Holiday rentals with a pool in Eastern Shore of Virginia

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Top-rated rentals with a pool in Eastern Shore of Virginia

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

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Guest favourite

Home in Rehoboth Beach

4.99 out of 5 average rating, 126 reviews

Secluded beach beauty with private, heated pool

The LV home by architect Rocio Romero is a modern classic, we love it… The heated, salt water pool is open mid-May to mid-October. You can cook in the fully equipped kitchen and eat indoors or on the large deck out back, play in the pool or fenced yard, lie in the hammocks, play games, do puzzles... We are right by the Junction and Breakwater bike trail; it's about 2 miles to the Rehoboth Boardwalk, 6 miles to Lewes. There's high speed WiFi, a Sonos audio system, and a Roku smart tv (no cable).

Guest favourite

Home in Cobbs Creek

4.9 out of 5 average rating, 149 reviews

Millionaire $ Views No Xtra Charge! Hot Tub! POOL!

Welcome to The Cottage at Misti Cove, where you can experience the epitome of relaxation and tranquility. Immerse yourself in the serene ambiance of our cottage, aptly named for its simplicity, which belies the luxurious amenities that await you. At The Cottage at Misti Cove, we understand that the essence of a fulfilling vacation lies in the delicate balance between embracing the simple life and indulging in modern comforts. Here, you will discover a haven that seamlessly blends these elements

Superhost

Home in Lancaster

4.63 out of 5 average rating, 19 reviews

One May wknd open!. Bay retreat, pool, fire pit

Peaceful get away on the sandy shores of the Corrotoman "Rivah" full of water activities. Fast WiFi, private saltwater pool(open May-Sept), kayaks, canoe, private sand beach, hot tub, full kitchen, pool table, firepit, deck with grill, outdoor dining tables. Deep water dock bring or rent a boat. Yankee Point Marina offers boat rentals, live music & restaurant w/in walking distance! Ride free ferry into Kilmarnock for shopping, restaurants & wineries. Kayak w/dolphins, watch Rock fish from dock

Guest favourite

Home in Cobbs Creek

4.98 out of 5 average rating, 152 reviews

Blue Heron WaterSide

Blue Heron Waterside awaits you...Private Hot Tub and Pool!Waterfront and Pier- Kayaks included! This retreat is set up with you in mind for a special get away.Relax.Enjoy being together plus space to have quiet time. Sunroom, spacious deck, private Pool, Hot tub and Pier create a waterfront living experience. Grab a book, go for a swim or lounge by the pool. Explore the water with a variety of Kayaks plus a Stand Up Paddle Board.Great location to fish and crab from the pier. Are you ready?

Guest favourite

Apartment in Dewey Beach

4.98 out of 5 average rating, 44 reviews

Stunning 2 bedroom with pool

Beautiful 2 bedroom condo in Dewey's most desired location. This condo is located at the Residences of Light House Cove with a stunning view of the bay and marina from your private balcony. The master suite boasts a king bed with a spacious private master bath. The comfortable 2nd bedroom has a queen bed with full bath easily accessible. The open floor plan allows ample room to spread out including a well equipped kitchen. The building has elevators for easy access and private parking.

Superhost

Home in Lewes

4.78 out of 5 average rating, 45 reviews

Bring your flip flops and relax! Adorable beach cottage in a quiet, gated community just a short drive from the hustle and bustle of downtown. Enjoy the outdoor area at home with a fire pit, grill, and games or explore the wooded trails, crabbing dock, or community pool. The pool is open on weekends only from the Saturday of Memorial Day weekend until full-time hours begin on or about the 12th of June each year. CLOSES Labor Day weekend. You must be at least 25 years of age to rent.

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

Home in Rehoboth Beach

4.96 out of 5 average rating, 71 reviews

Modern Home with Private Pool in Rehoboth Beach

Stunning modern home within biking or walking distance to Downtown Rehoboth. Location is key! We are just a stones throw from grocery stores, shopping, and many great restaurants! Our home features a large main house with 3 bedrooms (each with its own full bath), spacious living room, dining room, custom kitchen, a large screened porch, and heated saltwater pool. The property also includes a separate studio/4th bedroom with a powder room and outdoor shower area!

Superhost

Apartment in Ocean City

4.8 out of 5 average rating, 56 reviews

Renovated Downtown Townhome W/ Pool & Shuffleboard

Update- Outdoor pool closes 9/23/24 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

Apartment in Rehoboth Beach

4.93 out of 5 average rating, 102 reviews

Cozy condo, 3 pools, and 4 beds in Rehoboth Beach

Get ready to relax immediately in this cozy and bright condo in a quiet community. The condo is a WALK-UP 3rd floor with vaulted ceilings, multiple balconies, and a relaxing screened porch with a view. We provide linens for the beds, bath towels, boogie boards, and beach chairs. Just over a mile from the beach and within walking distance are 3 community pools, a brewery, a grocery store, seafood restaurants, a water park, and more.

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!