Your Paradise Vacation Destination: Indian Rocks Beach, Florida and Historic Downtown Annapolis, MD

Indian Rocks Beach, Florida and
Historic Annapolis, Maryland

Welcome to Your Paradise Vacation Destination!

We own two short term weekly rentals at Oceanway in Indian Rocks Beach , Florida (Oceanway 202 and Oceanway 203) and a large short-term rental home on coveted Shipwright Street in Historic Downtown Annapolis, Maryland (Historic Annapolis Treasure).

Please check out all the photos and details of our beautiful Indian Rocks Beach, Florida condos and our elegant and historic Victorian home in Historic Downtown Annapolis.

All of our properties are completely smoke-free (inside and outside). We do not rent to smokers because even if they only smoke outside, they will still bring smoke residue into our property. Our two condominium units at the friendly and upscale Oceanway Condominium in Indian Rocks Beach, Florida are adjoining units, and both accommodate up to six guests.

Our Historic Annapolis Treasure property is in Historic Downtown Annapolis and accommodates up to ten guests.

If you’re ready to book your next family vacation or business trip in Indian Rocks Beach, Florida, or in Historic Downtown Annapolis, please visit our Booking Page, where you can book directly and learn about payment and cancellation rules.

Oceanway Condos in Indian Rocks Beach, Florida

Both Indian Rocks Beach, Florida condo unit sleeps six people and has:

  • Two bedrooms with three queen beds (two queen beds in the master bedroom and one queen bed in the other bedroom),
  • Two bathrooms (one ensuite in the master bedroom with a large shower and one in the hallway next to the second bedroom, with a bathtub/shower combo, fully stocked with plenty of bath towels, makeup towels, body wash, shampoo, conditioner, etc.
  • Covered balcony with comfortable furniture for lounging and dining.
  • Washer and dryer with laundry detergent.
  • Fully stocked kitchen (refrigerator/freezer, stove/oven, microwave oven, dishwasher) with plenty of pots and pans, drinking glasses, wine glasses, plastic glasses for the pool, plates, utensils, Keurig and drip coffee makers, tea kettle, toaster, crock pot, paper towels, dish towels, dish soap, dishwasher detergent, seasonings, and much more
  • Fully stocked with all beach necessities, including beach towels, beach chairs, a large beach umbrella, and a beach wagon for hauling everything to and from the beach — all conveniently stored in a locker in the covered parking area near the pool.
  • And many other amenities. For more amenities, please visit our FAQ page.

Our two condominium units (Oceanway 202 and Oceanway 203) at Oceanway Condominium in Indian Rocks Beach, Florida — Oceanway 202 and Oceanway 203 — are adjacent to each other, set up almost exactly the same, and have full direct oceanfront views.

Our Oceanway condo building sits directly on the sugar-white sands of Indian Rocks Beach, Florida, a short distance between the hustle and bustle of Clearwater Beach and St. Pete Beach.

Indian Rocks Beach is the westernmost point of land on the Florida peninsula, and one of the most sought out family vacation spots in the country.

While Clearwater Beach and St. Pete Beach cater mostly to the younger college-age crowd, Indian Rocks Beach is a more family-friendly vibe and caters to a more respectful crowd, including families of all ages looking for a peaceful and quiet vacation at one of the most gorgeous beaches in Florida, with sugar white sand, amazing restaurants, and jaw-dropping ocean views and sunsets.

Dolphin sightings abound, and for the more adventurous, you will find almost every possible water activity nearby. There is also a family waterpark just a few blocks away.

Historic Annapolis Treasure

Our Historic Annapolis Treasure property is in Historic Downtown Annapolis and accommodates up to ten guests. We purchased our property in Historic Downtown Annapolis in 2024 and have been renting it since December 2024 after making significant upgrades and renovations. The name of our Annapolis property is Historic Annapolis Treasure.

  • Four bedrooms, 3.5 bathrooms (all with bidets), 4 level luxury home.
  • Covered balcony with comfortable furniture for lounging and dining.
  • Gourmet kitchen with water view.
  • Huge dining room.
  • Huge backyard dining area with water view.
  • Washer and dryer with laundry detergent.
  • Fully stocked kitchen (refrigerator/freezer, stove/oven, microwave oven, dishwasher) with plenty of pots and pans, drinking glasses, wine glasses, plastic glasses for the pool, plates, utensils, Keurig and drip coffee makers, tea kettle, toaster, crock pot, paper towels, dish towels, dish soap, dishwasher detergent, seasonings, and much more.
  • And many other amenities.

Thank you for considering our homes away from home for your next Paradise Vacation Destination!

We book directly via this website (with no service fees) or via VRBO and Airbnb (both of which have service fees, but may offer you the option to pay extra to purchase travel insurance). We have hundreds of 5-star reviews on these booking sites. If you book directly via this website, you will avoid service fees, and you can purchase travel insurance directly from many travel insurance companies after you book, but you must do so very shortly after you book — the exact timeframe is different for each insurance company, and we recommend you purchase CFAR (Cancel For Any Reason) insurance.

The links for all listings on Vrbo and Airbnb appear on our booking page, where you can read all the past reviews (you will see we have almost all five-star reviews) — we purchased Oceanway 202 in 2016, Oceanway 203 in 2017 and Historic Annapolis Treasure in 2024.

Please visit our Booking Page to book your next Paradise Vacation!

Your Hosts:
Evan and Jeannie