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Holiday Villas Chincoteague Island, VA

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All 332 Rentals in Chincoteague Island
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$1,965
Per Week
1 / 22
4 Bedrooms, 4 Bathrooms, Sleeps 10
Dishwasher, Air Conditioning, Grill & more
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From
$664
Per Week
1 / 12
3 Bedrooms, 2 Bathrooms, Sleeps 8
Internet Access, Dishwasher, Balcony & more
Details Reviews (2) Make Enquiry
From
$64
Per Night
1 / 7
1 Bedroom, 1 Bathroom, Sleeps 2
Air Conditioning, Dishwasher, Balcony
Details Reviews (1) Make Enquiry
Also consider
Endless Summer
4 Bedrooms, sleeps 9
$780 - $1,127 / week
Avalon
4 Bedrooms, sleeps 10
$1,358 - $2,282 / week
A Shore Thing
2 Bedrooms, sleeps 8
$664 - $1,098 / week
A Second Wind
2 Bedrooms, sleeps 8
$1,034 - $1,959 / week
From
$295
Per Night
1 / 18
4 Bedrooms, 3 Bathrooms, Sleeps 10
Fireplace, Dishwasher, Air Conditioning & more
Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 16 October 2014
The pics of the home make it appear very secluded. That is not the case. It is surrounded by 4 other homes with no direct access to the water. That being said - We had nice...
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From
$124
Per Night
1 / 19
2 Bedrooms, 2 Bathrooms, Sleeps 7
Washer, Grill, Air Conditioning & more
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5 of 5 stars Reviewed 21 November 2014
Coco Banana is the ideal vacation home on Chincoteague Island! The home is beautifully maintained, spacious, and comfortable for our family of 5. Everything we could possibly need...
5 of 5 stars Reviewed 21 November 2014
Being in the vacation rental business myself, I have very high standards. This is a beautifully furnished, well laid-out, comfortable home! Our family of 4 loves staying at Coco...
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From
$107
Per Night
1 / 15
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3 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Grill, Fireplace, Washer & more
Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 2 October 2014
This rental is located close to Main Street, and was perfect for my husband, my mom, and I. Although we visited during the off-season and most the of the businesses on Main Street...
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From
$119
Per Night
1 / 18
4 Bedrooms, 2 Bathrooms, Sleeps 9
Satellite TV, Air Conditioning, Washer & more
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5 of 5 stars Reviewed 1 September 2013
Really enjoyed ourselves here. It was large enough with enough porches and separate areas to allow everyone space to themselves
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From
$404
Per Night
1 / 13
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2 Bedrooms, 3 Bathrooms, Sleeps 15
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Grill, Dishwasher, Hot Tub & more
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5 of 5 stars Reviewed 19 August 2014
The owners (Tim and Coleen) were very responsive hosts and our stay in Chincoteague island in "Teaguers Delight" is one we remember for years to come. The house exceeded all of...
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From
$185
Per Night
1 / 13
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4 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (3) Make Enquiry
4 of 5 stars Reviewed 15 August 2014
We were pleasantly surprised at how much we enjoyed staying in this rental. We usually stay on the other side of the island. We were worried about it being one of the older homes...
5 of 5 stars Reviewed 3 August 2014
This house was great and the owner was very easy to work with. I highly recommend it for a peaceful family vacation.
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From
$58
Per Night
1 / 10
3 Bedrooms, 2 Bathrooms, Sleeps 6
Washer, Satellite TV, Grill & more
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5 of 5 stars Reviewed 10 October 2014
Loved the Sunshine Cottage! Immaculately clean and so cozy. A quick 10 minute drive to the beach and a 5 minute walk to the Main Street area which has several cute little shops...
5 of 5 stars Reviewed 8 October 2013
This was our first trip to Chincoteague and we loved it. In spite of the "government shutdown" which meant Assateague beaches were closed. Sunshine Cottage was very clean and just...
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From
$2,296
Per Week
1 / 18
2 Bedrooms, 2 Bathrooms, Sleeps 12
Fireplace, Water Views, Garden & more
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4 of 5 stars Reviewed 26 August 2014
We stayed from 8/16 - 8/22 and the house was wonderful. We had a party of 10, but were never in each other's way, even during meals. The kids LOVED fishing and crabbing and it...
5 of 5 stars Reviewed 28 May 2014
I booked last minute and we couldnt have had a better time. Andy was easy to coordinate with, gave great recommendations, and his place was just as described. Quiet, clean, with...
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From
$664
Per Week
1 / 19
2 Bedrooms, 2 Bathrooms, Sleeps 6
Air Conditioning, Grill, Dishwasher & more
Details Reviews (3) Make Enquiry
5 of 5 stars Reviewed 15 October 2014
We really enjoyed our stay at Sweet Retreat. This was a comfortable and very clean home. They had everything you would ever need. There was plenty of space for the 4 of us that...
5 of 5 stars Reviewed 3 September 2014
This petite, yet spacious cottage, was the perfect week-long vacation spot for my two Yorkshire terriers and me. The home smelled inviting the moment we entered, and the photos...
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From
$1,127
Per Week
1 / 13
3 Bedrooms, 2 Bathrooms, Sleeps 8
Balcony, Internet Access, Air Conditioning & more
Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 20 April 2014
We liked the open floor plan, five decks (!), and location in the pines next to a canal leading to Oyster Bay. The home is in a very nice development in a quiet location, The...
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From
$838
Per Week
1 / 11
3 Bedrooms, 4 Bathrooms, Sleeps 8
Balcony, Fireplace, Internet Access & more
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4 of 5 stars Reviewed 15 November 2011
We stayed during Columbus weekend and enjoyed the trip. The townhouse was the end unit and was perfect for our two families with 4 kids. The noise from the next door business...
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From
$1,127
Per Week
1 / 15
3 Bedrooms, 2 Bathrooms, Sleeps 8
Pool, Balcony, Hot Tub & more
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5 of 5 stars Reviewed 16 September 2013
This condo was very pretty, spacious and kitchen was well equipped (better than most resorts/condos). It is located on first floor, corner of building. Breath-taking views of...
3 of 5 stars Reviewed 3 July 2013
Sunset Bay Villas is a good choice. Being waterfront and having a deck is nice. Unit 101 is probably the best unit due to it's end location. It's weird and annoying that...
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From
$3,062
Per Week
1 / 19
5 Bedrooms, 4 Bathrooms, Sleeps 14
Air Conditioning, Internet Access, Grill & more
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5 of 5 stars Reviewed 5 September 2014
The house was beautiful and very spacious. The children loved the Captain's Quarters. Having our big family dinners in the large dining room across from the lighthouse was...
5 of 5 stars Reviewed 12 August 2014
The Ocean View Retreat is a wonderful place to stay to enjoy all that Chincoteague Island has to offer. The house is beautiful. It goes on and on. I was finding new nooks and...
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From
$1,034
Per Week
1 / 14
2 Bedrooms, 2 Bathrooms, Sleeps 6
Balcony, Dishwasher, Internet Access & more
Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 27 August 2014
We stayed at Sundance last week and it was great. Very roomy and bright and airy. The king bed in the master bedroom was very comfortable. The kitchen was well stocked and had...
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From
$607
Per Week
1 / 14
3 Bedrooms, 2 Bathrooms, Sleeps 8
Dishwasher, Hot Tub, Air Conditioning & more
Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 17 July 2013
I loved this property. This was the third time my family and I stayed at Island Thyme. The location is great, it's in the middle of the little town and less than half a mile from...
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From
$1,127
Per Week
1 / 15
3 Bedrooms, 2 Bathrooms, Sleeps 8
Pool, Internet Access, Air Conditioning & more
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5 of 5 stars Reviewed 15 July 2014
The unit we stayed in was beautifully decorated and clean. Being on the first floor, we have easy access to the pool and the marina. Loved that there is an outdoor shower by the...
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From
$740
Per Week
1 / 10
2 Bedrooms, 2 Bathrooms, Sleeps 6
Internet Access, Dishwasher, Balcony & more
Details Reviews (1) Make Enquiry
4 of 5 stars Reviewed 26 August 2012
Assateague Light is a very nice first-floor waterfront condo facing the Assateague Channel. The view from the deck is spectacular. When we were looking for vacation rentals on...
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From
$92
Per Night
1 / 6
4 Bedrooms, 2 Bathrooms, Sleeps 10
Air Conditioning, Washer, Dishwasher & more
Details Reviews (27) Make Enquiry
5 of 5 stars Reviewed 30 September 2014
Ducks Delight is our favorite rental on the island. It has ample space but is cozy and charming at the same time,. It is also very convenient to town and the beach, as it's an...
5 of 5 stars Reviewed 26 September 2014
Stayed at DD for a weekend. Sara is wonderful to deal with. Planning another trip in October with extended family. Very peaceful without a TV to distract you. We played games...
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From
$896
Per Week
1 / 15
3 Bedrooms, 2 Bathrooms, Sleeps 8
Dishwasher, Air Conditioning, Fireplace & more
Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 12 August 2014
Just returned from one of the best vacations ever. This house was nice and big. There were 8 in our party and there was plenty of room to speed out. The kitchen was well...
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From
$896
Per Week
1 / 14
3 Bedrooms, 3 Bathrooms, Sleeps 10
Pool, Dishwasher, Fireplace & more
Details Reviews (3) Make Enquiry
2 of 5 stars Reviewed 5 October 2013
We stayed with another couple for three nights at this property and were very disappointed from the start. It was advertised as being "waterfront" and a "luxury townhouse," but...
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From
$664
Per Week
1 / 12
3 Bedrooms, 2 Bathrooms, Sleeps 6
Air Conditioning, Balcony, Internet Access & more
Details Reviews (1) Make Enquiry
From
$595
Per Week
1 / 11
2 Bedrooms, 3 Bathrooms, Sleeps 8
Grill, Dishwasher, Air Conditioning & more
Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 5 May 2014
My family stayed at Marsh Point for a month Feb-March 2014. It was a really wonderful experience. The townhome was perfect for us, the location was great (1 mile walk to the park...
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From
$780
Per Week
1 / 11
2 Bedrooms, 2 Bathrooms, Sleeps 6
Air Conditioning, Dishwasher, Internet Access & more
Details Reviews (5) Make Enquiry
5 of 5 stars Reviewed 5 November 2014
To start, we live in Vermont & wanted to come south to get away, laugh, relax, smell, see & hear the ocean, see & hear the birds, get a weekly kayak rental, ride our bikes each...
5 of 5 stars Reviewed 19 September 2014
This little cottage was filled with whimsy and delight. It is NOT fancy and filled with the latest and greatest and shiniest. However, it is warm and welcoming and perfect for a...
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From
$231
Per Night
1 / 22
3 Bedrooms, 2 Bathrooms, Sleeps 6
Satellite TV, Air Conditioning, Internet Access & more
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5 of 5 stars Reviewed 12 August 2014
Lazy rocks on the screened in porch overlooking Chincoteague Island's west side's channel watching the pontoon boats and egrets. Badminton games on the back lawn next to the...
3 of 5 stars Reviewed 25 June 2013
This is an old cottage that has been renovated, altho not recently. The stairs to the second level are treacherous, and if you are a tall person the ceilings are so low that you...
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From
$290
Per Night
1 / 31
4 Bedrooms, 5 Bathrooms, Sleeps 10
Private Fishing Lake/River, Air Conditioning & more
Details Reviews (37) Make Enquiry
5 of 5 stars Reviewed 5 September 2014
We loved our stay at Epiphany on Chincoteague Island. The location was close to downtown, the beach, restaurants and ice cream!! It was a quick drive or bike ride away...
5 of 5 stars Reviewed 29 August 2014
Epiphany is a beautiful home and perfectly designed for a vacation with 2 families. I shared the home with my sister's family and both of our sets of teenagers. There are plenty...
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From
$595
Per Week
1 / 13
2 Bedrooms, 3 Bathrooms, Sleeps 8
Grill, Balcony, Air Conditioning & more
Details Reviews (1) Make Enquiry
From
$1,127
Per Week
1 / 14
3 Bedrooms, 2 Bathrooms, Sleeps 8
Pool, Dishwasher, Air Conditioning & more
Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 4 August 2014
This was a wonderful place to stay. The pictures don't do this place justice. Definitely will stay again.
3 of 5 stars Reviewed 27 August 2013
third floor rental with view of marina and bay...good living room couches....nice mbr furniture (if thats important)...but, I found it a struggle to find basic utensils in the...
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From
$693
Per Week
1 / 21
3 Bedrooms, 3 Bathrooms, Sleeps 10
Internet Access, Balcony, Dishwasher & more
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5 of 5 stars Reviewed 18 August 2014
I can't say enough about this beautiful rental!! Inside was perfect, kitchen and dining room was big enough for everyone and had everything we needed. The front porch was...
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From
$114
Per Night
1 / 59
4 Bedrooms, 4 Bathrooms, Sleeps 11
Pool, Housekeeping Optional, Dishwasher & more
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5 of 5 stars Reviewed 28 September 2014
We stayed at the Spinnaker to celebrate our birthday/anniversary. We were not disappointed. The house is a quaint and peaceful getaway. The views are absolutely gorgeous and it...
5 of 5 stars Reviewed 22 September 2014
Looked forward to a nice place for a vacation...and found the Spinnaker and it is WAY better than advertised! The pictures looked nice, and when you get there, it is much better...
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From
$114
Per Night
1 / 9
2 Bedrooms, 1 Bathroom, Sleeps 6
Air Conditioning, Dishwasher
Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 26 September 2014
I have went to chincoteague yearly since i was born and by far this is the first place i am going to stay for now on. Walking into this home i fell in love and instantly wanted to...
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From
$202
Per Night
1 / 9
3 Bedrooms, 2 Bathrooms, Sleeps 8
Air Conditioning, Dishwasher, Balcony
Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 14 July 2014
LOCATION: This was the first time we have stayed on the Northern end of Chincoteague Island. I will say that there is something to be said for the quiet neighborhood, tree...
5 of 5 stars Reviewed 29 May 2014
A group of friends and I rented this house for Memorial Day weekend, and it was perfect for our needs! Though the house does not look impressive from the outside, the interior...
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From
$1,034
Per Week
1 / 15
2 Bedrooms, 2 Bathrooms, Sleeps 8
Fireplace, Air Conditioning, Balcony & more
Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 17 January 2013
What a wonderful property. The water views are fantastic. The privacy is excellent. This is the perfect getaway location. We have visited this house three times and plan more...
5 of 5 stars Reviewed 2 November 2012
This was our second time here and I always feel right at home when I am there. Seriously if I could live anywhere in Chincoteague full time it would be in this home. The location...
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From
$107
Per Night
1 / 24
3 Bedrooms, 2 Bathrooms, Sleeps 6
Air Conditioning, Dishwasher, Washer & more
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5 of 5 stars Reviewed 17 July 2014
The house was well equipped with updates, private spot, wonderful screened porch. Comfortable furniture. Close enough to all the hustle of a beach town in Summer. Found out it...
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From
$141
Per Night
1 / 14
2 Bedrooms, 2 Bathrooms, Sleeps 6
Grill, Satellite TV, Dryer & more
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4 of 5 stars Reviewed 7 August 2012
Serenity was a great home to rent. It was very clean, updated, and beds comfortable. There was enough yard for the kids to kick the soccer ball. We have small children (5 & 8...
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From
$97
Per Night
1 / 8
2 Bedrooms, 1 Bathroom, Sleeps 6
Shared Indoor Pool, Grill, Air Conditioning & more
Details Reviews (14) Make Enquiry
5 of 5 stars Reviewed 14 November 2014
We stayed a few nights during the week. The unit was very clean and well stocked with needed items with the exception of a hair dryer which was an item that should have been...
3 of 5 stars Reviewed 30 August 2014
This was our first time visiting the Island and Dove Winds. I'll start with the Pro's (focusing mainly on Dove Winds). PRO'S- The indoor pool was great. It was actually...
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From
$83
Per Night
1 / 16
1 Bedroom, 1 Bathroom, Sleeps 4
Dryer, Washer, Satellite TV
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3 of 5 stars Reviewed 6 August 2014
$40 cleaning fee give me a break !!! yappy dog downstairs it did have great view would not stay here again would not recomend
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From
$676
Per Week
1 / 7
2 Bedrooms, 2 Bathrooms, Sleeps 6
Washer, Balcony, Dishwasher & more
Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 13 July 2014
We truly enjoyed our stay. The house was very clean and the decor made us feel right at home! Even the little odds and ends were not forgotten. If you needed something, it was...
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Suitability

  • Wheelchair access (12)
  • Elder access (18)
  • Suitable for children (26)
  • Pet friendly (60)
  • Smoking allowed (0)

Amenities

  • Air Conditioning (330)
  • Other outdoor space (321)
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  • Internet (186)
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Island vacation rentals - seaside villas, waterfront homes and condos

Browse through our vacation home rentals, and you’ll discover some very tempting choices for your family vacation. An historic Main Street home is surrounded by a private landscape with a screened porch, bikes and beach toys. A luxurious custom home overlooks beautiful Oyster Bay, and family-friendly condos feature waterside decks, swimming pool and marina.

Abundant outdoor recreation and attractions

Naturally, the seashore is the dominant focus for outdoor fun on Chincoteague Island. Fish from the dock or walk the beach. Take a bird-watching hike or bicycle ride through wildlife preserves and quaint island lanes. Enjoy dolphin watching, island tours and spectacular sunset views from your own guided cruise through remote bays and waterways. Either Assateague or Chincoteague beaches are ideal for family picnics and water sports.

Believe it or not, the wild Chincoteague Ponies are an unusual attraction on adjacent Assateague Island. The kids will love a trip to the Chincoteague Pony Center to enjoy pony rides, a show and riding competition. Book a small, charter deep-sea fishing trip that offers the opportunity to land big game fish from mahi-mahi and tuna to marlin and sharks.

Leisurely shopping and dining

As a contrast to all of that outdoor adventure, explore the village feel of the historic downtown and Maddox Boulevard areas. You’ll find exceptional hand-crafted duck decoys and original wildlife and landscape paintings and charming gift shops. To keep you entertained on a lazy sun-filled afternoon, stop in at Sundial Books to browse for book favorites and enjoy a cup of coffee or tea.

Fresh ocean fare dominates local restaurant menus that are loaded with clams, oysters, and all-you-can-eat seafood platters. Of course, you can’t take the kids on vacation without finding the perfect pizza place, and that would be Famous Pizza Family Restaurant. They’ve been serving home-fresh pizza, cheese steaks and more for over 30 years. And you positively have to stop in at The Sea Shell Café for a gourmet salad and authentic Smith Island Cakes. They even cater to your vacation home, if you want to skip the kitchen duties and enjoy their excellent dinner selections.

Villa and home rentals – the perfect seashore vacation choice

There is no better way to enjoy a lazy, leisurely island vacation than from your carefully-chosen home rental. You’ll have plenty of room to relax, waterside views to enjoy and some wonderful home-grilled meals or bountiful breakfasts that will long be memorable for your entire family.