Title: Rockland Key Cottages from CA $437 | Expedia.ca

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# Search Rockland Key Cottage Rentals from CA $437

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## Check prices for these dates

Next weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Rockland Key cottages

![Exterior](https://images.trvl-media.com/lodging/75000000/74240000/74237000/74236945/00dc7121.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/75000000/74240000/74237000/74236945/cd44e6df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/75000000/74240000/74237000/74236945/13a191dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/75000000/74240000/74237000/74236945/2be7fe30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Cudjoe Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Old-Florida-Style.h74236945.Hotel-Information)

8.2/10

Very good

(50)

"Great area. Quiet and comfortable "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

nancy c.

CA $186

CA $437 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Summerland-Key-Hotels-Old-Florida-Style.h74236945.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/5da801d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/fadc9b44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/515ffa6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/61e6cf8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Cudjoe Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Charming-Cottages.h33548243.Hotel-Information)

8.6/10

Excellent

(120)

"Jennifer was very nice and accommodating."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Randy G.

CA $220

CA $454 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Summerland-Key-Hotels-Charming-Cottages.h33548243.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/62000000/61590000/61585200/61585151/da754abc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/62000000/61590000/61585200/61585151/4681bad1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/62000000/61590000/61585200/61585151/16e13244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/62000000/61590000/61585200/61585151/8c79bc01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Cudjoe Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Canal-Front.h61585151.Hotel-Information)

9.0/10

Wonderful

(89)

"The facility is very nice with lots of amenities. It was clean and located close to everything we wanted to do."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer D.

CA $217

CA $510 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Summerland-Key-Hotels-Canal-Front.h61585151.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161406/119469de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161406/24f9aeaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161406/39474b4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161406/1e6e1b2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Old Town Key West

[](https://www.expedia.ca/Key-West-Hotels-Egret-Suite-Bright-Retreat.h110161406.Hotel-Information)

9.8/10

Exceptional

(33)

"Good place to stay loved it"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Charles I.

CA $194

CA $538 total

includes taxes & fees

Dec 20 - Dec 21

[](https://www.expedia.ca/Key-West-Hotels-Egret-Suite-Bright-Retreat.h110161406.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/72000000/71410000/71402800/71402765/6b090d7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71410000/71402800/71402765/d1e02db9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/72000000/71410000/71402800/71402765/442d52e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/72000000/71410000/71402800/71402765/49c68fa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Cudjoe Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Old-Florida-Style.h71402765.Hotel-Information)

8.6/10

Excellent

(52)

"We were very happy with our stay. Everything was as expected or above. Old Keys vibe was exactly what we wanted. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lauren R.

CA $186

CA $437 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Summerland-Key-Hotels-Old-Florida-Style.h71402765.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/76000000/75870000/75862800/75862770/792acc55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75870000/75862800/75862770/3bedcb76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75870000/75862800/75862770/4b744822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/76000000/75870000/75862800/75862770/1387427b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Cudjoe Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Old-Florida-Style.h75862770.Hotel-Information)

8.6/10

Excellent

(75)

"It was ok for what we needed. Needs some repairs though."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Craig M.

CA $186

CA $437 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Summerland-Key-Hotels-Old-Florida-Style.h75862770.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/102000000/101970000/101969900/101969867/591bb654.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/102000000/101970000/101969900/101969867/73021fc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101970000/101969900/101969867/9c903f98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101970000/101969900/101969867/fe66822e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Stock Island

[](https://www.expedia.ca/Key-West-Hotels-Living-Life-Dockside.h101969867.Hotel-Information)

CA $578

CA $862 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Key-West-Hotels-Living-Life-Dockside.h101969867.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/72000000/71430000/71420100/71420009/31f929e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/72000000/71430000/71420100/71420009/87670e64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/72000000/71430000/71420100/71420009/65220942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71430000/71420100/71420009/6dd601c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Cudjoe Key

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Old-Florida-Style.h71420009.Hotel-Information)

8.8/10

Excellent

(90)

"Nice place to vacation "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kevin D.

CA $217

CA $476 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Old-Florida-Style.h71420009.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/c1ab669a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/4d3ccae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/25ce0afb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/db40386c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Cudjoe Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Old-Florida-Style.h73238505.Hotel-Information)

8.8/10

Excellent

(52)

"Check in was easy, place nice & quiet. Kitchen facilities was good. Had a problem with the microwave, property manager took care of it within hours. WiFi great. Access was easy once you got used to it."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

myra c.

CA $341

CA $628 total

includes taxes & fees

Dec 26 - Dec 27

[](https://www.expedia.ca/Summerland-Key-Hotels-Old-Florida-Style.h73238505.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/68000000/67450000/67446300/67446229/90b1662b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/68000000/67450000/67446300/67446229/6b55a589.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/68000000/67450000/67446300/67446229/4b2fce7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/68000000/67450000/67446300/67446229/5250914d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Old Town Key West

[](https://www.expedia.ca/Key-West-Hotels-Southernmost-Retreat-2-Blocks-From-Duval-In-Old-Town.h67446229.Hotel-Information)

10/10

Exceptional

(131)

"Great place to stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

JEFFREY Z.

CA $544

CA $945 total

includes taxes & fees

Dec 19 - Dec 20

[](https://www.expedia.ca/Key-West-Hotels-Southernmost-Retreat-2-Blocks-From-Duval-In-Old-Town.h67446229.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/103000000/102190000/102186800/102186705/3ccd287c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, foosball, table tennis](https://images.trvl-media.com/lodging/103000000/102190000/102186800/102186705/w1280h854x0y1-3c29e84c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102190000/102186800/102186705/354705c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102190000/102186800/102186705/4147a5e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Cudjoe Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Beautiful-Cottage-Amenities-In-Gated-Community.h102186705.Hotel-Information)

10/10

Exceptional

(2)

"Beautiful home, perfect for our needs"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lindsay S.

[](https://www.expedia.ca/Summerland-Key-Hotels-Beautiful-Cottage-Amenities-In-Gated-Community.h102186705.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/012c9f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/1577bf53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/6c97b5f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/0b26cbe0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Cudjoe Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Quaint-Cottage.h33557696.Hotel-Information)

9.0/10

Wonderful

(146)

"great location, we are return visitors & will be back!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Shannon W.

CA $379

CA $655 total

includes taxes & fees

Dec 26 - Dec 27

[](https://www.expedia.ca/Summerland-Key-Hotels-Quaint-Cottage.h33557696.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161435/59200c69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161435/3b340556.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161435/0b2ab9b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161435/77611362.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Old Town Key West

[](https://www.expedia.ca/Key-West-Hotels-Pelican-Suite-Cozy-Cottage.h110161435.Hotel-Information)

10/10

Exceptional

(25)

"Wonderful clean place. It was an enjoyable experiance. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Chels J.

CA $180

CA $518 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Key-West-Hotels-Pelican-Suite-Cozy-Cottage.h110161435.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161439/a88c6d16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161439/a8c56ad8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161439/dc5dfbe8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161439/e2b37f05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Old Town Key West

[](https://www.expedia.ca/Key-West-Hotels-Seagull-Suite-Inviting-Studio.h110161439.Hotel-Information)

9.8/10

Exceptional

(23)

"Great little place, perfect for southernmost area."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lee G.

CA $180

CA $523 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Key-West-Hotels-Seagull-Suite-Inviting-Studio.h110161439.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/115000000/114430000/114429500/114429434/7ff914f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/115000000/114430000/114429500/114429434/c1f8574c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/115000000/114430000/114429500/114429434/228fc1fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/115000000/114430000/114429500/114429434/898be04c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Old Town Key West

[](https://www.expedia.ca/Key-West-Hotels-Coming-Soon-July-1-The-Jolly-RoosterNew-2BR2BA-Walk-To-Duval.h114429434.Hotel-Information)

9.6/10

Exceptional

(10)

"This was the perfect cottage for our stay. Very clean, nicely remodeled, great location to everything. It had everything we needed for or stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michael M.

CA $627

CA $1,054 total

includes taxes & fees

Jan 9 - Jan 10, 2026

[](https://www.expedia.ca/Key-West-Hotels-Coming-Soon-July-1-The-Jolly-RoosterNew-2BR2BA-Walk-To-Duval.h114429434.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161428/30d1aa29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161428/19aeadf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161428/537af082.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161428/f0bada72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Old Town Key West

[](https://www.expedia.ca/Key-West-Hotels-Osprey-Suite-Charming-Hideaway.h110161428.Hotel-Information)

9.8/10

Exceptional

(26)

"Great location! Fun place to stay! Responses to our questions/needs very promptly! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Teressa S.

CA $180

CA $518 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Key-West-Hotels-Osprey-Suite-Charming-Hideaway.h110161428.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/107000000/106170000/106161500/106161404/w2499h1667x1y0-498f0aa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/107000000/106170000/106161500/106161404/57815cac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106170000/106161500/106161404/w2499h1666x1y1-2340797d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106170000/106161500/106161404/w2500h1666x0y1-a7df3bb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Old Town Key West

[](https://www.expedia.ca/Key-West-Hotels-Find-Your-Zen-At-HIDDEN-TREASURE.h106161404.Hotel-Information)

8.8/10

Excellent

(10)

"Great place to stay! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

sarah R.

CA $709

CA $1,392 total

includes taxes & fees

Dec 24 - Dec 25

[](https://www.expedia.ca/Key-West-Hotels-Find-Your-Zen-At-HIDDEN-TREASURE.h106161404.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161415/c8d490fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161415/7a14c4ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161415/b9423d9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161415/c8088cd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Old Town Key West

[](https://www.expedia.ca/Key-West-Hotels-Heron-Suite-Vibrant-Retreat.h110161415.Hotel-Information)

10/10

Exceptional

(28)

"Clean room, amazing location, the host was very communicative and helpful. They had a car service ready to pick us up at the airport which was phenomenal. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lauren S.

CA $180

CA $518 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Key-West-Hotels-Heron-Suite-Vibrant-Retreat.h110161415.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161419/9f5b04c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161419/3b92efe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161419/6f555f0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161419/dfe1cfb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Old Town Key West

[](https://www.expedia.ca/Key-West-Hotels-Ibis-Suite-Bright-Hideaway.h110161419.Hotel-Information)

9.8/10

Exceptional

(26)

"Bar across street wonderful they didn’t clean room staff talked to great with anything you needed court yard could have been better maintained overall would go back and stay there "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Richele

CA $329

CA $725 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Key-West-Hotels-Ibis-Suite-Bright-Hideaway.h110161419.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-30&endDate=2025-12-31&regionId=553248635976197596&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

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Apartments

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Rockland+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197596&latLong=24.592217%2C-81.676102&adults=2&startDate=2026-03-16&d1=2026-03-16&endDate=2026-03-19&d2=2026-03-19&lodging=COTTAGE)

Villas

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Condos

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Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Rockland+Key%2C+Florida%2C+United+States+of+America&regionId=553248635976197596&latLong=24.592217%2C-81.676102&adults=2&startDate=2026-03-16&d1=2026-03-16&endDate=2026-03-19&d2=2026-03-19&lodging=VACATION_HOME)

Houseboats

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## Top Rockland Key Hotel Reviews

![Blue Flamingo Resort Key West](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/c4b850d1_y.jpg)

### Blue Flamingo Resort Key West

10/10 Excellent

"."

[](https://expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information)

![DoubleTree Resort by Hilton Grand Key - Key West](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/cefb5fc2_y.jpg)

### DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent

"shuttle"

[](https://expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.Hotel-Information)

![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg)

### Southernmost Beach Resort and Guesthouses

10/10 Excellent

"Beach and pool - bar, music and great staff"

[](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information)

![Pier House Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/19400/19307/c9267f77_y.jpg)

### Pier House Resort & Spa

10/10 Excellent

"Clean room, great amenities, very nice staff and close by foot to restaurants and stores."

[](https://expedia.ca/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information)

![Hilton Garden Inn Key West / The Keys Collection](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/449c6937_y.jpg)

### Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent

"clean room comfortable bed ,pool jacuzzi with bar make us amazing stay this hotel."

[](https://expedia.ca/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.Hotel-Information)

![La Concha Key West, Autograph Collection](https://images.trvl-media.com/lodging/1000000/10000/3900/3853/aebf156d_y.jpg)

### La Concha Key West, Autograph Collection

10/10 Excellent

"My husband and I enjoyed our stay at the hotel tremendously - everything was excellent! Location, cleanliness, pool, food, bedding, friendly staff, hotel decor, pleasant ambiance. Highly recommend this hotel to the guests who want to experience upscale services and hospitality of old Florida"

[](https://expedia.ca/Key-West-Hotels-Crowne-Plaza-Key-West-La-Concha.h3853.Hotel-Information)

![Winslow's Bungalows - Key West Historic Inns](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/7cf7d263_y.jpg)

### Winslow's Bungalows - Key West Historic Inns

10/10 Excellent

"Quaint hotel with beautiful grounds. Close to everything yet far away enough away from Duvall. Clean and comfortable rooms"

[](https://expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information)

![Beachside Resort & Residences](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg)

### Beachside Resort & Residences

10/10 Excellent

"The pool beach area was clean, water in pool and hot tub clean and warm Shuttle to Duvall street was very convent and helpful to get to shopping / dinning area "

[](https://expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information)

![Hyatt Vacation Club at Beach House, Key West](https://images.trvl-media.com/lodging/1000000/860000/858000/857962/fc0a2a7e_y.jpg)

### Hyatt Vacation Club at Beach House, Key West

10/10 Excellent

"Beautiful place"

[](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Beach-House.h857962.Hotel-Information)

## Find out more about Rockland Key

## Rockland Key Cottages information

| Number of reviews | 943          |
| ----------------- | ------------ |
| Accommodation     | 112 Cottages |
| Lowest Price      | CA $437      |
| Highest Price     | CA $1,392    |

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