Title: Rockland Key Vacation Home Rentals : 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

Next weekend

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976197596&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Rockland Key Vacation Homes

![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/9c267ac9.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/f111b153.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/f2ffe64a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/w1024h630x0y0-e267420a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### OCT. & NOV. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cudjoe Key

9.6/10

Exceptional

(98)

"Clean place with room for 2 couples. Everything you need."

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

Jason W.

CA $194

CA $591 total

includes taxes & fees

Oct 29 - Oct 30

[](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, a heated pool](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/28679789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/6bfc69e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/8e7ed1a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/7f597dff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### OCT. & NOV. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cudjoe Key

9.8/10

Exceptional

(81)

"The place is clean and convenient for anyone wanting to spend time on the water in the keys"

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

Ubaldo G.

CA $222

CA $626 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Ocean-Paradise-AT-Venture-OUT-4-Bikes-2-2-Person-Kayaks.h44556643.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/80000000/79690000/79683300/79683240/w905h683x60y0-701bb32b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/80000000/79690000/79683300/79683240/w907h683x59y0-59367592.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/80000000/79690000/79683300/79683240/w509h683x258y0-3618efad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/80000000/79690000/79683300/79683240/6b75217d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Paradise found

Stock Island

9.8/10

Exceptional

(30)

"Very nice! Had everything we needed and then some! Bonus there a a few great places for breakfast and lunch across the street! Thanks for a great vacation!"

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

Mandi C.

CA $349

CA $766 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Key-West-Hotels-Paradise-Found.h79683240.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/49000000/48230000/48220200/48220112/82f72492.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/49000000/48230000/48220200/48220112/2761e1ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/49000000/48230000/48220200/48220112/def4d659.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/49000000/48230000/48220200/48220112/0d75fd5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beach Getaway in the Florida Keys

SUGARLOAF KEY

8.4/10

Very good

(7)

"Amazing property and views. Tom was great and very helpful with places to go and things to do. Will definitely recommend!!"

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

Robyn M.

CA $1,224

CA $2,714 total

includes taxes & fees

Nov 5 - Nov 6

[](https://www.expedia.ca/Sugarloaf-Key-Hotels-Beach-House-At-Sugarloaf-Key-W430ft-Dock-5ft-Drft.h48220112.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/3c8eff21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/w2500h1666x0y1-8de3e595.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/c7065ca6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/e1bc9e10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Cudjoe Key

9.2/10

Wonderful

(7)

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

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

elisa b.

CA $264

CA $826 total

includes taxes & fees

Oct 26 - Oct 27

[](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/109000000/108500000/108496400/108496393/73acf8f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/f620b37f.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)

![Beach](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/22584e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Cudjoe Key

9.4/10

Exceptional

(10)

"Greta property, really enjoyed the water view and the bbq grill "

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

William B.

CA $294

CA $868 total

includes taxes & fees

Oct 29 - Oct 30

[](https://www.expedia.ca/Summerland-Key-Hotels-Island-Time-110-Ocean-Views-Cudjoe-Key.h108496393.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/85000000/84050000/84046300/84046253/2fb13370.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Summerland Key

9.8/10

Exceptional

(119)

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

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

Lisa K.

CA $283

CA $722 total

includes taxes & fees

Oct 27 - Oct 28

[](https://www.expedia.ca/Summerland-Key-Hotels-Kellys-Kabin-Adorable-Private-Summerland-Key-Cottage.h84046253.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/a7ddb2fb.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

Raccoon Key

CA $1,826

CA $3,415 total

includes taxes & fees

Oct 26 - Oct 27

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

![Outdoor pool](https://images.trvl-media.com/lodging/77000000/76590000/76584900/76584886/46a74ee5.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)

![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

Key West

9.8/10

Exceptional

(53)

"Nice area, quiet and clean"

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

Gary S.

CA $233

CA $414 total

includes taxes & fees

Oct 28 - Oct 29

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

![Pool](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/37a1453e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/c54b4cae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/95000000/94620000/94616500/94616487/7c92d095.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)

### Palm - Beach Houses Key West

Upper Sugarloaf Key

10/10

Exceptional

(14)

"We had a great time at this out-of-the-way spot. It was quiet, beautiful, and comfortable. Lots to do around the property. The pool area is especially beautiful. Highly recommend!"

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

Crystal G.

CA $885

CA $1,912 total

includes taxes & fees

Nov 4 - Nov 5

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76570000/76568300/76568286/w4000h2998x0y2-2789293b.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)

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

### Poolside Cottage #412

Key West

9.2/10

Wonderful

(26)

"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 $233

CA $414 total

includes taxes & fees

Oct 29 - Oct 30

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

![Property grounds](https://images.trvl-media.com/lodging/74000000/73240000/73238500/73238458/60b95cd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/74000000/73240000/73238500/73238458/ade06e4d.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)

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

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

Little Torch Key

9.6/10

Exceptional

(84)

"The secluded dock is a nice feature. The driveway is tricky to exit. "

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

drywall c.

CA $490

CA $1,053 total

includes taxes & fees

Nov 8 - Nov 9

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

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

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

Cutthroat Harbor Estates

8.4/10

Very good

(117)

"Deer in the front yard, perfect location, clean and friendly "

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

Sara H.

CA $315

CA $754 total

includes taxes & fees

Oct 29 - Oct 30

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

![A heated pool](https://images.trvl-media.com/lodging/107000000/106920000/106911800/106911727/a0a288d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, table tennis, books](https://images.trvl-media.com/lodging/107000000/106920000/106911800/106911727/54d787f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/107000000/106920000/106911800/106911727/62b4ca8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106920000/106911800/106911727/96aae30a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

Cudjoe Key

9.0/10

Wonderful

(7)

"Place was perfect for our trip. Staff was super nice and helpful as well. "

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

Rebecca G.

CA $330

CA $909 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Summerland-Key-Hotels-Salty-Breeze-161-Canal-Front-Venture-Out-Home-On-Cudjoe-Key.h106911727.Hotel-Information)

![On the beach, beach towels](https://images.trvl-media.com/lodging/20000000/19710000/19709400/19709378/f3afeb85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/20000000/19710000/19709400/19709378/94858c4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/20000000/19710000/19709400/19709378/356d9302.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/20000000/19710000/19709400/19709378/673fe9bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Upscale Luxury House on Open Water Gated Community, Dock, Pool, Kayaks, Bikes

Cudjoe Key

9.8/10

Exceptional

(238)

"Lovely property. Well equipped, nicely decorated, perfect for our stay."

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

Karen M.

CA $490

CA $1,144 total

includes taxes & fees

Oct 28 - Oct 29

[](https://www.expedia.ca/Summerland-Key-Hotels-Gated-Community-On-Open-Water-With-Dock.h19709378.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310574/51bad23a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310574/7f2df60c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310574/c2c1b6c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310574/80c5c4f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape

Cudjoe Key

CA $294

CA $863 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Summerland-Key-Hotels-Waterfront-2BR2BA-With-35-Dock.h121310574.Hotel-Information)

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

![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)

![Pool](https://images.trvl-media.com/lodging/109000000/108200000/108195400/108195321/1e7f74ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/109000000/108200000/108195400/108195321/d979d3d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Larkshine House at Lunara Bay

Raccoon Key

10/10

Exceptional

(6)

"well maintained, clean, easy to access"

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

Raj P.

CA $1,679

CA $3,425 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Key-West-Hotels-Brand-New-Build-Larkshine-House-Pool.h108195321.Hotel-Information)

![House](https://images.trvl-media.com/lodging/118000000/118000000/117995500/117995431/f42e4485.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/118000000/118000000/117995500/117995431/2a6c0772.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/118000000/118000000/117995500/117995431/208a6937.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/118000000/118000000/117995500/117995431/bfa871fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### New Waterfront Home - Dreamside House

Raccoon Key

CA $1,784

CA $3,368 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Key-West-Hotels-New-Waterfront-Home-Dreamside-House.h117995431.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/9d72c172.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/30527523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/130b2801.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/40a49494.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Cudjoe Key

CA $257

CA $818 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Summerland-Key-Hotels-Updated-2BR2BA-Venture-Out-Home-W-Pool-Access.h120816897.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/4480719e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/94e8538a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/04d12b41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/b5098a17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Reel Island Retreat #273 at Venture Out in the Florida Keys

Cudjoe Key

9.6/10

Exceptional

(7)

"We really enjoyed our stay here. We really loved sitting on the back porch by the water and the closeness to the community pool and courts. "

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

Lindsay C.

CA $294

CA $863 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Summerland-Key-Hotels-Reel-Island-Retreat-273-At-Venture-Out-In-The-Florida-Keys.h109794896.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=2025-11-08&endDate=2025-11-09&regionId=553248635976197596&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&openPlayBack=true)

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Save an average of 15% on thousands of hotels when you're signed in

[Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FRockland-Key-Private-Vacation-Homes.d553248635976197596-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FRockland-Key-Private-Vacation-Homes.d553248635976197596-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Top Rockland Key Hotel Reviews

![DoubleTree Resort by Hilton Grand Key - Key West](//images.trvl-media.com/lodging/1000000/480000/470900/470834/be4147fb_y.jpg)

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

10/10 Excellent

"Staff was very helpful reported to front desk that ac unit was not working properly. When we return to hotel they informed us they were going to switch our room and give us a balcony room too"

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

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

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

10/10 Excellent

"Was great!"

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

![Parrot Key Hotel & Villas](//images.trvl-media.com/lodging/1000000/30000/24700/24615/b83a5985_y.jpg)

### Parrot Key Hotel & Villas

10/10 Excellent

"."

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

![Hilton Garden Inn Key West / The Keys Collection](//images.trvl-media.com/lodging/1000000/10000/1400/1376/5c83029c_y.jpg)

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

10/10 Excellent

"Our stay at the Hilton Garden Inn Key West was fantastic. The rooms were well appointed, well stocked, and clean. The pool area is beautiful and includes an outdoor bar with great drinks and exceptional staff. The front desk team were all an absolute pleasure to deal with. And the free shuttle to downtown was a great way to explore the entertainment district in Key West. I can absolutely recommend a stay at this hotel. "

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

![Oceans Edge Key West Resort, Hotel & Marina](//images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/3a4457a0_y.jpg)

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

10/10 Excellent

"Beautiful setting - great water views. Room was clean and comfortable - pools were great. "

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

![Blue Flamingo Resort Key West](//images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/cb0a4c1e_y.jpg)

### Blue Flamingo Resort Key West

10/10 Excellent

"All great! "

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

![Hampton Inn Key West FL](//images.trvl-media.com/lodging/1000000/20000/15800/15720/4075e8ff_y.jpg)

### Hampton Inn Key West FL

10/10 Excellent

"Yes"

[](https://expedia.ca/Key-West-Hotels-Hampton-Inn-Key-West-FL.h15720.Hotel-Information)

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

### Beachside Resort & Residences

10/10 Excellent

"Wonderful room, Brilliant friendly staff that go the extra mile. Great shuttle service and amazing restaurant. All in all a very memerable stay to celebrate my husbands 60th Birthday. Thank you xx"

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

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

### Margaritaville Beach House Key West

10/10 Excellent

"Room was clean. Felt safe. Staff was great, very friendly."

[](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 | |
| --- | --- |
| Accommodation | Vacation Homes |
| Lowest Price | |
| Highest Price | |

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-   [Flights from Toronto (YYZ) to Key West (EYW)](https://www.expedia.ca/lp/flights/yyz/eyw/toronto-to-key-west)

-   [Visit Big Coppitt Key](https://www.expedia.ca/Big-Coppitt-Key.dx553248635975850102)
-   [Boca Chica Key Vacations](https://www.expedia.ca/Boca-Chica-Key.d553248635083916609.Destination-Travel-Guides)
-   [Visit Boca Chica Key](https://www.expedia.ca/Boca-Chica-Key.dx553248635083916609)
-   [Boca Chica Nude Beach](https://www.expedia.ca/Boca-Chica-Nude-Beach-Key-West.d553248635983994034.Vacation-Attraction)
-   [Raccoon Key Vacations](https://www.expedia.ca/Raccoon-Key.d180164.Destination-Travel-Guides)
-   [Stock Island Vacations](https://www.expedia.ca/Stock-Island.d180166.Destination-Travel-Guides)
-   [Visit Stock Island](https://www.expedia.ca/Stock-Island.dx180166)

-   [Auto Rent Rental Cars in Boca Chica Key](https://www.expedia.ca/Auto-Rent-Car-Rentals-In-Boca-Chica-Key.d553248635083916609-c1006.Car-Rental-Guide-Suppliers)
-   [Car rentals near Boca Chica Key](https://www.expedia.ca/Car-Rentals-In-Boca-Chica-Key.d553248635083916609.Car-Rental-Guide)
-   [Click & Rent Rental Cars in Key Haven](https://www.expedia.ca/Click-Rent-Car-Rentals-In-Key-Haven.d553248635976197997-c1089.Car-Rental-Guide-Suppliers)
-   [Easirent Rental Cars in Key Haven](https://www.expedia.ca/Easirent-Car-Rentals-In-Key-Haven.d553248635976197997-c1039.Car-Rental-Guide-Suppliers)

-   [Raccoon Key Vacation Rentals](https://www.expedia.ca/Raccoon-Key-Vacation-Rentals.d180164.Travel-Guide-VacationRentals)

-   [Things to do in Big Coppitt Key](https://www.expedia.ca/Things-To-Do-In-Big-Coppitt-Key.d553248635975850102.Travel-Guide-Activities)
-   [Things to do in Boca Chica Key](https://www.expedia.ca/Things-To-Do-In-Boca-Chica-Key.d553248635083916609.Travel-Guide-Activities)
-   [Things to do in Stock Island](https://www.expedia.ca/Things-To-Do-In-Stock-Island.d180166.Travel-Guide-Activities)

-   [Book Vacation Homes in Rockland Key on Expedia.com](https://www.expedia.com/Rockland-Key-Private-Vacation-Homes.d553248635976197596-aaPrivateVacationHomes.Travel-Guide-Accommodation)