
Condo holiday rentals in Cumberland Island
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Top-rated condo rentals in Cumberland Island
Guests agree: These condos are highly rated for location, cleanliness and more.

Oceanfront Amelia Island-Beach Views-Pool Oasis
"This is my favorite section of beach, rarely crowded like the other parts of the island” - Anne Looking over the gorgeous Amelia Island beach-front in multiple sunrise-facing directions from the top floor, this newly remodeled luxury retreat is unique fun. Hear the waves from both of the king bed suites. Steps to the sand. Minutes to the historic cobblestones downtown "Not your grandma’s beach house…a bit of oceanside luxe with amazing views... private beach access and a great pool" - C.H.
ValueLocationView
4.94 out of 5 average rating, 124 reviews
Beach Walk -optional BIKES-Pool-Walk 2 PierVillage
This cozy 1 bedroom condo has many upgrades. U will enjoy the south-island location close 2 many shops & restaurants. U can walk 2 Pier Village & other entertainment. King in Master & living room has queen sleeper sofa. Comes w/ new furnishings & BUSINESS CLASS WIFI. 2 tennis courts, 2 pools (1 heated), laundry facilities (coin operated), ping pong, fitness center, playground, private stocked lake, & USAGE OF BIKES your entire stay for an additional charge. NO PETS or ANIMALS ALLOWED. SEE RULES
FamilyLocationTV
4.91 out of 5 average rating, 463 reviews
Beach Escape, a block from the Beach-POOL/Pklball
Beachy vibes, 1 block from the Beach. Relax and unwind in this comfy beautifully designed space. Newly renovated kitchen & well stocked (pots, pans, coffee maker, toaster, etc.) ready for use. Condo includes everything you need for a day of fun at the beach (beach chairs, umbrella's, boogie boards, beach towels and beach toys) or just enjoy the amenities(in ground pool, tennis and pickleball courts, playground, and BBQ area). Includes tennis racquets & more. Tropical wooded view, pet friendly
LocationValueParks
4.94 out of 5 average rating, 202 reviews
Cool Beachy Vibes! KING Beds, Bikes! POOL/Pickle!
HIGHLY sought after quiet north side condo. 100's of 5 star reviews! Cool, relaxing vibes. Beautifully renovated w/ a well equipped kitchen, 3 streaming TV’s high speed internet, KING BEDS in both huge masters w/ a large tropical loo. 800 feet to the sand! ENJOY Pool and Tennis/Pickle steps away, FREE Beach Bikes! The North side is the locals favorite for Sharks Teeth! Main Beach, Skate Park, Ft. Clinch. Walking distance to Basketball, Sandbar & Salt Life restaurants plus a Quickie mart.
ValueLocationBreakfast
4.98 out of 5 average rating, 225 reviews
Oceanfront with Included Golf Cart & Kayak
This fully renovated condo is in The Sandcastles complex within Amelia Island Plantation. It has 1 bedroom, 1 bath, a flex room that can be used as an office or a sleeping space with a king trundle bed. Single kayaks & gas golf cart are included to explore Drummond Park, Walker's Landing, Nature Center, mini golf, multiple shops and restaurants all within Amelia Island Plantation. The location is great, views are incredible and is a very comfortable space for couples, and small families!
FamilyLocationCheckout
4.96 out of 5 average rating, 148 reviews
Perfect Island Private Getaway-Walk2Beach-Village
If you are interested in a great little getaway, this is it. Gated UPDATED BEACHY condo with private gated parking & pool. IDEAL LOCATION. Walk/Bike to the Beach, Pier Village Shopping, Restaurants & Entertainment. Custom made book with local recommendations included. Condo is setup similarly to a hotel suite with Kitchenette *see photos. Relaxing jetted tub&large shower Has washer/dryer, full refrigerator, Keurig coffee, WiFi, Roku Stick, Alexa, Amazon Music, Amazon Prime, Netflix.
ValueLocationIndoor spaces
4.97 out of 5 average rating, 353 reviews
Driftwood paradise, ocean view!
Enjoy amazing ocean sunrises from spacious 1-BR Jekyll Island condo! Next to secluded beach and short walk to famous Driftwood Beach. Updated, ground-level unit sleeps 4 (with pullout sofa). Extended patio offers panoramic shoreline view. Condo complex has pool, fitness center, volleyball, basketball, playground, bike rentals, picnic tables/grills, restaurant and more. One dog (60 lbs. max) OK with $75 fee. Sorry, no cats. For stays longer than 7 nights, contact host for special discount.
FamilyLocationAccuracy
4.86 out of 5 average rating, 120 reviews
Jack & Laurel Welcome You To Our Beach Club Condo!
Comfort, relaxation, and beauty await you here - On the quieter and most private side of the Beach Club - with direct, gated beach access . Enjoy our oceanside pool, 2 hot tubs, and lush gardens - in the perfect spot, on one of the prettiest beaches in the South! Primary suite with king bed, walk-in shower/soaking tub. Second bedroom with 1 queen/ 1 twin, full bathroom. Well-equipped kitchen, full balcony... Come on, the dolphins are waiting for you!
ValueLocationLaundry
4.98 out of 5 average rating, 248 reviews
Ocean Vibes Retreat (dog friendly)
This serene ground floor 3 bedrooms and 2 bathrooms condo available on St. Simons Island. We live up to our name “Ocean Vibes Retreat”. You walk in and see all the upgrades and new furnishings this home has to offer for you and your group. The complex is gated and located in walking distance to many restaurants, Redfern Village, and one of our grocery stores. We also offer a pool, workout room, tennis court and play ground. Come stay and let the salt air cure what ails you!
ValueFamilyKitchen
4.98 out of 5 average rating, 150 reviews
Oceanview Condo, 2 bedrooms, 1 bath
Clean, beautiful and all the comforts of home. 2 bedroom/1 bath with walk in shower, condo with the ocean so close that you can almost touch it! Sleeps 4. A 20 ft balcony gives you the best seat in the house for sunrises, sunsets and dolphin viewing. Master bedroom is on ocean side. 2nd bedroom has a queen bed. A fully furnished kitchen means you don't have to eat out every meal .. enjoy dinner on the great balcony! Perfect for a romantic getaway or a family vacation.
LocationValueLayout
4.97 out of 5 average rating, 203 reviews
2 king Oceanfront bedrooms just steps to the Ritz!
PURE LUXURY. If you are looking for a space for up to 4 adults that rivals a suite at the Ritz, YOU'VE FOUND IT! STUNNING total renovation of this 2 bedroom, 6th floor Surf & Racquet Club condo! Almost 40 feet of VERY PRIVATE uninterrupted views of the ocean between the living room & the 2 balconies off of each of the 2 BEACHFRONT KING BEDROOM SUITES! Completely new kitchen & baths! Sweeping beach views from every room. Come experience it for yourself...
FamilyValueIndoor spaces
4.99 out of 5 average rating, 159 reviews
Amelia Island Paradise Rental!
Tranquil Island Retreat: Cozy 2-bedroom, 1-bath condo nestled amidst lush greenery. Sunlit living space, coastal-inspired decor, granite kitchen, and King and Queen-sized beds. Private patio for coffee and sunsets. Take a stroll to the nearby beach, where seashells await discovery. Explore the historic district, dine at charming seafood restaurants, and immerse yourself in the island’s laid-back vibe. License # BTR-000354-2025, RRDP # RRDP-000353-2025
ValueFamilyIndoor spaces
4.91 out of 5 average rating, 120 reviewsPopular amenities for Cumberland Island condo rentals
Weekly condo rentals

Guest favorite! 130+five-star reviews!
FamilyValueCondition
4.99 out of 5 average rating, 139 reviews
Surf a Wave • Oceanfront • Perfect for Couples
FamilyLocationAccuracy
4.95 out of 5 average rating, 196 reviews
Newly Renovated Island Condo
ValueLocationPets
4.96 out of 5 average rating, 156 reviews
Million Dollar Ocean View!
FamilyLocationAmenities
4.98 out of 5 average rating, 180 reviews
Lovely 2-Bedroom Condo with Pool
ValueFamilyWalkability
4.98 out of 5 average rating, 106 reviews
Seaview Oasis: Beachfront | Resort Access
LocationFamilyBiking
4.87 out of 5 average rating, 155 reviews
Location! WALK to BEACH, Village & PIER! 2 POOLS*
ValueFamilyIndoor spaces
4.89 out of 5 average rating, 152 reviews
Oceanfront Condo w/view! | Free Bikes! | Updated!
ValueFamilyHospitality
4.99 out of 5 average rating, 114 reviewsPet-friendly condo rentals

Selah and Sea • Quiet Oceanfront + Dogs Welcome
FamilyValueDecor
4.96 out of 5 average rating, 162 reviews
Condo of Curiosity - Unique, cozy, fun and clean!
FamilyLocationIndoor spaces
4.95 out of 5 average rating, 166 reviews
St Simons Townhouse Close to Beach and Village
LocationFamilyCleanliness
4.88 out of 5 average rating, 225 reviews
The Reef | Cozy Hideaway | Steps from the Beach
FamilyValuePool
4.83 out of 5 average rating, 152 reviews
One bedroom condo w/ pool in the SSI Village 2100
LocationFamilyQuiet
4.82 out of 5 average rating, 115 reviews
Ocean Views from EVERY Room! | Newly Updated!
LocationFamilyNearby
4.91 out of 5 average rating, 11 reviews
The Tipsea Turtle
FamilyLocationIndoor spaces
4.94 out of 5 average rating, 52 reviews
Freshly Renovated Beachfront First Floor Condo
ValueFamilyQuiet
4.93 out of 5 average rating, 54 reviewsCondo rentals with a pool

Perfect getaway
LocationFamilyLong stay
4.83 out of 5 average rating, 292 reviews
A Super Host Best Favorite on St. Simon's Island
ValueLocationBeach
4.93 out of 5 average rating, 122 reviews
Sea-Esta Retreat, a Great Golden Isles Location!
FamilyLocationParking
4.92 out of 5 average rating, 107 reviews
Fall Special (1BR + Beach/Pool) Amelia Island
FamilyLocationHospitality
4.94 out of 5 average rating, 33 reviews
Oceanfront Walkout · Steps to Ritz · Fireplace
LocationValueIndoor spaces
5.0 out of 5 average rating, 47 reviews
Beachy Keen
FamilyLocationComfort
4.96 out of 5 average rating, 28 reviews
Beach Please! Balcony Ocean View*Top Floor*Pool
FamilyLocationNearby
5.0 out of 5 average rating, 63 reviews
Island Dream | Tranquil Coastal Condo
FamilyLocationCleanliness
5.0 out of 5 average rating, 21 reviewsDestinations to explore
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- EverBank Stadium
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- East Beach
- St Johns Town Center
- Kathryn Abbey Hanna Park
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- Memorial Park
- Little Talbot
- Catty Shack Ranch Wildlife Sanctuary
- Kingsley Plantation
- Southbank Riverwalk
- Jacksonville Beach Fishing Pier
- Fort Frederica National Monument
- Jacksonville Zoo & Gardens
- Saint Simons Island Lighthouse Museum
- Museum of Science and History
- South Beach Park and Sunshine Playground
- Autobahn Indoor Speedway & Events - Jacksonville, FL
- Daily's Place
- St Simons Island Pier





