
Home rentals with a pool near Assateague Island National Seashore
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Top-rated rentals with a pool near Assateague Island National Seashore
Guests agree: these stays are highly rated for location, cleanliness and more.

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB
After relaxing at the beach (just a 7 min walk away), unwind on our deck "watchin' the tide rollin' away!" Get the best of the bay & the beach with this dog-friendly hidden gem! Imagine evenings enjoying the bay breeze as you crack crabs on the deck! Relax inside our open-concept great room that allows everyone to be together. Fish on our private dock or use it for your own boat or jet-ski to dock there. Witness spectacular sunsets with our Kayaks. Enjoy a well lit, private work space to virtual work w/ high speed internet! A new wood CRIB now in master suite for restful sleep! The pools and tennis/pickleball courts are only a few blocks away for your enjoyment! Plus, a truly unique OUTDOOR MOVIE EXPERIENCE for all our guests to make for the best Vacay EVER!

Oceanfront Family Oasis: Pool, Beach & Parking!
CONSTRUCTION NOTICE NOV 24 to MAY 25, noise may be heard Wake up to the ocean sunrise in this modern 2 bedroom, completely renovated, condo. Prime location on 29th street, 2 blocks north of the famous OC Boardwalk, 2 blocks east of OC's premier amusement and water park along with two famous crab house and other restaurants within walking distance. One hassle free off street parking spot, free WIFI, full size washer & dryer, and a beautiful outdoor pool steps from the beach. Enjoy the bay sun

Ocean Pines Retreat
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

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! 🌊☀️

Stay Salty OC Beach House
Welcome to your ultimate getaway near Assateague State Park & Ocean City! Our spacious retreat sleeps 14 guests and boasts resort-style amenities including pools, a gym, kayaks, and tennis courts. Located just moments from beaches, charming towns, and exciting attractions, you'll have everything you need for an unforgettable vacation. With a fully stocked kitchen, game rooms, cozy reading nooks, puzzles, and a balcony, there's something for everyone. Book now and let the relaxation begin!

Stunning waterfront panoramic view getaway house
Welcome to this thoughtfully remodeled waterfront property on the beautiful eastern shore of Virginia. Immerse yourself in jaw-dropping panoramic canal views of the Chincoteague Bay. Secluded escape for the nature enthusiast, balanced with country club amenities. Pools, boating and a golf course are within walking distance. Outdoor adventures and pristine beaches are just a short drive away! This property was designed to gather, recharge, explore, love, work remotely and inspire.

Bayside community, near OCMD, great rates
Welcome to MERMAID DREAMS where you can have FUN or just RELAX! We are ONLY 5 miles from OC, MD beaches & Assateague National Park/beaches. Our gated, beautiful community, is bayside, has 2 awesome pools, big splash pool, rec center, a fishing/crabbing pier, pond with paddle boats, 2 playgrounds+ more For kiddos of all ages, we are located right next door to Frontier Town, which has awesome water slides , western shows, mini golf, a rope course, ice cream shop.. short term stay

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.

Mosaic Life Escapes -Bayfront Million Dollar Views
At Mosaic Life Escapes the BAYFRONT is our back yard! Safe gated community home. Water access for paddle boards & kayaks. Community fishing/crabbing pier 2 pools 3 ponds arcade room, playgrounds, paddle boats. 2 bd home w/a million dollar view. Minutes from Ocean City, Assateague Island & Casino. WiFi + 3 smart TVs We have implemented additional sanitizing procedures between guest stays to ensure a clean house! Perfect for a family or romantic get away!

Sun, Sand & Sea | Your Cozy Oceanfront Hideaway
-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! **2025 guests: Our pool and hot tub are in the process of being renovated and will be closed during your stay. This does not impact our condo, but you will not be able to use these amenities.**

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck
Book 3 nights, get 1 night FREE stays thru March 10. inquire before booking This is a Ocbeachfrontrentals .com premier property 24/7 SUPPORT LINEN & TOWELS PROVIDED 8TH FLOOR PENTHOUSE! This stunning top floor 3 b 2.5 ba unit is the ULTIMATE friends & family beach trip, located in a premier building in Ocean City. Enjoy the ocean breeze and stunning views from over 150 square ft of private balcony. Wake up to ocean views from every room!

WraparoundBalcony-2 Bed-Sleeps 8-Pool-Laundry-WiFi
Welcome to our stunning oceanfront retreat! This luxurious property offers the perfect combination of comfort, style, and breathtaking views. With a spacious J-shaped wraparound balcony, you can indulge in panoramic vistas of the sparkling ocean waves from every angle. Ideal for groups of up to 8 guests, this two-bedroom, two-bathroom getaway provides ample space for everyone to unwind. Book today for the vacation you'll never forget!
Popular amenities for rentals with a pool near Assateague Island National Seashore
House rentals with a pool

Cozy beach home away from home!

Sunshine at Ocean Pines

Private pool, waterfront, kayaks, bikes, firepits!

Beach Paradise IV-Downtown Luxury Condo Bay View

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

Cozy 3 BR Pet Friendly Beach, Bay & Pond nearby.

Bayside West

Seaside Escape Mansion
Apartment rentals with a pool

𝙂𝙪𝙚𝙨𝙩 𝙛𝙖𝙫𝙤𝙧𝙞𝙩𝙚 Lovely 2lvl Condo Steps 2Beach+Pool

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE

Luxury Oceanfront Getaway!

Top Rated! Beautful Sunsets! Midtown Bayside Condo

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

Ultra Luxe Direct Oceanfront Escape - Marigot 1004

Love Above the Waves-Best Ocean View & Heated Pool

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom
Other holiday rentals with a pool

Mermaid Cove

NEW Beautiful Peaceful Costal Getaway

Coastal Cottage! Walk to Beach!

OC Gateway: Modern 4BR/2.5BA home (dog friendly)

Holiday Cottages - Sea Star cottage

Nautical at 82 Newport- private dock & waterfront

Pristine 4+ acre waterfront in Bethany Beach area

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines
Quick stats about rentals with a pool near Assateague Island National Seashore
Total rentals
20 properties
Nightly prices starting at
€ 137 before taxes and fees
Total number of reviews
280 reviews
Family-friendly rentals
20 properties are a good fit for families
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
Destinations to explore
- Rentals with a firepit Assateague Island National Seashore
- Waterfront rentals Assateague Island National Seashore
- Pet-friendly rentals Assateague Island National Seashore
- Family-friendly rentals Assateague Island National Seashore
- Rentals with outdoor seating Assateague Island National Seashore
- Rentals with a patio Assateague Island National Seashore
- Rentals with a fireplace Assateague Island National Seashore
- Rentals with a kayak Assateague Island National Seashore
- Rentals with a washing machine and dryer Assateague Island National Seashore
- Rentals with beach access Assateague Island National Seashore
- House rentals Assateague Island National Seashore
- Rentals with pools Maryland
- Rentals with pools United States
- Ocean City Beach
- Ocean City Boardwalk
- Dewey Beach Access
- Cape Henlopen State Park
- Assateague Beach
- Jolly Roger Amusement Park
- Peninsula Golf & Country Club
- Poodle Beach
- Assateague State Park
- Bear Trap Dunes
- Northside Park
- Bayside Resort Golf Club
- Towers Beach
- Baywood Greens Golf Maintenance
- Jolly Roger at the Pier
- Whiskey Beach
- Delaware Seashore State Park
- Plantation Lakes Golf and Country Club
- Fenwick Island State Park Beach
- North Shores Beach
- Coin Beach
- Lewes Beach
- Splash Mountain Water Park
- Heritage Shores