
Holiday rentals with a pool in Ocean City
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Ocean City
Guests agree: These homes with a pool 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!

DownByTheBay 115- Waterfront/4BR/Sleep 15/Pool
On The Bay, Beautifully furnished 4BR/3.5BR located in the heart of Midtown Ocean city, MD. * 1 block to beach- 5 min walk * Bonfire Buffet, Dough Roller, Ice cream Parlor - 2 min walk * Mini golf - 2 min walk * Bowling - 5 min walk * OC Boardwalk -7 minute by car * Seacrets - 5 minute by car * Convention Center - 5 minute by car * bus stop -1min walk * Market64- 2min drive *This property DOES NOT provide linens/towels* **Please FIND us at Down by the Bay OCMD For current Promotion**

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom
Launch your fabulous beach getaway at amenity-rich Sunset Cove at Sea Watch, part of an oceanfront condo complex offering 3 pools, complimentary movie theater, game room, gym, and much more. Enjoy spectacular ocean and bay views from 2 balconies, smart TVs in every bedroom and living room with provided satellite programming, fully equipped kitchen, comfortable living and bedroom spaces–and that’s just the beginning as your group has a blast at the beach and all of Ocean City’s fun attractions.

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

IslandCoveParadise:LuxNewlyBuilt-Brdwk pool/2CarGg
We welcome you, your family and friends to stay at our luxury, Newly Built, beautifully furnished, & decorated 3 BR 3.5 BA 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.

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.

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

Beachfront 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 a breathtaking view of the beach and ocean.

Love Above the Waves-Best Ocean View & Heated Pool
🥂 Complimentary champagne, oceanfront sunrises, breathtaking views, and warm swims in the heated pool—your romantic escape is ready. Whether you're celebrating a birthday, anniversary, engagement, or simply falling in love all over again, Love Above the Waves is more than a stay—it's a shared experience, both intimate and enduring. Let the ocean be your witness, the champagne your spark, and the sunrise your reminder: some escapes are meant to be unforgettable.

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!

Oceanfront & Amazing views! Time to book for 2025!
Great Mid-Town location! Direct Ocean front, 3 bedroom 2 full bath condo. Breathtaking views from very room. Natural light flows in from sliding glass doors and new windows, brightening the entire condo. When the surf gets too rough, go for a swim in the outdoor pool. 3 elevators and 2 assigned parking spaces. Make our home your home for vacation. Come stay at the Sandpiper Dunes and make wonderful memories that will last a lifetime!
Popular amenities for Ocean City rentals with a pool
House rentals with a pool

Upscale Family Home, Community Pool, Grill!

Beach Oasis w/ King Suite + Outdoor Shower & Pool

Ocean City Escape | Spacious Home | Pool & Golf

Beautiful Cottage W/ shared pool & close 2 beach

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

Ocean Palms II - Renovated, Ocean Block, Midtown

Mosaic Life Escapes -Bayfront Million Dollar Views

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines
Condo rentals with a pool

Gorgeous oceanfront Capri Beach and Bay Views!!!!

Well maintained 1 bedroom condo- midtown

Spectacular Ocean Front Condo on Boardwalk!

Oceanview 3 BR/3 BA 1800+sq ft!

Oceanfront Condo pools/Gameroom/Theatre/Restaurant

Updated 2-Bedroom Oceanview Condo

Beautiful 2BR 2BA oceanfront condo at the Atlantis

Dazzling Views Ocean Front one bedroom
Other holiday rentals with a pool

2 BR Ocean Front Condo w/Pool, Expansive Views

Beautiful Direct Oceanfront Condo on Boardwalk

Your Comfortable Beach Get-A-Way

Bayside Condo in Midtown Ocean City MD

NEW: Oceanfront End-Unit Condo w/ 100ft Balcony

OC Beach Life

OceanViewBeachClub-minutes from Bethany Beach/Golf

Ocean Front Pools Tiki Bar Self-Check-in Parking
When is the best time to visit Ocean City?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $252 AUD | $247 AUD | $242 AUD | $259 AUD | $332 AUD | $427 AUD | $489 AUD | $467 AUD | $342 AUD | $281 AUD | $256 AUD | $253 AUD |
| Avg. temp | 3°C | 4°C | 7°C | 13°C | 18°C | 23°C | 26°C | 24°C | 21°C | 15°C | 9°C | 5°C |
Quick stats about holiday rentals with a pool in Ocean City

Total holiday rentals
Explore 3,120 holiday rentals in Ocean City

Nightly prices starting at
Ocean City holiday rentals start at $15 AUD per night before taxes and fees

Verified guest reviews
Over 62,280 verified reviews to help you choose

Family-friendly holiday rentals
2,440 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 120 rentals that welcome pets

Rentals with dedicated workspaces
1,460 properties have a dedicated workspace

Wi-Fi availability
2,940 of Ocean City holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Ocean City rentals

4.6 Average rating
Ocean City stays receive an average rating of 4.6 out of 5 from guests
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- Ocean City Beach
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- Assateague Island National Seashore
- Ocean City Boardwalk
- Dewey Beach Access
- Willow Creek Winery & Farm
- Assateague Beach
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