Holiday rentals with a pool in Kent Island

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Top-rated rentals with a pool in Kent Island

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

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Top guest favourite

Guest house in Annapolis

5 out of 5 average rating, 156 reviews

Private Art-Filled Guesthouse near Naval Academy

Slip under a colorful quilt and get a great night's sleep in a secluded walk-up guesthouse. An intriguing blend of antique curios and Americana populates the room. The result is a comforting space that also has a modern kitchen and updated bathroom. Homeowners on site and available to book your Treetop Getaway! Key code access will be provided. Check in time is 3pm. Check out time is 11am. Contact me via phone or through messages here and I will respond as soon as possible. The guesthouse is in West Annapolis, a residential neighborhood bounded by Weems Creek and the Severn River. It's close to downtown, the Naval Academy, and the Stadium. Quaint shops and restaurants are just around the corner.

Guest favourite

Flat in Upper Marlboro

4.95 out of 5 average rating, 121 reviews

DC Oasis- hot tub, pool, theater/game rm, & more

Have fun and relax at this stylish oasis! Packed w/ amenities. Huge Pool w/multiple cabanas, HOT TUB, trampoline, playground, axe throwing, pool/ice hockey table, arcade,huge theater room and outdoor projector too, basketball court, grill, spa/library with sauna and full gym!! 5 comfy beds. Rooms split for privacy. Open kitchen/dining/living room. Cold DeerPark water fountain. Basement apt so there is some movement noise. Updated bath and an outdoor shower. 20 mins from Downtown DC & 6Flags.

Guest favourite

Guest suite in Arnold

4.87 out of 5 average rating, 132 reviews

Cozy Comfort - only 7.5 Miles to Annapolis & USNA

Close to historic Annapolis, our cozy first floor guest apartment of our home in a quiet large single family home neighborhood. 'The Oasis' is private and spacious with 2-bedrooms, a living room, mini sit-in kitchen, bathroom, and laundry room. Close to waterfront restaurants, B & A trail, Sandy Point Public Beach and Park, festivals, shopping, bowling, miniature golf, wineries and more. Our guests are welcome to enjoy some time relaxing in our wooded backyard with pool (unheated) and gazebo.

Top guest favourite

Flat in Stevensville

4.98 out of 5 average rating, 274 reviews

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Guest favourite

Guest suite in Arnold

4.94 out of 5 average rating, 169 reviews

Coastal Comfort Suite Near Annapolis, Hottub, EV

Hot tub is open for the season. Pool will be open May 12 through Labor Day weekend. Ideal for a couple's retreat, this king suite guest room has a massive bedroom with a seating area, mounted TV, and coffee bar with microwave/mini-fridge. An ensuite bathroom provides a luxurious shower with dual shower heads and a spacious closet. The pool and hot tub are seasonal. Please don’t hesitate to reach out with any questions, concerns, or expectations so that we can address them prior to your stay.

Guest favourite

Home in Severn

4.88 out of 5 average rating, 162 reviews

Large Home with Pool & 7 bedrooms; sleeps 21

Relax at this large 7-bedroom spacious top-quality home that is ideal for large gatherings where all can be together in one place. All will be comfortable in large open areas both inside (4,125 sq ft, tall ceilings) & outside (1 acre). Enjoy a huge first-class kitchen with all the granite countertop space, cooking & serving supplies you will ever need. Enjoy the large fenced-in backyard with pool, grill, & fire pit. Ideal for family events, quiet getaways, sports teams, & business meetings

Top guest favourite

Casa particular in Chestertown

4.92 out of 5 average rating, 143 reviews

Red, White & Waterview Studio Apt with pool

One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, seasonal hot tub, lush grounds and outdoor seating. The space is well equipped w/ a queen sized bed, linens, washer/dryer, microwave, fridge, dinette, full size sofa bed, toiletries... everything you could possibly need to escape the hustle and bustle of life. Flat walk to the historic Chestertown waterfront!

Guest favourite

Flat in Arnold

4.96 out of 5 average rating, 174 reviews

Celebrate Summer by Your Private Pool

Lovely 2 acre waterfront lower level attached apartment with separate private entrance. Exceptional amenities include an inground pool, a pier with kayaks and paddle boards, pickleball and basketball courts, a swing set with a rock wall for kids, a gas grill, and a pool table. This amazing water front home is conveniently located only seven miles from the Naval Academy and downtown Annapolis. We do not host parties or events. Only registered guests are permitted on the property.

Top guest favourite

Guest house in Stevensville

4.99 out of 5 average rating, 268 reviews

Waterfront Getaway - View of bay from your bed

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.

Top guest favourite

Home in Harwood

4.95 out of 5 average rating, 136 reviews

Luxury Home, Sleeps 15, Private Pool, Close to DC

Stunning 6 bedroom, 5½ bath home on 34 acres with panoramic woodland views and private salt water pool, perfect for that special gathering. Secluded yet just 35 minutes from Capitol Hill and 20 minutes from Annapolis. The home, with its high ceilings, huge windows and expansive decks comprises over 8000 square feet, so there is plenty of room to stretch out. *** IMPORTANT Please send AN INQUIRY with a little about you PRIOR to requesting a booking.

Top guest favourite

Cottage in Easton

5 out of 5 average rating, 102 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

Guest favourite

Home in Fort Washington

4.91 out of 5 average rating, 148 reviews

5 BEDR, Inground Pool+Billiard Table, Close To D.C

Enjoy the comfort of this fully remodeled, beautifully decorated single family home. This home is located within minutes of National Harbor Waterfront, MGM, Tanger outlets, many restaurants and shops, and only 20 minutes from Washington DC and 20 minutes away from DCA - Ronald Reagan Washington National Airport. The home is built on half an acre of land, with a brand new in-ground pool in the backyard for enjoyment in the summer months.