Title: Rockland Key Vacation Home Rentals from CA $644: Search Top Private Vacation Homes for Rent | 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)[Vacation Rentals in Rockland Key](https://expedia.ca/Rockland-Key-Vacation-Rentals.d553248635976197596.Travel-Guide-VacationRentals)[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 homes

![House](https://images.trvl-media.com/lodging/121000000/120240000/120239600/120239529/2a1c9fc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120240000/120239600/120239529/5ac36685.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/121000000/120240000/120239600/120239529/10b16cb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/121000000/120240000/120239600/120239529/eafa7da5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.ca/Key-West-Hotels-The-Fairhaven-House-At-Solaire-Lunara-Bay.h120239529.Hotel-Information)

CA $1,519

CA $3,099 total

includes taxes & fees

Feb 2 - Feb 3

[](https://www.expedia.ca/Key-West-Hotels-The-Fairhaven-House-At-Solaire-Lunara-Bay.h120239529.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)

![Property grounds](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/d57de0d1.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)

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

### Vacation Home in Cudjoe Key

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

9.4/10

Exceptional

(102 reviews)

"Great location. "

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

Davian k.

CA $337

CA $763 total

includes taxes & fees

Feb 4 - Feb 5

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

![A heated pool](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/a01f4162.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/e29d300c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table tennis, books](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/99097ad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/67b94030.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Cudjoe Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Blue-Lobster-Lodge-Venture-Out-543-Cudjoe-Key.h107116554.Hotel-Information)

9.2/10

Wonderful

(7 reviews)

"Close to Key West. Would stay there again!!"

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

elisa b.

CA $270

CA $824 total

includes taxes & fees

Feb 3 - Feb 4

[](https://www.expedia.ca/Summerland-Key-Hotels-Blue-Lobster-Lodge-Venture-Out-543-Cudjoe-Key.h107116554.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/121000000/120870000/120862100/120862073/4c3dc49f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120870000/120862100/120862073/a935335c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120870000/120862100/120862073/c8d44015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120870000/120862100/120862073/393a2acc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Cudjoe Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Waterfront-2BR2BA-35-Seawall-For-32-Boat-Beautiful-Sunrises-On-Cudjoe-Key.h120862073.Hotel-Information)

10/10

Exceptional

(1 review)

"Very clean! Good location. "

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

January M.

CA $464

CA $1,071 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Summerland-Key-Hotels-Waterfront-2BR2BA-35-Seawall-For-32-Boat-Beautiful-Sunrises-On-Cudjoe-Key.h120862073.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/71000000/70550000/70541400/70541336/6e3c9448.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/71000000/70550000/70541400/70541336/w1284h2247x0y0-fe8bc1e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/71000000/70550000/70541400/70541336/w1282h837x1y0-05f17a6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach towels](https://images.trvl-media.com/lodging/71000000/70550000/70541400/70541336/86d1247e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Cudjoe Key

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Oceanview-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h70541336.Hotel-Information)

7.6/10

Good

(13 reviews)

"Good experience. The property is well place and the Venture is really nice and quiet."

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

Primeau J.

CA $335

CA $699 total

includes taxes & fees

Feb 4 - Feb 5

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Oceanview-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h70541336.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/37ba1c6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sport court](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/25a85f73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/00d34243.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/4a876812.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Cudjoe Key

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Spanish-Queen-Venture-Out.h90010009.Hotel-Information)

9.4/10

Exceptional

(19 reviews)

"This is our third time staying here. It is a great property and works perfectly for a three-person family."

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

Kimberly G.

CA $476

CA $930 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Spanish-Queen-Venture-Out.h90010009.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132624/2885e075.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132624/8d434b6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132624/33a62704.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132624/3593d5fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.ca/Key-West-Hotels-The-Seagate-Estate-At-Lunara-Bay.h74132624.Hotel-Information)

10/10

Exceptional

(19 reviews)

"The perfect House , everything was good "

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

CARLOS G.

CA $1,082

CA $2,315 total

includes taxes & fees

Feb 3 - Feb 4

[](https://www.expedia.ca/Key-West-Hotels-The-Seagate-Estate-At-Lunara-Bay.h74132624.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132647/22e311d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132647/66fe5222.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132647/65dacfe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132647/d8e3a0a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.ca/Key-West-Hotels-Mirador-House-At-Lunara-Bay.h74132647.Hotel-Information)

9.6/10

Exceptional

(34 reviews)

"Fantastic property! Fantastic hosts! Fantastic pool! Would highly recommend staying here, we had an amazing time. "

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

Claudia S.

CA $2,655

CA $4,540 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Key-West-Hotels-Mirador-House-At-Lunara-Bay.h74132647.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)

![Dining](https://images.trvl-media.com/lodging/34000000/33500000/33496300/33496206/bd64b13f.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)

### Vacation Home in Old Town Key West

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

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 $347

CA $644 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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97540000/97538200/97538167/46f398f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/98000000/97540000/97538200/97538167/53e705db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/98000000/97540000/97538200/97538167/07101baf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97540000/97538200/97538167/5cc75497.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.ca/Key-West-Hotels-Altair-House-At-Lunara-Bay.h97538167.Hotel-Information)

9.8/10

Exceptional

(12 reviews)

"Great house. Large space, everything you need is there. "

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

CRIMSON A.

CA $1,217

CA $2,830 total

includes taxes & fees

Feb 2 - Feb 3

[](https://www.expedia.ca/Key-West-Hotels-Altair-House-At-Lunara-Bay.h97538167.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/116000000/116000000/115993700/115993610/b85cd3d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/116000000/116000000/115993700/115993610/93c22143.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/116000000/115993700/115993610/ee43d350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/116000000/116000000/115993700/115993610/5e338074.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.ca/Key-West-Hotels-Waterfront-Luxury-Home-Tidelands-House.h115993610.Hotel-Information)

CA $1,505

CA $3,082 total

includes taxes & fees

Feb 4 - Feb 5

[](https://www.expedia.ca/Key-West-Hotels-Waterfront-Luxury-Home-Tidelands-House.h115993610.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994655/61fc156d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, stereo, offices](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994655/cf94feca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994655/0ce6f815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/116000000/116000000/115994700/115994655/e32b0a4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.ca/Key-West-Hotels-Parking.h115994655.Hotel-Information)

10/10

Exceptional

(2 reviews)

"Beautiful home with great outdoor space and we loved the pool and private dock"

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

Sharon L.

CA $1,217

CA $2,916 total

includes taxes & fees

Feb 2 - Feb 3

[](https://www.expedia.ca/Key-West-Hotels-Parking.h115994655.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/7303809e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/bea2cf35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/357cfc90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/2b45d993.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Cudjoe Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Island-Time-110-Ocean-Views-Cudjoe-Key.h108496393.Hotel-Information)

9.4/10

Exceptional

(12 reviews)

"Our family had an amazing vacation! We love the house and hope to come back!! "

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

Tammy G.

CA $462

CA $1,069 total

includes taxes & fees

Feb 21 - Feb 22

[](https://www.expedia.ca/Summerland-Key-Hotels-Island-Time-110-Ocean-Views-Cudjoe-Key.h108496393.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)

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33490000/33483800/33483790/w1917h1268x0y0-ddb8f2af.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)

### Vacation Home in Cudjoe Key

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

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 $476

CA $948 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)

![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106410000/106408200/106408147/89820818.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106410000/106408200/106408147/4c30df1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sun loungers, beach towels](https://images.trvl-media.com/lodging/107000000/106410000/106408200/106408147/34f632fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106410000/106408200/106408147/c5a1cb5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Cudjoe Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Tropical-Tides-In-Cudjoe-Key-135.h106408147.Hotel-Information)

10/10

Exceptional

(5 reviews)

"Our house was beautiful and right on the water! Great sunrises and beautiful views! Fully equipped with everything you need or want! This home is the best VRBO we have rented! Would love to come back!!"

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

Loretta F.

CA $313

CA $940 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Summerland-Key-Hotels-Tropical-Tides-In-Cudjoe-Key-135.h106408147.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76570000/76568300/76568286/d7a848f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/77000000/76570000/76568300/76568286/w4000h2998x0y2-ffef9e21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/77000000/76570000/76568300/76568286/ea75861d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/77000000/76570000/76568300/76568286/cd6c698d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Key West

[](https://www.expedia.ca/Key-West-Hotels-Poolside-Cottage-412.h76568286.Hotel-Information)

9.2/10

Wonderful

(28 reviews)

"Everything you need for a great stay!!"

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

Karen D.

CA $409

CA $648 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/Key-West-Hotels-Poolside-Cottage-412.h76568286.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/117000000/116810000/116800200/116800175/eacdb869.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116810000/116800200/116800175/w1666h2499x1y1-3446235e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table tennis](https://images.trvl-media.com/lodging/117000000/116810000/116800200/116800175/w2500h1666x0y1-ee87ad68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116810000/116800200/116800175/w2499h1666x1y1-11741275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Cudjoe Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Oceanfront-2BR-In-Venture-Out-35-Dock.h116800175.Hotel-Information)

10/10

Exceptional

(5 reviews)

"Beautiful "

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

Lisa P.

CA $711

CA $1,382 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Summerland-Key-Hotels-Oceanfront-2BR-In-Venture-Out-35-Dock.h116800175.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/78000000/77070000/77064100/77064022/2f0f66a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/78000000/77070000/77064100/77064022/a7e2aa66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/78000000/77070000/77064100/77064022/b5a934e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/78000000/77070000/77064100/77064022/d9484c64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Upper Sugarloaf Key

[](https://www.expedia.ca/Sugarloaf-Key-Hotels-Bungalows-At-Sugarloaf-Beach-The-Hemingway.h77064022.Hotel-Information)

9.6/10

Exceptional

(8 reviews)

"Perfect location way off the path if you like seclusion."

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

Jonathan L.

CA $1,333

CA $2,581 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Sugarloaf-Key-Hotels-Bungalows-At-Sugarloaf-Beach-The-Hemingway.h77064022.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)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/b25eb073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Cutthroat Harbor Estates

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

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 $948 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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120240000/120238500/120238462/bd124994.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, stereo, offices](https://images.trvl-media.com/lodging/121000000/120240000/120238500/120238462/36229ea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/121000000/120240000/120238500/120238462/e05557f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120240000/120238500/120238462/660ee6b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Raccoon Key

[](https://www.expedia.ca/Key-West-Hotels-Brand-New-The-Greenmoor-House-With-Pool.h120238462.Hotel-Information)

CA $1,217

CA $2,916 total

includes taxes & fees

Feb 2 - Feb 3

[](https://www.expedia.ca/Key-West-Hotels-Brand-New-The-Greenmoor-House-With-Pool.h120238462.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=2026-02-12&endDate=2026-02-13&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=2026-04-29&d1=2026-04-29&endDate=2026-05-02&d2=2026-05-02&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=2026-04-29&d1=2026-04-29&endDate=2026-05-02&d2=2026-05-02&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=2026-04-29&d1=2026-04-29&endDate=2026-05-02&d2=2026-05-02&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=2026-04-29&d1=2026-04-29&endDate=2026-05-02&d2=2026-05-02&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=2026-04-29&d1=2026-04-29&endDate=2026-05-02&d2=2026-05-02&lodging=HOUSE_BOAT)

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## Top Rockland Key Hotel Reviews

![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)

![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)

![Hyatt Vacation Club at Windward Pointe, Key West](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/481a771e_y.jpg)

### Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent

"Everything was great. "

[](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Windward-Pointe.h868697.Hotel-Information)

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

### Duval House

10/10 Excellent

"The Duvall house was the icing on the cake for our stay in Key West. The staff was friendly (especially the gentleman that we spoke with for awhile), the grounds were so beautiful. Nice and clean, very comfortable beds, showers had great water pressure and hot water. We were surprised to be given an upgrade from a nice room in the rear to a suite that overlooked the Main Street with a balcony. Thank you so very much for that! The house is located in the central of downtown. Walking everywhere was a breeze. The town gets quiet about 10pm. We didn’t have a noise issue at all. The rear of the grounds offers a good size swimming pool and small gym. You can even bbq if you wanted. Perfect place for couples or ladies getaway. "

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

![Ibis Bay Beach Resort](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/4a09d86c_y.jpg)

### Ibis Bay Beach Resort

10/10 Excellent

"We had a last minute cancellation on our VRBO. Ibis Bay was able to accommodate us immediately. The staff was awesome and the room was clean."

[](https://expedia.ca/Key-West-Hotels-Ibis-Bay-Beach-Resort.h4218809.Hotel-Information)

![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg)

### Oceans Edge Key West Resort, Hotel & Marina

10/10 Excellent

"This place exceeded our expectations!! The rooms were spacious and clean, and we somehow lucked out with incredible water and marina views from the top floor. Food at the Yellowfin restaurant was better than we could have imagined (a few delicious fish dishes, belgian waffle breakfast, and even something as simple as a chicken quesadilla was great. Great coffee and breakfast cocktail selection as well.) I will say that leading up to the resort, we had our reservations, but the resort itself was perfect for a relaxing few days. 6 heated pools, a few outside games, ample outdoor lounge chairs and cabanas for laying out, and a beautiful marina setting and full bar to cater to just about everyones needs. Shuttle is very close by and comes every hour to take you downtown to enjoy a day or night out. Staff was also very accomodating. And with a quick ten minute drive from the airport, the planes that flew over the resort was very cool touch. If you want a vacation where you can choose to have a few drinks (or not at all, as my wife is pregnant) in a very relaxing serene setting, I wouldn't sleep on this place. We would go back here again in a second!!"

[](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information)

## Find out more about Rockland Key

## Rockland Key Vacation Homes information

| Number of reviews | 683                |
| ----------------- | ------------------ |
| Accommodation     | 806 Vacation Homes |
| Lowest Price      | CA $644            |
| Highest Price     | CA $4,540          |

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