
Condo holiday rentals in Cumberland Island
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Top-rated condo rentals in Cumberland Island
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Location! WALK to BEACH, Village & PIER! 2 POOLS*
After a relaxing nights sleep, walk out to the balcony and enjoy the amazing lake views & the sounds & smells of the salty ocean breeze, which is just down the street. Enjoy a workout in the gym, a game of pingpong/corn hole next to the lake, or a dip in one of the luxurious pools. Sit back & relax after a day at the beach & watch a movie on one of the smart TVs. This condo is nestled in the heart of SSI, a short walk to shopping, golfing, restaurants, historic sites, parks, the pier, & more.

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!

Large Open 2 Bed 2 bath Condo Overlooks Pool
You have found one of the best vacation rental condos on St. Simons Island. Comfortable and spacious, 1,100 sq ft, 2 bedroom, 2 bathroom in South Island gated complex, just two miles from the beach and Pier area. Upstairs. Perfect for as little as 1 guest or as many as 6. This condo is kept immaculately clean and fresh. Along with king in the master, the 2nd bedroom has a new queen full memory foam mattress. Pool, fitness room, fast Wifi, free gated parking, laundry. Lots of natural light!

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 saltwater 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!

Resort~ Amelia Island~ Ocean Front~ Condo
Welcome to the GORGEOUS Turtle Watch Condo! Imagine sitting on a private patio, with a crisp cup of coffee, as the warm ocean breeze splashes against your face. This two story, split floor plan condo, gives your late risers the quiet haven they seek while the early birds in your party can enjoy starting breakfast, sitting on the patio, or simply catching up on the morning news! This condo is truly a joy, the proximity to the ocean, pool, and outdoor spaces is unmatched on Amelia Island!

Quick Beach Access, Huge Deck -POOL & Tennis
First floor villa, two bedrooms, two full bath beautifully updated Villa, within walking distance of the beach. The open floor plan provides a spacious feel and leads you to the massive screened in deck with a tropical wooded view. The Villa also has a sleeper sofa that sleeps 2 more! Just steps from pool and tennis courts. fully stocked for cooking ,kitchen table that seats 6 and washer and dryer. High speed internet and 2 smart TV's. First building in the complex. Free parking

Beach Hideaway~great location~pool~ground floor
GROUND FLOOR unit~GREAT LOCATION(mid/South Island)~walk to Redfern Village(many shops and restaurants), Southern Soul, Chickfila, Starbucks, etc~quick drive to the beach and pier~NEWLY REMODELED~GATED FAMILY ORIENTED COMMUNITY~ reliable WiFi~TV and sofa in living room~king bed & TV in master~queen bed & TV in spare~twin sleeper sofa in sunroom~pool & tennis court~NO PETS or ANIMALS ALLOWED, SEE RULES FOR HIGH PET FEE. **Parking -- My HOA does not allow work/business vehicles**

Luxe Azul Oasis Minutes to Beach
Luxury condo near the Ritz Carlton and Omni hotels. You'll approach your oasis on a tree lined canopy street reminiscent of the romantic south. Large fully stocked chef kitchen. You don't need to bring anything from home. Great for family dinners. Gorgeous master king suite. Stylish and romantic. Comfortable screened in porch. The vacation is steps away from the pool and minutes walk to the beachy sand on a shaded beach path. Beach tent, towels, wagon, and 2 bikes.

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.

Million Dollar Ocean View!
Beautiful 1 bedroom (king), 1 bath ocean-front condo on the 4th floor at Amelia Surf & Racquet Club. Walking distance to the Ritz Carlton. Relax and unwind with spectacular views from every room. Kitchen is well appointed and ready for some cooking! There are 2 flat screen TVs (32” and 50”), Condo is smoke-free and pet-free. Two beautiful swimming pools, beach chairs and four clay tennis courts. Island has bike paths, 4 State parks, great restaurants, and shopping.

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 ft 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!!

TOP SHELF*Private Fishing Pier-Pool-Oceanfront*
Come and make treasured memories at the ocean front, Top Shelf Beach Condo located on 7th (top) floor at Amelia By the Sea! Wake up to beautiful panoramic sunrises, fish from the private pier, stroll the beach or simply grab a chair & chill. The ocean front pool is irresistibly refreshing, the only suit required on Amelia Island is your bathing suit! We look forward to sharing our island sanctuary with you. Permit #BTR-000681-2022
Popular amenities for Cumberland Island condo rentals
Weekly condo rentals

Ocean Place 22 - Sea Forever

Vitamin Sea Oceanfront 2/2 Condo in Amelia Island

Oceanfront Condominium with Great Amenities

Paradise Palms! Oceanfront @ Amelia Surf & Racquet

Surf & Racquet Club B156 | 5th Floor Ocean Front

Enjoy the Creek view! Safe & peaceful.

Amelia Island Paradise Rental!

Escape to Paradise | Oceanfront, Beach, Pool
Pet-friendly condo rentals

1384 Shipwatch - Oceanfront with amazing views, 2

Ocean Front Condo at St. Simons Grand

Island Retreat Condo (Pet Friendly!)

Pool | Parking | Beach | Food | Bars | Stores, etc

Amelia Island Villa 2/2-Beach, Pool, Shops, Golf

Enchanting Sandcastles Villa-Ocean Front-Amelia

Moss Oak Golf Course Lake view

Beachcomber's Nook~ quiet and serene setting
Condo rentals with a pool

Seashell Sunrise 2BR | Beach + Pool

Steps to Beach and Restaurants/Balcony Ocean View

Oceanfront - Pool - Short walk to The Ritz

Oceanfront. SSI, Ga Beach Club

A Super Host Best Favorite on St. Simon's Island

Remodeled 5th-Floor Sandcastles Villa

Beachfront, Pier, Pool, Kitchen, Amelia By The Sea

Walk to Beach, Pool, Hot Tub, Balcony NEWER FURN
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Atlanta Holiday rentals
- Four Corners Holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- Myrtle Beach Holiday rentals
- Tampa Bay Holiday rentals
- Panama City Beach Holiday rentals
- Charleston Holiday rentals
- EverBank Stadium
- East Beach
- Kathryn Abbey Hanna Park
- Adventure Landing Jacksonville Beach
- Little Talbot
- VyStar Veterans Memorial Arena
- Fort Clinch State Park
- Memorial Park
- Autobahn Indoor Speedway & Events - Jacksonville, FL
- University of North Florida
- St Johns Town Center
- TPC Sawgrass
- Fort Frederica National Monument
- Museum of Science and History
- Friendship Fountain
- Kingsley Plantation
- Saint Simons Island Lighthouse Museum
- Cummer Museum of Art & Gardens
- Southbank Riverwalk
- South Beach Park and Sunshine Playground
- Jacksonville Zoo & Gardens
- Catty Shack Ranch Wildlife Sanctuary
- Jacksonville Beach Fishing Pier
- Daily's Place




