Cumberland Island Vacation Rentals

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Our top choices for Cumberland Island vacation rentals

Island getaway

Island getaway
Fernandina Beach
9.4 out of 10, Exceptional, (53 reviews)
"House was clean and worked well for our weekend trip."
United States
Adrienne L.
The price is CA $244
CA $581 total
includes taxes & fees
May 3 - May 4
Island getaway

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 CA $335
CA $689 total
includes taxes & fees
May 7 - May 8
Third-floor Oceanfront Condo With Balcony, W/d, Pool & Tennis

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
9.6 out of 10, Exceptional, (35 reviews)
"Excellent communication with host regarding check-in. Incredibly comfortable beds. Great stay!"
United States
Melissa
The price is CA $159
CA $470 total
includes taxes & fees
May 3 - May 4
Swim, bike, relax: South Side Condo near East Beach with 4 bikes included

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 CA $199
CA $422 total
includes taxes & fees
May 12 - May 13
Beach 5 Villas - Immaculate 300 steps from the Ocean

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 CA $190
CA $768 total
includes taxes & fees
May 21 - May 22
Close Beach Access, Walk to Lighthouse & Village!

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, (54 reviews)
"It was convient and relaxing for a short weekend"
United States
Damon C.
The price is CA $183
CA $500 total
includes taxes & fees
May 5 - May 6
Cozy condo sleeps 6! Convenient to beach, shopping and all restaurants.

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 CA $150
CA $452 total
includes taxes & fees
May 3 - May 4
Summer Special! Steps to Village & Pier

3 Mi to St Simons Beach: Gem w/ Pool Access & Deck

3 Mi to St Simons Beach: Gem w/ Pool Access & Deck
3.5 star property
St. Simons Island
8.0 out of 10, Very good, (2 reviews)
"Very easy to communicate with the property manager. A delightful visit."
United States
Josephine
3 Mi to St Simons Beach: Gem w/ Pool Access & Deck

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 CA $161
CA $441 total
includes taxes & fees
May 7 - May 8
NEW- Discount! POOL - near beach and golf course!

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, (168 reviews)
"Great location, great space."
United States
Cindy K.
The price is CA $340
CA $614 total
includes taxes & fees
May 6 - May 7
Elegant St. Simons Island Honeymoon Beach Cottage near Pier Village

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 CA $342
CA $612 total
includes taxes & fees
May 30 - May 31
Original island cottage 3 bedroom well maintained

*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 CA $204
CA $522 total
includes taxes & fees
May 31 - Jun 1
*NEW* Sunny Circle SSI| 1.4 Miles from the Beach!

Apartment near downtown.

Apartment near downtown.
St. Simons Island
9.4 out of 10, Exceptional, (13 reviews)
"Nice place, nice hood, nice time."
United States
mark w.
The price is CA $139
CA $395 total
includes taxes & fees
May 4 - May 5
Apartment near downtown.

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 CA $128
CA $681 total
includes taxes & fees
May 2 - May 3
Cowboy Studio, Pet Friendly, Walk to Village

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 CA $216
CA $614 total
includes taxes & fees
May 4 - May 5
ISLAND VIBE ~ Close to Beach, Downtown, Egan’s Creek with Fire Pit! KQQ~2Ba

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 CA $185
CA $393 total
includes taxes & fees
May 3 - May 4
One Bedroom just across the street from the Beach!

Beach House -optional BIKES - Walk 2 Shops & Fun

Beach House -optional BIKES - Walk 2 Shops & Fun
Saint Simons Island
9.8 out of 10, Exceptional, (138 reviews)
"The host was most welcoming and communicated with us well. The house was cleaned and well arranged. We had all we need to make our stay pleasant"
United States
Judeen R.
The price is CA $50
CA $257 total
includes taxes & fees
May 3 - May 4
Beach House -optional BIKES - Walk 2 Shops & Fun

Beautiful Oceanfront Condo With Breathtaking Beach Views

Beautiful Oceanfront Condo With Breathtaking Beach Views
Amelia City
10.0 out of 10, Exceptional, (336 reviews)
"Beautiful location and accommodations."
United States
Janice R.
The price is CA $324
CA $534 total
includes taxes & fees
May 4 - May 5
Beautiful Oceanfront Condo With Breathtaking Beach Views

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

♥ of SSI Bungalow, Quick walk to beach and food ☼
St. Simons Island
10.0 out of 10, Exceptional, (12 reviews)
"Great place for a great weekend! Super clean and close to some great restaurants. "
United States
JT M.
♥ of SSI Bungalow, Quick walk to beach and food ☼

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
9.8 out of 10, Exceptional, (8 reviews)
"Condo was beautiful, clean and offered all the amenities needed. It was located in a perfect place, easy to walk/ride bikes everywhere!"
United States
Stephanie D.
The price is CA $227
CA $546 total
includes taxes & fees
May 5 - May 6
2-bedroom Condo on St. Simons Island. Pool/Parking/Beach/Food/Bars/Stores, etc..
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Cumberland Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Cumberland Island?

Yes, we have vacation rentals near the most popular local attractions in Cumberland Island, or you can go with a more remote option if you want a relaxing place to 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 vacation rentals in Cumberland Island?

The Villas of Amelia Island: This vacation 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 you can immerse yourself in your vacation.

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 vacation rental in Cumberland Island like?

Vacation rentals are private properties you can stay in for short or long periods in Cumberland Island. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for family gatherings.