Holiday rentals with a pool in Anne Arundel County

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.

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.

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

Chesapeake Bay View 3BR/2BA Duplex*Hot Tub*

*Hot tub* “Chesapeake Bay View Paradise" (3BR/2BA Penthouse Suite). Private penthouse level of a 2-level duplex, new deck, gorgeous Chesapeake Bay views, steps to sandy beach. 3 car parking. Gourmet kitchen, SS appl, granite counters, bar. Comfy living & dining areas. Entry handrail installed 9/20/24. 2 King BR, 1 Queen BR + Queen sleeper sofa in living area. Sleeps 8. 2 spa inspired baths, 1 jetted 2-person Jacuzzi tub inside. Outdoor Spa with Jets * Best Places To Stay Annapolis

Celebrate Summer by Your Private Pool

Lovely two 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 waterfront home is conveniently located only eight miles from the Naval Academy and downtown Annapolis. We do not host parties or events. Only registered guests are permitted on the property.

Waterfront | Pool | Hot tub | Beach Access

Recently renovated home near gorgeous Chesapeake Bay beaches! Located on a quiet street between Beverly Triton Nature Park and Mayo Beach Park. Your Big Pond retreat has a primary king room with ensuite bathroom, private pool, hottub, pond access & an expansive outdoor living area! This luxurious open floor plan living is on one level & sleeps 8. Less than 25 minutes from downtown Annapolis with amazing shopping & restaurants with a view! The perfect getaway for fun & relaxation.

Annapolis Waterfront Condo - Unit #: A-203

BOOK NOW FOR SUMMER 2025! SPRING and FALL BOAT SHOW AVAILABILITY! Free reserved parking! Walk to show in minutes! Great views - 2nd flr. condo (12 stairs, no elevator.) Pool hours are fixed: Mon: 4pm-8 Tues: Closed Wed: 4-8 Thurs: 4-8 Fri: 3-8 Sat/Sun/Holidays: 12pm-8 The pool is one of the best places to be on a hot summer day. If hours are unacceptable, pls select another location. 15 min. walk to downtown Annapolis/USNA. MULTIPLE Free parking options.

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.

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.