Chincoteague Rentals With Pools

Chincoteague Rentals with Pool Access

Browse Chincoteague Rentals with Pool Access

Need a rental with more options than just the open water of the VA 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 vacation rental provides several amenities to ensure a fun-filled vacation and a great location to 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 55 properties available
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 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Changes in Latitude, Changes in Attitude….Jimmy Buffet sure does know what he’s talking about, doesn’t he?! 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
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Sunset Bay Villa 309 - Changes in Latitude
Condominium Pet Friendly
$150 - $495 / 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 220 - Vista Costiera
Condominium
$150 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
There’s nothing like the smell of salt in the air, the sound of the trees swaying, and a warm breeze through your hair - and that’s just what you’ll find at The Shore Shanty in Captain’s Cove Golf and Yacht Club. One of the best kept secrets on the Eastern Shore of Virginia, Captain’s Cove sits directly on the Chincoteague Bay, just 25 short minut
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The Shore Shanty
House Pet Friendly
$125 - $250 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Welcome to beautiful Sunset Bay Villas on the Chincoteague Bay - a Water Lover’s 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
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Sunset Bay Villa 310 - Nauti Girl
Condominium Pet Friendly
$150 - $475 / 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 - $350 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
Ahhh, Chincoteague Island—where the salty marsh breeze greets you, and wild ponies roam Assateague as if they’re welcoming you home. One trip here, and it’s love at first sight—it’s the kind of place that sticks with you forever. But let’s face it, life’s a whirlwind, and carving out a whole week to escape isn’t always in the cards. Maybe you’re mo
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Assateague Inn 110-S
Condominium
$62 - $310 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Welcome to Assateague Inn 107 in the heart of Chincoteague Island at the The Assteague Inn. The Inn is a long time favorite of Beach Lovers, and sits less than 5 minutes from Assateague National Seashore, where our Wild Ponies roam free!What makes Assateague Inn 107 different from the other Suites at this beloved building? It’s the ONLY Suite that
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Assateague Inn 107-A
Condominium
$65 - $300 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Calypso - Dance to the Song of the Sea.....You know that feeling you get while relaxing on the beach and listening to steel drums play while the Sea Breeze blows through your hair? Enjoy this feeling every day at fabulous Calypso in Captain's Cove Golf and Yacht Club - one of the Best Kept Secrets on the Eastern Shore of Virginia. This stunning 4 B
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Calypso
House
$150 - $375 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Bella Vista - Everything is better with a Water View…..Welcome to Sunset Bay 319 - Bella Vista - at fabulous Sunset Bay Villas on the Chincoteague Bay. Bella Vista, which is Italian for ‘beautiful View’, more than lives up to its name with stunning Direct Bayfront Views all around. These gorgeous condos sit directly on the Bay with spectacular View
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Sunset Bay Villa 319 - Bella Vista
Condominium
$150 - $495 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Cove’s Point - Of all the paths you take in life, make sure a few of them are sandy…….When was the last time you had a vacation that took your breath away? If this is what you’ve been craving, Cove’s Point is the place for you. Located in gorgeous Captain’s Cove Golf and Yacht Club - one of the best kept secrets on the Eastern Shore of Virginia, yo
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Coves Point
House
$135 - $450 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Welcome to Sunset Bay 109 at fabulous 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 Comm
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Sunset Bay Villa 109
Condominium
$125 - $525 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests

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