Welcome to Keys On Jamaica, a waterfront retreat on Ramrod Key offering 170 feet of canal frontage, up to 30 feet of dockage, and easy access to some of the best fishing, diving, snorkeling, and boating in the Lower Florida Keys. Perfect for snowbirds, anglers, boaters, and extended stays, this spacious canal front home combines the laid-back Keys lifestyle with all the comforts of home.
Wake up to tropical breezes and waterfront views, sip your morning coffee while watching boats drift by, and spend your days exploring the crystal-clear waters surrounding Ramrod Key. Bring your boat and enjoy convenient dockage along the seawall, making it easy to access world-class offshore fishing, backcountry fishing, and nearby Looe Key Reef.
Located on a large corner lot, this inviting home offers plenty of space to relax after a day on the water. Whether you're planning a month-long fishing adventure, escaping winter weather, or simply looking to experience authentic island living, Keys On Jamaica is the perfect home base.
Experience waterfront living, world-class fishing, and the relaxed charm of the Lower Florida Keys at Keys On Jamaica.
Living Area
The open and comfortable living room features ample seating, Smart TV, and a welcoming space to gather with family and friends. Large windows bring in natural light and showcase the tropical surroundings.
Kitchen & Dining
The fully equipped kitchen includes everything needed to prepare and serve meals during your stay. Enjoy casual breakfasts before heading out on the water or gather around the dining table to share stories from the day's adventures.
Sleeping Accommodations
Sleeps up to 8 Guests
Bedroom 1
• King Bed
• En-Suite Bathroom
• Smart TV
Bedroom 2
• Queen Bed
• Smart TV
Bedroom 3
• Two Full Beds
• Twin Bed
Outdoor Living
Step outside and embrace the Florida Keys lifestyle.
• 170 Feet of Waterfront
• Maximum Boat Length 30 Feet
• Fish Cleaning Station with Water
• Outdoor Seating Areas
• Propane BBQ Grill
• Large Corner Lot
Whether you're grilling the day's catch, relaxing with a sunset cocktail, or preparing for tomorrow's fishing trip, the outdoor spaces are designed for enjoying life on the water.
Explore the Lower Florida Keys
Keys On Jamaica places you in the heart of the Lower Keys, close to many of the area's most popular attractions.
Nearby:
• Looe Key Reef
• Bahia Honda State Park
• Big Pine Key
• Local waterfront restaurants and bars
• Shopping and marinas
Day Trips:
• Key West – approximately 35 minutes
• Marathon – approximately 25 minutes
Amenities
• Canal Front Location
• Up to 30' Boat Dockage
• Fish Cleaning Station
• Smart TVs
• Fully Equipped Kitchen
• Propane BBQ Grill
• Linens & Towels Provided
• Parking for up to 4 Vehicles (including boat trailers)
Important Policies & Booking Information
Minimum Stay Requirement:
County zoning requires a minimum rental period of 28 nights. No exceptions can be made.
Age & Occupancy Requirements:
The booking tenant must be at least 25 years old and must occupy the property for the entire duration of the stay. This property is licensed exclusively as a vacation rental and may not be used for worker or employee housing.
Peak Season Monthly Bookings (December–March):
Reservations during peak season must begin on the first day of the month and end on the last day of the month. Consecutive monthly bookings are permitted when they follow this requirement. Reservations that do not comply may be subject to cancellation. Please contact us prior to booking if you wish to discuss alternative dates.
Smoking Policy:
Smoking and vaping are strictly prohibited anywhere on the property.
Pet Policy:
Pets are not permitted. To help maintain a pet-free environment, all guests must complete a simple pet verification process after booking. The verification is free and does not require creating an account.
Mid-Stay Cleaning Requirement:
For stays of 28 nights or longer, a mid-stay cleaning may be required to maintain the property. For extended stays, additional cleanings may be required every 28 nights thereafter. Applicable cleaning fees will be collected separately after booking.
Boating & Dockage Advisory:
Guests bringing a boat are responsible for confirming that their vessel can safely navigate local waters, canal depths, bridge clearances, and fit within the available dockage before booking. While we are happy to provide general information about the area, guests assume responsibility for safe boating practices and compliance with all local regulations.
Local Wildlife & Pest Control:
The Florida Keys are a unique tropical environment home to mosquitoes, no-see-ums, termites, reptiles, Key deer, free-roaming chickens, and other wildlife. Routine pest control services are performed; however, complete elimination of insects and wildlife is not possible. Guests are encouraged to use insect repellent and keep doors and windows closed when possible.
Construction & Renovation Notice:
Due to ongoing growth throughout the Florida Keys, nearby construction, renovations, road work, and infrastructure improvements may occur without advance notice. While we strive to provide a peaceful vacation experience, iTrip Key West cannot guarantee freedom from construction-related disturbances outside of the property.
Photo Disclaimer:
Photos are provided for illustrative purposes only. Furnishings, décor, bedding, appliances, electronics, amenities, colors, and other property features may vary as updates and improvements are made by the homeowner. Lighting conditions and screen settings may also affect appearance. Please rely on the written description for the most accurate representation of the property and contact us with any questions prior to booking.
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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
On-site parties or group events are strictly prohibited
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
About the area
Summerland Key
Located on the waterfront, this holiday home is in Breezeswept Beach Estates, a neighbourhood in Summerland Key. The area's natural beauty can be seen at Florida Keys Beaches and Bahia Honda State Park. Blue Hole and Big Munson Island are also worth visiting.
How much does it cost to stay at Keys On Jamaica: waterfront, Ramrod Key?
As of 4 July 2026, prices found for a 1-night stay for 2 adults at Keys On Jamaica: waterfront, Ramrod Key on 1 Nov 2026 start from AU$354, 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.
How much is parking at Boater's Paradise | 170' Waterfront | 30' Dockage | Ramrod Key Retreat?
On-site parking is available at the property.
What time is check-in at Boater's Paradise | 170' Waterfront | 30' Dockage | Ramrod Key Retreat?
Check-in begins at 4:00 PM.
What time is check-out at Boater's Paradise | 170' Waterfront | 30' Dockage | Ramrod Key Retreat?
Checkout is at 10:00 AM.
Where is Boater's Paradise | 170' Waterfront | 30' Dockage | Ramrod Key Retreat located?
Located in Breezeswept Beach Estates, this holiday home is 1.1 mi (1.7 km) from Boondocks Grille & Draft House and within 6 miles (10 km) of Florida Keys Beaches and Big Pine Key Flea Market. National Key Deer Refuge Visitor Center and Crab Key are also within 6 miles (10 km).
Reviews
9.6
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
We loved our stay at this house. It was very clean and well stocked. The location is perfect for access to all the keys have to offer. The owner was very easy to work with and quickly responded to all of our questions.
Susan D.
Stayed 29 nights in Dec 2022
Response from VrboOwner on 24 Jan 2023
Thank you Susan. I am glad to hear that you and your family enjoyed your stay in my home and found it well appointed! I am so happy to hear that you were able to take great advantage of all the wonderful things that the Keys has to offer!
The house was nice and comfortable. The spiral staircase to the beds upstairs is very narrow, designed for young children or very petite adults. Parking was also very tight in the fenced in area and your boat trailer has to be backed in for the length of Jamaica Lane.
Monique O.
Stayed 29 nights in Jul 2025
Response from VrboOwner on 23 Aug 2025
Thank you for your review! We’re glad to hear that you found Keys On Jamaica to be nice and comfortable. We appreciate your feedback regarding the spiral staircase and parking situation. We understand that these aspects can be challenging, and we’re always looking for ways to improve our guests’ experience. Your insights are invaluable to us, and we hope to welcome you back for another enjoyable stay in the future!
The house was comfortable and well stocked.
You won't need any paper products or laundry detergents. Also dish washer detergent was plentiful. The dock in the pictures has been rebuilt. New dock is shorter. Also if you are a boater you need to watch out for a large rock at the beginning of the dock that can damage your boat at low tide. I placed a 15" round bouy on the pilings to keep my boat away from the dock. Overall a nice home to stay at . Had a great time.
Pete P.
Stayed 28 nights in Aug 2019
Response from VrboOwner on 8 Feb 2022
Thank you Pete for staying with us. The re-built dock post Irma is shorter(pictures are updated) and accommodated our boat of 30' well. We have a post marker identifying the coral at high tide.
vertical blinds broken or missing, hvac filthy, washing machine in need of repair, bedroom furniture damaged, shower curtain so dirty it had to be replaced, vinyl siding loose and falling off, porch and siding covered with mildew and there's more...
Lee H.
Stayed 29 nights in Apr 2022
Response from VrboOwner on 27 May 2022
Home has been closed for occupancy and scheduled for maintenance and repairs June of 2022.
Great place, great property, had all the amenities you'd want. Lots of fis hinges from the boat and the dock.
Jose D.
Stayed 44 nights in Sep 2018
Verified
10/10 Excellent
Marcia B.
11 June 2018
Nice location
The home on Ramrod Key was comfortable and inviting. The beds were comfortable. The location on the canal made it easy to dock the boat. There was a lot of construction in the Month of May 2018,in the surrounding homes due to hurricane Irma, but that should be done soon. Joe's lot was landscaped beautifully. The boat launch is next to Joe's property making it very convenient.
Marcia B.
Stayed 30 nights in May 2018
Verified
10/10 Excellent
david s.
7 Apr 2018
Another year, another great time
Once again we very much enjoyed our stay on Ramrod Key. Every year the house has more than lived up to our expectations! Very resonably priced, great canal location, and always clean and ready for us to arrive.
The owners are always interested in making sure our stay is a good one, and it showed even more this year, as everything was well back to normal from the hurricane.
After spending the last 7 winter's on Ramrod, I believe that this home to be the best value on the key.
david s.
Stayed 31 nights in Mar 2018
Verified
10/10 Excellent
Verified traveller
12 Mar 2018
Absolutely amazing recovery from Hurricane Irma!
I love the location of this house at the end of the street so you can watch the boats going up and down the main canal. And now with the mangroves across the canal being thinned out by the hurricane, you can see the ocean and the next Key from the porch. The house is clean, comfortable, and bright. The owners stock it with all the paper towels, toilet paper, laundry detergent, and cleaning supplies you’ll ever need. And there are kayaks and two brand new cruiser bikes in the storage area. Can’t go wrong with this house!
Verified traveller
Stayed 27 nights in Feb 2018
Verified
10/10 Excellent
William D.
6 Mar 2018
A bit storm battered, but still a wonderful place to be - location, location, location.
This property is close to just about everything in the Keys - beaches, shopping, and, of course, Key West. We were concerned, with reports of Hurricane Irma's impact, that the Keys might not be the best vacation spot for us. We shouldn't have been. We've stayed here for several years now and working with the landlord is easy with any problems (there weren't any this stay) quickly resolved. While the evidence of the storm was everywhere, the progress in removing debris and restoring things to normal (if ever the Keys can be "normal") in the month we were there was remarkable. This property had been cleaned up and the only evidence of the storm were some damaged palm trees and a missing deck. The main canal was blocked when we arrived, but cleared out enough to allow the large dive boat to resume trips to the reef. The biking trail along Highway 1 was also blocked, but that too was cleared within a couple of weeks. This property sustained no observable damage to the living quarters which remain well-equipped and comfortable - really everything you'd need to enjoy the stay - fully equipped kitchen, good cable TV channels (who stays indoors???), laundry supplies, extra paper towels and TP, detergents - everything you'd need is provided. The only issue we had was with the bedroom pillows but we travel everywhere with our own so that wasn't really an issue. You're on your own for food if you don't want to prepare your own but there are several choices for eating out on this Key - Boondocks and Five Brothers and the Dive Tiki locally, and too many other choices in the area to mention. And Big Pine Key is a short drive away and has a good grocery store and other shopping choices, including a weekly weekend flea market. The kayaks and the new bikes are an added plus and the new dock to replace the one destroyed in the storm is great. We missed the big deck, but there was gravel placed there and that area was great for sunning and watching the boats go up and down the canals. The neighborhood was buzzing with repairs to homes that had been damaged (tornadoes, we were told, did much of the damage on this Key) but that was not as much a distraction as a sign of a resilient group of neighbors, who, to a person, were friendly and helpful in spite of the losses that some had suffered. I can't think of a better place to stay, which is why we've returned here the past few years and look forward to returning again next winter.
William D.
Stayed 31 nights in Jan 2018
Verified
10/10 Excellent
Thomas D.
24 Jan 2018
House was very nice and clean
This place is very nice with a vaulted ceiling and walk in tile shower in the master bath .
Dock space is good and the neighborhood is of course very good .
The owners are very professional and do an excellent job maintaining this property.
I would certainly rent from them again were I venturing to the keys !!
Thomas D.
Stayed 30 nights in Dec 2017
Archival
10/10 Excellent
Jose D.
3 June 2017
Great house, great location.
Lots of things to do, fishing was great even from the dock. We caught dinner from the dock several times.
Jose D.
Archival
10/10 Excellent
Patricia Q.
9 May 2017
Great vacation getaway
Had a wonderful stay at this beautiful home on Ramrod Key. It was very comfortable and well equipped. This home fit our needs perfectly. The loft bedroom was great to have when two of our grandchildren came to visit for a week. They loved it ! Having two kayaks and four bikes available was a big plus. The access ramp to the canals is another big plus making it easy to launch the kayaks. We love the central location and being at the end of the street where you have the canal on two sides of the property. We would highly recommend this home to anyone.
Also want to say what a pleasure it was working with the owner. He made everything run seamlessly. Great Experience!
Patricia Q.
Stayed 29 nights in Apr 2017
Archival
10/10 Excellent
david s.
11 Apr 2017
Got to really relax for a month!!
We had a wonderful stay! The house suited all of our needs perfectly, and the location is perfect. We have already booked for next year, and will book this same house every year til I can no longer tow a boat. The bikes and the kayaks made the trip even more fun. The owners are very easy to deal with, and the house is clean and well stocked. My wife and I would very much recommend renting this house. Can't wait till next year!
david s.
Archival
10/10 Excellent
William D.
27 Feb 2017
Perfect place to spend time in the Keys
We're a retired couple and we've been here now in January for several years - fantastic location, close to everything you might need - restaurants, shopping, and, of course, Key West. Nightlife or wildlife and beaches (we enjoy Bahai Honda state park) are close by and the home is comfortable and well-equipped with plenty of space for an occasional guest in a quiet and peaceful neighborhood. There's also a primitive park nearby on the Key which offers fantastic views of sunsets. We especially enjoy watching the boats leave and come back into the canals and there's a surprising variety of fish swimming next to the spacious deck. Ramrod is also a good place to walk, or with the equipment provided by the owners, bike or kayak. The owners are friendly and exceptionally easy to work with, communicating well and resolving problems (and in three years there was only one, with an ice maker) quickly. If we're not here, you, and your family should be! Love it!
William D.
Archival
10/10 Excellent
michael c.
15 Jan 2017
A great place to relax
We spent 2 months in this lovely home and loved every minute of it. The home looks like the photos, very clean and neat. Even the first floor (where kayaks and bicycles are stored was clean and dry) As you climb the outside stairs you have access to the covered patio or enter the house in the kitchen/dining area. The living room is visible as the home has an open concept. Down the hall is a bathroom, 2nd bedroom and master suite with a nice stand up shower in the bathroom. The king size bed was very comfortable. An additional bedroom can be found at the top of the spiral staircase.
The canal along side of the property empties into a shallow bay (it does have a channel deep enough for boats) the shallow areas are great for kayaks because boats can't access the area. We saw a variety of fish, found an island to picnic on and treasure the time spent exploring the area.
There are two restaurants within walking distance. We ate at
both many times and found that Taco Tuesday at Lookeys is very popular so get there early.
This is a quiet area with friendly neighbors. Our visit was fantastic on the happy scale and Joe is a wonderful host. He was always available when we had a question and his directions were easy to follow. We have stayed in many vacation rentals and our experience here with Joe has been the best. I hope we have an opportunity to visit again soon.
michael c.
Archival
10/10 Excellent
Jose D.
10 Oct 2016
Jose DeAra
Excellent property, very well equipped, with lots of activities for the entire family. Centrally located, yet far enough away to avoid congestion and not be isolated. All needs are supplied within a 5 mile radius, food, beverages, air fills, gas, bait and tackle.
Jose D.
Archival
10/10 Excellent
Jim P.
8 Apr 2016
The best home we've ever rented!
Exactly as described in the VRBO ad and even better. House is extremely clean and well stocked with all the cleaning supplies and paper products needed for doing dishes, laundry, etc. That's a first for us in renting houses as we've always had to buy all those supplies before. Location is perfect for easy access to great fishing (Bahia Honda State Park, for example), and it's only 30 minutes from Key West. Only house we've ever rented that provided bikes and kayaks for our use. Love the corner canal location for watching all the boat traffic in and out. The only suggestion for improvement would be to screen in the porch so it could be used more bug free. The owners are a pleasure to work with and really care that you enjoy your stay in their beautiful home.
Jim P.
Stayed 29 nights in Feb 2016
Archival
10/10 Excellent
Margaret G.
10 Nov 2013
Jamaica Ln
This home rental was excellent. The home is in a perfect location for water access, on a main canal to the ocean. The home was clean, well equipped, and easy to maintain while there. There is a great storage room downstairs to keep all your boating and diving equipment.The deck , dock, and cleaning table are in great shape, the deck is amazingly spacious. The owners are friendly, and always accessible for questions. We thoroughly enjoyed our stay at this home, and hope we can do it gain next year. An excellent value for a great vacation getaway.
Margaret G.
Response from VrboOwner on 30 Mar 2020
Dear M and J,
Thank you for the positive reponse to our home. It was a pleasure working with you. I'd like to thank you for being so communicative with us as well. We really enjoy hearing from our guests.
Thanks for taking such great care of our home while you stayed. Hope to hear from you soon.
Sincerely,
Danielle and Joe
Archival
10/10 Excellent
4 Oct 2013
Exactly As Promised
Our stay was wonderful from beginning to end. We found everything just as promised in the vrbo photos, description and correspondence with the owner. The corner lot is lovely and an easy few minutes to open water. There are plenty of decks and seating options to enjoy the evening breezes after sunny days boating, kayaking or riding bikes. The house is well appointed. The beds are all quite comfortable with plenty of linens and the kitchen is equipped with all the necessities plus a few extras. Everything about our stay was a pleasure, from first contact with the owner to the prompt refund of the deposit and all available to enjoy in between.
Archival
10/10 Excellent
Ernie K.
26 June 2013
Super Comfy
We chose this home for our 3rd annual Keys vacation and were very happy with our choice. A very nice home with all the amenities including kayaks and bicycles allowed for a very nice stay. Very comfortable and clean, a nice neighborhood (corner lot) and the owners were very cordial and accomdating in every way, including a prompt refund or our security deposit (This has not been the case with some other homes we've rented in the past). If I had to be overly critical, the one "issue" I can think of would be that even though this house is positioned for some beautiful sunsets from the decks, there is a limited area between other homes to allow for a sunset view all the way to the water and we were not there at the right time of the year to be able to take advantage of that. Had we been, everything about this home would have been perfect. That said, this home did offer a better sunset view than any other we've stayed in to date, and probably as good as it can get for anything in this price range. All in all, we left very satisfied and enjoyed our entire stay immensely. We would recommend this home to anyone looking for the features this home has to offer.
Ernie K.
About the host
Hosted by iTrip Vacations Key West
Premier Host
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