Holiday Homes in Ramrod Key

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Holiday Homes in Ramrod Key

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

9.0 out of 10, Wonderful, (67)
"House needs many minor repairs but is very functional. Good location."
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Kelly's Kabin - Adorable Private Summerland Key Cottage

9.8 out of 10, Exceptional, (104)
"Check in was super easy.Over all was a very comfortable place.Air condition was nice and cold..Everything worked properly.Located just South of Boondocks Bar&Grille which os one of our favorite spots.Easy to get back and forth to Key West.Would definately stay here again."
The price is AU$941
includes taxes & fees
1 Dec - 2 Dec
Kelly's Kabin - Adorable Private Summerland Key Cottage

20 MINUTES TO KEY WEST , BOATERS PARADISE

9.6 out of 10, Exceptional, (44)
"The property is perfect for a couple maybe 3. Its on the smaller side but we loved our time there. Property owner was very attentive even went and bought fishing poles when we asked if there were some available! We will be back!"
20 MINUTES TO KEY WEST , BOATERS PARADISE

WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

9.6 out of 10, Exceptional, (79)
"The stay was good. It was close enough to wedding venue. Few things wrong when we got there. My husband fixed the closet door because it would not open n shut also a door knob was about to fall off so he tightened it."
The price is AU$777
includes taxes & fees
25 Nov - 26 Nov
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

9.4 out of 10, Exceptional, (26)
"Super nice place Comfortable Couch Comfortable Bed"
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

9.0 out of 10, Wonderful, (184)
"Loved this ocean view property! Very nice location and very comfortable home!"
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

8.4 out of 10, Very good, (95)
"Great property. Brought our boat and had a great time. Quick drive to Key Wedt."
The price is AU$829
includes taxes & fees
22 Dec - 23 Dec
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear

9.8 out of 10, Exceptional, (106)
"Everything was great and Melanie was very easy to communicate with! "
Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear

Latitudes - Ocean front with pool

10.0 out of 10, Exceptional, (22)
"Beautiful home located on the water and nearby several great restaurants. Only 25 min to Key West. I would highly recommend this property to anyone searching this area for a vacation rental."
Latitudes - Ocean front with pool

Tropical Paradise - Ocean front with swim spa

9.6 out of 10, Exceptional, (74)
"Second time here and everything was great! Location, views, kayaks, bikes just needed a little air. Nice biking and walking. Quiet but not far if you want key West action."
Tropical Paradise - Ocean front with swim spa

Island Therapy

9.8 out of 10, Exceptional, (47)
"The ice maker wasn’t working. The tray on the inside was broken. There wasn’t any dish soap. I thought it came with my stay. But overall we have stayed in this place 3 times. And Wii come back again"
Island Therapy

Amazing Open Water Views - Venture Out Unit #374

10.0 out of 10, Exceptional, (12)
"This property is as listed. It was clean and the views are great. The location is also good as it is not far from Key West. I rated cleanliness as 4 stars because there was a small ant problem in the unit, lots of traps set up but they were on the kitchen floor. Also, no toiletries were provided such as shampoo and body wash and although the kitchen was well stocked with all things needed for cooking, there were no basics such as salt and pepper or cooking oil and any soaps provided were of...
Amazing Open Water Views - Venture Out Unit #374

One of the very few beach houses with a daily, rental license in the Keys.

9.0 out of 10, Wonderful, (54)
"Our trip was supposed to be a boys fishing trip but that was derailed by the hurricane. We were not able to reschedule the trip so my wife and I decided to come down for a private retreat. The house is much more than two people need but we had a great time. The morning views are spectacular. The only thing I would change would be the addition of a full size oven for those who like to cook at the house. "
The price is AU$2,049
includes taxes & fees
26 Nov - 27 Nov
One of the very few beach houses with a daily, rental license in the Keys.

Relax by Florida Keys Beaches, just a 7-min drive away

9.8 out of 10, Exceptional, (182)
"We enjoyed our visit to Cudjoe Key. We rented a boat for two days to enjoy snorkeling. It was great being able to tie up the boat outside our rental."
Relax by Florida Keys Beaches, just a 7-min drive away

Ocean/Canal Views 21ft Dock - Venture Out #357

8.6 out of 10, Excellent, (12)
"My travel buddy and I stayed here for 5 days. Peaceful, serene, so relaxing!"
Ocean/Canal Views 21ft Dock - Venture Out #357

OCEANFront Gem! True Southern Exposure - Venture Out Unit 93

9.0 out of 10, Wonderful, (6)
"It would be nice if beach chairs, umbrella and a cooler were provided"
OCEANFront Gem! True Southern Exposure - Venture Out Unit 93

Dickey's Dockside Retreat

10.0 out of 10, Exceptional, (1)
"What a way to check out of the weather up north and check into paradise - that's exactly what we did. We'll be back next year."
Dickey's Dockside Retreat

Fun in the Sun in Cudjoe Key! #51

2.0 star property
8.0 out of 10, Very good, (2)
"Great property unbelievable views would definitely come back"
Fun in the Sun in Cudjoe Key! #51

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (216)
"Property was clean and had everything to have an enjoyable stay."
The price is AU$1,115
includes taxes & fees
25 Nov - 26 Nov
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

Old Florida Style, wrap around porch, boat basin for dockage, open water

9.8 out of 10, Exceptional, (57)
"Our family of five adults and a dog had a fantastic week at this beautiful house! We had plenty of space, it was super clean and well kept. The countertop ice maker was definitely appreciated! We didn’t cook but all the tools you could need are there. We did place an Instacart order from Publix for a few things and delivery was no problem. Lots of restaurants are within a short drive and Kiki’s right down the road was a plus and had great food. We spent most mornings and evenings hanging out on...
Old Florida Style, wrap around porch, boat basin for dockage, open water
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Ramrod Key
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Ramrod Key

Old Wooden Bridge Resort and Marina

2.5 star property
8.4 out of 10, Very good, (161)
"The houseboat was a delight. Super comfortable and a full kitchen. Very dog-friendly. The woman who checked us in was super nice, and the salt-water pool felt great!"
The price is AU$377
includes taxes & fees
25 Nov - 26 Nov
Old Wooden Bridge Resort and Marina

Knight's Key Suites

3.0 star property
9.0 out of 10, Wonderful, (1064)
"I liked full kitchen. Balcony door dos not close, but it’s not a big deal. Location is central to Fla Keys. "
The price is AU$196
includes taxes & fees
9 Dec - 10 Dec
Knight's Key Suites

34’ Catamaran Sailboat

9.6 out of 10, Exceptional, (27)
"Overall it was a great experience."
34’ Catamaran Sailboat
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.