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Browse Select Rockland Key Cottages

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

9.0 out of 10, Wonderful, (40)
"The cottage was clean and well appointed. Loved the little porch to sit in late in the evening or drink coffee in early in the morning. Beds were comfy, shower was not as strong as I like (but I'm spoiled by my home one, so . . . ) Only problem we noted was sometimes the toilet would not refill after flushing - simple fix, but kind of annoying. Pool was much smaller than it looked in the picture, though. Really enjoyed our stay and would not hesitate to stay again!"
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

ISLE BE BACK To The Sunny Keys

9.6 out of 10, Exceptional, (24)
"Rxcellent"
ISLE BE BACK To The Sunny Keys

Waterfront Home

8.8 out of 10, Excellent, (154)
"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

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

8.6 out of 10, Excellent, (37)
"Well located to visit Key West as well as other Keys both East and West. House needs some attention. "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

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

9.8 out of 10, Exceptional, (9)
"We arrived to a spotless cabana! The bed was perfect! Just awesome accommodations that I would definitely book again!!! Highly recommend- it was close to Key West but quiet and relaxing. And our pet stayed with us."
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

Conch Republic Consul General's Cottage.-Historic District

9.4 out of 10, Exceptional, (150)
"Very clean and well equipped kitchen although we didn’t cook! Quiet neighborhood but not far from everything! Pool was very nice and relaxing!"
Conch Republic Consul General's Cottage.-Historic District

The Dancing Rooster: 2 Blocks from Duval in Old Town.

10.0 out of 10, Exceptional, (108)
"Our 3 bedroom, 2 bathroom bungalow accommodated the 5 of us perfectly. Kitchen had all that we needed, space to sit outside, and so close to the action on Duval St. "
The Dancing Rooster: 2 Blocks from Duval in Old Town.

Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.

10.0 out of 10, Exceptional, (16)
"We were very happy with our stay at this property! It was perfect for a couple! A lot of the properties I looked at were two bedrooms and much more expensive. I was happy to find this one. The gated community was awesome and friendly. The communication with the manager was prompt and helpful. I read some of the reviews complaining about all the "rules". We had ZERO problems with all the rules in the Venture Out Community. It was so quiet and everyone was friendly. We will definitely...
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.

Riley's Retreat - Venture Out 107

8.8 out of 10, Excellent, (6)
"Quiet neighborhood close enough yet far enough from Key West madness "
Riley's Retreat - Venture Out 107

Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

9.4 out of 10, Exceptional, (214)
"Very clean. Could use some updating such as fresh paint. "
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

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

9.6 out of 10, Exceptional, (43)
"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

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!

SEA SHELL COTTAGE UNIT #2

9.4 out of 10, Exceptional, (14)
"Made sure to get ahold of me when I wasn’t reponding, emails were going to junk, and straightened out my reservation. Very appreciated! Was a great property for a good price 4 miles from my family so absolutely perfect for Christmas. "
SEA SHELL COTTAGE UNIT #2

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

8.8 out of 10, Excellent, (57)
"Spent Monday through Friday enjoying the peace and tranquility of this beautiful location. We brought a 22 foot center console with us and had no problems launching at the onsite boat ramp or tying up to the dock. Had to pay particular attention to the tides for fishing excursions as the immediate waters are very shallow. The cabin was adequately appointed for our needs and clean upon our arrival. The pool was also spotless and there were plenty of chairs/lounges for sitting pool and/or...
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

9.2 out of 10, Wonderful, (65)
"The cottage worked great for our sister trip. It was a good halfway point to many of the Key's attractions and was in a nice quieter community. The cottage was cozy and clean, but don't expect a fancy accommodation. The property was right on some water which was really nice."
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

8.0 out of 10, Very good, (32)
"It's a good quiet place about 20 miles from Key West. The property itself has seen its best years-- it has aged now but functional. The entrance is a bit tricky to find, right off of the highway. Overall a good place if you don't mind driving back and forth between Key West attractions. "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!

3.5 star property
8.0 out of 10, Very good, (2)
"The living room furniture and mattresses are not the most comfortable. Worn. Mattresses in small bedroom need replacement. Air conditioner does not reach small bedroom. "
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!

Blue Mind - Venture Out Unit 225

9.4 out of 10, Exceptional, (66)
"nice place 3rd time there"
Blue Mind - Venture Out Unit 225

**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool

10.0 out of 10, Exceptional, (204)
"Stunning views. Very clean. Loved it all!!!"
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
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 Rockland Key

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (109)
"Family had a great time "
The price is CA $323
CA $565 total
includes taxes & fees
Jan 28 - Jan 29
Aqua Lodges at Hurricane Hole Marina

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (361)
"Fun little place with a great pool. Ken was very helpful in all aspects. Highly recommended. Be aware its a small place but very comfortable."
The price is CA $258
CA $492 total
includes taxes & fees
Feb 9 - Feb 10
Steps from Duval, Pool on Site & Bikes Included!

34’ Catamaran Sailboat

9.4 out of 10, Exceptional, (30)
"We had a wonderful time. It is an older, smaller boat but we enjoyed it. There is a port a pot in the cabin but there is a huge shower and bathroom under the carport. We were able to fish right off the boat. Frank will answer texts pretty quickly. "
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.