
Home rentals with a pool near Chincoteague Island
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool near Chincoteague Island
Guests agree: these stays are highly rated for location, cleanliness and more.

Nature's retreat @ the Bug-a-Boo. Beaches nearby
We're inside a lovely gated campground community with full amenities @ the Club House: Wi-Fi, pool, fishing n crabbing, boat ramp, laundry, and bath houses. The Bug-a-Boo is a lovely single dwelling home. It is ADA handicap accessible. There's an outdoor fire pit and space for camping. We are 20 miles from Chincoteague National Wildlife Refuge with miles of protected beaches. This is a peaceful place for soul searching & social distancing. We are also 42 mi from Assateague Is. Nat. Seashore.

Ocean Pines 2-bedroom marina view getaway
Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

DirectOceanFront on Boardwalk/Newly Remodeled/Pool
Newly renovated and beautifully decorated direct oceanfront condo 1BR/1BA on the 4th floor, 12th St. on the center of the Boardwalk. Enjoy AMAZING VIEWS of the sunrises over the ocean and refreshing ocean breeze from the top floor. You can watch Ocean City’s best access to entertainment like the air show, fireworks, car shows and more on your private balcony. Within walking distance are great restaurants, shopping, nightlife, amusement parks, and plenty of water activities, and Pet Friendly.

Gone Coastal *Pool* Bayside with view* Top Floor
Welcome to Gone Coastal! Relax in this beautiful 2BR/2BA getaway featuring: 🛏 1 King (Master) | 1 Twin-over-Full Bunk | 1 Sleeper Sofa 🏊♂️ Outdoor Community Pools – Lap & Family Pool (Directly Across!) 🔑 Keyless, Contactless Check-in 🌅 Spacious Deck – Outdoor Dining + Bay & Pool Views 📺 Smart TVs + YouTube TV 🛒 1-Minute to Grocery Store 🍽 Fully Equipped Kitchen 📍 Prime Location – 120th St, Heron Harbor 🚗 Ample Free Onsite Parking A perfect retreat for families & beach lovers! 🌊☀️

Heartsong Farmhouse , a nature lover's retreat.
Heartsong Farmhouse was completely renovated in 2019. Beautiful hardwood floors, brand new furniture, in a modern farmhouse style with a Boho vibe. The entire home is filled with beautiful natural light and the brick walls ensure a peaceful nights sleep. The yard is completely surrounded by a 15ft hedgerow of holly, magnolia and camellias, like walking into a secret garden. You will feel welcome from the moment you drive up. The Farmhouse is also beautifully decorated for the holidays.

Oceanfront 1 Bedroom, Balcony, Sitting Room, Pool
Opal Osprey: This OVERSIZE one-bedroom condo has been completely remodeled... giant oceanfront balcony PLUS a large patio room on the bayside! Expansive ocean views from every angle, super easy beach access, wonderful atmosphere in the quiet north end of OC. Linens included! Property Amenities - King size bed & queen sleeper - Large outdoor pool - Elevators - Dedicated high-speed WiFi and router w/ ethernet (Xfinity 100Mbps) - 2 Smart TVS with Xfinity, Roku - Keyless check-in 24/7

Direct Oceanfront with a View and Amenities Galore
Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.

Farmhouse located on a horse farm
Farmhouse located just minutes off of Route 13 in Princess Anne, MD. Enjoy a peaceful farm experience while staying in a charming farmhouse with lots of character. You can walk the grounds of the farm, including a trail through the woods, or take a swim in the pool. We do not offer horseback riding lessons but you can interact with the horses. We are minutes to shopping, groceries, restaurants, UMES, and a short ride to Chincoteague (32 miles) and Ocean City (40 miles).

Caramar Couples Retreat
This cute little first floor efficiency condo is ocean front for a perfect vacation to the beach. It’s an older building but has been partially renovated and updated. You can get to the beach by a very short walk through a private walkway from the condo building. The view from the private balcony is perfect and relaxing. WiFi provided upon check in- xfinity, Netflix, and internet. Indoor and outdoor dining areas and a full kitchen. Closet and dresser for storage use.

Fresh renovated beach home~12 street
Enjoy a stylish experience at this centrally-located place. Our brand new remodeled beach home is located on a quiet street. You don’t need to worry about driving because the beach and Ocean city’s famous Boardwalk are only 2 minutes walking away from us. Peaceful nights with no loud vehicles speeding around. Our residential area is quiet with lovely pool which you can enjoy. The unit is stylish and clean. Great for couples or small family.

Water Front Condo w/Pool Short Walk to Beach
FIRST FLOOR UNIT Bayside Condominium Sleeps 4 - 6 max Walking Distance to Northside Park Walk to the Ocean , don't worry about beach parking NON SMOKING 1 Bedroom 1 Bath condo, First floor unit with an outside deck This Air Conditioned, One Bedroom Condo has a fully equipped kitchen, washer/dryer, full refrigerator. There is a Queen bed and a full bed along with 1 Queen Sleep sofa in the living room *MUST BE 21 OR OVER* No Pets!

Oceanfront Paradise | Pool | Hot Tub | Beach
-Oceanfront -Indoor pool & Hot tub -Walk to local dining and shopping -Elevator accessible plus luggage carts -Full kitchen for cooking meals -Fast Wifi and Streaming TVs -Fully Stocked Home: Clean linens, towels, toilet paper, paper towels & more! **2026 guests: Our pool and hot tub are in the process of being renovated and will be closed during your stay. They will re-open after Memorial Day**
Popular amenities for rentals with a pool near Chincoteague Island
House rentals with a pool

2 BR Ocean Front Condo w/Pool, Expansive Views

Salty Serenity

Beach Paradise 2101-Downtown Luxury Condo Bay View

Bayside community, near OCMD, great rates

Upscale House Steps 2 Ocean 3 Balconies Pool Bikes

Oceanfront | Pool | Steps to beach | Elevator

Right behind Alley Oops & Crab Bag. Walk to beach

Island Creek Retreat - Great Views, Pool, Pier
Apartment rentals with a pool

Oceanfront Carousel building, Swimming Pools!

Spectacular Oceanfront Penthouse - Unit 1204

Oceanfront Family Oasis: Pool, Beach & Parking!

Ocean Block - Clean, cozy 1 Bedroom. Pool, Wifi

DownByTheBay 4601-Midtown/Oversize Sleep 15 w/Pool

🌊Oceanfront studio w/ amazing views & amenities🏖

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom

Love Above the Waves-Best Ocean View & Heated Pool
Other holiday rentals with a pool

Welcome to Splash Pad-pools, beach + private patio

Boardwalk, pool, Great Unit!

9400 Building #1506| Great Location | Outdoor Pool

South Beach Boardwalk Condo

Oceanfront condo with pool, sleeps 4, free Wi-Fi

Bury Oasis: Pool, Hottub, Movie Theatre, Game Room

BaysideGetaway | 2 Blk to Beach & Boardwalk | Pool

Assateague Views! Top Floor -Assateague House #505
Destinations to explore
- Rentals with a patio Chincoteague Island
- House rentals Chincoteague Island
- Rentals with beach access Chincoteague Island
- Rentals with outdoor seating Chincoteague Island
- Rentals with a firepit Chincoteague Island
- Pet-friendly rentals Chincoteague Island
- Family-friendly rentals Chincoteague Island
- Rentals with a fireplace Chincoteague Island
- Rentals with a washing machine and dryer Chincoteague Island
- Waterfront rentals Chincoteague Island
- Rentals with pools Chincoteague
- Rentals with pools Accomack County
- Rentals with pools Virginia
- Rentals with pools United States
- Chesapeake Bay
- Ocean City Beach
- Ocean City Boardwalk
- Assateague Island National Seashore
- Jolly Roger Amusement Park
- Northside Park
- Bayside Resort Golf Club
- Bear Trap Dunes
- Assateague State Park
- Fenwick Island State Park Beach
- Delaware Seashore State Park
- Trimper Rides of Ocean City
- Roland E Powell Convention Center
- Old Pro Golf
- Ocean City Boardwalk
- Salisbury Zoo
- Bethany Beach Boardwalk




