Chincoteague Rentals With Pools

Chincoteague Rentals with Pool Access

Browse Rentals with Pool Access

Need a rental with more options than just the open water of the Virginia shore? Check out these Chincoteague Island Rentals with pools. With over 30 vacation homes and condos with pools or pool access, you are sure to have plenty of swim time and water fun. Each Chincoteague Island vacation rental provides several amenities to ensure a fun-filled vacation and great locations near the major attractions, shops, and dining.

Chincoteague Island has lots to do for your vacation. After a day at the beach, followed by lounging in your vacation rental's pool, maybe be a little adventure is what you need. Check out Maui Jacks Water Park & other fun activities on our Entertainment and Activities page!


Properties Available 65 properties available
Looking for a different kind of Beach Vacation? Dad likes to golf, Mom and the kids want the beach, and you don't want to leave Fido behind? How do you please everyone, you ask? We’ve got the answer right here at Paws and Relax in beautiful Captain’s Cove Golf and Yacht Club!One of the Best Kept Secrets on the Eastern Shore of Virginia, Captain’s C
Hot HOT 53
Paws and Relax
House Pet Friendly
$150 - $300 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
Ahhhhh, Chincoteague Island - the smell of Salt Marsh in the air - the visions of our Wild Ponies wandering through the Refuge. Once you visit our beautiful Island, it stays with you forever. But life is so busy - it's hard to get away for a whole week every year, isn't it? Or maybe you're one who prefers to take many shorter trips over the course
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Assateague Inn 207-S
Condominium
$45 - $215 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Relax, Rejuvenate, and Reconnect…..Welcome to ‘Shellfish Time’ on the beautiful Eastern Shore of Virginia! If you have been looking for a “different” kind of Vacation - a totally new Experience, yet not too far from Home, boy, do we have the place for you! Get ready for an awesome Adventure at this fabulous Brand New Home - the Beach, Wild Ponies,
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Shellfish Time
House Pet Friendly
$125 - $242 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Looking for the perfect beach break close to everywhere you want to be? The Assateague Inn is a long time favorite of Chincoteague Island Lovers, and sits less than 5 minutes from the Beach! Assateague National Seashore is one of the most visited beaches in America - after a visit, you will understand why! Home of our famous Wild Ponies, our pristi
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Assateague Inn 103-S
Condominium
$45 - $215 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Welcome to A Seagull’s Perch - Sunset Bay 320 - where salt in the air brings peace to the soul….Ahhh, Sunset Bay Villas on the Chincoteague Bay - pure Paradise! These gorgeous condos sit directly on the Bay with stunning Views of the Bay, Drawbridge, and the best Sunsets to be found. Lounge by the Bayfront Pool and watch Herons and Egrets frolic ov
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Sunset Bay Villa 320 - A Seagull's Perch
Condominium
$141 - $500 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Welcome to beautiful Sunset Bay Villas on the Chincoteague Bay - pure Paradise! These gorgeous condos sit directly on the Bay with stunning Views of the Bay, Drawbridge, and the best Sunsets to be found. Lounge by the Bayfront Pool and watch Herons and Egrets frolic over the water. Try your hand at crabbing or fishing from the Community Dock - or w
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Sunset Bay Villa 216
Condominium
$150 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Life is a collection of Moments….Longing for a new Experience - a different kind of Beach Getaway? Let us introduce you to a truly ‘Hidden Gem’ in Captain’s Cove Golf and Yacht Club - one of the Best Kept Secrets on the Eastern Shore of Virginia!Captain’s Cove is only 25 short minutes by boat or car from Chincoteague Island and Assateague National
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Hidden Gem
House
$145 - $283 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
A day spent at the Beach is never a wasted day…..Ready for a Vacation that will thrill everyone in your family? You’ve found ‘The Sweets Spot’ right here in Captain’s Cove, for sure! Captain’s Cove Golf and Yacht Club is one of the Best Kept Secrets on the Eastern Shore of Virginia. Located at the water’s edge directly on the Chincoteague Bay, Capt
Hot HOT 38
The Sweets Spot
House
$135 - $350 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
‘Off the Record’, we have to tell you - you are in for quite a treat!Ready for a Vacation that will take your breath away?! We’ve got the perfect place for you - welcome to fabulous ‘Off the Record’ in Captain’s Cove Golf and Yacht Club - one of the Best Kept Secrets on the Eastern Shore of Virginia. This stunning 3 Bedroom Waterfront Dream Home ha
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Off the Record
House Pet Friendly
$135 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Bliss by the Bay - If you’re wearing flip flops, you’re overdressed!There’s nothing like the smell of salt in the air and a warm breeze through your hair - and that’s just what you’ll find at Bliss by the Bay in beautiful Captain’s Cove Golf and Yacht Club. One of the best kept secrets on the Eastern Shore of Virginia, Captain’s Cove sits directly
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Bliss by the Bay
House
$125 - $351 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Casa Del Canal - Captivating. Canalfront. Calling your name.....Looking for the perfect Eastern Shore Vacation Destination? Look no further than Casa Del Canal in gorgeous Captain's Cove - one of the best kept secrets on the Eastern Shore of Virginia. This stunning 3 Bedroom/2 Bath Waterfront Home has something for everyone in the family. Located C
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Casa Del Canal
House
$140 - $250 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Welcome to Casa Del Sol - “Live in the Sunshine, swim the Sea, drink the Wild Air….”When was the last time your Vacation took your breath away? If that is what you’ve been yearning for, clear your schedule - Paradise awaits you in beautiful Captain’s Cove Golf and Yacht Club!Casa Del Sol is Brand New Construction in 2024, and beyond stunning. Tucke
Hot HOT 107
Casa Del Sol
House
$200 - $532 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests

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