Holiday rentals with a pool in West Ocean City

4.95 out of 5 average rating, 255 reviews

Home in Montego Bay

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!

4.91 out of 5 average rating, 311 reviews

Apartment in Ocean City

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

4.96 out of 5 average rating, 75 reviews

Private pool, waterfront, kayaks, bikes, firepits!

The Golden Quarter Farm is 150-acre waterfront, nature preserve, centrally located 5 miles from Assateague Island and its wild ponies, small town charm of Berlin, and OC Boardwalk. With a pool, kayaks, SUP, hiking trails, bikes, and birding, there's little reason to leave the property! Max of 8 adults. No parties. No Pets. Renters must sign a Rental Agreement & provide $250 refundable damage deposit. Pool open April-Sept 30th, NOT heated. 5% local room tax will be collected after booking.

4.97 out of 5 average rating, 172 reviews

Apartment in Ocean Pines

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

4.9 out of 5 average rating, 208 reviews

Flat in Ocean City

Newly renovated cute apartment 🏄 12 street 🌸

Welcome to our sweet, quite, enhanced clean and cozy place! Our apartment is the perfect escape for couples looking to spend some lovely days on the beach! We’ve got 1 bedroom but also a nice sofa where your friend can sleep if decides to join you! With its location being only couple minutes walking distance away from the beach and the Boardwalk, our beach home is the perfect place to stay. You will not have to worry about your car because we’ve got free parking spot for you! See you soon! 🌸

4.95 out of 5 average rating, 41 reviews

Luxury Townhome WestOC -4 BRS / golf / asssateague

This luxurious 2,700 foot sq. foot townhouse is the perfect place to enjoy golf, fishing, or enjoying nearby attractions like Assateague or Frontier Town. Only rents to age 25 and above. 4 stories of living space - 1st floor - 1 bedroom 2nd floor - all living / entertaining space 3rd floor -3 bedrooms 4th floor - loft play room Bedrooms: 1 - King - attached bathroom - ground floor 2- King - attached bathroom - 3rd floor 3 - Queen - 3rd floor 4 - 2 twin beds - 3rd floor 4 cars MAXIMUM.

5 out of 5 average rating, 106 reviews

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!

5 out of 5 average rating, 12 reviews

Apartment in Ocean City

Remodeled 1st flr condo-sleeps 6

Beach days and boardwalk nights start here! This newly remodeled 1st-floor condo is the perfect home base for your getaway. With two comfy queen beds and a pull-out couch, it sleeps up to 6 and has everything you need to relax. Enjoy the pool just steps away, free parking, and a location that puts you close to all the action—walk to restaurants, parks, the boardwalk, and the ocean in minutes. Clean, cozy, and convenient, this spot makes your beach trip easy and fun from start to finish.

4.8 out of 5 average rating, 198 reviews

OC MD trip bayside, great amenities

Welcome to MERMAID DREAMS where you can have FUN or just RELAX! We are ONLY 5 miles from OC/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

4.92 out of 5 average rating, 36 reviews

Ocean City beach house with bay view

A perfect getaway house for up to 4 ADULTS ONLY (age 25 & older) looking to relax, unwind and enjoy some peace and quiet. Rental is NOT SUITABLE for children. Max occupancy is 4 adults only. Enjoy this cozy bay view, sunshine filled, 2-bedroom home directly across from Sinepuxent Bay. Home is located on Stephen Decatur Highway within a gated community. It's conveniently located 5mi to Ocean City's inlet boardwalk & 5 miles to Assateague Island Seashore Beach.

Superhost

4.8 out of 5 average rating, 110 reviews

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!