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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.

Celebrate Summer In Your Private Pool & Hot Tub

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 eight miles from the Naval Academy and downtown Annapolis. WE DO NOT HOST PARTIES OR EVENTS, AND UNREGISTERED GUESTS ARE NOT PERMITTED ON THE PROPERTY AT ANY TIME.

Secluded Tiny House With your own Private Pool

Secluded Tiny Guest House Retreat with Private Pool – Near Baltimore & Annapolis As you pull into the driveway, the city noise melts away—replaced by the serenity of trees and the inviting sparkle of your private in-ground swimming pool. This 320 sq. ft. Pool House is cozy. A large window fills the space with natural light to the ever-changing views of the wooded setting. Completely private stay – no shared spaces Self check-in with no contact Private pool exclusively yours during your stay

Annapolis Condo-1 bedroom King

Brand New Vacation Rental – Prime Annapolis Location! 1 bedroom. Experience the best of Annapolis in this newly renovated, beautifully furnished 1-bedroom condo with a king bed and NO chore list! This open-concept retreat offers a bright, modern interior and a private balcony to unwind. Start your day with a scenic walk through Truxton Park trails or head to the boat ramp to catch a water taxi to downtown Annapolis! Whether you're here for relaxation or adventure, this is the perfect spot.

The General's House-Spacious Home w/Pool & Hot Tub

Look no further for your next vacation home in Annapolis! Relax, unwind or entertain friends and family in this spacious, updated 4-bedroom, 4 bathroom home in the heart of Annapolis. Our home features multiple spaces for entertaining both indoor and outdoors. You can swim in the pool, cozy up by the fire place or enjoy a movie night in our theater room. When you stay here, you will find this home provides everything you need to create lasting memories and truly enjoy your time in the area.

Kone Oasis- hot tub, pool, theater/game rm.

Have fun and relax! Near every amenity. Huge Pool w/multiple cabanas, hot tub, trampoline, playground, axe throwing, pool/ice hockey table, arcade,huge theater room, 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. Now offering RV for additional cost to add additonal sleeping space. Basement apt so there is some movement noise. 20 mins to DC & National Harbor

Captains Quarters | Waterfront & Pool

Welcome to Captains Quarters — your waterfront home in the Yacht Club Condominiums. Fall asleep to the sound of the water, wake up to views of Spa Creek, and walk to Eastport's best restaurants in minutes. Relax on the covered patio, swim in the community pool, or stroll across the Eastport Bridge to Downtown Annapolis. Two bedrooms, a full kitchen with Keurig and bean grinder, cable TV, and 2 free parking spots. Everything you need for an Annapolis stay on the water.

Annapolis Garden Suite

Welcome to our oasis, tucked away on a forested residential street. ~7 minutes from the Annapolis Towne Centre, ~15m from the coast, and ~30m from Baltimore and DC. Tl;dr: This is a ground-level guest suite. Inside, you’ll find 3 beds, 2 bedrooms, 1 desk, 1 kitchen with a dishwasher, oven, Nespresso/pour over, 2 TVs, a laundry room, fast wifi, a pool, patio and a forest view. We live on the top floor (separated by stairs and a locked door; separate entrances).

Waterfront-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.

1st Floor Condo in Annapolis

This newly renovated, 1st floor studio is perfectly located just across Spa Creek from historic Annapolis in Eastport. Within easy walking distance of restaurants (3 min), Main Street/City Dock (10 min) & USNA's Gate 1 entrance (14 min), our studio includes a full kitchen, high-speed wifi, free onsite parking lot, a secure building entrance, dock (limited access) and a rooftop patio (with a seasonal pool) that offers beautiful views of downtown Annapolis.

Captains Quarters Oasis Near Annapolis, Sleeps 4

This updated suite is designed for comfort & convenience. Enjoy a king bed and a (queen bed) LoveSac sofa perfect for 2-4 guests. The suite includes a private en-suite bathroom, high-speed internet, a fully furnished kitchen, and a coffee bar to make you feel right at home. Located just 4 miles from Annapolis, you're close to all the best spots. Whether you’re here to relax or explore, this suite has everything you need!

*Waterfront* 5BR w/ Pool + Firepit on Kent Island!

Welcome to The Landing at Kent Island — a beautifully designed waterfront home where families and friends can relax, spread out, and enjoy being together. As featured in Bethesda Magazine in the July 2026 issue - Best of the Bay feature! Wake up to panoramic water views, spend afternoons by the private pool or playground, and end the day around the firepit with s’mores. We love Kent Island - enjoy the Island life!