Cumberland Island Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Cumberland Island holiday rentals

Living area

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 HK$1,164
HK$3,504 total
includes taxes & fees
16 May - 17 May
Charming Villa Just Steps to Beach & Shared Pool W/central AC, Private WD, Wifi
TV

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 HK$916
HK$2,712 total
includes taxes & fees
13 May - 14 May
Swim, bike, relax: South Side Condo near East Beach with 4 bikes included
3 bedrooms, free WiFi

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 HK$1,409
HK$3,310 total
includes taxes & fees
14 May - 15 May
Island getaway
30-inch flat-screen TV with satellite channels, Hulu, streaming services

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 HK$387
HK$794 total
includes taxes & fees
3 Jun - 4 Jun
Beach GO BO-HO
Beach nearby, beach umbrellas, beach towels, surfing

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 HK$1,102
HK$2,374 total
includes taxes & fees
18 May - 19 May
Beach 5 Villas - Immaculate 300 steps from the Ocean
Sun-loungers

♥ 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 HK$1,184
HK$2,135 total
includes taxes & fees
14 May - 15 May
♥ of SSI Bungalow 2, Quick walk to beach and food ☼
Pool

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 HK$867
HK$2,608 total
includes taxes & fees
13 May - 14 May
Summer Special! Steps to Village & Pier
Beach nearby, sun-loungers, beach towels

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 HK$1,284
HK$3,418 total
includes taxes & fees
13 May - 14 May
ISLAND VIBE ~ Close to Beach, Downtown, Egan’s Creek with Fire Pit! KQQ~2Ba
1 bedroom, WiFi

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 HK$735
HK$3,920 total
includes taxes & fees
13 May - 14 May
Cowboy Studio, Pet Friendly, Walk to Village
Smart TV

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 HK$1,578
HK$3,432 total
includes taxes & fees
17 May - 18 May
Steps to East Beach & Pet Friendly w/ 2 King Beds
Living area

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 HK$1,922
HK$3,959 total
includes taxes & fees
16 May - 17 May
Third-floor Oceanfront Condo With Balcony, W/d, Pool & Tennis
Property grounds

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 HK$1,445
HK$4,850 total
includes taxes & fees
13 May - 14 May
Steps to the Sand! 2BR/2BA, 1st Level, Beach Gear
1 bedroom, iron/ironing board, bed sheets

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 HK$1,125
HK$2,666 total
includes taxes & fees
14 May - 15 May
Luxury Studio Steps to Beach Kitchenette Outdoor Seating Partial View Upstairs
TV

*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 HK$1,174
HK$2,936 total
includes taxes & fees
27 May - 28 May
*NEW* Sunny Circle SSI| 1.4 Miles from the Beach!
Beach nearby, sun-loungers

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 HK$1,174
HK$3,014 total
includes taxes & fees
31 May - 1 Jun
Cozy condo sleeps 6! Convenient to beach, shopping and all restaurants.
TV

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 HK$736
HK$3,922 total
includes taxes & fees
13 May - 14 May
Close Beach Access, Walk to Lighthouse & Village!
Beach nearby

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 HK$822
HK$2,391 total
includes taxes & fees
17 May - 18 May
NEW- Discount! POOL - near beach and golf course!
Beach

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 HK$1,235
HK$2,464 total
includes taxes & fees
18 May - 19 May
One Bedroom just across the street from the Beach!
Exterior

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 HK$1,057
HK$2,843 total
includes taxes & fees
25 May - 26 May
2-bedroom Condo on St. Simons Island. Pool/Parking/Beach/Food/Bars/Stores, etc..
Outdoor dining

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 HK$1,973
HK$3,510 total
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

Queens Court

Queens Court

6/10 Okay
"Room was clean and has it expected however, the pool wasn’t ready. It was green with algae. It would’ve been nice to know and we would’ve booked somewhere else because that was the selling point for us."
Matthew 2-night trip
Posted 1 hour ago
Queens Court

Find out more about Cumberland Island

Search for holiday rentals in Cumberland Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Cumberland Island using one of the methods below:

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Look no further and take a look at our great range of rental properties in Cumberland Island!

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.