacation rentals in The Landings, and over 20 vacation rentals in Rio Vista.

  • Are there vacation rentals with a dedicated workspace in Skidaway Island?

    Yes! Work meets play with ease at over 40 vacation rentals in Skidaway Island featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in house rentals in Skidaway Island?

    Experience the best of Skidaway Island with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Skidaway Island?

    Four-legged friends are welcome in Skidaway Island. Choose from more than 30 vacation rentals for guests traveling with pets.

  • Do house rentals in Skidaway Island have wifi?

    Absolutely! We offer over 50 house rentals with wifi in Skidaway Island. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Skidaway Island have self check-in?

    Absolutely! We offer over 10 house rentals with self check-in in Skidaway Island. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Skidaway Island have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Skidaway Island. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Skidaway Island?

    Skidaway Island has more than 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore