Title: Rockland Key Vacation Rentals from CA $426: Short-Term Rentals for 2026 | Expedia.ca

[Rockland Key Travel Guide](https://expedia.ca/Rockland-Key.dx553248635976197596)[Hotels in Rockland Key](https://expedia.ca/Rockland-Key-Hotels.d553248635976197596.Travel-Guide-Hotels)[Flights to Rockland Key](https://expedia.ca/Cheap-Flights-To-Rockland-Key.d553248635976197596.Travel-Guide-Flights)[Rockland Key Car Rentals](https://expedia.ca/Car-Rentals-In-Rockland-Key.d553248635976197596.Car-Rental-Guide)[Rockland Key Vacation Packages](https://expedia.ca/Rockland-Key.d553248635976197596.Destination-Travel-Guides)

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## Check prices for these dates

In two weeks

[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)

In two months

[Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2026-05-22&endDate=2026-05-24&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 vacation rentals

![Apartment | Exterior](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003134/11dbf1c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003134/e8ea6ec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | Exterior](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003134/03c0fc45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003134/c247b637.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Resort View 1BR Suite With Direct Pool Access

[](https://www.expedia.ca/Key-West-Hotels-Resort-View-1BR-Suite-With-Direct-Pool-Access.h109003134.Hotel-Information)

Key West

CA $657

CA $862 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Key-West-Hotels-Resort-View-1BR-Suite-With-Direct-Pool-Access.h109003134.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/90000000/89840000/89832400/89832384/721053af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/90000000/89840000/89832400/89832384/3a268cdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Cabin | Living area](https://images.trvl-media.com/lodging/90000000/89840000/89832400/89832384/c267004f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/90000000/89840000/89832400/89832384/bc5aedd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aqua Lodges at Hurricane Hole Marina

[](https://www.expedia.ca/Key-West-Hotels-Aqua-Lodges-At-Hurricane-Hole-Marina.h89832384.Hotel-Information)

Stock Island

8.8/10

Excellent

(174 reviews)

"Unique place to stay! We loved the nature and the location! "

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

Sara

CA $256

CA $516 total

includes taxes & fees

Feb 4 - Feb 5

[](https://www.expedia.ca/Key-West-Hotels-Aqua-Lodges-At-Hurricane-Hole-Marina.h89832384.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)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71410000/71402800/71402765/7140cd13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/72000000/71410000/71402800/71402765/2cf2f4c1.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)

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

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

Cudjoe Key

8.6/10

Excellent

(52 reviews)

"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 $337

CA $623 total

includes taxes & fees

Feb 1 - Feb 2

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

![Exterior](https://images.trvl-media.com/lodging/34000000/33920000/33912100/33912031/2c7b5ad1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/34000000/33920000/33912100/33912031/3ff004d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33920000/33912100/33912031/a14e8a95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33920000/33912100/33912031/761d8c20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage with Pool and Boat Dockage just minutes to Key West!

[](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Pool-And-Boat-Dockage-Just-Minutes-To-Key-West.h33912031.Hotel-Information)

Cudjoe Key

8.6/10

Excellent

(157 reviews)

"This cottage served our purpose well, very close to our family’s home and was very clean and comfortable for a short stay."

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

Richard S.

CA $272

CA $473 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Pool-And-Boat-Dockage-Just-Minutes-To-Key-West.h33912031.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w2720h1531x0y0-d54bbbc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Villa, Ocean View | Garden view](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w1153h1530x0y2-2909ca24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Villa, Ocean View](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w2304h1532x8y4-86de2f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w2722h1530x2y6-b30f2be4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Atlantic View Luxury Villa with Pool

[](https://www.expedia.ca/Summerland-Key-Hotels-Atlantic-View-Luxury-Villa-With-Pool.h111535402.Hotel-Information)

Summerland Key

10/10

Exceptional

(1 review)

"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "

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

Preetam

[](https://www.expedia.ca/Summerland-Key-Hotels-Atlantic-View-Luxury-Villa-With-Pool.h111535402.Hotel-Information)

![Miscellaneous](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/49b733bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/bc83e7d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/f3c522ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/00d423f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage with swimming pool and dockage, just minutes to Key West!

[](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Swimming-Pool-And-Dockage.h33566283.Hotel-Information)

Cudjoe Key

9.0/10

Wonderful

(164 reviews)

"Everything was there that I needed. Very nice area for my dog."

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

Terry

CA $270

CA $471 total

includes taxes & fees

Feb 15 - Feb 16

[](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Swimming-Pool-And-Dockage.h33566283.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/62000000/61590000/61585200/61585151/94e4b670.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)

![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)

![Smart TV](https://images.trvl-media.com/lodging/62000000/61590000/61585200/61585151/bce2dd72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Canal front, dockage, 2 bedroom, 2 bath

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

Cudjoe Key

9.0/10

Wonderful

(92 reviews)

"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 $349

CA $673 total

includes taxes & fees

Feb 1 - Feb 2

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

![Interior](https://images.trvl-media.com/lodging/34000000/33500000/33496300/33496206/237d62a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33500000/33496300/33496206/8267d923.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33500000/33496300/33496206/55f445db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33500000/33496300/33496206/a8959ffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Low Rates.& spec. early & late book spec. & 10% wk stays & close all& beach! 

[](https://www.expedia.ca/Key-West-Hotels-Year-Rd-W7-Night-Stay-Get-10-OffFull-Kitchen-Outside-Area12-Mile-Beach.h33496206.Hotel-Information)

Old Town Key West

9.0/10

Wonderful

(184 reviews)

"We had such a delightful time staying here! While the space is small, it was absolutely perfect for two people. Everything was clean, comfortable, and conveniently located. We really enjoyed our time in Key West and would definitely stay here again! "

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

ALISHA

CA $349

CA $647 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Key-West-Hotels-Year-Rd-W7-Night-Stay-Get-10-OffFull-Kitchen-Outside-Area12-Mile-Beach.h33496206.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413504/ccc6991c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413504/2903bcd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413504/586730d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413504/61ab05a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Summerland-Key-Hotels-Acreage-Beach-House-W-Pool-Billiards.h38413504.Hotel-Information)

Summerland Key

8.8/10

Excellent

(65 reviews)

"Excellent secluded location but near everything Thanks!!!!!"

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

Gary D.

CA $611

CA $1,636 total

includes taxes & fees

Feb 5 - Feb 6

[](https://www.expedia.ca/Summerland-Key-Hotels-Acreage-Beach-House-W-Pool-Billiards.h38413504.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/34000000/33570000/33564800/33564734/ef0fcc3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33570000/33564800/33564734/070ba9c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33570000/33564800/33564734/a7df710a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33570000/33564800/33564734/f4a6c5c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private Oceanfront Cottage with dockage, pool just minutes to Key West!

[](https://www.expedia.ca/Summerland-Key-Hotels-Private-Oceanfront-Cottage-With-Dockage.h33564734.Hotel-Information)

Cudjoe Key

8.6/10

Excellent

(165 reviews)

"Everything was nice and clean. Loved the location . Would definitely stay at the property again. "

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

Shawn M.

CA $304

CA $513 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Summerland-Key-Hotels-Private-Oceanfront-Cottage-With-Dockage.h33564734.Hotel-Information)

![Apartment | Exterior](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003146/40c4cfb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003146/cf637b4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | Exterior](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003146/9bc9a0a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | Exterior](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003146/b1bfe41a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Island View 1BR Residence With Balcony

[](https://www.expedia.ca/Key-West-Hotels-Island-View-1BR-Residence-With-Balcony.h109003146.Hotel-Information)

Key West

10/10

Exceptional

(2 reviews)

"Great place it is a full apartment with everything you could need and very clean "

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

Luis

CA $591

CA $788 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Key-West-Hotels-Island-View-1BR-Residence-With-Balcony.h109003146.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/d56a9a80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![LED TV, DVD player, table tennis, books](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/787fb31a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/9e0e4056.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/9c267ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Waterfront-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h32660303.Hotel-Information)

Cudjoe Key

9.4/10

Exceptional

(102 reviews)

"Great location. "

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

Davian k.

CA $336

CA $760 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Waterfront-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h32660303.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/93000000/92970000/92966000/92965988/681d666f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/93000000/92970000/92966000/92965988/fded6d82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92970000/92966000/92965988/682ba7e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/93000000/92970000/92966000/92965988/6d55c844.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

[](https://www.expedia.ca/Key-West-Hotels-Viking-Yacht-Getaway-In-The-Keys-NEW-LOCATION-Tons-Of-Amenities.h92965988.Hotel-Information)

Stock Island

7.8/10

Good

(26 reviews)

"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."

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

Julie

CA $337

CA $684 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Key-West-Hotels-Viking-Yacht-Getaway-In-The-Keys-NEW-LOCATION-Tons-Of-Amenities.h92965988.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/32000000/31900000/31892500/31892418/78df4af0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/32000000/31900000/31892500/31892418/98e9c6b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/32000000/31900000/31892500/31892418/39a5429b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/32000000/31900000/31892500/31892418/6a3c7406.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront Home

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Waterfront-Home.h31892418.Hotel-Information)

Cudjoe Key

8.6/10

Excellent

(177 reviews)

"Great location if you bring a boat. Secure location. Venture Out is a nice community. "

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

Georgiana V.

CA $306

CA $622 total

includes taxes & fees

Feb 6 - Feb 7

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Waterfront-Home.h31892418.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/100000000/99890000/99882200/99882182/532693cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/100000000/99890000/99882200/99882182/017ce471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99890000/99882200/99882182/44ae2c6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99890000/99882200/99882182/3d90235f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Living the Dream Key West Style

[](https://www.expedia.ca/Key-West-Hotels-Living-The-Dream-Key-West-Style.h99882182.Hotel-Information)

Stock Island

9.8/10

Exceptional

(40 reviews)

"Perfect, just perfect!"

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

Mikael

CA $567

CA $718 total

includes taxes & fees

Feb 3 - Feb 4

[](https://www.expedia.ca/Key-West-Hotels-Living-The-Dream-Key-West-Style.h99882182.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132652/4d522535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132652/b47188e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132652/02900870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132652/ad59ca22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Capmar House at Lunara Bay

[](https://www.expedia.ca/Key-West-Hotels-Capmar-House-At-Lunara-Bay.h74132652.Hotel-Information)

Raccoon Key

9.8/10

Exceptional

(29 reviews)

"House was spotless. Pool lights blinked on and off all night but not a problem. "

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

Emmett A.

CA $1,078

CA $2,306 total

includes taxes & fees

Feb 3 - Feb 4

[](https://www.expedia.ca/Key-West-Hotels-Capmar-House-At-Lunara-Bay.h74132652.Hotel-Information)

![Balcony](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/0c89d58b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/3835dc3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/e93bd5d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/b653e8ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Summerland-Key-Hotels-Just-20-Miles-From-Key-West-Oceanfront.h33547859.Hotel-Information)

Cutthroat Harbor Estates

8.4/10

Very good

(121 reviews)

"Great experience "

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

Peyton S.

CA $476

CA $950 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Summerland-Key-Hotels-Just-20-Miles-From-Key-West-Oceanfront.h33547859.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/34000000/33490000/33483800/33483790/w1917h1435x0y0-13878f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33490000/33483800/33483790/w1917h1148x0y0-e3e5de04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/34000000/33490000/33483800/33483790/w1916h1147x0y0-2466c03b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/34000000/33490000/33483800/33483790/ac960d77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

[](https://www.expedia.ca/Summerland-Key-Hotels-Direct-Oceanfront-Atlantic-Side-Dockage-Pool-And-20-Miles-From-Key-West.h33483790.Hotel-Information)

Cudjoe Key

8.8/10

Excellent

(158 reviews)

"Great location , clear communications and listing accuracy. Will be coming back again "

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

Kirk D.

CA $472

CA $941 total

includes taxes & fees

Feb 15 - Feb 16

[](https://www.expedia.ca/Summerland-Key-Hotels-Direct-Oceanfront-Atlantic-Side-Dockage-Pool-And-20-Miles-From-Key-West.h33483790.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132629/f12238b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132629/74f74be0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132629/02e9b6e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132629/466c62c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Suncoast House at Lunara Bay

[](https://www.expedia.ca/Key-West-Hotels-Suncoast-House-At-Lunara-Bay.h74132629.Hotel-Information)

Raccoon Key

9.6/10

Exceptional

(41 reviews)

"Beautiful House, super clean, perfect location "

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

carlos s.

CA $1,078

CA $2,537 total

includes taxes & fees

Feb 3 - Feb 4

[](https://www.expedia.ca/Key-West-Hotels-Suncoast-House-At-Lunara-Bay.h74132629.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/77000000/76490000/76481200/76481154/9d55a4ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76490000/76481200/76481154/6497e910.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/77000000/76490000/76481200/76481154/b3743fa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/77000000/76490000/76481200/76481154/b4eb767b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### SUGAR PALM STUDIO \~ Adult Only Studio w/ Community Pool & Close to Town!

[](https://www.expedia.ca/Key-West-Hotels-SUGAR-PALM-STUDIO-Tranquil-Studio-W-Community-Pool-Close-To-Town.h76481154.Hotel-Information)

Old Town Key West

9.8/10

Exceptional

(116 reviews)

"we had a wonderful room with a great location. It was too cold to use the pool, but it looked very inviting. Would definitely stay again."

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

Richard

CA $499

CA $836 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Key-West-Hotels-SUGAR-PALM-STUDIO-Tranquil-Studio-W-Community-Pool-Close-To-Town.h76481154.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=2026-02-14&endDate=2026-02-15&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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Villas

[](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=2026-05-01&d1=2026-05-01&endDate=2026-05-04&d2=2026-05-04&lodging=VILLA)

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=2026-05-01&d1=2026-05-01&endDate=2026-05-04&d2=2026-05-04&lodging=COTTAGE)

Condos

[](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=2026-05-01&d1=2026-05-01&endDate=2026-05-04&d2=2026-05-04&lodging=CONDO)

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=2026-05-01&d1=2026-05-01&endDate=2026-05-04&d2=2026-05-04&lodging=VACATION_HOME)

Houseboats

[](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=2026-05-01&d1=2026-05-01&endDate=2026-05-04&d2=2026-05-04&lodging=HOUSE_BOAT)

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## Top Rockland Key Hotel Reviews

![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

"Room was neat and staff was very courteous"

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

![Havana Cabana at Key West ](https://images.trvl-media.com/lodging/22000000/21250000/21241100/21241090/becea015_y.jpg)

### Havana Cabana at Key West 

10/10 Excellent

"Staff friendly, rooms clean, lobby smelled amazing, transportation was key. Could just drop your bags and enjoy island life!"

[](https://expedia.ca/Key-West-Hotels-Havana-Cabana-At-Key-West.h21241090.Hotel-Information)

![Duval House](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/d8706fe9_y.jpg)

### Duval House

10/10 Excellent

"Clean room"

[](https://expedia.ca/Key-West-Hotels-Duval-House.h900423.Hotel-Information)

![Margaritaville Beach House Key West](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/32e70782_y.jpg)

### Margaritaville Beach House Key West

10/10 Excellent

"The property was wonderful. Great pool, restaurant, and the room was clean and well kept. Staff was all wonderful, from the welcome cocktail, help with a relentless alarm clock, daily free smoothies at poolside, great pool towels and lots of chaise lounges under umbrellas. Also enjoyed the 'air show' with the naval jets flying over a couple times a day. Great location for the beach too!"

[](https://expedia.ca/Key-West-Hotels-Margaritaville-Beach-House-Key-West.h48713884.Hotel-Information)

![Parrot Key Hotel & Villas](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/67735d0c_y.jpg)

### Parrot Key Hotel & Villas

10/10 Excellent

"Cleanliness, staff and the spacious room"

[](https://expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.Hotel-Information)

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

### Beachside Resort & Residences

10/10 Excellent

"Wonderful staff. Beautiful "

[](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

"Very nice resort, and clean"

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

![The Perry Hotel & Marina Key West](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/e4eb7fd5_y.jpg)

### The Perry Hotel & Marina Key West

10/10 Excellent

"Wonderful place to stay. Facilities were great. There were three bar/ restaurants to choose from with all very good food. You could walk off site to a few other local places with very good food also. The room was clean. Staff was helpful."

[](https://expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information)

![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

"Shuttle"

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

## Find out more about Rockland Key

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Rockland Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Rockland Key ](https://expedia.ca/Rockland-Key-Private-Vacation-Homes.d553248635976197596-aaPrivateVacationHomes.Travel-Guide-Accommodation)
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- [Dredgers Key Luxury Hotels](https://expedia.ca/Dredgers-Key-Hotels-Luxury-Hotel.0-0-d180165-tLuxuryHotel.Travel-Guide-Filter-Hotels)

Flights

- [Flights to JAX](https://expedia.ca/Cheap-Flights-To-Southeast-Jacksonville.d6062932.Travel-Guide-Flights)
- [Cheap Tickets from Raccoon Key](https://expedia.ca/lp/flights/180164/flights-from-raccoon-key)

Cars

- [Right Cars Car Rentals In Northeast Orlando](https://expedia.ca/Right-Cars-Car-Rentals-In-Northeast-Orlando.d553248635976480125-c1070.Car-Rental-Guide-Suppliers)

Activities

- [Things to do in Boca Chica Key](https://expedia.ca/Things-To-Do-In-Boca-Chica-Key.d553248635083916609.Travel-Guide-Activities)
- [Things to do in South Tampa](https://expedia.ca/Things-To-Do-In-South-Tampa.d6321582.Travel-Guide-Activities)

Packages

- [Duval Street](https://expedia.ca/Duval-Street-Key-West-Historic-District.d6068616.Vacation-Attraction)
- [South Beach](https://expedia.ca/South-Beach-Old-Town-Key-West.d6246827.Vacation-Attraction)
- [Smathers Beach](https://expedia.ca/Smathers-Beach-Beachside.d6069255.Vacation-Attraction)
- [Mallory Square](https://expedia.ca/Mallory-Square-Key-West-Historic-District.d501385.Vacation-Attraction)
- [Florida Keys Eco - Discovery Center](https://expedia.ca/Florida-Keys-Eco-Discovery-Center-Old-Town-Key-West.d6069247.Vacation-Attraction)
- [Southernmost Point](https://expedia.ca/Southernmost-Point-Old-Town-Key-West.d501380.Vacation-Attraction)
- [Raccoon Key Vacation Packages](https://expedia.ca/Raccoon-Key.d180164.Destination-Travel-Guides)

Vacation Rentals

- [Vacation Rental Gasparilla Island](https://expedia.ca/Gasparilla-Island-Vacation-Rentals.d6128516.Travel-Guide-VacationRentals)

General

- [Visit Venetian Islands](https://expedia.ca/Venetian-Islands.dx553248635976481890)
- [Visit Little Torch Key](https://expedia.ca/Little-Torch-Key.dx177498)
- [Visit Sugarloaf Key](https://expedia.ca/Sugarloaf-Key.dx183126)
- [Visit Honeymoon Island State Park](https://expedia.ca/Honeymoon-Island-State-Park.dx6160046)

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