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Rockland Key Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Rockland Key vacation rentals

A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

1. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (199 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is ￥17,093
￥46,344 total
includes taxes & fees
Oct 13 - Oct 14
Aqua Lodges at Hurricane Hole Marina
A hot tub with a view of a marina and boats during sunset.

2. Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (62 reviews)
"Great would definitely stay again "
United States
Zach C.
The price is ￥66,490
￥83,983 total
includes taxes & fees
Oct 13 - Oct 14
Living the Dream Key West Style
A beachside resort with a wooden deck, palm trees, and a sunset view.

3. Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
2.0 star property
Stock Island
10.0 out of 10, Exceptional, (3 reviews)
"Nice place "
United States
Pawel
The price is ￥64,953
￥111,542 total
includes taxes & fees
Oct 13 - Oct 14
Grand Marina Suite by Brightwild Waterfront
A tropical garden pathway leading to a building with a yellow facade and green shutters.

4. SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (138 reviews)
"Great place to stay"
United States
walter l.
The price is ￥28,179
￥59,387 total
includes taxes & fees
Oct 25 - Oct 26
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
A modern living room with a sofa, coffee table, and a painting of a beach scene.

5. The Saint Kitts Suite | Breathtaking View, Heated Pool

The Saint Kitts Suite | Breathtaking View, Heated Pool
Key West
9.6 out of 10, Exceptional, (9 reviews)
"Beautifully decorated and great location. The condo was clean, comfortable, quiet and well stocked. Would recommend and definitely stay there again!"
United States
Linda W.
The price is ￥27,514
￥79,267 total
includes taxes & fees
Oct 13 - Oct 14
The Saint Kitts Suite | Breathtaking View, Heated Pool
A wide sandy beach with palm trees and a clear sky.

6. Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.

Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
Key West
9.2 out of 10, Wonderful, (115 reviews)
"I enjoyed my stay at the resort, highly recommend!"
United States
Michelaine a.
The price is ￥47,335
￥74,683 total
includes taxes & fees
Oct 15 - Oct 16
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
A wooden boardwalk leading to a building with a green roof, surrounded by lush greenery and palm trees.

7. The Cat Island Suite | Charmingly Renovated w/ Pool

The Cat Island Suite | Charmingly Renovated w/ Pool
Key West
9.8 out of 10, Exceptional, (47 reviews)
"I liked that it was pretty centrally located to everything very nice Thank you we had a great time "
United States
Patti E.
The Cat Island Suite | Charmingly Renovated w/ Pool
A narrow alleyway with white buildings, a stone pathway, and various plants.

8. Welcome Matt's - Truman @ Duval | Perfect Hideaway!

Welcome Matt's - Truman @ Duval | Perfect Hideaway!
Old Town Key West
9.8 out of 10, Exceptional, (33 reviews)
"The apartment was perfect for a trip to Key West!! Super good communication with the host. Their bus happened to be at the airport when I landed and even got to enjoy a complimentary ride from the airport! They went the extra mile and I can’t wait to book again!"
United States
John
The price is ￥24,031
￥73,435 total
includes taxes & fees
Oct 13 - Oct 14
Welcome Matt's - Truman @ Duval | Perfect Hideaway!
A wide sandy beach with palm trees and a clear sky.

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

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Key West
9.0 out of 10, Wonderful, (49 reviews)
"Great place for our 1 night in key west "
United States
Thadd W.
The price is ￥56,200
￥85,764 total
includes taxes & fees
Oct 25 - Oct 26
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
A wooden signpost with city names and distances in miles.

10. Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!
Old Town Key West
9.6 out of 10, Exceptional, (458 reviews)
"This studio is in a wonderful location and comes with bikes and a pool spa. It is a fabulous place to stay for a relaxing get-away island-style."
United States
Laura D.
The price is ￥15,530
￥37,776 total
includes taxes & fees
Oct 13 - Oct 14
Steps from Duval, Pool on Site & Bikes Included!
A beach with lounge chairs, palm trees, and a water body.

11. Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.6 out of 10, Exceptional, (35 reviews)
"Pool was great! Just far enough from Duval street to get away and relax if needed or jump in the car and head down for live music! "
United States
Brent H.
The price is ￥47,493
￥99,973 total
includes taxes & fees
Oct 13 - Oct 14
Grand Marina Suite - Poolside & Waterfront Condo
A wooden boardwalk leading to a hotel with a green roof, surrounded by palm trees and a water feature.

12. The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
Key West
10.0 out of 10, Exceptional, (35 reviews)
"Very nice clean place. Had a minor problem with the beds after checking in but property manager was quick to respond and correct issue. Would stay here again. "
United States
Teri K.
The price is ￥27,514
￥78,476 total
includes taxes & fees
Oct 26 - Oct 27
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
Exterior

13. Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (3 reviews)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
The price is ￥34,036
￥53,000 total
includes taxes & fees
Oct 13 - Oct 14
Island View 1BR Residence With Balcony
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

14. Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
Stock Island
9.6 out of 10, Exceptional, (136 reviews)
"I can't say enough about how wonderful this property is or the host."
United States
Linda
The price is ￥33,483
￥82,312 total
includes taxes & fees
Oct 13 - Oct 14
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A wooden deck with rows of green lounge chairs facing the ocean, a rope barrier, and a distant view of the sunset over the water.

15. Luxury Waterfront at Galion Resort in Old Town

Luxury Waterfront at Galion Resort in Old Town
Key West Historic District
9.6 out of 10, Exceptional, (113 reviews)
"A great place for my family to stay on our trip! Lots of room and all the amenities you could need for a perfect trip to Key West."
United States
Katie C.
The price is ￥106,859
￥135,415 total
includes taxes & fees
Nov 3 - Nov 4
Luxury Waterfront at Galion Resort in Old Town
A narrow brick pathway flanked by white buildings with potted plants and a bench.

16. Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West

Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West
Old Town Key West
9.8 out of 10, Exceptional, (27 reviews)
"Awesome location & very helpful host!"
United States
Jay M.
The price is ￥18,807
￥59,151 total
includes taxes & fees
Oct 25 - Oct 26
Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West
A bedroom with two beds, a ceiling fan, a window with curtains, a wall clock, and a decorative plate.

17. Waterfront Condo Dock Pool Downtown Near Duval

Waterfront Condo Dock Pool Downtown Near Duval
Meadows
9.6 out of 10, Exceptional, (30 reviews)
"Wow, this was one of the best short term rentals we've done. Well appointed, extremely clean, convenient location, and everything pretty much top of the line."
United States
John L.
Waterfront Condo Dock Pool Downtown Near Duval
A fish cleaning station with a sign, wooden structure, and water.

18. Waterfront Dock Pool Key West Near Duval

Waterfront Dock Pool Key West Near Duval
Meadows
10.0 out of 10, Exceptional, (40 reviews)
"We loved our stay! Beautiful room with a wonderful view. We loved how quiet and relaxing it was!"
United States
Jesse B.
Waterfront Dock Pool Key West Near Duval
A wooden deck with a large tree, outdoor seating, and a marina in the background.

19. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Wonderful stay. Thank you."
United States
shannon b.
The price is ￥26,359
￥48,236 total
includes taxes & fees
Oct 18 - Oct 19
Poolside Cottage #412
A living room with a sofa, two chairs, a coffee table, a TV, and a ceiling fan.

20. Hollinsed House Studio - Great Location!!

Hollinsed House Studio - Great Location!!
Old Town Key West
9.6 out of 10, Exceptional, (162 reviews)
"Nice location, clean, & would stay there again"
United States
Karen L.
The price is ￥21,006
￥69,025 total
includes taxes & fees
Oct 13 - Oct 14
Hollinsed House Studio - Great Location!!
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

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

8/10 Good
"Not applicable."
Nhia 2-night trip
Posted 2 hours ago
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

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