Ramrod Key Vacation Rentals, Cottages & Private Rental Homes.
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Vacation Rentals by Owner in Ramrod Key Florida -- We have partnered directly with a major provider for By Owner Rentals, and now have the selection and value to offer our visitors searching for places to rent in Florida. Choose from Rental Homes or Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities to make your stay enjoyable.
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Beautiful Oceanfront Home on Ramrod Key - Three Lots, Dock & Poolside Tiki Bar
Private Vacation Home in Ramrod Key
***We are taking the recommended steps as presented by the Center for Disease Control and Prevention (CDC) for cleaning, disinfecting, and preparing this home for your arrival. We are following the protocols laid out by the CDC and using the EPA-approved disinfectants for Hard (non-porous) Surfaces, Soft (Porous) Surfaces and Electronics. We look forward to welcoming you to Island View on Ramrod Key.***
Island View is a charming three bedroom estate situated on three tropical landscaped l.......
10.0 Star Review Looe Key Villa - Beautiful Ocean View - 3 Balconies
Private Vacation Home in Ramrod Key
The view is breathtaking. This spacious home is great for 3 couples with 1 master BR with queen & private balcony overlooking Newfound Harbor, 1 BR with 2 twins & private balcony with view of salt pond, 1 BR with queen. It is one mile off route 1, the first house at the opening of a deep water canal facing the ocean; there is easy access to the Gulf;
Keywords: closest mainland house to Looe Key Sanctuary; great deep water canal + dock. Sleeps 6........
Canal Front Home to Dock and lift your boat in Lower Keys Paradise
Private Vacation Home in Ramrod Key
This comfortable elegant 3B/3B stilt home offers paradise in the Lower Keys. CAN BE RENTED AS A 4B/4B DETAILS BELOW. Newly renovated kitchen with granite countertops, new refrigerator, dishwasher and microwave. New wood solid maple floors in Master suite and Guest Bedroom 2. New Central air and heat, as well as ceiling fans throughout the home offer total comfort. There is a full washer and dryer for use with your rental. Comfortable elegant beach decor throughout with very large open an.......
Lower Keys Retreat and Boaters Paradise
Private Vacation Home in Ramrod Key
Enjoy your stay at our beautiful Keys home! With a 60 ft waterfront dock--- only 3 canals from the Atlantic, there is plenty of room to keep your boat, use our kayaks and paddleboards, or sit and sip your favorite cocktail (the picture is older and all foliage around the dock has been removed, approx 32 ft of dockage before the boat lift). The 1,300 sq ft house features an open floorplan, 2 bedrooms (sleeping 6), pullout sofa bed (sleeps 2), and 2 bathrooms. We also have a "pack-n-play" and a.......
Mermaid House: Heated Pool, Dual Dockage & Outdoor Bar on the Canal
Private Vacation Home in Ramrod Key
Mermaid House is a renovated second-level home sitting right on a canal corner in Ramrod Key, with 30 feet of dockage on one side and 20 feet on the other. The backyard is where most guests end up spending their time. There's a private saltwater pool available (heater available for additional fee), a big wooden island table next to the grill, an outdoor dining area, a fire pit, and an outdoor shower to rinse off after a day on the water. A kayak and two bikes are included for guests to use.
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Private House Facing the Ocean with Heated Pool/Spa
Private Vacation Home in RAMROD KEY
Come enjoy the cool clear blue waters of the Florida Keys. The weather is great, lobster season is open. This is a spacious oceanfront home with breathtaking open water views! It is located on beautiful Ramrod Key 110 ft concrete seawall facing the priceless Atlantic ocean teaming with lobsters, parrot fish, queen angels, snappers, and many others.A private boat slip cuts into the backyard...NOW WITH A NEW POOL/SPA
With nearly 25 feet of deep water dockage and you will have quick access.......
Relaxation in Paradise - Open Water Canal
Private Vacation Home in Ramrod Key
Relaxing in the beautiful Florida Keys, it does not get any better than this! Swimming and snorkeling in the crystal clear open water canal, docking your boat to go to world renowned Looe Key Marine Sanctuary, or heading down to Key West for all the night life and fine dining that it has to offer. This 3 bedroom has all the comforts of home in this tropical paradise island setting.
The master bedroom is furnished with a king-size memory foam mattress, sleeping on this is a dream. T.......
Beachfront 3B/3B Fishing Oasis
Private Vacation Home in Ramrod Key
Relax with the whole family at this peaceful place to stay. The main house boasts a 2B/2B spacious home, and there is a private 1B/1B efficiency downstairs (with separate A/C) The home has the luxuries of Instacart (to deliver groceries), has its own private dip pool and there is a local bait and tackle shop that will deliver bait!
Our home is a short kayak ride to the iconic, PICNIC ISLAND and we have a private pool and the only kayak launch on the beach! This home is a private slice of heav.......
Cayman Cottage | 3 bed/2 bath canalfront home
Private Vacation Home in Ramrod Key
Summary:
Great canalfront 3 bed/2 bath boating home on Ramrod Key
The Space:
Escape to Cayman Cottage, a charming three-bedroom, two-bathroom monthly vacation rental in Breezeswept Beach Estates on the oceanside of Ramrod Key. Just four canals away from the ocean, this idyllic retreat is a haven for anglers, divers and kayakers seeking the ultimate coastal getaway.
Boasting a prime location, Cayman Cottage offers 30 feet of available composite dock spa.......
Cozy Corner 2A
Private Vacation Home in Ramrod Key
This family friendly neighbor is peaceful and relaxing, very close to many restaurants and also 35 min from key west. There is a brand new boat dock where you can dock up to 30 ft boat and many bikes to take out riding around the neighborhood........
2 Bedrooms
- Sleeps 4
Vacation Rental in Ramrod Key
Lower Keys Home getaway
Private Vacation Home in Ramrod Key
This lovely 2 bedroom is close to many popular restaurants and is only 35 min from key west. Very close to several boat ramps and very close to the bay, there is a brand new boat dock that will allow up to a 33 foot vessel........
2 Bedrooms
- Sleeps 30
Vacation Rental in Ramrod Key
Breezeswept Beach, Waterfront with heated pool
Private Vacation Home in Ramrod Key
Located on the ocean side of Ramrod Key, this home offers open water sunrise views, a heated pool, a private sandy beach, and shallow lagoon access for kayaking and shallow boating. With the swimming pool, this home will be an excellent escape for those seeking a relaxed, quiet getaway. You will find everything you need to make your time here easy and comfortable. Washer/Dryer. There are two bedrooms with two baths and for sleeping King bed in the master and king in the 2nd bedroom... Nearby you.......
2 Bedrooms
- Sleeps 4
Vacation Rental in Ramrod Key
Pets Allowed 
Beautiful 3 Bedroom Canal Home in Ramrod Key, FL with Open Water Views!
Private Vacation Home in Ramrod Key
Welcome to Cape Cod South! This comfortable home is located 4 lots from the open water on the Gulf side of Ramrod Key. It sleeps 6, has a beautiful clean lot with a concrete dock, and sneak peak views of the open water. There is plenty of storage downstairs for your gear along with an extra bait freezer and refrigerator.
It's all about location and this home is located in a very nice quiet neighborhood with quick access for boating and it is super close to some of the best fishing and di.......
3 Bedrooms
- Sleeps 6
Vacation Rental in Ramrod Key
Pets Allowed
Casa Sirena, FL Keys Canalfront 3BD/2BA home offers a small pool & private dock
Private Vacation Home in Ramrod Key
Welcome to “Casa Sirena”, a canal-front paradise home nestled in the peaceful lower Florida Keys. Upon entering your rental property instantly access the private and spacious parking area out front. Enjoy the breeze as you walk through the covered patio area where you can enjoy a game of pool or simply take a seat and relax. The backyard offers lounging areas, seating areas, a grill, small pool and screened-in patio with arcade-style games. For the avid fishermen and boaters of the group, ta.......
Pool coming soon! Beautiful House on Ramrod Key with boat slip & water access.
Private Vacation Home in Ramrod Key
The house is very spacious. Large front & back decks. Newer furniture through-out. The house is on a lagoon and you can bring a boat. Fits a 30 foot boat. Ocean access is close. Enjoy water access and other activities such as paddle boarding, biking, and fishing. Pool coming soon! The main level consists of 1 queen bedroom, a hallway bath and the master suit that consists of 1 king bed and private bathroom. Upstairs is for owner use only and will be locked otherwise. Outdoor surveillance devices.......
Canal-Front Keys Getaway w/ Dock, Pet-Friendly, Near Looe Key & Key West!
Private Vacation Home in Ramrod Key
Breezy Keys – Canal front Retreat on Ramrod Key | Pet Friendly w/ Dock, Fire Pit & RV Parking
Welcome to Breezy Keys, your perfect Florida Keys escape. This 2BR/2BA canal front home on Ramrod Key combines coastal charm with modern comfort, just 27 miles from Key West and minutes from world-famous Looe Key Reef. Whether you're boating, fishing, diving, or simply soaking up the island lifestyle, Breezy Keys offers the ideal home base.
Highlights - Canal front Living – Private 11.5' dock .......
Peaceful Florida Retreat with Stunning Waterfront Views, Game Room & High-Speed
Private Vacation Home in Ramrod Key
Escape to Your Oceanfront Paradise in Ramrod Key, FL
Discover the perfect blend of relaxation and adventure at this vibrant oceanfront retreat in beautiful Ramrod Key! Designed for families, friends, and thrill-seekers alike—plus it's dog-friendly, so your four-legged family members are welcome too!
Wake up just steps from the turquoise waters, ready for a day of kayaking, sailing, or snorkeling—three guest kayaks are waiting for you to launch your next adventure. Prefer to sta.......
3 Bedrooms
- Sleeps 5
Vacation Rental in Ramrod Key
Pets Allowed
Gorgeous 4 bedroom 5 bath pool home with excellent boating
Private Vacation Home in Ramrod Key
Welcome to 333 Indies Rd! This 4 bedroom 5 and half bath pool home is ready for you to enjoy. Located on a great boating canal with excellent access to World Class off shore fishing and beautiful Looe Key reef for incredible snorkeling and diving. This spacious home features a chef 's kitchen with plenty of counter space, eat in bar area and dining area with seating for 10. The bedrooms feature s 2 queens and 2 king size beds each room has its own bath. There is plenty of out door space great fo.......
4 Bedrooms
- Sleeps 8
Vacation Rental in Ramrod Key
Gorgeous 3 Bedroom 2 Bath Canal Front Home With Great Boating
Private Vacation Home in Ramrod Key
If you are looking for a light, bright, and tropical rental home this is it!! This 3 bedroom 2 bath home is beautifully decorated, fully equipped and ready for your enjoyment. Featuring an open living area with eat in kitchen, screen porch and spacious bedrooms. Located on Ramrod Key with great boating access to the Atlantic and the Gulf and just a short ride to Looe Key Reef a virtual aquarium in your back yard! Plenty of dockage for your water toys and tropically landscaped yard offers shade t.......
3 Bedrooms
- Sleeps 6
Vacation Rental in Ramrod Key
Pets Allowed
Gorgeous 3 Bedroom 2 Bath Canal Front Home With Great Boating
Private Vacation Home in Ramrod Key
Stunning 3 bedroom 2 bath home located in Breezeswpt Beach Estates on Ramrod Key. This beautiful home features an open living area with a gorgeous fully equipped kitchen and huge island perfect for entertaining. The spacious bedrooms features a king bed in the master, queen bed in the guest bedroom and 2 twins in the 2nd guest bedroom. The large open porch has plenty of outdoor seating and dining area great for catching the southern winds. Downstairs also features an outdoor living area with TV,.......
3 Bedrooms
- Sleeps 6
Vacation Rental in Ramrod Key
Cozy 2 Bedroom 1 Bath Canal Front Home On Ramrod Key
Private Vacation Home in Ramrod Key
Charming Canal-Front Getaway on Ramrod Key Escape to this cozy 2-bedroom, 1-bath fishing cottage, perfectly situated in a quiet neighborhood on beautiful Ramrod Key, FL. This charming canal-front home offers direct boating access to open waters, making it a dream destination for boaters, anglers, and water enthusiasts. Just minutes from world-famous Looe Key Reef, you'll experience incredible diving and snorkeling in one of the best coral reef ecosystems in the Florida Keys. Spend your days fish.......
2 Bedrooms
- Sleeps 7
Vacation Rental in Ramrod Key
Boater's Paradise | 170' Waterfront | 30' Dockage | Ramrod Key Retreat
Private Vacation Home in Ramrod Key
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 boa.......
Super Cute, Well Maintained 2BR Canal Home in Ramrod Key - Great Boating Access!
Private Vacation Home in Ramrod Key
Welcome to Castaway Cottage, your home away from home in the heart of the Florida Keys! This beautiful 2-bedroom, 2-bathroom vacation rental offers the perfect blend of comfort and a “Keysie” style! Located in Ramrod Key, it is central to everything the Lower Keys has to offer including a quick ride out to the open ocean with no bridges.
Inside the home, you’ll find a beautiful kitchen equipped with everything necessary, plenty of areas to lounge, a master suite with private bath p.......
Casa Palma – Canalfront 3BR Home w/ Dock, Pet Friendly, Near Looe Key Reef
Private Vacation Home in Ramrod Key
Casa Palma – Canalfront 3BR/2BA Vacation Rental on Ramrod Key, Florida Keys Escape to the Lower Florida Keys and experience the perfect blend of relaxation, boating, and island living at Casa Palma. This beautifully updated 3-bedroom, 2-bath canalfront vacation rental on Ramrod Key offers direct access to the open waters of the Atlantic and Gulf, making it ideal for boaters, anglers, and ocean lovers. With a 30-foot concrete dock, this pet-friendly home provides convenient water access for you.......
Lux Canal Front Home w/ Dock, Near Looe Key – Fishing, Diving & Sunsets!
Private Vacation Home in Ramrod Key
Welcome to Diver's Den – A Luxurious Canal-Front Florida Keys Getaway
Escape to Diver's Den, a stunning canal-front vacation home in the Florida Keys, where comfort, style, and location come together for the ultimate island experience. Located in a peaceful and private neighborhood, this 3-bedroom, 2-bath waterfront home offers top-tier amenities, boating access, and beautiful sunset views over the salt ponds.
Inside, you'll find an airy, light-filled layout with two spacious living room.......
3 Bedrooms
- Sleeps 6
Vacation Rental in Ramrod Key
Pets Allowed
Charming shared 1-bedroom house with AC and WiFi also has a 37 foot dock
Private Vacation Home in Ramrod Key
Summerland Beauty located 35 min north of Key West. Many charming restaurants located nearby. Plenty of activities and fishing in the area, just a short thirty five minute drive to lovely Key West where you can go on many tours........
1 Bedrooms
- Sleeps 1
Vacation Rental in Ramrod Key
Cozy keys getaway
Private Vacation Home in Ramrod Key
Your home away from home in Ramrod Key with 1 bedroom. This wonderful house is equipped with all the essentials for a comfortable stay, including iron, hair dryer, AC, heating, washing machine, and WiFi. Experience what Ramrod Key has to offer with a stay at our house........
1 Bedrooms
- Sleeps 1
Vacation Rental in Ramrod Key
Villa Lucie | Canalfront pool home, 5 bedrooms
Private Vacation Home in Ramrod Key
Summary:
5 bedroom canalfront home with pool & boat lift on Ramrod Key
The Space:
Welcome to Villa Lucie, your slice of paradise on Ramrod Key.
Escape to the Keys in style at this stunning stilted concrete pool home in the oceanside Breezeswept Beach Estates neighborhood. Designed for relaxation, entertaining and the ultimate Keys lifestyle, this nearly new 5 bedroom, 4.5 bath retreat offers resort-style living with the privacy and space of a luxury ho.......
5 Bedrooms
- Sleeps 10
Vacation Rental in Ramrod Key
Paradise in the Lower Keys
Cottage in Ramrod Key
About this space
Escape to paradise at this charming cottage in Ramrod Key, Florida Keys. Ideal for families, the property offers a perfect getaway with a dock that leads to ocean access.
Located in the Lower Keys, guests can explore nearby attractions like Bahia Honda State Park and Looe Key Reef Resort & Dive Center. Key West, with its historic district and numerous attractions, is about 27 miles away, and Key West International Airport is 26 miles from the property........
3 Bedrooms
- Sleeps 6
Vacation Rental in Ramrod Key
Pets Allowed
Mangrove Hideaway: 3BR Canal Front Ramrod Key Home w/ Dockage, Gulf + Atlantic Access & Parking
Private Vacation Home in Ramrod Key
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below.
Welcome to Mangrove Hideaway, your perfect canal-front escape on Ramrod Key, where laid-back island living meets easy access to everything the Lower Keys have to offer.
This inviting 3-bedroom home sits along a canal with up to 30 feet of dockage available, making it an excellent choice for boaters and anglers. From here, you’ll .......
3 Bedrooms
- Sleeps 8
Vacation Rental in Ramrod Key