Title: Rockland Key Vacation Home Rentals from CA $424: 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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# Rockland Key Vacation Rentals

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## Check prices for these dates

In two weeks

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

In two months

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2026-04-03&endDate=2026-04-05&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

![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)

![Property grounds](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/d57de0d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### DECEMBER SAVE 60% OFF! 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

(101)

"Great location. "

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

Davian k.

CA $205

CA $598 total

includes taxes & fees

Dec 15 - Dec 16

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84050000/84046300/84046253/78d41425.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84050000/84046300/84046253/03f59755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/85000000/84050000/84046300/84046253/359e6f94.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/85000000/84050000/84046300/84046253/c7aff2d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kelly's Kabin - Adorable Private Summerland Key Cottage

[](https://www.expedia.ca/Summerland-Key-Hotels-Kellys-Kabin-Adorable-Private-Summerland-Key-Cottage.h84046253.Hotel-Information)

Summerland Key

9.8/10

Exceptional

(122)

"We enjoyed our stay! Great little house and location. "

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

Lisa K.

CA $279

CA $710 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Summerland-Key-Hotels-Kellys-Kabin-Adorable-Private-Summerland-Key-Cottage.h84046253.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)

![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/22d297cd.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)

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

### Island Time #110 Ocean Views - Cudjoe Key

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

Cudjoe Key

9.6/10

Exceptional

(11)

"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 $325

CA $895 total

includes taxes & fees

Dec 15 - Dec 16

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

![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/27d3efc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/ca8e91e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/e65d43dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/5018018b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Starlight Serenity - Hideaway with Stunning Views

[](https://www.expedia.ca/Summerland-Key-Hotels-Starlight-Serenity-Hideaway-W-Stunning-Views.h111873736.Hotel-Information)

Summerland Key

CA $262

CA $807 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Summerland-Key-Hotels-Starlight-Serenity-Hideaway-W-Stunning-Views.h111873736.Hotel-Information)

![House](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)

![House](https://images.trvl-media.com/lodging/116000000/116000000/115993700/115993610/a00c4a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Waterfront Luxury Home - Tidelands House

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

Raccoon Key

CA $2,514

CA $4,166 total

includes taxes & fees

Dec 16 - Dec 17

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

![A heated pool](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/8bf693c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/09f11ae8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/d1732c67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/35103395.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

[](https://www.expedia.ca/Summerland-Key-Hotels-Planktons-Palace-Cozy-2BR-Getaway-In-Oceanfront-Resort-Community-With-Patio-Island-Vibes.h116667062.Hotel-Information)

Cudjoe Key

CA $260

CA $813 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Summerland-Key-Hotels-Planktons-Palace-Cozy-2BR-Getaway-In-Oceanfront-Resort-Community-With-Patio-Island-Vibes.h116667062.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76590000/76584900/76584886/53dba367.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/77000000/76590000/76584900/76584886/w3000h1999x0y1-e258b195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76590000/76584900/76584886/w2998h1999x1y1-68fba4ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/77000000/76590000/76584900/76584886/w3000h1999x0y1-09a4d9ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Poolside Cottage #411

[](https://www.expedia.ca/Key-West-Hotels-Poolside-Cottage-411.h76584886.Hotel-Information)

Key West

9.8/10

Exceptional

(53)

"Perfect for our family! Recommend 10/10!"

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

Melissa F.

CA $231

CA $424 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Key-West-Hotels-Poolside-Cottage-411.h76584886.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)

![Marina](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/e93bd5d2.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)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/b25eb073.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

(118)

"Great experience "

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

Peyton S.

CA $310

CA $738 total

includes taxes & fees

Dec 15 - Dec 16

[](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)

![Marina](https://images.trvl-media.com/lodging/34000000/33490000/33483800/33483790/ac960d77.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)

![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)

### 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

(155)

"The property was excellent. The location was perfect. Quiet and relaxing. "

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

Jonathan K.

CA $341

CA $777 total

includes taxes & fees

Dec 15 - Dec 16

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

### The Shellstone House at Solaire Lunara Bay

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

Raccoon Key

CA $1,927

CA $3,838 total

includes taxes & fees

Dec 15 - Dec 16

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

![Pool](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/d62d627a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/a03560e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/2ea056a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/bf68a65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Palm - Beach Houses Key West

[](https://www.expedia.ca/Summerland-Key-Hotels-Bungalows-At-Sugarloaf-Beach-The-Palm.h94616487.Hotel-Information)

Upper Sugarloaf Key

10/10

Exceptional

(14)

"Beautiful grounds and pool area. Enjoyed all the abundant wildlife as well as fishing from one of the piers."

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

Harvey(Tabb) M.

CA $1,280

CA $2,445 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Summerland-Key-Hotels-Bungalows-At-Sugarloaf-Beach-The-Palm.h94616487.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/74000000/73240000/73238500/73238458/21ae09eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/74000000/73240000/73238500/73238458/c9d78c2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/74000000/73240000/73238500/73238458/8ea08bd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/74000000/73240000/73238500/73238458/2c3a4e8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Old Florida Style, wrap around porch, boat basin for dockage, open water

[](https://www.expedia.ca/Little-Torch-Key-Hotels-Old-Florida-Style.h73238458.Hotel-Information)

Little Torch Key

9.6/10

Exceptional

(87)

"This place really had it all , one of my best stays yet anywhere. "

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

Charles M.

CA $558

CA $1,133 total

includes taxes & fees

Dec 26 - Dec 27

[](https://www.expedia.ca/Little-Torch-Key-Hotels-Old-Florida-Style.h73238458.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)

![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)

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

### Spanish Queen @Venture Out, Cudjoe Key

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

Cudjoe Key

9.4/10

Exceptional

(19)

"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 $482

CA $937 total

includes taxes & fees

Dec 15 - Dec 16

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

![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)

![Terrace/patio](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413504/5c8f33a8.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)

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

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

Gary D.

CA $742

CA $1,812 total

includes taxes & fees

Dec 15 - Dec 16

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

![House](https://images.trvl-media.com/lodging/112000000/111880000/111873000/111872953/3d9bbd48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/112000000/111880000/111873000/111872953/1f10acb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/112000000/111880000/111873000/111872953/w3000h1968x0y0-d4c36356.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/112000000/111880000/111873000/111872953/f9199920.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Starlight Serenity - Hideaway w Stunning Views

[](https://www.expedia.ca/Summerland-Key-Hotels-Starlight-Serenity-Hideaway-W-Stunning-Views.h111872953.Hotel-Information)

Summerland Key

CA $374

CA $881 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Summerland-Key-Hotels-Starlight-Serenity-Hideaway-W-Stunning-Views.h111872953.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132637/8e393104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132637/1ebee8e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132637/c41273fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132637/6154370f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Springtide House at Lunara Bay

[](https://www.expedia.ca/Key-West-Hotels-Parking.h74132637.Hotel-Information)

Raccoon Key

9.8/10

Exceptional

(43)

"It was great. House was amazing"

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

Ernest H.

CA $1,122

CA $2,382 total

includes taxes & fees

Dec 23 - Dec 24

[](https://www.expedia.ca/Key-West-Hotels-Parking.h74132637.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)

![Exterior](https://images.trvl-media.com/lodging/77000000/76570000/76568300/76568286/w4000h2998x0y2-41f21691.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)

### Poolside Cottage #412

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

Key West

9.2/10

Wonderful

(28)

"The property and our place was really nice. Would definitely stay again. "

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

Sarah M.

CA $373

CA $602 total

includes taxes & fees

Jan 7 - Jan 8, 2026

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

![Exterior](https://images.trvl-media.com/lodging/58000000/57260000/57259300/57259241/3f698bba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/58000000/57260000/57259300/57259241/fd63c9b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/58000000/57260000/57259300/57259241/84aef88f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/58000000/57260000/57259300/57259241/c22ecf5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

[](https://www.expedia.ca/Summerland-Key-Hotels-Oceanfront-Home-Shared-Swimming-Pool.h57259241.Hotel-Information)

Cudjoe Key

8.6/10

Excellent

(89)

"We had a great time and will be back. "

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

Michelle K.

CA $413

CA $954 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Summerland-Key-Hotels-Oceanfront-Home-Shared-Swimming-Pool.h57259241.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132624/8fe35e26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132624/1b44d2b2.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/c7cec569.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74140000/74132700/74132624/e6a3d753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Seagate Estate at Lunara Bay

[](https://www.expedia.ca/Key-West-Hotels-Parking.h74132624.Hotel-Information)

Raccoon Key

10/10

Exceptional

(18)

"The perfect House , everything was good "

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

CARLOS G.

CA $1,032

CA $2,267 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Key-West-Hotels-Parking.h74132624.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108200000/108195400/108195321/f4cb0461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/109000000/108200000/108195400/108195321/c3afe913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108200000/108195400/108195321/2f1a1fda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/109000000/108200000/108195400/108195321/e3fefed1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Larkshine House at Lunara Bay

[](https://www.expedia.ca/Key-West-Hotels-Larkshine-House-At-Lunara-Bay.h108195321.Hotel-Information)

Raccoon Key

10/10

Exceptional

(7)

"well maintained, clean, easy to access"

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

Raj P.

CA $1,789

CA $3,575 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Key-West-Hotels-Larkshine-House-At-Lunara-Bay.h108195321.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-28&endDate=2025-12-29&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=2026-03-13&d1=2026-03-13&endDate=2026-03-16&d2=2026-03-16&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=2026-03-13&d1=2026-03-13&endDate=2026-03-16&d2=2026-03-16&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=2026-03-13&d1=2026-03-13&endDate=2026-03-16&d2=2026-03-16&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=2026-03-13&d1=2026-03-13&endDate=2026-03-16&d2=2026-03-16&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=2026-03-13&d1=2026-03-13&endDate=2026-03-16&d2=2026-03-16&lodging=HOUSE_BOAT)

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## Top Rockland Key Hotel Reviews

![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)

![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)

![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

"They went the extra mile! Was a lovely stay"

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

![Hyatt Centric Key West Resort and Spa](https://images.trvl-media.com/lodging/1000000/10000/1000/901/0b72a249_y.jpg)

### Hyatt Centric Key West Resort and Spa

10/10 Excellent

"Nice. Cold weather but still charged $65 for use of pool towels & facilities"

[](https://expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.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

"The facility was really well taken care of and the staff was very helpful. We had three meals at the restaurant and thought it was exceptional"

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

"Rooms were beautiful"

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

"Great place. Relatively quiet, but with great shuttle service to old town for more lively entertainment and more island food!"

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

## Find out more about Rockland Key

## Rockland Key Vacation Homes information

| Number of reviews | 906                |
| ----------------- | ------------------ |
| Accommodation     | 806 Vacation Homes |
| Lowest Price      | CA $424            |
| Highest Price     | CA $4,166          |

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