50 Best Saint Simons Island Vacation rentals on Holiday Lettings - Apartments

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81 Vacation rentals

(7) Excellent 

Certificate of Excellence

22

Apartment rental in Saint Simons Island with shared pool

Golden Isles of Georgia / Saint Simons Island

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 5 mi
  • Swimming pool
  • Child friendly
2 bedroom / 2 1/2 bath Condo in quiet Brockinton Marsh. Short ride to beach, close to stores and restaurants. Fully equipped condo. Pool in Complex. King Bed, 2 twin beds, 1 inflatable twin. 3 LED TVs, high speed internet. …see more

Certificate of Excellence

from $100 / night

$700 / week

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Responds fast!
avg. 1 hour 35 minutes

from $100 / night

(1) Excellent 

22

Vacation apartment in Saint Simons Island

Golden Isles of Georgia / Saint Simons Island

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Purple Dog Vacation Rentals is pleased to offer this residence in one of St. Simons Island’s newest locations, Salt Air Villas. This great, new Island community is nestled in a quiet location, just minutes from the pier and village area! Our Salt Air Villa is well appoi …see more

from $165 / night

$750 / week

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from $165 / night

31

Condo rental in Saint Simons Island with shared pool

Golden Isles of Georgia / Saint Simons Island

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our tastefully decorated condo is on the 2nd floor and is located beside a large, beautiful pool with adjacent tennis court and small playground. The kitchen and bathroom have been updated with granite countertops, and bath has a tiled shower/tub combo. There is a livi …see more

from $99 / night

$650 - $750 / week

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Responds fast!
avg. 1 hour 26 minutes

from $99 / night

10

Condo rental in Saint Simons Island

Golden Isles of Georgia / Saint Simons Island

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Ask about pets
Get away from it all in beautiful Saint Simons and relax in our beautifully decorated, centrally located home away from home. Our first year of new ownership was amazing, and we have worked to make our condo even more accommodating! This year, we added a new ceiling fan …see more

from $99 / night

$693 / week

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from $99 / night

(1) Very Good 

36

Saint Simons Island Vacation home rental

Golden Isles of Georgia / Saint Simons Island

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
If you’re looking for a relaxing beach vacation, St. Simons Island is the destination for you, and ‘Banana House,’ this uniquely charming vacation property, is your perfect homebase. Boasting 2 bedrooms and 2 bathrooms with accommodations for 8, there’s plenty of room f …see more

from $155 / night

$1,085 - $1,575 / week

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Responds fast!
avg. 59 minutes

from $155 / night

23

Vacation condo with shared pool in Saint Simons Island

Golden Isles of Georgia / Saint Simons Island

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Located within walking distance of the St. Simons Island pier, our community has 2 pools (one heated), 2 tennis courts, a large playground, and a private stocked lake. The clubhouse has WiFi, a business center, and a fitness center. Plenty of shopping and restaurants a …see more

from $115 / night

$650 - $750 / week

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from $115 / night

(1) Excellent 

24

Vacation home rental

Golden Isles of Georgia / Saint Simons Island

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Captain's Bluff is a newly renovated historical house on the Frederica River. Come and see St. Simons the way it used to be on 18 acres of undeveloped wilderness. There are 3 bedrooms and 2.5 bathrooms in this 1800 sf home. Two bedrooms have queen beds with pr …see more

from $425 / night

$2,375 / week

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Responds fast!
avg. 3 hours 40 minutes

from $425 / night

36

Saint Simons Island Vacation condo rental

Golden Isles of Georgia / Saint Simons Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Discover the Golden Isles Don't miss out for your next great vacation! St.Simons, Sea Island, Jekyll Island, Little St.Simons Island, and Brunswick Georgia. This island square oasis has everything that you need to stay and relax at the beach. Very spacious, extra clean …see more

from $99 / night

$699 - $2,200 / week

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Responds fast!
avg. 13 minutes

from $99 / night

30

Saint Simons Island Vacation home rental

Golden Isles of Georgia / Saint Simons Island

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Child friendly
  • Air conditioning
Discover the light-filled island charm of this beautiful four-bedroom home, a recently redecorated St. Simons Island retreat with family-friendly amenities, a screened porch, a fenced backyard, updated furnishings and appliances, and a perfect location close to shops, r …see more

from $123 / night

$861 / week

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Responds fast!
avg. 37 minutes

from $123 / night

(1) Excellent 

13

Vacation condo with shared pool in Saint Simons Island

Golden Isles of Georgia / Saint Simons Island

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Your home away from home awaits you here on beautiful Saint Simons Island Ga. Welcome to Shipwatch, a family friendly complex right on the beach where this condo will have all of the necessities for a perfect beach vacation. There is some excellent restaurants within wa …see more

from $250 / night

$1,400 / week

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Responds fast!
avg. 3 hours 40 minutes

from $250 / night

17

Vacation apartment in Saint Simons Island

Golden Isles of Georgia / Saint Simons Island

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning
This ground floor, two bedroom condominium is located 74 steps from the tide contingent beach and a five minute walk to the quaint village of St. Simons. A private patio overlooks the Atlantic ocean - offering fantastic sunrise and sunset vistas! Direct ocean views fro …see more

from $190 / night

$950 / week

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from $190 / night

(1) Good 

20

Vacation apartment in Saint Simons Island

Golden Isles of Georgia / Saint Simons Island

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
This two bedroom condominium is located just 74 steps from the tide contingent beach and a five minute walk to the quaint village of St. Simons. A private balcony overlooks the Atlantic ocean - offering fantastic sunrise and sunset vistas! Direct ocean views from the …see more

from $200 / night

$1,000 / week

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from $200 / night

(1) Excellent 

17

Vacation apartment rental

Golden Isles of Georgia / Saint Simons Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
ST SIMONS ISLAND IS A MAGNIFICENT PLACE YEAR ROUND WITH PLENTY TO DO IN ADDITION TO THE WONDERFUL BEACH! Catch a wonderful vacation BEFORE rates go up for the high season!!!! This wonderful 2B/2B condo is located in the King & Prince Area. You enter a 24hr secure are …see more

from $300 / night

$1,900 - $2,600 / week

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from $300 / night

(8) Excellent 

Certificate of Excellence

21

Saint Simons Island Vacation villa rental

Golden Isles of Georgia / Saint Simons Island

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Two story unit located within walking distance to the charming Pier Village of St. Simons and its famous lighthouse. This beautiful unit offers unique style, amazing décor and outstanding comfort throughout. Features include: luxurious master suite, gorgeous dining area …see more

Certificate of Excellence

from $150 / night

$925 / week

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Responds fast!
avg. 43 minutes

from $150 / night

(37) Excellent 

15

Vacation townhouse with shared pool in Saint Simons Island

Golden Isles of Georgia / Saint Simons Island

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This charming townhouse offers easy access to all St. Simon’s has to offer. Located just steps from the beach, this 3 bedroom 3 1/2 bathrooms get-away is uniquely decorated and newly furnished. Enjoy views of the marsh with your morning coffee in the recently updat …see more

from $110 / night

$950 - $1,600 / week

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Responds fast!
avg. 3 hours 27 minutes

from $110 / night

24

Vacation home rental

Golden Isles of Georgia / Saint Simons Island

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
This stunning designer decorated home is located in the gorgeous East Beach neighborhood. East Beach was just rated as the best 'Neighborhood on St. Simons Island' by Elegant Island Living Magazine. If you are looking for wide, sandy beaches without rocks, this is the a …see more

from $275 / night

$2,100 / week

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from $275 / night

(1) Excellent 

29

Vacation home in Saint Simons Island

Golden Isles of Georgia / Saint Simons Island

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
This St. Simons Island condo for six is just what your family or group of friends need to truly relax. Take advantage of home essentials and enjoy a seasonal community pool. Marshland views can be seen from the balcony of your vacation rental. Plus, you can easily make …see more

from $125 / night

$875 / week

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Responds fast!
avg. 37 minutes

from $125 / night

(2) Excellent 

24

Saint Simons Island Vacation home rental

Golden Isles of Georgia / Saint Simons Island

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Beautifully appointed and tastefully decorated, this gorgeous home is located in a quiet neighborhood and has an updated, gourmet kitchen, furnished patio, private, enclosed yard, and room for up to six guests to stretch out and relax. It's even dog-friendly. Located c …see more

from $126 / night

$882 / week

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Responds fast!
avg. 37 minutes

from $126 / night

(3) Very Good 

27

Vacation home in Saint Simons Island

Golden Isles of Georgia / Saint Simons Island

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Child friendly
  • Air conditioning
Cute and cozy 3 bedroom, 2 bath cottage in a great location : short walk to the village with all its amenities including restaurants, shops, pier, pool and beach. This totally renovated house sleeps 6. This home is newly purchased and features a large, updated kitchen …see more

from $211 / night

$1,300 / week

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from $211 / night

(1) Excellent 

23

Townhouse rental in Saint Simons Island with shared pool, golf nearby

Golden Isles of Georgia / Saint Simons Island

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Relax on the beaches of charming St. Simons Island in this quiet, beautifully renovated two story townhome. We have brand new comfortable mattresses & bedding, gorgeous kitchen cabinets with granite counters, attractive plank flooring & carpet and new bathroom vanities …see more

from $125 / night

$875 / week

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Responds fast!
avg. 2 hours 21 minutes

from $125 / night

(9) Excellent 

15

Apartment rental in Saint Simons Island

Golden Isles of Georgia / Saint Simons Island

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Whether you are looking for some fun in the sun or just some well deserved R & R, this beautiful condo is the perfect spot for enjoying all that this unique island has to offer! It is very conveniently located about half way between East Beach and the St. Simons villag …see more

from $300 / night

$1,800 / week

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from $300 / night

33

Vacation home in Saint Simons Island

Golden Isles of Georgia / Saint Simons Island

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
Old-world elegance meets modern comfort with this beautiful home on the south Georgia coast. Surrounded by moss-draped oak trees and adorned with double front porches, this elegant two-story vacation home is the perfect location to celebrate a special occasion with the …see more

from $400 / night

$2,800 / week

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Responds fast!
avg. 37 minutes

from $400 / night

(10) Very Good 

Certificate of Excellence

29

Vacation apartment with shared pool, golf nearby in Saint Simons Island

Golden Isles of Georgia / Saint Simons Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
ONE STUNNING LOCATION. Discover the Golden Isles. St Simons, Sea Island, Jekyll Island, Little St. Simons Island, and Brunswick Georgia.This island oasis has everything that you need to stay and relax at the beach. Very spacious, extra clean 2 bedroom condo, 1.5 bath w …see more

Certificate of Excellence

from $92 / night

$699 - $2,500 / week

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Responds fast!
avg. 1 hour 53 minutes

from $92 / night

(2) Excellent 

33

Saint Simons Island Vacation home rental

Golden Isles of Georgia / Saint Simons Island

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Experience the picturesque Southern charm of St. Simons Island at this four-bedroom cottage, a dog-friendly bungalow with a private hot tub and pool, a balcony and screened-in porch, and an enviable location close to the village and beaches. Wonderfully situated on a t …see more

from $400 / night

$2,800 / week

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Responds fast!
avg. 37 minutes

from $400 / night

(4) Excellent 

13

Vacation apartment rental

Golden Isles of Georgia / Saint Simons Island

2 8 6 nights min

  • 2 bedrooms
  • Sleeps 8
  • 6 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
Accommodations: Condominium, 2 Bedrooms + Convertible bed(s), 2 Baths (Sleeps 4-6) Georgia's Atlantic Coastline is only about 100 miles long, but along this green corridor you'll see some of America's most breathtaking natural landscapes... It's a region richly woven …see more

from $275 / night

$1,650 / week

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from $275 / night

(2) Very Good 

18

Vacation townhouse in Saint Simons Island

Golden Isles of Georgia / Saint Simons Island

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Air conditioning
Beth's Beachcomber is a four bedroom townhouse that has a view of the Atlantic from the top floor patio. With remodeled baths and kitchen this condo is stunning! Amenities include 5 new flat screen TVs, a renovated kitchen and renovated baths and WIFI. The condo is jus …see more

from $295 / night

$1,800 / week

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from $295 / night

22

Vacation home rental

Golden Isles of Georgia / Saint Simons Island

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
FLETC Rental Properties is excited to announce this new pet friendly home just a 3 minute walk from one of the islands best beaches. This cottage located just 2 blocks from the beach has 3 bedrooms and 2 bathrooms. This open concept floor plan is pet friendly with a gre …see more

from $235 / night

$1,500 / week

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Responds fast!
avg. 38 minutes

from $235 / night

(1) Excellent 

14

Vacation home in Saint Simons Island

Golden Isles of Georgia / Saint Simons Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Large two story home featuring three bedrooms and two bathrooms with beautiful hardwood floors throughout. Enclosed outside shower with hot water is available to rinse off from those trips to the beach. Open floor plan with exit out to large second story deck, includes …see more

from $200 / night

$1,400 / week

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Responds fast!
avg. 1 hour 25 minutes

from $200 / night

(2) Very Good 

20

Vacation condo in Saint Simons Island

Golden Isles of Georgia / Saint Simons Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
2 BR/2 BA condo at Northbreakers Condominiums on beautiful Saint Simons. Come and enjoy St. Simons, named NO. 1 BEACH TOWN IN AMERICA last year by Travel & Leisure Magazine! Relax by the large pool that is limited to only property guests. This well-stocked condo slee …see more

from $180 / night

$1,045 - $1,750 / week

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from $180 / night

(2) Excellent 

13

Vacation condo in Saint Simons Island

Golden Isles of Georgia / Saint Simons Island

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
In between the hustle and bustle of the larger condos along ocean blvd is Ocean wood condos. A quiet little complex tucked under the live oaks right in the middle of all the beach action. This condo has all the amenities for a perfect beach vacation. The condo has 2 b …see more

from $225 / night

$1,250 / week

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Responds fast!
avg. 3 hours 40 minutes

from $225 / night

28

Saint Simons Island Vacation home rental

Golden Isles of Georgia / Saint Simons Island

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
Listen to the waves crash on the beach and feel the ocean breeze from the private upstairs balcony! Renovated Kitchen & Bedrooms in January 2017. All new furniture! First year on the market a 2 Bedroom 1 Bathroom upstairs unit in a duplex property. Bedroom one has a K …see more

from $145 / night

$1,100 - $1,240 / week

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from $145 / night

28

Condo rental in Saint Simons Island with shared pool, golf nearby

Golden Isles of Georgia / Saint Simons Island

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
New on the market.... an "Oasis of Relaxation"! This 2300 square-foot condo on the north end of Saint Simons, is ready for occupancy. Bring your golfing buddies for a fun and relaxing getaway. Enjoy peaceful tranquility as you sip your morning coffee overlooking the eig …see more

from $177 / night

$1,228 / week

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from $177 / night

(3) Very Good 

12

Cottage rental in Saint Simons Island

Golden Isles of Georgia / Saint Simons Island

3 4 7 nights min

  • 3 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Quiet, private French cottage with pool and spa in garden setting. Minutes from beach, restaurants and shopping. Freshly renovated cottage with European charm set in custom designed garden set around a new salt water pool. Extremely quiet neighborhood provides ultimate …see more

from $200 / night

$1,400 / week

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from $200 / night

22

Vacation apartment in Saint Simons Island

Golden Isles of Georgia / Saint Simons Island

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
This condo is located in the heart of the St. Simons Island pier and village area. It is directly across the street from tide contingent beach access. Just steps away are the St. Simons lighthouse, oceanfront Neptune Park with resort-style pool, playground, miniature g …see more

from $200 / night

$1,400 / week

Book View

from $200 / night

(9) Very Good 

Certificate of Excellence

36

Vacation apartment with shared pool, golf nearby in Saint Simons Island

Golden Isles of Georgia / Saint Simons Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
ONE STUNNING LOCATION Discover the Golden Isles St. Simons, Sea Island, Jekyll Island, Little St. Simons Island, and Brunswick Georgia.This island oasis has everything that you need to stay and relax at the beach. Very spacious, extra clean 2 bedroom condo, 1.5 baths w …see more

Certificate of Excellence

from $99 / night

$699 - $2,200 / week

Book View

Responds fast!
avg. 26 minutes

from $99 / night

(10) Very Good 

11

Saint Simons Island Vacation apartment rental

Golden Isles of Georgia / Saint Simons Island

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Island tropical condos featuring pool, wireless internet access. Close to St. Simons Village and East Beach. Bikes included: 2 Adult / 2 child. Comfortable beds (1K,2Q,1Q sofa:sleeps 6-8), towels and furniture makes this the spot to be on the island! …see more

from $125 / night

$900 / week

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Responds fast!
avg. 2 hours 54 minutes

from $125 / night

20

Vacation home in Saint Simons Island

Golden Isles of Georgia / Saint Simons Island

5 13 Min stay varies

  • 5 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Hideaway Cottage, one of the most popular ocean front homes on St Simons Island. Fully renovated in 2013, Hideaway is beautifully decorated, has incredible ocean views, a heated private pool, a fully equipped cooks kitchen and recreation room for the kids. …see more

from $850 / night

$5,800 - $8,000 / week

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Responds fast!
avg. 3 hours 19 minutes

from $850 / night

19

Vacation home in Saint Simons Island

Golden Isles of Georgia / Saint Simons Island

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
This house is truly spectacular!...definitely one of the best on St. Simons Island. There is ample room for several people, lots of parking, and you are just steps from the beach! Enjoy a full kitchen, 3 bedrooms, 2 fully renovated baths, a large living room with a new …see more

from $211 / night

$1,477 / week

Book View

from $211 / night

(8) Excellent 

Certificate of Excellence

33

Vacation condo rental

Golden Isles of Georgia / Saint Simons Island

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
May 2018 - 15% Discount off 7 nights or more!! Excellent ocean views from this top floor unit! Top to bottom renovation completed December 2016 with new tile, carpets, bath and kitchen granite, fixtures, cabinetry and furnishings. Soothing colors and top of the line …see more

Certificate of Excellence

from $149 / night

$1,050 - $1,875 / week

Book View

Responds fast!
avg. 2 hours 14 minutes

from $149 / night

(1) Good 

18

Saint Simons Island Vacation condo rental

Golden Isles of Georgia / Saint Simons Island

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
Your home away from home awaits you here on beautiful Saint Simons Island Ga. Welcome to Shipwatch, a family friendly complex right on the beach where this condo will have all of the necessities for a perfect beach vacation. There is some excellent restaurants within wa …see more

from $225 / night

$1,250 - $1,400 / week

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Responds fast!
avg. 3 hours 40 minutes

from $225 / night