Title: Rockland Key Vacation Rentals from CA $414: Short-Term Rentals for 2026 | Expedia.ca

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# Rockland Key Vacation Rentals

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## Check prices for these dates

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 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)

In three months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2026-04-10&endDate=2026-04-12&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

![Restaurant](https://images.trvl-media.com/lodging/90000000/89840000/89832400/89832384/d6422035.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)

![Deluxe Bungalow | Private kitchen](https://images.trvl-media.com/lodging/90000000/89840000/89832400/89832384/920119e4.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

(170)

"Location , staff , and aqua lodge were perfect."

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

William

CA $162

CA $414 total

includes taxes & fees

Dec 17 - Dec 18

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

![Exterior](https://images.trvl-media.com/lodging/1000000/860000/858000/857964/eca90904.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/860000/858000/857964/489ad80a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Two Bedroom Villa | Private kitchen](https://images.trvl-media.com/lodging/1000000/860000/858000/857964/639869f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/1000000/860000/858000/857964/376faaf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Vacation Club at Sunset Harbor, Key West

[](https://www.expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Sunset-Harbor.h857964.Hotel-Information)

Old Town Key West

8.6/10

Excellent

(321)

"Place was great bed was comfy and the water was HOT!!! "

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

Angela

CA $330

CA $418 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Sunset-Harbor.h857964.Hotel-Information)

![Apartment](https://images.trvl-media.com/lodging/110000000/109010000/109003300/109003218/54f28351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/110000000/109010000/109003300/109003218/63aa365b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/110000000/109010000/109003300/109003218/b77f7c60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/110000000/109010000/109003300/109003218/b1d63d4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ocean Front One Bedroom Residence

[](https://www.expedia.ca/Key-West-Hotels-Ocean-Front-One-Bedroom-Residence.h109003218.Hotel-Information)

Key West

[](https://www.expedia.ca/Key-West-Hotels-Ocean-Front-One-Bedroom-Residence.h109003218.Hotel-Information)

![Apartment](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003146/db32ae29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003146/a9dabced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003146/6b9536d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003146/w2994h2000x6y0-c109b53e.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)

"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 $413

CA $582 total

includes taxes & fees

Dec 18 - Dec 19

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

![Apartment](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003158/cfc92383.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003158/ddcb4189.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003158/714967b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/110000000/109010000/109003200/109003158/02c51bbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ocean Front 1BR Suite With Direct Beach Access

[](https://www.expedia.ca/Key-West-Hotels-Ocean-Front-1BR-Suite-With-Direct-Beach-Access.h109003158.Hotel-Information)

Key West

10/10

Exceptional

(2)

CA $550

CA $736 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Key-West-Hotels-Ocean-Front-1BR-Suite-With-Direct-Beach-Access.h109003158.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/28000000/27690000/27682400/27682303/79d0a981.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/28000000/27690000/27682400/27682303/7b599af0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach towels](https://images.trvl-media.com/lodging/28000000/27690000/27682400/27682303/3a198a15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27690000/27682400/27682303/0fa3fcec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Steps from Duval, Pool on Site & Bikes Included!

[](https://www.expedia.ca/Key-West-Hotels-Steps-From-Duval.h27682303.Hotel-Information)

Old Town Key West

9.6/10

Exceptional

(413)

"Everything was excellent!"

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

Susan L.

CA $296

CA $533 total

includes taxes & fees

Jan 14 - Jan 15, 2026

[](https://www.expedia.ca/Key-West-Hotels-Steps-From-Duval.h27682303.Hotel-Information)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/130000/120600/120544/fde9bad6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 outdoor pools](https://images.trvl-media.com/lodging/1000000/130000/120600/120544/e2a89efd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/1000000/130000/120600/120544/9652c070.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dock](https://images.trvl-media.com/lodging/1000000/130000/120600/120544/fdc5083f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Coconut Mallory Resort And Marina By Kees Vacations

[](https://www.expedia.ca/Key-West-Hotels-Coconut-Mallory-Resort-And-Marina-By-Kees-Vacations.h120544.Hotel-Information)

Key West

8.2/10

Very good

(821)

"The staff goes above and beyond very, very warm and nice people"

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

erik

[](https://www.expedia.ca/Key-West-Hotels-Coconut-Mallory-Resort-And-Marina-By-Kees-Vacations.h120544.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)

![Dining](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161415/c8088cd5.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)

![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)

### Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

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

Old Town Key West

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)

![Exterior](https://images.trvl-media.com/lodging/64000000/63730000/63723300/63723258/db6f8e09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bathtub, hair dryer, towels, soap](https://images.trvl-media.com/lodging/64000000/63730000/63723300/63723258/caaa3ab9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/64000000/63730000/63723300/63723258/738506c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63730000/63723300/63723258/4bc41e4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Heart of Downtown Key West Cottage With Off-Street Parking

[](https://www.expedia.ca/Key-West-Hotels-Heart-Of-Downtown-Key-West-Cottage-With-Off-Street-Parking.h63723258.Hotel-Information)

Key West Historic District

10/10

Exceptional

(142)

"As always, the host and house provided a great experience in KW. We have stayed there multiple times and will continue coming back!"

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

Tom H.

[](https://www.expedia.ca/Key-West-Hotels-Heart-Of-Downtown-Key-West-Cottage-With-Off-Street-Parking.h63723258.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/93000000/92970000/92966000/92965988/5017edad.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)

![Marina](https://images.trvl-media.com/lodging/93000000/92970000/92966000/92965988/a6298f91.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)

"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 $344

CA $690 total

includes taxes & fees

Dec 20 - Dec 21

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

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74060000/74054100/74054085/cf599eaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/75000000/74060000/74054100/74054085/15f1bcfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/75000000/74060000/74054100/74054085/25cbbbcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/75000000/74060000/74054100/74054085/05958025.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private Parking, Heated Pool - Sweet Caroline

[](https://www.expedia.ca/Key-West-Hotels-Sweet-Caroline-Spacious-2BR-Suite-W-Heated-Pool-Parking.h74054085.Hotel-Information)

Key West Historic District

8.6/10

Excellent

(20)

"It is definitely an historic property with some cracks in the floor boards and bathrooms but it has its charms and the location is excellent! I would stay there again!"

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

Martha B.

CA $556

CA $1,132 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Key-West-Hotels-Sweet-Caroline-Spacious-2BR-Suite-W-Heated-Pool-Parking.h74054085.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/124000000/123010000/123004300/123004292/w507h683x259y0-7393737d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/124000000/123010000/123004300/123004292/6c45e1c0_edited_b737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/124000000/123010000/123004300/123004292/8f5ff0fd_edited_c87f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123010000/123004300/123004292/89c3ec4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 3-bedroom houseboat with AC in perfect Key West, Sleeps 10 Guests!

[](https://www.expedia.ca/Key-West-Hotels-Charming-3-Bedroom-Houseboat-With-AC-In-Perfect-Key-West.h123004292.Hotel-Information)

Stock Island

[](https://www.expedia.ca/Key-West-Hotels-Charming-3-Bedroom-Houseboat-With-AC-In-Perfect-Key-West.h123004292.Hotel-Information)

![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)

![Property grounds](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161435/0b2ab9b0.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)

![Dining](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161435/97f1383f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

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

Old Town Key West

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)

![Sport court](https://images.trvl-media.com/lodging/84000000/83030000/83022100/83022015/f7b9230a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83030000/83022100/83022015/97e57def.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/84000000/83030000/83022100/83022015/af555929.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/84000000/83030000/83022100/83022015/235235dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

[](https://www.expedia.ca/Key-West-Hotels-Two-Bedroom.h83022015.Hotel-Information)

Key West

9.0/10

Wonderful

(31)

"Great place, great location, great communication from host!"

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

Lara P.

CA $523

CA $776 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Key-West-Hotels-Two-Bedroom.h83022015.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/122000000/121250000/121243800/121243734/4ae43588.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121250000/121243800/121243734/ebce7c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121250000/121243800/121243734/5d32a789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121250000/121243800/121243734/cb8b2cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Treehouse Condo 2nd Floor Balcony sleeps 6 free parking

[](https://www.expedia.ca/Key-West-Hotels-Treehouse-Condo-2nd-Floor-Balcony.h121243734.Hotel-Information)

Old Town Key West

8.0/10

Very good

(1)

"We had 3 people in the space. While there is sleeping for 6, there is not comfortable seating for 6 (not at table or in general area). Note that there is no couch, only a trundle day bed in general area. Kitchen was sparse - don’t expect to do much beyond boil water or use the toaster. Thought we wouldn’t mind bring off the beaten path, but this was too far out."

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

Michelle J.

[](https://www.expedia.ca/Key-West-Hotels-Treehouse-Condo-2nd-Floor-Balcony.h121243734.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/74000000/73980000/73974900/73974831/dc297b02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![9 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/74000000/73980000/73974900/73974831/a5d8c09c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/74000000/73980000/73974900/73974831/60f019a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/74000000/73980000/73974900/73974831/d96bf391.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private Heated Pool & Near Duval - The Curry House

[](https://www.expedia.ca/Key-West-Hotels-The-Curry-House-By-Brightwild-Historic-Guesthome.h73974831.Hotel-Information)

Old Town Key West

10/10

Exceptional

(6)

CA $2,980

CA $5,869 total

includes taxes & fees

Jan 12 - Jan 13, 2026

[](https://www.expedia.ca/Key-West-Hotels-The-Curry-House-By-Brightwild-Historic-Guesthome.h73974831.Hotel-Information)

![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/100000000/99890000/99882200/99882182/74a49171.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)

![Marina](https://images.trvl-media.com/lodging/100000000/99890000/99882200/99882182/480812c7.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

(36)

"Everything was very nice. Staff was friendly and helpful ."

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

Debra

CA $371

CA $458 total

includes taxes & fees

Dec 17 - Dec 18

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

![Pool](https://images.trvl-media.com/lodging/77000000/76900000/76890200/76890111/e5cfe110.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76900000/76890200/76890111/5ee4438b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76900000/76890200/76890111/33b8d82f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/77000000/76900000/76890200/76890111/79100c4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Keys Breeze - Walk to Duval, Private Pool

[](https://www.expedia.ca/Key-West-Hotels-Keys-Breeze-Walk-To-Duval.h76890111.Hotel-Information)

Old Town Key West

10/10

Exceptional

(17)

"Great location. Very clean and hospitable."

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

Derrick H.

CA $792

CA $1,693 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Key-West-Hotels-Keys-Breeze-Walk-To-Duval.h76890111.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/36000000/35060000/35053400/35053355/3bbf9cc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35060000/35053400/35053355/8ca3f11b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books, music library](https://images.trvl-media.com/lodging/36000000/35060000/35053400/35053355/6940d922.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35060000/35053400/35053355/b7fc350c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Perfect Location, Private Heated Pool, Pristine Luxury Home!

[](https://www.expedia.ca/Key-West-Hotels-Steps-From-Duval-St-Historical-Charm-Meets-Modern-Design-In-Old-Town-Key-West.h35053355.Hotel-Information)

Old Town Key West

10/10

Exceptional

(195)

"Outstanding place to stay, centrally located!"

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

Elizabeth Y.

CA $1,859

CA $3,307 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Key-West-Hotels-Steps-From-Duval-St-Historical-Charm-Meets-Modern-Design-In-Old-Town-Key-West.h35053355.Hotel-Information)

![Fridge, stovetop, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/121000000/120530000/120524700/120524691/76ab7cff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, internet, bed sheets](https://images.trvl-media.com/lodging/121000000/120530000/120524700/120524691/eec5154b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120530000/120524700/120524691/2c771588.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/121000000/120530000/120524700/120524691/113d1995.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Super-Cozy boat in Key West!

[](https://www.expedia.ca/Key-West-Hotels-Super-Cozy-Boat-In-Key-West.h120524691.Hotel-Information)

Key West

8.0/10

Very good

(1)

"Yes, Troy was very welcoming. Met me at the airport and gave me a ride to his boat. Very accomodating. 2 diff.options for sleeping and boat was very comfortable. Plenty of fresh towels.Picked up whatever I needed and brought it out to me. Thx!"

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

rachael K.

CA $343

CA $430 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Key-West-Hotels-Super-Cozy-Boat-In-Key-West.h120524691.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.

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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

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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