Holiday rentals with a pool in Maryland Beach

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!

Beautiful waterview 2B condo w/Dock&Close to Beach

Welcome to the Canal Bungalow! A stylish 1000 sq. foot retreat to enjoy all the fun & relaxation of the coastal lifestyle in North Oc. Bring your boat with you and dock alongside your back porch, enjoy pool access in a private gated community, or bring your sports gear for Northside Park. We are tucked away on the quiet bayside of OC & only a few minutes walk to the beach. Unwind on our beautiful balcony while watching the boats go by & finally understand the true meaning of a coastal lifestyle!

2BRCapri: Indoor Pool, Game Room, Massage Chair

ALL THE COMFORTS OF HOME AT THE BEACH! BRAND NEW RENOVATED BATHROOMS! -ALL LINENS INCLUDED -Comfortable electric-reclining sofas -65-in smart Roku TV with soundbar. -Massage chair in master bedroom -Balcony & Dining Area w/ Ocean +Bay Views -In-unit W/D -Many conventional & USB Outlets -Arcade level features b-ball hoop, pool tables, ping-pong, shuffleboard, air-hockey -Outdoor tennis court -Large heated indoor pools -can swim full laps -Sauna and Gym -Board games in unit -Fast Wifi

3 BR Waterfront Home, Minutes to the Beach

Recently updated waterfront house located in the family-friendly Montego Bay community. Enjoy beautiful sunsets on the back deck or hop in one of the kayaks for a paddle around the wide-open canal. Try your hand at crabbing or fishing off the dock to catch your dinner. Within easy walking distance of the beach and Northside Park (about 10 minutes walk to both). Beach chairs, toys, boogie boards, and umbrellas are yours to use for fun in the sand and surf. The dock is available for boat tie-ups.

SeaGate Serenity | Oceanfront Condo with Balcony

Wake up to the sound of the waves crashing outside your window and finish your days relaxing on the private balcony as you watch the pastel skies over the ocean at sunset. Come find your serenity by the sea in our newly renovated oceanfront condo. Located in midtown, you can keep your car parked in our reserved spot and walk to many of the towns best restaurants, bars, and entertainment as well as the World Famous Ocean City Boardwalk. Morning beach strolls, pool days, and evening sips await :)

Rare Private Patio+Deck, Minutes Walk to OC Beach

Look no further–this upgraded 2-BR 2-BA bayside condo will be perfect for your family vacation! Whether you choose to spend your family getaway enjoying the beach, swimming at the indoor/outdoor pool, or enjoying a beautiful night on our one of a kind patio, you’ll be sure to have the vacation of a lifetime. We look forward to you staying at our favorite vacation spot! If your desired dates are unavailable/ you have a group of 7+, please click on our profile and look at our other properties!

1st Floor Canal Front POOL 2 Blocks 2 Beach/Park

Sit along the canal-front deck, watch boats, birds, and walk to beach, restaurants, shopping, Northside Park Fully equipped kitchen, washer/dryer, comfy queen bed and queen sleeper, plenty of blankets and pillows are provided. PLEASE PACK BED LINENS, BEACH and BATH TOWELS We enjoy hosting families and singles 25 years + NON SMOKING Provided: Hand/Dish/laundry detergents Starter Toilet Paper / Paper towel Hair dryer FREE parking Hi speed Wifi Pool OPEN Memorial-Labor Day 9:15am-8pm

Ultra Luxe Oceanfront Escape w/Breathtaking Views!

Enjoy a rare beach-house feel from this renovated first-floor oceanfront condo in North Ocean City. Set just one level up, the unit offers a spectacular perspective of the dunes, beach, ocean, and waves breaking right outside. Enjoy direct beach access, two reserved parking spaces, elevators, linens and towels, a heated indoor pool and hot tub, and a new 4,000 SF ocean-view sun deck. Inside, this warm coastal retreat sleeps 8 with pine ceilings, luxury finishes, and private balcony views.

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.

21st Floor Carousel - 2 BR Oceanfront & Bay View

NEW!! Welcome to our direct oceanfront 2 bedroom & 2 bath unit at the Carousel! Bringing the comfort of your home to the beach! Bring the whole family for lots of fun memories! We strive to take care of this condo to ensure you have a relaxing, comfortable, and clean stay! Our condo includes 2 DOUBLE SIZED balconies! An oceanfront balcony and a bay view balcony! You can enjoy both the sunrise and sunset!

Oceanfront 2 Bedroom-Sleeps 6-Indoor/Outdoor Pool

Kick back and relax in this beautiful and modern newly remodeled condo in Golden Sands! This rare 2 bedroom, 1.5 bathroom unit has an amazing Master Suite with full-length windows providing panoramic views down the coastline, and direct access to the private patio. Renowned building amenities include outdoor pool, top floor indoor pool, gym, tiki bar, sun deck & more. Linens & towels included!

4 Bd/3 Ba - 1 mi from beach, pool, linens included

Get ready for your best beach vacation yet in this bright 4 bed/3 bath home! Our home is located in Montego Bay and was updated in 2022. It features vaulted ceilings, a gas fireplace, and a sunroom lounge with a nugget ice maker (the "good ice") and commercial juicer to enjoy those orange crushes all vacation long! NEW FOR 2025: Linens and towels are now included!