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Pasadena, Maryland Boat Rentals

Page 1 of 124 listings

Still Crazy II - Cruise the Chesapeake in luxury! (Captain Included)
Powerboats in Pasadena · 10 guests

Still Crazy II - Cruise the Chesapeake in luxury! (Captain Included)

New
Snoozed - Active 02 Aug 2025
2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland
Powerboats in Severna Park · 4 guests

2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland

5.0
$120/hour
Pro line Center Console Magothy River - Perfect for fishing exploring cruising
Powerboats in Severna Park · 12 guests

Pro line Center Console Magothy River - Perfect for fishing exploring cruising

5.0
$65+/hour
Instant Book
Enjoy your day on the water with a Yamaha Waverunner EX Jet ski!
Water Sports in Riviera Beach · 6 guests

Enjoy your day on the water with a Yamaha Waverunner EX Jet ski!

New
$65+/hour
Fishing Charter in Pasadena, Maryland
Fishing in Riviera Beach · 6 guests

Fishing Charter in Pasadena, Maryland

5.0
$840/day
Instant Book
2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island
Powerboats in Annapolis · 8 guests

2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island

4.9
Best of 2025
$225/hour
Just Repowered Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis
Powerboats in Annapolis · 6 guests

Just Repowered Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis

4.8
$95+/hour
Instant Book
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$250/hour
38-ft Hunter 376 Sailing Adventure in Annapolis
Sailing in Annapolis · 6 guests

38-ft Hunter 376 Sailing Adventure in Annapolis

5.0
Superowner
$138+/hour
Instant Book
Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways
Events in Annapolis · 8 guests

Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

5.0
$250/hour
New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
Sailing in Annapolis · 13 guests

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

5.0
$1,100/hour
46′ CARMEN | Take Everybody With You! | Captain Included
Events in Annapolis · 30 guests

46′ CARMEN | Take Everybody With You! | Captain Included

New
$670+/hour
21′ KENCRAFT | Center Console | Located On The South River
Powerboats in Annapolis · 6 guests

21′ KENCRAFT | Center Console | Located On The South River

New
$125+/hour
50′ VIKING - Your Chartered Experience Awaits!
Events in Annapolis · 12 guests

50′ VIKING - Your Chartered Experience Awaits!

New
$841+/hour
26’ CREST TRITOON | Excellent Pontoon | Seats 12
Powerboats in Annapolis · 12 guests

26’ CREST TRITOON | Excellent Pontoon | Seats 12

New
$194+/hour
19' Hurricane (S) | Seats 6 | Ready For Adventure On The Chesapeake
Powerboats in Annapolis · 6 guests

19' Hurricane (S) | Seats 6 | Ready For Adventure On The Chesapeake

New
$125+/hour
26′ BENNINGTON PONTOON | Adventure Awaits | Seats 12
Powerboats in Annapolis · 12 guests

26′ BENNINGTON PONTOON | Adventure Awaits | Seats 12

5.0
$194+/hour
19' Hurricane (S) | Seats 6 | Ready For Adventure On The Chesapeake
Powerboats in Annapolis · 6 guests

19' Hurricane (S) | Seats 6 | Ready For Adventure On The Chesapeake

New
$125+/hour
19' Hurricane (S) | Seats 6 | Ready For Adventure On The Chesapeake
Powerboats in Annapolis · 6 guests

19' Hurricane (S) | Seats 6 | Ready For Adventure On The Chesapeake

New
$125+/hour
Parker Southwestern | Seats 6 | 23'
Powerboats in Annapolis · 6 guests

Parker Southwestern | Seats 6 | 23'

New
$125+/hour
Cruise on the Shannon Brendan
Fishing in Annapolis · 6 guests

Cruise on the Shannon Brendan

New
$350/hour
Relaxing Excitement of the Chesapeake Bay and tributaries on our Yacht
Events in Annapolis · 6 guests

Relaxing Excitement of the Chesapeake Bay and tributaries on our Yacht

New
$300/hour
Discover the Spirit of the Chesapeake Bay with our Nautical-Themed Photography
Events in Annapolis · 6 guests

Discover the Spirit of the Chesapeake Bay with our Nautical-Themed Photography

New
$255/hour
Charter 42' Lagoon Catamaran in Annapolis, MD
Sailing in Edgewater · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

5.0
$425/hour

Pasadena Reviews

  1. ET

    Eris

    Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

    This is everything you could want. Great boat and captain. McCoy has everything you need for a great trip. Plenty of space onboard for all your food and drink and all the toys you could want for a fun day on the water. We count thank him enough fro a such great experience and a great price! We will be booking again for sure!

  2. AI

    Amy

    2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island

    Dushaune was amazing! The best boat ride we have ever had. He is extremely nice and drove us to a swimming area that was amazing. We enjoyed just hanging in the water, talking with him. We lost track of time because we were having so much fun. Would definitely love to go on a ride with him again.

  3. DC

    Donte

    New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

    From start to finish, the entire experience was seamless and professional. There was zero chaos—everything ran like clockwork. The crew was exceptional: friendly, attentive, and incredibly knowledgeable about the Chesapeake Bay and Annapolis. The yacht itself was spotless and in pristine condition. From the moment we arrived, the crew went above and beyond—helping us load in, beautifully setting up our catering, keeping our group refreshed with drinks and snacks, and later packing up leftovers and loading them into our car. Every detail was handled with care. If you’re considering a yacht rental, don’t hesitate—this experience was truly top-notch. We’re already looking forward to booking again!

  4. HT

    Hien

    2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island

    Dushaune is a great captain and great host, he is down to earth, knowledgeable, funny. We are a group of 6 with very different characters and age (from 7-50) but all of us had fun. We felt great after the ride. Thanks Dushaune. Highly recommended

  5. GA

    Giselle

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Capt. Alberto and Graciela, the best! We had a great time and enjoyed learning about sailing with them. Everything was as described and much better. You’ll have a great time too! ⛵️☀️🩵

  6. Ashraf

    Ashraf

    2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland

    The whole experience was above and beyond the expectations the boat is tidy and clean and Sunmi is very helpful and knowledgeable. Elevate your experience and book this boat with Sunmi.