Holiday rentals with a pool in Worcester County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Worcester County

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Apartment in Ocean City

4.82 out of 5 average rating, 85 reviews

Bay View Condo, Pool @59th street

This condo is newly renovated and and has a stunning view of the bay with the most spectacular sunsets. It is also located in walking distance of popular restaurants, family attractions and is only a short walk to the beach. There is all day and night public transportation, and a conveniently located 7-11 for those last-minute snacks and pizza. The building has a private pool for all units with access to the dock on the bay, so grab your kayak for those beautiful Maryland sunrises and sunsets.

Guest favourite

Townhouse in Ocean City

4.93 out of 5 average rating, 153 reviews

IslandCoveParadise: Lux 5minsWALKto BdwalkBch/Pool

We welcome you, your family and friends to stay at our luxury, Newly Built, beautifully furnished, & decorated 3 BA 3.5 BR w/ 2 parking garage spaces plus free street parking, and an outdoor pool on 25th street. Relax and enjoy the AMAZING VIEW on the water front from our triple balconies, just 2 blocks (3-4 minutes walk) from the boardwalk & the beach. Steps from Jolly Rogers Amusement Park and many miniature golf courses. Within walking distance are restaurants/, shopping, & nightlife.

Guest favourite

Townhouse in Ocean City

4.93 out of 5 average rating, 116 reviews

Beach Paradise VII-New Townhouse with Pool, Garage

Welcome to Island Cove Townhouses! Newly built, spacious and beautifully furnished 3 bedrooms, 3.5 baths, 3 levels, luxury townhouse with garage. The community is located next to the bay in prime downtown location, 2 blocks from the beach and Ocean City's famous Boardwalk. This water front community offers not only boat docks, but also a private pier and community outdoor pool. Along with all the modern amenities, this south facing unit offers water views of BOTH the bay and the ocean.

Superhost

Flat in Ocean City

4.71 out of 5 average rating, 28 reviews

3br Waterfront Assateague Island Best View

3br/2 full bath with the best view in OC . great pool. View over the Bay, Inlet & Assat. Island. You can see the wild ponies on the beach. 2 1/2 off street parking spots. Quiet & right in the middle of the action. Beautiful Sunsets. Walk to Beach and many restaurants nearby. better Info call us 410two - 2 four137 hundred - and watch the video of the house/ or any doubt. Marcia Palmisano GoodtimesinOCcom Vacation Rentals.- please bring sheets/towels & call with questions & under 25.

Guest favourite

Apartment in Ocean City

4.87 out of 5 average rating, 31 reviews

Ocean View, Large Condo, Heated Pool

☀️🌊⛱️🐬🦀☀️ OC Searenity - We treat Our Guests like Friends. Enjoy summer vacation with this amazing, clean, fun oceanfront rental. This bright condo is one of the most spacious you will find! Wake up with coffee and the ocean view, and end the day with sunset on the second balcony. Everything you need to relax and enjoy your time away and make memories with your closest loved ones. Must be 25 years or older to rent. 🐬

Guest favourite

Apartment in Ocean City

4.94 out of 5 average rating, 16 reviews

Condo with Pool in the Heart of OC

First floor family friendly condominium with pool located within walking distance to the boardwalk, beach, amusement park, mini golf, and many restaurants. It has one bedroom with 2 queen beds and a pull-out sofa in the living room. Linens, bath towels, washcloths, and beach towels are provided for your convenience. The pool is located in the middle of the beautiful courtyard. There is a patio to enjoy the sunrise or sunsets.

Guest favourite

Home in Ocean City

4.98 out of 5 average rating, 132 reviews

Stunning Bayview Home with Own Private Pool

This home can be occupied by a max of 12 adults with a total of 15 including children. Come relax in this gorgeous bay view single-family home in the lovely Caine's Woods neighborhood of Ocean City, adjacent to Fenwick Island. Imagine lazy days spent on the beach followed by a dip in the pool outside the kitchen door! The pool is open from May 1- September 30. Obviously we can’t have it open during cold temperatures!

Guest favourite

Apartment in Ocean City

4.98 out of 5 average rating, 40 reviews

Charming Northside Park Condo w Pool, Walk 2 Beach

This charming 1 bedroom, 1 bathroom condo w/ a Pool is only a block and a half from the beach. You'll love relaxing on the deck that overlooks scenic Northside Park and the bay. An ideal getaway for couples or a small family. This unit has an Eat-in kitchen, washer & dryer, 2 TVs, Central Air, and high speed WiFi. This third floor two-story condo is in the Raffles Condominium complex, located on 127th Street in OCMD.

Guest favourite

Townhouse in Ocean City

4.85 out of 5 average rating, 27 reviews

Spacious 3 Bedroom, 3 Bath Townhouse, Pool, Pier

Very Family oriented, 10-minute walk, 2-minute drive to the beach, 1 block up from the boardwalk! Private shared pool, private pier, Grill. Bring your boat up to the house. lagoon sunsets. Perfect kayaking/paddle boarding. Two car parking. 3 bedrooms and 3 bathrooms. It's a spacious home away from home you'll love returning to. Sorry, but we don't rent to people under 25 and the Association doesn't allow pets.

Superhost

Apartment in Ocean City

4.8 out of 5 average rating, 56 reviews

Renovated Downtown Townhome W/ Pool & Shuffleboard

Modern, downtown Bayside 2-level townhouse w/ large community pool. Prepare to relax and unwind in this 2-level beach house! This central location makes it very easy to walk to the beach, boardwalk, and many restaurants & shops. The kitchen is fully stocked with all your cooking needs. Enjoy the pool view from right outside your sliding door. There isn't much more you could ask for. Bath and bed linens provided.

Guest favourite

Holiday home in Fenwick Island

4.94 out of 5 average rating, 34 reviews

Cozy, updated condo. Pool, tennis, walk to beach.

NEW KITCHEN COMING FOR 2025! Updated 2 bedroom condo in quiet beautifully maintained community, with screened in porch overlooking zen-like garden. Quick walk to beach, plus a resort style pool and tennis court. New furniture, beds, carpet and paint. Refreshed kitchen and baths, and super clean!

Guest favourite

Apartment in Ocean City

5 out of 5 average rating, 8 reviews

Bayfront Condo 46th St *2 POOLS*Free Linens/Towels

FREE Linen & Towel package! Very spacious, 2 Bedrooms with en-suite Bathrooms, Indoor & Outdoor Pools, SMART TV, Fireplace, NEW Full size Washer/Dryer & Dishwasher, Central A/C, Parking for 2, Central a/c **NO High School or College Groups, No Bachelor/Bachelorette Groups, Family Rentals ONLY**