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Condo Rentals in Highland Beach

Romantic Two Bedroom Condo
Enjoy cooking in this well-equipped kitchen with a refrigerator, dishwasher, microwave, oven, and granite countertop.

Romantic Two Bedroom Condo

10.0 out of 10, Exceptional, (81)
"Excellent stay. We look forward to returning."
Romantic Two Bedroom Condo
Annapolis Condominium in the heart of the historic center
Enjoy the city view from this balcony with a sofa and wicker chairs.

Annapolis Condominium in the heart of the historic center

9.8 out of 10, Exceptional, (279)
"The location and amenities are great. The host are very friendly, helpful and easy to make contact with. My family used this location for commission week and could not have asked for more. "
Annapolis Condominium in the heart of the historic center
Beautiful Condo - Water View Near City Dock
Stroll along the pier to a tranquil dock area with moored boats.

Beautiful Condo - Water View Near City Dock

9.6 out of 10, Exceptional, (145)
"Clean, quiet, and very close to both downtown and Eastport restaurants."
Beautiful Condo - Water View Near City Dock
Waterfront 2-Bedroom Condo on Spa Creek
Smart TV

Waterfront 2-Bedroom Condo on Spa Creek

10.0 out of 10, Exceptional, (8)
"This is a great location. Walking distance to everything. Near all the sailing clubs! Property manager was the best we have ever experienced."
Waterfront 2-Bedroom Condo on Spa Creek
Waterfront Condo with Rooftop Pool, Spa Creek Views & Prime Eastport Location with Parking
Relax by the pool with a view of the city skyline.

Waterfront Condo with Rooftop Pool, Spa Creek Views & Prime Eastport Location with Parking

10.0 out of 10, Exceptional, (18)
"Can’t have a better location near everything in Eastport and Main St Annapolis!"
Waterfront Condo with Rooftop Pool, Spa Creek Views & Prime Eastport Location with Parking
Kent Island Waterfront Cottage
Enjoy cooking in this well-equipped kitchen with a sink, microwave, oven, and refrigerator.

Kent Island Waterfront Cottage

8.8 out of 10, Excellent, (11)
"Enjoyed fishing at the pier and sitting on the porch"
Kent Island Waterfront Cottage
Unbelievable beach views for 6
Guests can enjoy a festive atmosphere in our outdoor public space, featuring a beautifully decorated Christmas tree.

Unbelievable beach views for 6

2.0 star property
10.0 out of 10, Exceptional, (8)
"It was unbelievable stay with fantastic sunrise and moon rise on the day of the eclipse"
Unbelievable beach views for 6
New Downtown Annapolis Condo With Free Parking
Relax on the balcony with a wooden table and two cushioned chairs, surrounded by a railing and offering a view of the surrounding buildings and greenery.

New Downtown Annapolis Condo With Free Parking

10.0 out of 10, Exceptional, (26)
"Clean, modern apartment walking distance from all of Annapolis harbor and restaurants. "
New Downtown Annapolis Condo With Free Parking
Chic Condo w/ Balcony in the Heart of Annapolis!
Relax in a stylish space with a plush sofa, potted plant, and abstract artworks.

Chic Condo w/ Balcony in the Heart of Annapolis!

9.8 out of 10, Exceptional, (58)
"This cute condo is as pictured; charming and clean. Nice bathrooms. Comfortable beds. Great location. Loved the parking ease as well. Host was very receptive and flexible with my arrival/departure times.Would highly recommend and would stay here again."
Chic Condo w/ Balcony in the Heart of Annapolis!
Unique 2-Bedroom Condo in Renovated Church Parish House
Stroll along the marina, surrounded by boats and historic architecture.

Unique 2-Bedroom Condo in Renovated Church Parish House

Unique 2-Bedroom Condo in Renovated Church Parish House
Upscale Condo in Annapolis
Terrace/patio

Upscale Condo in Annapolis

Upscale Condo in Annapolis
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Highland Beach Hotel Reviews

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

10/10 Excellent
"Great place"
Patrick 2-night trip
Posted 5 hours ago
SpringHill Suites by Marriott Annapolis