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Holiday Homes in Rockland Key

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Our top choices for Rockland Key holiday homes

1. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (68 reviews)
"Excellent cottage in a quiet location. Our family of 4 enjoyed the stay & plan to return in the future!"
United States
Jennifer W.
Poolside Cottage #411

2. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (36 reviews)
"Very pleasant and generally a nice quiet community. "
United States
Julia M.
The price is AU$431
includes taxes & fees
23 Aug - 24 Aug
Poolside Cottage #412

3. TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking

TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking
Stock Island
10.0 out of 10, Exceptional, (23 reviews)
"Great place nice and clean easy access to the pool short drive to the beach"
United States
Nathan W.
The price is AU$1,352
includes taxes & fees
23 Aug - 24 Aug
TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking

4. Aug.-Sept. Special@125.lodging Only 129. + extras. From.8-17 to 9-30

Aug.-Sept. Special@125.lodging Only 129. + extras. From.8-17 to 9-30
Old Town Key West
9.0 out of 10, Wonderful, (198 reviews)
"Fantastic location! Close enough to walk to all the things, but very quiet and relaxing to hang out. Loved the back deck. Owner was very responsive and helpful. Neighbors were nice as well."
United States
Jeanine
The price is AU$448
includes taxes & fees
31 Aug - 1 Sept
Aug.-Sept. Special@125.lodging Only 129. + extras. From.8-17 to 9-30

5. Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (38 reviews)
"Great to stay. Good places to eat close by."
United States
Robert B.
The price is AU$917
includes taxes & fees
8 Sept - 9 Sept
Paradise found

6. Gone Coastal

Gone Coastal
Stock Island
9.6 out of 10, Exceptional, (22 reviews)
"Great place , clean and close to everything!"
United States
april
The price is AU$861
includes taxes & fees
23 Aug - 24 Aug
Gone Coastal

7. Spacious 3-bedroom townhome on Stock Island with resort style pool.

Spacious 3-bedroom townhome on Stock Island with resort style pool.
Stock Island
10.0 out of 10, Exceptional, (7 reviews)
"Perfect for our family trip to Key West. Great location and we enjoyed the pool and nearby restaurants. Easy check in and check out process and clear, timely communication with the owner. "
United States
Samantha P.
The price is AU$855
includes taxes & fees
11 Aug - 12 Aug
Spacious 3-bedroom townhome on Stock Island with resort style pool.

8. Road's End | Prime Old Town Location! Updated Home w/ Pool

Road's End | Prime Old Town Location! Updated Home w/ Pool
Old Town Key West
9.8 out of 10, Exceptional, (20 reviews)
"The property was very clean with an excellent location. "
United States
Mike T.
The price is AU$729
includes taxes & fees
8 Sept - 9 Sept
Road's End | Prime Old Town Location! Updated Home w/ Pool

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

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Excellent location - clean, quiet, well-kept community. Boat launch was key for us. Pool and beach looked very nice, but we didn't use. The unit is as described and has a nice patio out back that we used every day."
United States
Cheryl V.
The price is AU$768
includes taxes & fees
1 Sept - 2 Sept
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

10. Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food."
United States
max
The price is AU$928
includes taxes & fees
17 Aug - 18 Aug
Starlight Serenity - Hideaway w Stunning Views

11. Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West

Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West
Cudjoe Key
The price is AU$917
includes taxes & fees
15 Aug - 16 Aug
Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West

12. SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (95 reviews)
"Great location, very clean, and a responsive host. We enjoyed our stay and highly recommended this spot!"
United States
David T.
The price is AU$607
includes taxes & fees
12 Aug - 13 Aug
SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

13. Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (5 reviews)
"Property was perfectly located and very clean and comfortable."
United States
Kiara
The price is AU$842
includes taxes & fees
17 Aug - 18 Aug
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

14. SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (110 reviews)
"Stay was great. We met the hosts and they were wonderful people."
United States
James B.
The price is AU$607
includes taxes & fees
16 Aug - 17 Aug
SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

15. Luxury two floor apartment in prime location of famous Duval Street

Luxury two floor apartment in prime location of famous Duval Street
Old Town Key West
9.6 out of 10, Exceptional, (103 reviews)
"Great stay at a great location. Apartment was very clean. Enjoyed the balcony overlooking Duval St. "
United States
Gregory L.
The price is AU$834
includes taxes & fees
11 Aug - 12 Aug
Luxury two floor apartment in prime location of famous Duval Street

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

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Cudjoe Key
8.0 out of 10, Very good, (3 reviews)
" Great 2 bedroom home in a lovely vacation community . We enjoyed the 2 recliners to relax after a full day of exploring as well as in the morning with our coffee. The screened in patio was a nice perk as well . At check in , a calendar of events was provided and the staff were friendly and helpful. FYI : We enjoyed a gorgeous sunrise right by the beach near the pool ."
United States
jim b.
The price is AU$796
includes taxes & fees
1 Sept - 2 Sept
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

17. Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (128 reviews)
"Very nice place. Centrally located near good restaurants, markets, etc.. Pet friendly which worked for us. Nice long walking trail behind cottage."
United States
John B.
The price is AU$747
includes taxes & fees
11 Aug - 12 Aug
Kelly's Kabin - Adorable Private Summerland Key Cottage

18. Aquaria House at Lunara Bay

Aquaria House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (44 reviews)
"Absolutely amazing property with great access to the water and an amazing pool. Our fishing guide picked us up at the dock, very convenient. The back porch was a treat, plenty of room to sit and visit. The community the house is in is really nice. Highly recommend this property."
United States
John-Ryan H.
The price is AU$2,017
includes taxes & fees
11 Aug - 12 Aug
Aquaria House at Lunara Bay

19. Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29 reviews)
"The Best VRBO I have stayed in "
United States
Wilbert C.
The price is AU$1,997
includes taxes & fees
17 Aug - 18 Aug
Capmar House at Lunara Bay

20. Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Cudjoe Key
9.6 out of 10, Exceptional, (4 reviews)
"Stayed with family and good location for family vacations. "
United States
Phani U.
The price is AU$870
includes taxes & fees
17 Aug - 18 Aug
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
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

Find out more about Rockland Key

Rockland Key Holiday Homes information

Number of reviews
787
Accommodation
856 Holiday Homes
Lowest Price
AU$431
Highest Price
AU$2,017

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