Cumberland Island Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Cumberland Island holiday rentals

Short walk to East beach on St Simons Island.

Short walk to East beach on St Simons Island.
East End
9.2 out of 10, Wonderful, (5 reviews)
"X"
United States
Cheryl H.
The price is AU$375
includes taxes & fees
11 Mar - 12 Mar
Short walk to East beach on St Simons Island.

Island getaway

Island getaway
Fernandina Beach
9.6 out of 10, Exceptional, (48 reviews)
"Great location. "
United States
Greg B.
The price is AU$601
includes taxes & fees
22 Mar - 23 Mar
Island getaway

Hodnett Cooper's Shipwatch

Hodnett Cooper's Shipwatch
2.5 star property
East End
8.6 out of 10, Excellent, (45 reviews)
"All good only one issue mattress was a bit tired"
United States
bryan s.
Hodnett Cooper's Shipwatch

Original island cottage 3 bedroom well maintained

Original island cottage 3 bedroom well maintained
Kings Terrace
9.0 out of 10, Wonderful, (2 reviews)
"We love the property because is close to the beach ,restaurants the pier it is only 18 minutes away from the house we loved!! the house was really cozy we had a grate vacation "
United States
Jessica
The price is AU$630
includes taxes & fees
13 Mar - 14 Mar
Original island cottage 3 bedroom well maintained

The Angel`s Share: Hideaway in the treetops w/ Cowboy Pool

The Angel`s Share: Hideaway in the treetops w/ Cowboy Pool
St. Simons Island
10.0 out of 10, Exceptional, (4 reviews)
"I had a wonderful stay at this lovely and spotless unit—everything was just as expected. The owners were incredibly helpful and a pleasure to work with; I would definitely stay here again!"
United States
Robert B.
The price is AU$360
includes taxes & fees
11 Mar - 12 Mar
The Angel`s Share: Hideaway in the treetops w/ Cowboy Pool

Cowboy Studio, Pet Friendly, Walk to Village

Cowboy Studio, Pet Friendly, Walk to Village
St Simons
9.8 out of 10, Exceptional, (77 reviews)
"Fantastic location, across from a gorgeous park and just a couple of blocks from all that downtown has to offer! "
United States
Barbara R.
The price is AU$754
includes taxes & fees
13 Mar - 14 Mar
Cowboy Studio, Pet Friendly, Walk to Village

Elegant St. Simons Island Honeymoon Beach Cottage near Pier Village

Elegant St. Simons Island Honeymoon Beach Cottage near Pier Village
King City
9.8 out of 10, Exceptional, (163 reviews)
"Great location, great space."
United States
Cindy K.
The price is AU$590
includes taxes & fees
29 Mar - 30 Mar
Elegant St. Simons Island Honeymoon Beach Cottage near Pier Village

Newly Renovated 2 Bedroom Cottage! One block to Beach! Walk to King & Prince!

Newly Renovated 2 Bedroom Cottage! One block to Beach! Walk to King & Prince!
St Simons
10.0 out of 10, Exceptional, (87 reviews)
"Very convenient and easy check in and out!"
United States
Kaitlan N.
The price is AU$600
includes taxes & fees
15 Mar - 16 Mar
Newly Renovated 2 Bedroom Cottage! One block to Beach! Walk to King & Prince!

Snowbird Special! Steps to Village & Pier

Snowbird Special! Steps to Village & Pier
St. Simons Island
9.2 out of 10, Wonderful, (26 reviews)
"Great communication from host, very clean place, great neighborhood, perfect location!"
United States
natalie h.
The price is AU$525
includes taxes & fees
25 Mar - 26 Mar
Snowbird Special! Steps to Village & Pier

Close Beach Access, Walk to Lighthouse & Village!

Close Beach Access, Walk to Lighthouse & Village!
St. Simons
9.4 out of 10, Exceptional, (16 reviews)
"Excellent location and the management company was very responsive and informative. "
United States
Olivia Y.
The price is AU$782
includes taxes & fees
18 Mar - 19 Mar
Close Beach Access, Walk to Lighthouse & Village!

Beach Air -optional BIKES-Pool-Walk 2 Pier Village

Beach Air -optional BIKES-Pool-Walk 2 Pier Village
St Simons
10.0 out of 10, Exceptional, (139 reviews)
"It was a awesome place to stay "
United States
Dilara L.
The price is AU$254
includes taxes & fees
16 Mar - 17 Mar
Beach Air -optional BIKES-Pool-Walk 2 Pier Village

Apartment near downtown.

Apartment near downtown.
St. Simons Island
9.8 out of 10, Exceptional, (12 reviews)
"Nice place, nice hood, nice time."
United States
mark w.
The price is AU$511
includes taxes & fees
17 Mar - 18 Mar
Apartment near downtown.

Ocean Lodge Resort

Ocean Lodge Resort
4.0 star property
St. Simons Island
8.4 out of 10, Very good, (348 reviews)
"Great location "
United States
Debra
The price is AU$279
includes taxes & fees
11 Mar - 12 Mar
Ocean Lodge Resort

ISLAND VIBE ~ Close to Beach, Downtown, Egan’s Creek with Fire Pit! KQQ~2Ba

ISLAND VIBE ~ Close to Beach, Downtown, Egan’s Creek with Fire Pit! KQQ~2Ba
Fernandina Beach
10.0 out of 10, Exceptional, (29 reviews)
"The house was great. The location and accommodations were excellent. Very nice attention to details that made our stay comfortable. We will choose it again when we return Fernandina Beach. "
United States
jeanne f.
The price is AU$680
includes taxes & fees
24 Mar - 25 Mar
ISLAND VIBE ~ Close to Beach, Downtown, Egan’s Creek with Fire Pit! KQQ~2Ba

Quick Beach Access- Beautiful Screened in Deck and POOL

Quick Beach Access- Beautiful Screened in Deck and POOL
Fernandina Beach
9.8 out of 10, Exceptional, (30 reviews)
"Great location and very clean. Great place to stay!"
United States
Stephanie W.
The price is AU$431
includes taxes & fees
22 Mar - 23 Mar
Quick Beach Access- Beautiful Screened in Deck and POOL

Beach 5 Villas - Immaculate 300 steps from the Ocean

Beach 5 Villas - Immaculate 300 steps from the Ocean
4.5 star property
Fernandina Beach
9.6 out of 10, Exceptional, (21 reviews)
"Everything was spotless. Perfect proximity to the beach. Was stocked with everything we needed, and the host was very attentive will definitely return"
United States
Tiffany
The price is AU$435
includes taxes & fees
11 Mar - 12 Mar
Beach 5 Villas - Immaculate 300 steps from the Ocean

Beach&Village! 2 BR, 2 BA 1st Lvl, Beach Gear

Beach&Village! 2 BR, 2 BA 1st Lvl, Beach Gear
Saint Simons Island
9.6 out of 10, Exceptional, (42 reviews)
"We have stayed at Bill’s beach bungalow once before and would definitely stay again. The unit was VERY clean and orderly when we checked in, as was previously. This unit is perfect for a long weekend and we enjoyed our time here. The location is primary reason we chose to stay a second time. Cross one little street and down a path to beach!"
United States
Susan R.
The price is AU$830
includes taxes & fees
11 Mar - 12 Mar
Beach&Village! 2 BR, 2 BA 1st Lvl, Beach Gear

Beach Walk -optional BIKES-Pool-Walk 2 PierVillage

Beach Walk -optional BIKES-Pool-Walk 2 PierVillage
Saint Simons Island
9.8 out of 10, Exceptional, (147 reviews)
"Such a nice quiet nice neighborhood. Excellent stay for the price."
United States
Heather
The price is AU$272
includes taxes & fees
15 Mar - 16 Mar
Beach Walk -optional BIKES-Pool-Walk 2 PierVillage

♥ of SSI Bungalow, Quick walk to beach and food ☼

♥ of SSI Bungalow, Quick walk to beach and food ☼
St. Simons Island
9.8 out of 10, Exceptional, (9 reviews)
"Host was very welcoming & always available! "
United States
Teresa W.
The price is AU$373
includes taxes & fees
12 Mar - 13 Mar
♥ of SSI Bungalow, Quick walk to beach and food ☼

Amelia Surf & Racquet Club Condo B138 | 4th Floor Oceanfront | Pools| Tennis Courts | Sleeps 4

Amelia Surf & Racquet Club Condo B138 | 4th Floor Oceanfront | Pools| Tennis Courts | Sleeps 4
Amelia City
10.0 out of 10, Exceptional, (64 reviews)
"Excellent accommodations!"
United States
Denise P.
The price is AU$791
includes taxes & fees
12 Mar - 13 Mar
Amelia Surf & Racquet Club Condo B138 | 4th Floor Oceanfront | Pools| Tennis Courts | Sleeps 4
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Cumberland Island Hotel Reviews

Find out more about Cumberland Island

Everything you need to know about Cumberland Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cumberland Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cumberland Island holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Cumberland Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cumberland Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cumberland Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cumberland Island holiday rentals we have selected for you start as low as AU$279 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Cumberland Island rentals

At Expedia, we put the best Cumberland Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cumberland Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cumberland Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cumberland Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Cumberland Island?

Yes, there are holiday rentals close to the most popular sights in Cumberland Island, or you can select a more secluded option if you're looking for a relaxing stay. Cumberland Island is known for its beaches and shopping. Make sure you have time to check out the restaurants and museums during your trip.

What are some of the best holiday rentals that Cumberland Island has to offer?

The Villas of Amelia Island: This holiday home rental outside of Cumberland Island is located on the beach, and has an indoor pool, a furnished balcony and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a coffee maker to make your meal-planning easier. It offers a terrace, a garden and a selection of games so that you can immerse yourself in your holiday.

What’s there to see and do in Cumberland Island?

Explore the area and family-friendly sights such as Fernandina Beach Main Beach Park, or get out into nature at a spot like Crooked River State Park. Other places in town to visit include Plum Orchard Mansion and First African Baptist Church.

What’s a holiday rental in Cumberland Island like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cumberland Island. Holiday rentals feature extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for a family getaway.