Cumberland Island Holiday Rentals

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Our top choices for Cumberland Island holiday rentals

Charming Villa Just Steps to Beach & Shared Pool W/central AC, Private WD, Wifi

Charming Villa Just Steps to Beach & Shared Pool W/central AC, Private WD, Wifi
2.0 star property
Fernandina Beach
The price is NZ$718
includes taxes & fees
16 May - 17 May
Charming Villa Just Steps to Beach & Shared Pool W/central AC, Private WD, Wifi

Swim, bike, relax: South Side Condo near East Beach with 4 bikes included

Swim, bike, relax: South Side Condo near East Beach with 4 bikes included
St. Simons Island
9.8 out of 10, Exceptional, (36 reviews)
"Excellent communication with host regarding check-in. Incredibly comfortable beds. Great stay!"
United States
Melissa
The price is NZ$577
includes taxes & fees
17 May - 18 May
Swim, bike, relax: South Side Condo near East Beach with 4 bikes included

Island getaway

Island getaway
Fernandina Beach
9.4 out of 10, Exceptional, (54 reviews)
"House was clean and worked well for our weekend trip."
United States
Adrienne L.
The price is NZ$709
includes taxes & fees
14 May - 15 May
Island getaway

Beach GO BO-HO

Beach GO BO-HO
3.5 star property
Brunswick
10.0 out of 10, Exceptional, (2 reviews)
"The owner was wonderful, the room was beautiful and the bed was heavenly. Will definitely be back again."
United States
Antinette
The price is NZ$170
includes taxes & fees
3 June - 4 June
Beach GO BO-HO

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, (25 reviews)
"Excellent property with great proximity to the beach. The property is exactly as listed with a well equipped kitchen. "
United States
Marshell
The price is NZ$517
includes taxes & fees
21 May - 22 May
Beach 5 Villas - Immaculate 300 steps from the Ocean

♥ of SSI Bungalow 2, Quick walk to beach and food ☼

♥ of SSI Bungalow 2, Quick walk to beach and food ☼
St. Simons Island
9.6 out of 10, Exceptional, (20 reviews)
"Great location, very clean and comfortable!"
United States
Charles F.
The price is NZ$458
includes taxes & fees
14 May - 15 May
♥ of SSI Bungalow 2, Quick walk to beach and food ☼

Summer Special! Steps to Village & Pier

Summer Special! Steps to Village & Pier
St. Simons Island
9.2 out of 10, Wonderful, (27 reviews)
"Great communication from host, very clean place, great neighborhood, perfect location!"
United States
natalie h.
The price is NZ$555
includes taxes & fees
20 May - 21 May
Summer Special! Steps to Village & Pier

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)
"One of the best kept secrets in around Amelia Island. We were there for the auction at Goodings and I was impressed at how clean quiet and how close everything was to the home. I can’t express enough how much we enjoyed our stay."
United States
Traci
The price is NZ$804
includes taxes & fees
26 May - 27 May
ISLAND VIBE ~ Close to Beach, Downtown, Egan’s Creek with Fire Pit! KQQ~2Ba

Cowboy Studio, Pet Friendly, Walk to Village

Cowboy Studio, Pet Friendly, Walk to Village
St Simons
9.8 out of 10, Exceptional, (77 reviews)
"Loved the location, nice private location and very walkable to the pier and beach. Comfortable place, would definitely stay here again. "
United States
Dana S.
The price is NZ$828
includes taxes & fees
14 May - 15 May
Cowboy Studio, Pet Friendly, Walk to Village

Steps to East Beach & Pet Friendly w/ 2 King Beds

Steps to East Beach & Pet Friendly w/ 2 King Beds
East End
9.2 out of 10, Wonderful, (36 reviews)
"Great location and great host. The property was exactly what we needed for a short stay on SSI."
United States
Shawn P.
The price is NZ$716
includes taxes & fees
17 May - 18 May
Steps to East Beach & Pet Friendly w/ 2 King Beds

Third-floor Oceanfront Condo With Balcony, W/d, Pool & Tennis

Third-floor Oceanfront Condo With Balcony, W/d, Pool & Tennis
2.0 star property
Amelia City
The price is NZ$850
includes taxes & fees
16 May - 17 May
Third-floor Oceanfront Condo With Balcony, W/d, Pool & Tennis

Steps to the Sand! 2BR/2BA, 1st Level, Beach Gear

Steps to the Sand! 2BR/2BA, 1st Level, Beach Gear
St Simons Island
9.4 out of 10, Exceptional, (96 reviews)
"Great little place, clean, comfortable. "
United States
Jenifer
The price is NZ$1,026
includes taxes & fees
14 May - 15 May
Steps to the Sand! 2BR/2BA, 1st Level, Beach Gear

Luxury Studio Steps to Beach Kitchenette Outdoor Seating Partial View Upstairs

Luxury Studio Steps to Beach Kitchenette Outdoor Seating Partial View Upstairs
Fernandina Beach
10.0 out of 10, Exceptional, (8 reviews)
The price is NZ$567
includes taxes & fees
14 May - 15 May
Luxury Studio Steps to Beach Kitchenette Outdoor Seating Partial View Upstairs

*NEW* Sunny Circle SSI| 1.4 Miles from the Beach!

*NEW* Sunny Circle SSI| 1.4 Miles from the Beach!
Saint Simons Heights
The price is NZ$642
includes taxes & fees
27 May - 28 May
*NEW* Sunny Circle SSI| 1.4 Miles from the Beach!

Cozy condo sleeps 6! Convenient to beach, shopping and all restaurants.

Cozy condo sleeps 6! Convenient to beach, shopping and all restaurants.
St. Simons Island
9.6 out of 10, Exceptional, (56 reviews)
"It was convient and relaxing for a short weekend"
United States
Damon C.
The price is NZ$618
includes taxes & fees
22 May - 23 May
Cozy condo sleeps 6! Convenient to beach, shopping and all restaurants.

Close Beach Access, Walk to Lighthouse & Village!

Close Beach Access, Walk to Lighthouse & Village!
St. Simons
9.6 out of 10, Exceptional, (18 reviews)
"Excellent location and the management company was very responsive and informative. "
United States
Olivia Y.
The price is NZ$828
includes taxes & fees
14 May - 15 May
Close Beach Access, Walk to Lighthouse & Village!

NEW- Discount! POOL - near beach and golf course!

NEW- Discount! POOL - near beach and golf course!
Fernandina Beach
9.2 out of 10, Wonderful, (12 reviews)
"Great weekend getaway for my husband, daughter and I! We loved that the pool was right there!"
United States
Diana W.
The price is NZ$506
includes taxes & fees
17 May - 18 May
NEW- Discount! POOL - near beach and golf course!

One Bedroom just across the street from the Beach!

One Bedroom just across the street from the Beach!
Saint Simons Island
10.0 out of 10, Exceptional, (3 reviews)
"It was a great stay. Perfect location - walkable to EVERYTHING! The only thing missing was ceiling fans, especially in the bedroom."
United States
Marikay B.
The price is NZ$514
includes taxes & fees
15 May - 16 May
One Bedroom just across the street from the Beach!

2-bedroom Condo on St. Simons Island. Pool/Parking/Beach/Food/Bars/Stores, etc..

2-bedroom Condo on St. Simons Island. Pool/Parking/Beach/Food/Bars/Stores, etc..
King City
9.6 out of 10, Exceptional, (9 reviews)
"Property was clean and comfortable."
United States
Karen
The price is NZ$599
includes taxes & fees
25 May - 26 May
2-bedroom Condo on St. Simons Island. Pool/Parking/Beach/Food/Bars/Stores, etc..

Original island cottage 3 bedroom well maintained

Original island cottage 3 bedroom well maintained
Kings Terrace
9.4 out of 10, Exceptional, (3 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 NZ$743
includes taxes & fees
29 May - 30 May
Original island cottage 3 bedroom well maintained
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.
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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 favorite 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 depends 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 NZ$332 per night. Entering your travel dates in the search wizard you might find 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.