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Sailing catamaran vacation rentals in Pensacola Beach

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On the beach
Interior
Property grounds
Interior

Reviews

10 out of 10
Exceptional

Entire house boat

2 bedrooms2 bathroomsSleeps 556 sq m

Popular amenities

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

About this property

Entire place

You'll have the entire house boat to yourself and will only share it with other guests in your party.

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

Property manager

Kevin Darden

Languages

English

Property amenities

Beach

  • On the beach

Parking and transportation

  • Car not required

Kitchen

  • Refrigerator
  • Stovetop
  • Oven
  • Coffee/tea maker
  • Cookware/dishes/utensils

Bedrooms

  • 2 bedrooms
  • Bed sheets provided

Bathrooms

  • 2 bathrooms
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Outdoor areas

  • Patio
  • Barbecue grill

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • 2 total (up to 50 lbs per pet)
  • Welcoming dogs only

Suitability/Accessibility

  • Smoke-free property

Location highlights

  • Near the ocean
  • Near the sea
  • On the waterfront

Things to do

  • Kayak on site
  • Power boating nearby
  • Sailing nearby
  • Scuba diving nearby
  • Swimming nearby
  • Kayaking nearby
  • Marina nearby
  • Ecotours nearby
  • Snorkeling nearby
  • Fishing nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

General

  • Unit size: 600 sq ft (56 sq m)

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Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total (up to 50 lbs per pet)
Note from host: Pets transported to shore in dinghy by owners.

Children and extra beds

Children are welcome
Note from host: We can't allow food/drinks in the bedrooms.

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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

A car is not required for transportation to and from this property

Property is also known as

Sailing Catamaran Vacation Rental Pensacola Beach Houseboat
Sailing Catamaran Vacation Rental Pensacola Beach
Sailing Catamaran Vacation Re
Sailing Catamaran Vacation Rental in Pensacola Beach Houseboat

About the neighborhood

Map
Pensacola Beach, FL

What's nearby

  • Quietwater Beach - 1 min walk - 0.1 km
  • Pensacola Beach Boardwalk - 2 min walk - 0.2 km
  • Pensacola Beach Gulf Pier - 10 min walk - 0.8 km
  • Casino Beach - 10 min walk - 0.9 km
  • Park West On-Leash Dog Beach - 7 min drive - 4.8 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 - ‬9 min walk
  • ‪Sandshaker Lounge & Package - ‬5 min walk
  • ‪Shaggy's Pensacola Beach - ‬2 min walk
  • ‪The Dock At Pensacola - ‬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.

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 11:00 AM.

Where is Sailing catamaran vacation rentals in Pensacola Beach located?

Nestled on the beach, this Pensacola Beach houseboat is just steps from Santa Rosa Sound and Pensacola Beach Boardwalk. Pensacola Beach Beaches and Quietwater Beach are also within 10 minutes.

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Sailing catamaran vacation rentals in Pensacola Beach Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 15 out of 15 reviews
Rating 8 - Good. 0 out of 15 reviews
Rating 6 - Okay. 0 out of 15 reviews
Rating 4 - Poor. 0 out of 15 reviews
Rating 2 - Terrible. 0 out of 15 reviews

10/10

Cleanliness

Reviews

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

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

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

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

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

10/10 Excellent

jeff n., Colleyville

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

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

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

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!

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

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

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.

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.

10/10 Excellent

Tammy D., Denham Springs, Louisiana

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
This review was submitted before 2018 and has not been verified.

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!!!