Holiday Homes in Lower Keys

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Featured Holiday Homes in Lower Keys

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

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

9.8 out of 10, Exceptional, (61)
"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
Beachside @ Torchview Waterfront Retreat
On the beach, beach towels

Beachside @ Torchview Waterfront Retreat

9.8 out of 10, Exceptional, (37)
"I had a wonderful 3 weeks stay at Beachside@Torchview. I loved the privacy of the house, the gorgeous sunset views, and the peaceful mornings sitting out on the deck while drinking my morning coffee. I would highly recommend this house for anyone looking for a quiet getaway in the busy Florida Keys. It was everything I had hoped for, and I will definitely be staying here again if I decide to return to the Keys next year. The house was very clean and suited my needs perfectly, and the host...
Beachside @ Torchview Waterfront Retreat
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
On the beach, sun-loungers, beach towels

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

9.8 out of 10, Exceptional, (220)
"Perfect location with sunset views and kayaking "
The price is AU$1,216
includes taxes & fees
7 Jan - 8 Jan
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
3 night minimum! Spectacular Ocean Views!
A heated pool

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

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
Grand Opening! New Construction in Venture Out! 3 night minimum stay.
Private kitchen

Grand Opening! New Construction in Venture Out! 3 night minimum stay.

10.0 out of 10, Exceptional, (1)
"We stayed 4 nights. This unit was much nicer than the pictures show. Essentially everything was immaculate and brand new. The resort was also much nicer than we expected. Would definitely stay again!"
Grand Opening! New Construction in Venture Out! 3 night minimum stay.
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Balcony

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

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
Oceanfront Paradise w Dock for your 35' boat and Huge Tiki and Firepit. Dogs OK
Property grounds

Oceanfront Paradise w Dock for your 35' boat and Huge Tiki and Firepit. Dogs OK

10.0 out of 10, Exceptional, (11)
"Verry nice location and the best Tikihut and bar ever, quiet palce, wonderful sunrises and a lot of space outside and perfect breakfast place on the balcony, inside also plenty of space, clean and tastefully furnished, renovated bathrooms, wildlife wonderful with the trusting deer++++ also a lot of fish, sharks in front of the house wow+++++Big Pine Key area is nice and wonderful peaceful, Could be use new windows and blinds are old and not functional, the sand in living area is nice and you...
Oceanfront Paradise w Dock for your 35' boat and Huge Tiki and Firepit. Dogs OK
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Outdoor dining

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

9.4 out of 10, Exceptional, (29)
"Super nice place Comfortable Couch Comfortable Bed"
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Island Therapy
A heated pool

Island Therapy

9.8 out of 10, Exceptional, (48)
"We enjoyed everything about this rental. Perfect location. Just beautiful."
Island Therapy
Waterfront Captain House with Boat Basin & Ramp!
Outdoor dining

Waterfront Captain House with Boat Basin & Ramp!

9.8 out of 10, Exceptional, (7)
"Beautiful property comfortable beds! We enjoyed fishing in the lagoon. This is a beautiful home!"
Waterfront Captain House with Boat Basin & Ramp!
Ocean Front - Private 56' Dock
Terrace/patio

Ocean Front - Private 56' Dock

9.8 out of 10, Exceptional, (135)
"We are experienced Florida renters and we were blown away by this unit. The view alone is worth the stay but we found Venture Out to be absolutely charming. Clean, comfortable, safe, kitchen is well stocked. We will be back for sure!"
The price is AU$1,266
includes taxes & fees
6 Jan - 7 Jan
Ocean Front - Private 56' Dock
20 MINUTES TO KEY WEST , BOATERS PARADISE
Exterior

20 MINUTES TO KEY WEST , BOATERS PARADISE

9.4 out of 10, Exceptional, (47)
"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
Amazing Open Water Views - Venture Out Unit #374
Exterior

Amazing Open Water Views - Venture Out Unit #374

9.8 out of 10, Exceptional, (13)
"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
Dickey's Dockside Retreat
Fridge, microwave, oven, stovetop

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
Southern Exposure in Cudjoe Key #49
Beach

Southern Exposure in Cudjoe Key #49

2.0 star property
Southern Exposure in Cudjoe Key #49
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Outdoor dining

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

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
A heated pool

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

9.8 out of 10, Exceptional, (200)
"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
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 property types in Lower Keys

Old Wooden Bridge Resort and Marina
2 Bedroom Aqua Lodge # 13 Barracuda | Living area

Old Wooden Bridge Resort and Marina

2.5 star property
8.4 out of 10, Very good, (173)
"It was a nice experience staying in the houseboat. Everyone there was very friendly and accommodating. "
The price is AU$394
includes taxes & fees
6 Jan - 7 Jan
Old Wooden Bridge Resort and Marina
34’ Catamaran Sailboat
Interior

34’ Catamaran Sailboat

9.4 out of 10, Exceptional, (30)
"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
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
On the beach, sun-loungers, beach towels

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

9.8 out of 10, Exceptional, (220)
"Perfect location with sunset views and kayaking "
The price is AU$1,216
includes taxes & fees
7 Jan - 8 Jan
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
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.