0 Bedrooms for 1 Guest
Price $10 - $1000+

Highland Beach Vacation Rentals

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews. Compare Highland Beach vacation rentals from 8 rental sites including HomeAway, VRBO, TripAdvisor, and more, ranging from $54 to $1,500 a night. 
Showing 364 personalized results
    $250 / night
    TreeHouse
    TreeHouse
    3 bed / 2 bath
    Annapolis, MD
    $300 / night
    2. Private 20 acre waterfront estate - studio apt
    2. Private 20 acre waterfront estate - studio apt
    1 bed / 1 bath
    Annapolis, MD
    $1500 / night
    1. Private 20 acre waterfront estate - main house
    1. Private 20 acre waterfront estate - main house
    4 bed / 4 bath
    Annapolis, MD
    $700 / night
    Naval Academy Rental Home
    Naval Academy Rental Home
    5 bed / 6 bath
    Annapolis, MD
    $700 / night
    Naval Academy Rental Home
    Naval Academy Rental Home
    5 bed / 6 bath
    Annapolis, MD
    $425 / night
    Beautiful Murray Hill Home (Annapolis)
    Beautiful Murray Hill Home (Annapolis)
    4 bed / 3 bath
    Annapolis, MD
    $200 / night
    Snug Harbor USNA Cottage in Eastport Annapolis
    Snug Harbor USNA Cottage in Eastport Annapolis
    4 bed / 2 bath
    Annapolis, Maryland
    $595 / night
    Annapolis Crows Nest Cottage:  Chesapeake Bay View
    Annapolis Crows Nest Cottage: Chesapeake Bay View
    5 bed / 3 bath
    Annapolis, MD
    $800 / night
    Beautifully water front Contemporary Home in Bay Ridge, Annapolis
    Beautifully water front Contemporary Home in Bay Ridge, Annapolis
    3 bed / 3 bath
    Annapolis, MD
    $450 / night
    Charming Townhouse - Steps to City Dock and USNA
    Charming Townhouse - Steps to City Dock and USNA
    3 bed / 2 bath
    Annapolis, MD
    $300 / night
    2. Private 20 acre waterfront estate - studio apt
    2. Private 20 acre waterfront estate - studio apt
    1 bed / 1 bath
    Annapolis, MD
    $1500 / night
    1. Private 20 acre waterfront estate - main house
    1. Private 20 acre waterfront estate - main house
    4 bed / 4 bath
    Annapolis, MD