Vacation rentals with a pool in Delmarva Peninsula

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Top-rated rentals with a pool in Delmarva Peninsula

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

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Top guest favorite
The living area features comfortable electric reclining sofas facing a coffee table. Large windows provide views of the ocean, while a dining area and modern kitchen are visible in the background, creating a spacious and inviting atmosphere.
Condo in Ocean City
5 out of 5 average rating, 117 reviews

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

Top guest favorite
A dining area is showcased with a grey table set for six, surrounded by vibrant yellow chairs and a metal wire-frame chair. A modern light fixture hangs above, and a decorative wreath adorns the wall, complemented by abstract artwork on either side.
Condo in Rehoboth Beach
4.99 out of 5 average rating, 200 reviews

Renovated Condo Near Outlets, 3.5 Miles to Beach

Enjoy your stay in this recently renovated and beautifully furnished two-bedroom, two-bathroom 3rd-floor condo conveniently located 3.5 miles from the Rehoboth Beach boardwalk, and 4.5 miles from Lewes Beach. The proximity to the beaches, stores, and restaurants make this condo a great spot to spend a fun-filled vacation at the beach. Our condo amenities include a community pool*( seasonal), free parking, free WiFi, smart TV, washer, and dryer. We supply all the sheets & towels for your stay.

Top guest favorite
A cozy living area features a spacious sectional couch adorned with patterned cushions. A wooden coffee table sits centrally, with a decorative rug beneath. A brick fireplace is present, flanked by windows allowing natural light, and a green door leads to the exterior.
Guesthouse in Cambridge
4.99 out of 5 average rating, 131 reviews

Rosses Chance Guest House

This lovely guest cottage is located on a historic 16 acre waterfront estate on Hudson Creek that includes a main house, barn, pool, dock and pond. Built in the 18th century tidewater style, the guesthouse is charming and well decorated and completely self efficient. A special place for your romantic getaway at any season of the year. Recently cell phone service has improved and is reliable. However, in the country, WiFi internetl can be slow at times as well as the Wifi TV streaming.

Guest favorite
A charming two-story cottage is set on a lush green lawn, with a clear view of the Chesapeake Bay in the background. The cottage features large windows and a sloped roof, with a small wooden addition on one side, surrounded by well-maintained grass.
Tiny home in Cape Charles
4.98 out of 5 average rating, 340 reviews

The Laughing King Retreat Honeymoon Island Cottage

Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

Top guest favorite
A bright living area features wooden beams and large windows adorned with plaid curtains. A variety of cushions decorate a sectional sofa and a leather couch. A television offers a view of a sports event, while an area rug adds pattern to the wooden floor.
Farm stay in Princess Anne
4.95 out of 5 average rating, 113 reviews

Farmhouse located on a horse farm

Farmhouse located just minutes off of Route 13 in Princess Anne, MD. Enjoy a peaceful farm experience while staying in a charming farmhouse with lots of character. You can walk the grounds of the farm, including a trail through the woods, or take a swim in the pool. We do not offer horseback riding lessons but you can interact with the horses. We are minutes to shopping, groceries, restaurants, UMES, and a short ride to Chincoteague (32 miles) and Ocean City (40 miles).

Top guest favorite
A modern guesthouse features a peaked roof and large windows, set against a vibrant sunset sky. The surrounding landscape includes wild grasses and a paved pathway, suggesting a serene connection to nature.
Cottage in Saint Michaels
4.97 out of 5 average rating, 178 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

Top guest favorite
Guesthouse in Stevensville
4.99 out of 5 average rating, 319 reviews

Waterfront-View of Bay from your Bed-Steamy Sauna

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Guest favorite
An open-plan kitchen and living area feature a light wooden counter with three stools. A fully equipped kitchen is visible, including a refrigerator, while a comfortable seating area with a cream-colored armchair and a coffee table is also present. Natural light enhances the inviting space.
Condo in Ocean City
4.88 out of 5 average rating, 162 reviews

Water Front Condo w/Pool Short Walk to Beach

FIRST FLOOR UNIT Bayside Condominium Sleeps 4 - 6 max Walking Distance to Northside Park Walk to the Ocean , don't worry about beach parking NON SMOKING 1 Bedroom 1 Bath condo, First floor unit with an outside deck This Air Conditioned, One Bedroom Condo has a fully equipped kitchen, washer/dryer, full refrigerator. There is a Queen bed and a full bed along with 1 Queen Sleep sofa in the living room *MUST BE 21 OR OVER* No Pets!

Top guest favorite
A wrap-around deck overlooks a tranquil waterfront view, featuring lush greenery and calm waters. A seating arrangement includes four chairs with cushioned backs, positioned for relaxation. The scene is punctuated by nearby trees, contributing to a serene atmosphere.
Home in Lewes
4.99 out of 5 average rating, 214 reviews

Beautiful Waterfront Home-Private, Clean, Relaxing

A beautiful and peaceful get-away all year round! Bright and sunny 3 bed/2 bath waterfront home with wrap-around deck. Fully stocked, community pool, walking trails, kayaks and more! Visit Rehoboth or Lewes Beaches (10 miles away), Cape Henlopen and tax-free outlet shopping (6 miles away)! Great for families, water lovers, and bird lovers! Sunday to Sunday weekly rentals *only* and no pets from Memorial Day to Labor Day.

Superhost
A modern living area features a light-colored sofa paired with two brown leather armchairs. A round wooden coffee table graces the floor, complemented by a textured area rug. Floor-to-ceiling glass doors provide unobstructed ocean views, while floor curtains add a pop of color.
Condo in Ocean City
4.91 out of 5 average rating, 141 reviews

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!

Top guest favorite
The kitchen area features modern cabinetry and stainless steel appliances. A large kitchen island with seating is complemented by woven bar stools. Natural light enters through a window, enhancing the open space and inviting atmosphere.
Apartment in Frankford
4.98 out of 5 average rating, 124 reviews

Sunshine By The Sea near Bethany Beach

Enjoy Southern Delaware and everything it has to offer in this stylish, family friendly condo located just 1.5 miles from the beach. Completely remodeled in 2022 and thoughtfully furnished to create modern, relaxing coastal getaway. Pool access 2026 Opens Memorial Day Weekend Closes TBD (through LDW possibly still open first week in September) Hours: 11am-7:45pm

Top guest favorite
A light-filled living area features a comfortable seating arrangement with two red chairs and a cozy couch, accompanied by a round coffee table. A wall-mounted TV is situated above an electric fireplace, enhancing the space's inviting atmosphere. Large windows offer views of the outside.
Condo in Lewes
4.94 out of 5 average rating, 296 reviews

Spacious| Modern & Cozy| Pool| Close to the Beach

Perfect getaway conveniently nested just off the Costal Highway and just few minutes from the Nassau Valley Vineyard. Less then 5 miles to Lewes Beach and 7 miles to Rehoboth and Dewey Beach to enjoy the Ocean! Cape Henlopen State Park, Great Restaurants, Breweries, Historic Downtown Lewes, Tax free shopping at the Tanger Outlets and much more.

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