Lower Florida Keys Holiday Rentals

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Holiday Rentals in Lower Florida Keys

34’ Catamaran Sailboat

9.4 out of 10, Exceptional, (29)
"It was 6 miles from key west which we liked. It sits in an inlet so you don’t see much ocean or beach. Property had a separate bath house. Bathroom wasn’t really usable & tv cord was missing so no tv (wasn’t there to watch tv) If you have problems with close spaces, it wouldn’t be for you "
34’ Catamaran Sailboat

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

9.8 out of 10, Exceptional, (59)
"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

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

9.8 out of 10, Exceptional, (219)
"Perfect location with sunset views and kayaking "
The price is AU$1,215
includes taxes & fees
28 Jan - 29 Jan 2025
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

3 night minimum! Spectacular Ocean Views!

8.4 out of 10, Very good, (18)
"Venture out is a great location for being on the water. This rental was reasonable, spacious and clean! We had an amazing stay with no issues!"
3 night minimum! Spectacular Ocean Views!

Waterfront Home

8.8 out of 10, Excellent, (152)
"Has a nice seawall that can accomodate about a 30 foot boat. Cleaning station for fish was nice also. Actual house unit was older, but nice. We really just used it for cooking our fish and sleeping. The main perks of this place is that it has a seawall on a protected canal to keep a boat, has good channel access to both the oceanside and gulf, and is clean. Marina with boat fuel and boat ramp is in Venture Out neighborhood just a few hundred feet away from this actual unit. Overall a good...
Waterfront Home

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

9.8 out of 10, Exceptional, (108)
"This place was beautiful. When staying in a rental, there can always be a little something that is not right or goes wrong. Nothing went wrong with this place. The master bed evidently has an older form top mattress that doesn't dissipate heat, so it you are warm sleeping you will want to sleep in the second bedroom. It's not quite as bad. You may want to bring your own King Sheets and pillowcases. They were very rough!! All in all, I would recommend this place! They seemed to have everything...
Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear

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

8.4 out of 10, Very good, (96)
"This place was nice and came as advertised. Location is solid and near a few good restaurants and bars. It could have been a little cleaner but overall was in good shape. Would stay again. Price is good for what you get. "
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)

9.8 out of 10, Exceptional, (8)
"Our stay was amazing. The property was immaculate. The amenities were great. We will be back next year. The location was perfect. Close to Key West and alot to do in the area. Thank you for making our stay wonderful. See you next year!"
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)

Canal front, dockage, 2 bedroom, 2 bath

9.0 out of 10, Wonderful, (74)
"Property was just as advertised and looked as nice in person as in ads"
Canal front, dockage, 2 bedroom, 2 bath

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

9.8 out of 10, Exceptional, (183)
"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

Springs Venture Out Dolphin House (#386) with beautiful open water views

9.4 out of 10, Exceptional, (87)
"Weve stayed here twice now. It offers great views, great location, great hosts, my only suggestions is the beds could use some upgrading."
Springs Venture Out Dolphin House (#386) with beautiful open water views

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

9.0 out of 10, Wonderful, (188)
"We picked this place for the view and it didnt disappoint. We brought our electric bikes and used them pretty much everywhere. "
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4

9.6 out of 10, Exceptional, (42)
"This place was a gem. Clean, well kept and charming. The owner was very sweet and helpful."
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

9.8 out of 10, Exceptional, (233)
"The unit was spotless and perhaps one of the best equipped places we have stayed at with VRBO. Everything worked, the utensil drawers were overflowing, extra towels and bedding were provided. There was even a printer available. There were 6 bicycles to pick from and several kayaks (although it was too windy to use this time). Everything in the description is accurate. 5 of 5 rating."
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

9.8 out of 10, Exceptional, (199)
"The Property was as advertised. Great location, had everything we needed, served as both a fantastic base camp between outings and home base. We were able to experience everything we wanted for Thanksgiving as well as hit all the Florida Key highlights (Key West, Bahia Honda , and Piegon Key to list a few), the Venture Out location amenities and activities were a fantastic fit for us as well. Would 100% come back and we are even looking for future dates already. "
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

Ocean Front Luxury Vacation Rental Near Key West

9.4 out of 10, Exceptional, (40)
"Entering the Villa was pure ‘Candy to the Eye!’ All amenities were over the top. We absolutely loved the beach, kayaks and canoes. So much fun. The pool was fabulous. The outdoor furniture was so beachy, comfy and many fun seating arrangements. Enjoyed coffee on the balcony every morning. Views, views, views, just stunning. We would love to return to the Villa in the future and stay longer!"
Ocean Front Luxury Vacation Rental Near Key West

Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West

9.6 out of 10, Exceptional, (177)
"Excellent location, our house was perfect for fishing off the bulkhead and traveling to Key West! "
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West

Waterfront Cozy Cottage with Boat Ramp & Dock!

10.0 out of 10, Exceptional, (53)
"Cottage was great pier was great too! "
Waterfront Cozy Cottage with Boat Ramp & Dock!

Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5

10.0 out of 10, Exceptional, (208)
"Had two retired couples in the unit. Wanted to enjoy the Keys. This unit was a great location for exploration both ways. (South to Key West and north to Marathon) Had a great time. The owners were very quick with answering questions and providing a GREAT PLACE."
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5

SEA SHELL COTTAGE UNIT #2

9.4 out of 10, Exceptional, (13)
"Hidden Hammock was a gem for sure. Quiet, clean, located near lots of restaurants, stores, and things to do, Manager Hope was very kind and helpful giving us tips where to go, where to eat etc. Property sits on Summerland Key and close to everything North or South of us. I would recommend this place highly. Cheryl Zelsman "
SEA SHELL COTTAGE UNIT #2
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.
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Other types of properties in Lower Florida Keys you may be interested in

Parmer's Resort

2.5 star property
8.8 out of 10, Excellent, (1006)
"Overall nice. Staff was friendly and helpful. Just wish breakfast offered had more choices, perhaps some protein. Room was very small with no view, just one small window. But it was very clean and bed was comfortable. "
The price is AU$420
includes taxes & fees
8 Jan - 9 Jan 2025
Parmer's Resort

Sugarloaf Key Hotel at KOA Resort

3.0 star property
9.8 out of 10, Exceptional, (277)
"Wonderful resort hotel at Sugarloaf KOA. Fantastic accommodations for our entire family and dog. Great location and friendly staff. "
Sugarloaf Key Hotel at KOA Resort

Sugar Loaf Lodge

2.5 star property
8.0 out of 10, Very good, (1002)
"Ambience and the place is cool. The property is well maintained, staff courteous and helpful"
The price is AU$360
includes taxes & fees
5 Jan - 6 Jan 2025
Sugar Loaf Lodge
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.