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Sailing catamaran vacation rentals in Pensacola Beach

Photo gallery for Sailing catamaran vacation rentals in Pensacola Beach

Trinity taking guests for a sail.
Trinity at rest waiting on her guests.
Sailing downwind with two sails.
Walking the deserted beach at Fort McRee.
Trinity in Naples, FL for a long two week trip.

Reviews

10 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 4

Popular amenities

  • Ocean view
  • Kitchen
  • Pet friendly
  • Air conditioning
  • Outdoor Space
  • Barbecue grill

Explore the area

View in a map
Pensacola Beach, FL
  • Place, Pensacola Beach Boardwalk
    ‪2 min walk‬
  • Place, Casino Beach
    ‪8 min walk‬
  • Place, Pensacola Beach Beaches
    ‪10 min walk‬
  • Airport, Pensacola, FL (PNS-Pensacola Intl.)
    ‪25 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 1

1 Queen Bed

2 bathrooms

Bathroom 1

Bathroom 2

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Dining area

About this property

Sailing catamaran vacation rentals in Pensacola Beach

Admit it, you have always wanted to sail your own private yacht. Definitely on a short Bucket list!!!!Let's go sailing!! If you want to experience Pensacola Beach and surrounding sailing area like you have never have before, look no further. Enjoy your wine and cheese during a sunset sail. Kayak at Fort McRee. Wander the deserted beaches at Redfish Point or enjoy a local band at Pirates Cove. "Trinity" is a sailing catamaran that is a very stable 20 feet wide (no tilting) with two queen size berths and one full size berth. She has two bathrooms and air conditioning. She is able to sail to local anchorages or stay at Pensacola Beach. Guests will be transported to Trinity while at anchor at Pensacola Beach or at convenient marina. Guests have a choice to stay and enjoy the Pensacola Beach or sail to local anchorages. She has a full galley, spacious deck, salon, and cockpit. Enjoy a unique luxury experience aboard S/V Trinity, and wake up every morning on the water to a dark roast poured from a French Press. Trinity comes with her full time captain to insure the guests receive full attention while aboard. Guests are encouraged to participate and learn sailing during their unforgettable vacation. We also offer day Snorkel/Kayak trips and Wine/cheese pairing sunset sails in addition to our overnight charter sailing excursions.

Your sailing adventure starts here!!! Charter this pristine and luxurious Catamaran for up to 5 guests. See the Fee Section on Rates page for charter rates. This sailing yacht is specially equipped with all the amenities to make your sailing experience comfortable and stately. All berths are made to feel like a first class cabin. You will always be comfortable with air conditioning at night and hot showers. A well-appointed kitchen/Galley is ready for gourmet meals and fine dining. Dine in the spacious saloon or move outside for dining in the cockpit and enjoy the view. This is no ordinary sail boat. This is your floating condo with an amazing view.

*We are also now taking Reservations for week long trips to?? Where do you want to go? Already know how to sail, feel free to design your own trip. Captain Kevin wants everyone to enjoy Trinity as much as he has.

Captain Kevin has over 30 years of boating experience with 4 years sailing in the Pensacola area. He has taught sailing several years for the Red Cross. He is an avid airplane pilot with aerobatics training. He has practiced as a Chiropractor for the last 18 years. He has written a book "Mommies with Migraines" for headache sufferers. He doesn't want any aches on his boat. This perfect combination of experience means you can have the peace of mind of having a qualified Captain to take you to your destinations along with someone who knows how to make your guest experience first class. From cocktails at sunset with a seafood extravaganza to a morning fresh pressed coffee. Captain Kevin will guarantee that your charter experience will be unlike any other.

S/V Trinity has 3 kayaks and a stand up paddle board. She also has a dinghy to transport back and forth to beach or bar.

Captain Kevin's main priority is your safety (and having an amazingly fun experience is right behind that priority).
We absolutely love dogs and kids are always welcome. Face it, dogs are already barefoot, like the guests.

Keywords: luxury, yacht, Pensacola, Pensacola Beach, Fort McRee, Redfish Point, sailing catamaran, sailing, sunset sail, snorkel, kayaking, stand up paddle board, beach combing, beach, dolphins
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
We can't allow food/drinks in the bedrooms.
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Events

Events allowed: family gatherings, birthday parties, weddings
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Pets

Pets allowed: dogs less than 50 lbs per pet (limit 2 pets total)
Pets transported to shore in dinghy by owners.
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site; maximum attendees: 6
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property

About the neighborhood

Pensacola Beach

Located in Pensacola Beach, this houseboat is on the beach. Fort Pickens is a notable landmark, and the area's natural beauty can be seen at Pensacola Beach Beaches and Opal Beach. Water Warrior and Pensacola Children's Museum are also worth visiting. Kayaking, scuba diving, and snorkeling offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours nearby.
View more Houseboats in Pensacola BeachOpens in a new window
Map
Pensacola Beach, FL

What's nearby

  • Quietwater Beach - 1 min walk - 0.1 km
  • Pensacola Beach Boardwalk - 2 min walk - 0.2 km
  • Casino Beach - 8 min walk - 0.7 km
  • Pensacola Beach Gulf Pier - 10 min walk - 0.9 km
  • Pensacola Beach Beaches - 10 min walk - 0.9 km

Getting around

  • Pensacola Station - 20 min drive
  • Pensacola Intl. Airport (PNS) - 23 min drive

Restaurants

  • ‪Crabs We Got 'em! - ‬11 min walk
  • ‪Flounder's Chowder House - ‬7 min walk
  • ‪Hilton - ‬13 min walk
  • ‪Circle K - ‬4 min walk
  • ‪The Dock - ‬11 min walk

Frequently asked questions

Is Sailing catamaran vacation rentals in Pensacola Beach pet-friendly?

Yes, this houseboat allows dogs (limit 2 total) with a maximum weight of up to 50 lbs per pet.

How much does it cost to stay at Sailing catamaran vacation rentals in Pensacola Beach?

As of May 6, 2026, prices found for a 1-night stay for 2 adults at Sailing catamaran vacation rentals in Pensacola Beach on Jun 11, 2026 start from $408, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

What time is check-in at Sailing catamaran vacation rentals in Pensacola Beach?

Check-in begins at 4:00 PM.

What time is check-out at Sailing catamaran vacation rentals in Pensacola Beach?

Check-out is at 10:00 AM.

Where is Sailing catamaran vacation rentals in Pensacola Beach located?

Nestled on the beach, this Pensacola Beach houseboat is within a 10-minute walk of Santa Rosa Sound, Pensacola Beach Beaches, and Pensacola Beach Gulf Pier. Quietwater Beach and Pensacola Beach Boardwalk are also within 5 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 18 out of 18 reviews
Rating 8 - Good. 0 out of 18 reviews
Rating 6 - Okay. 0 out of 18 reviews
Rating 4 - Poor. 0 out of 18 reviews
Rating 2 - Terrible. 0 out of 18 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Teri M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
What a wonderful experience! We loved our sailing and captain Kevin was fantastic and showed us a great time! We will definitely be back to sail again!!
Stayed 3 nights in Jun 2025
Verified

10/10 Excellent

Shelley W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was just the little adventure my family was looking for! My husband and I took our 14 yr old daughter and her friend. Captain Kevin was an amazing host. From cooking, to sailing, to finding semi-private beaches, etc. He encouraged the girls to kayak and explore. We were lucky enough that the Blue Angels had an air show and we got front row seats out on the bay. It was a perfect way to spend our family vacation.
Stayed 5 nights in Jul 2025
Verified

10/10 Excellent

Kayla O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Kevin is the most warming and welcoming host ever and he could as well be a chief! Me and my boyfriend joined Kevin for three days for July 2-5 and I am definitely spoiled now lol. This was a trip full of bunch of firsts and I enjoyed it all. If you are looking for a once in a life time experience and making a new friend definitely book with Kevin. Thanks again Kevin for keeping our belly full and the fun going, all while feeling safe.
Stayed 3 nights in Jul 2025
Verified

10/10 Excellent

Rhonda M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Catamaran Cruise

The trip was too short but wonderful. Kevin is a great host. He has the perfect blend of professionalism and friendliness. I enjoyed his cooking and service. The boat was clean and had everything we needed to be comfortable while sailing. I hope to buy my own catamaran after this great experience.
Stayed 3 nights in May 2024
Verified

10/10 Excellent

Cindy G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Getaway

We all SO enjoyed our stay with Kevin on his boat!!! He was such a gracious host…feel like we made and have a new friend for sure! He was knowledgeable of where to take us so that we could enjoy the things we love. The secluded beach area was our favorite!!! If we would have had our beach chairs and umbrella we’d have have stayed there all day! Can’t wait to do it again!!
Stayed 3 nights in Jun 2023
Verified

10/10 Excellent

Paul C.

Great sailing with Captain Kevin

Trinity is very comfortable and easy to get around on. We really enjoyed sailing to the pass and Big Lagoon areas. Meals on board were excellent. Kevin is a very good cook. He is also a good sailing instructor and encourages, but doesn't demand participation. Although he is the skipper of Trinity, he can drop you off and pick you up almost anywhere with a dock or beach, at your request. Can't wait to book another cruise on Trinity!
Stayed 3 nights in May 2018
Verified

10/10 Excellent

Heather I.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Most unique vacation ever!

I booked this as a surprise for my husband and teenage son. I had no idea how perfect of a vacation this would turn out to be. Kevin was an incredible host and teacher! He continuously taught us about sailing and gave us opportunities to try things on our own. We spent 4 nights on Trinity, and each night we anchored somewhere new that brought its own magical things. Kevin always made sure we were comfortable and made the most of our trip. He made us breakfast every morning and dinner every night. I can’t say enough great things about our sailing adventure. It truly was one of a kind!
Stayed 4 nights in Jun 2024
Archival

10/10 Excellent

Kristen S.

Sailing on Trinity around Pensacola Bay for a week was a fantastic vacation!

We booked Trinity on VRBO and I must say that the owner Kevin was a pleasure to work with. He responded quickly, and was very informative about the booking process. Trinity is VERY comfortable. If you feel like cooking you have a nice galley that has everything you need and there is also a grill. Or you can dinghy ashore to a restaurant for dining. We really enjoyed the paddle board that is provided. lots of family fun. the dolphins were out swimming with us! We anchored out for a night a Fort Pickens and got to see the most amazing sunset! Thank you so much to Kevin and Amy for a wonderful time on Trinity! Hope to do it again soon!!!
Verified

10/10 Excellent

Megan G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Memories to last a lifetime!

Where do I begin?! This trip was an amazing experience from start to finish and just kept getting better each day! Kevin is so welcoming and becomes part of the family while you’re on his vessel, the Trinity. He plans each day around your interests and is an amazing host. Kevin starts each morning off with the smell of coffee & breakfast cooked as you roll out of bed! He chartered us to white sand beaches and clear water where we saw stingrays and other marine life on our first day then we headed out and discovered our own personal dolphin cove (Literally, a TON of dolphins putting on a show for us both mornings we had anchored there!) and our last night we watched Pensacola’s 4th of July firework show right over the boat front & center! The whole trip was epic and full of sailing, swimming, laughter, and memories for a lifetime… even our 12 year old daughter enjoyed the whole experience! Thank you for your gracious hospitality, Kevin! We will be back on the Trinity again in the future for sure! :)
Stayed 4 nights in Jul 2023
Verified

10/10 Excellent

Stacey H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing, once-in-a-lifetime experience

I honestly didn’t know quite what to expect going into this vacation- I had really no idea it would be so awesome! A ton of I-never-would-have-thought-I-would-do-this moments every day. Running for miles on the beach seeing basically no one. Kayaking with dolphins. Sunrise, dolphin splashes, and a rainbow, at the same time. Sailing through the bay - no engines. Letting out 7lengths of anchor chain and helping anchor down for the night. Watching my kids pilot the dinghy to shore. Shrimp boil and tuna steaks. Napping in a hammock, on a catamaran. Yeah, that all happened. Captain Kevin was amazing. Totally laid back, totally real, totally flexible, and totally focused on ensuring we had a great time. Not only is he a more than capable captain, but he’s a great cook, and he thoroughly enjoys doing this, which totally shows when he’s at the helm. Our family had an unforgettable experience doing this and we’re grateful Kevin has shared this lifestyle with us; we are definitely spoiled now and can’t do the beach any other way. Definitely want to do this again.
Stayed 3 nights in Oct 2019
Verified

10/10 Excellent

David S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

An Unforgettable Sailing Adventure with Captain Kevin

Our stay on Kevin's sailboat was incredible. Having never stayed on a sailboat before, my wife and I were thrilled by every aspect of the trip. Kevin was an exceptional host, ensuring we were comfortable and well taken care of. We enjoyed gourmet meals, indulged in wine, and experienced a level of relaxation that's hard to find in everyday life. Kevin allowed us to use his dinghy to explore secluded beaches, and we saw dolphins, sea turtles, sharks, hermit crabs, and various birds. This trip was unforgettable for my wife and I. Being disconnected from the busyness of life, having minimal contact with people, and leaving our cell phones in our berths allowed us to truly lose track of time. We plan on taking this trip again and hope to share the experience with others. For those who haven’t tried this, think of it as camping in an RV. You won't have all the luxuries of home, but there's something rewarding about "roughing it" for a bit. You can't ask for a better host than Kevin. We spent hours talking about life; he is knowledgeable, humble, and always encouraged us to relax, watch the sunset, or lay on the trampoline at the front of the boat to count stars. His presence was so unobtrusive that we often forgot he was even there. In summary, our sailing adventure with Kevin was extraordinary. If you're looking for a unique getaway combining adventure, relaxation, and nature, this is the perfect trip for you.
Stayed 7 nights in May 2024
Verified

10/10 Excellent

jeff n.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Life changing experience

If you are looking for a truly unique vacation experience, I highly recommend taking a trip with Captain Kevin on his catamaran. My recent trip on Kevin's cat was an absolute dream come true. From the moment we set sail, I felt completely at home and relaxed. The catamaran experience far exceeded my expectations. Captain Kevin is extremely knowledgeable and was a great instructor. Jennifer (my girlfriend) was appointed the rank of Admiral and given 1st class treatment throughout our voyage. I requested to be 1st mate and learn the "ropes" of sailing. After spending a few days under Captain Kevin's tutelage, I quickly became comfortable at the helm. The highlight of the trip was undoubtedly the time spent on the water. Each day we woke up to stunning views and spent our days exploring hidden coves, watching the Blue Angels practice their aerobatics and strolling along on beautiful beaches. As a host, Kevin was absolutely wonderful. He cooked delicious meals and we spent hours talking about sailing and life. Kevin was incredibly knowledgeable about the area and provided us with great recommendations for places to explore and things to see. The time we spent with Kevin on his beautiful boat convinced us to pursue a life aboard a catamaran. Until then we will definitely set sail with Captain Kevin on one of his future adventures.
Stayed 3 nights in Jun 2023
Verified

10/10 Excellent

Kristine V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Mother’s Day Holiday

The Catamaran and Capt. Kevin are very impressive. It was a very relaxing time, we loved sailing around with the wind in our faces! My 1 year old did amazing on the trip. We spent most of the time on the trampoline. We also were able to use the kayaks which was amazing! Capt. Kevin made us breakfast and dinner but also gave us full access to the kitchen if we wanted to make anything ourselves. He is extremely friendly and made us feel extra welcome. We had a wonderful time! Thank you again!
Verified

10/10 Excellent

Angelle P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Unique experience

We really enjoyed sailing and would love to do it again. Kevin was great, taught us much about sailing and the areas we visited, and was very patient with our 5 & 7 year old boys. Highly recommend. I don't think anyone would be disappointed.
Stayed 3 nights in Aug 2020
Verified

10/10 Excellent

Vincent R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Best experience ever!

Great experience. Sailing is exceptional, the owner teaches as much as you want to learn. Run the AC at night, sail all day. The meals are to die for. What am I waiting for to go back?
Stayed 4 nights in Jul 2020
Verified

10/10 Excellent

Morgan E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Unique vacation experience

Surely, no doubt, a wonderfully fantastic vacation. Captain Kevin was so helpful throughout the whole trip. From making sure we had the right gear and food before the trip to helping us off load our gear right up to our car. We wanted to test the waters of live-aboard and he was more than eager to show us the "ropes" so to speak. Every day was a new adventure with a new surprise in store! We are so glad we took each of his suggestions as every one of them was so much fun.
Verified

10/10 Excellent

Jason H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Unique getaway!

My kids and I had a great time on Captain Kevins vessel. It was a totally unique experience. We loved the clean boat and felt pampered throughout the three day trip. Florida beaches are beautiful and what better way to experience them through the ultimate private boating experience. We got to experience some excellent meals prepared by Captain Kevin. We always felt safe and totally relaxed. Yes, you will be learning boating 101 but that is part of the experience. Captain Kevin allowed me to bring kiteboading gear which is no easy feat due to the amount of extra stuff. We got lucky with the wind on one day which allowed me a chance to kiteboard....definite highlight. The kids will remember this trip for the rest of their lives. Thanks, Captain Kevin and Trinity.
Verified

10/10 Excellent

Tammy D.

Very memorable experience.

Capt. Kevin made our experience on Trinity very memorable. He has a wonderful personality that made it feel like we were sailing with our best friend. We had two adults and three 19 year old girls who thought Capt. Kevin was so cool. He gave everyone lessons on sailing and even let us drive the boat which made us feel like he wanted us to have a part in the whole experience. The kayaks and paddle board were so much fun. Capt. Kevin made sure to anchor us in the perfect spot to watch the Blue Angels. He also cooked up some amazing dinners! The girls loved his scrambled eggs in the mornings. The beds are very comfortable and if needed, the a/c can be run at night. Trinity has everything you need to stay on the boat or if you want to go ashore for shopping or restaurants, Capt. Kevin will bring you in the dinghy. He took the time to find out what everyone wanted to experience on the boat and he made sure to accommodate everyone and we all had an amazing time.
Stayed 4 nights in Jul 2018

About the host

Hosted by Kevin Darden

Host profile image
I want everyone to enjoy life!! I fly aerobatics. I do flips off the bow of boat. I sail boats across big water. I scuba dive. Kayak with dolphins. Etc. Etc.
I want everyone around me to enjoy what life has to offer. This boat is incredible. She offers a playground for kids of all ages. I absolutely love having kids (young or not) on the boat to experience a fun experience.
I also believe in naps and relaxing. Definitely bring a book to read that can offer many naps. Play hard then relax.
Guests definitely won't have to fight crowds or stand in lines like a hotel or condo.

Why they chose this property

Sailboat allows the guests to get away from the stress of everyday life. Let's face it crowded hotels, crowded traffic, or crowded beaches can't begin to compare to the seclusion allowed by Trinity. She can find the places that offer the secluded lifestyle we all desire. She also carries all her toys with her. Guests don't have to rent toys. Guests can really get "lost" for hours, days, or weeks. Take a picnic to a deserted beach or take a nap on the trampoline of Trinity. This trip should be on a short bucket list. You will forever remember your trip on Trinity.

What makes this property unique

Who wouldn't want to live on a sailboat for a week or forever?
Trinity is not an ordinary sailboat. She sails flat and has so much room for her guests. There is certainly a place to lounge and relax. If you don't find it on the boat, you can find yourself while paddle boarding or kayaking.
Parents are allowed to have fun as well while Captain Kevin takes the kids to the beach or kayaking. Captain Kevin can also fix popcorn and play games with kids while the adults play on shore.

Languages:

English

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