
Rockland Key Holiday Rentals
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Our top choices for Rockland Key holiday rentals

1. Aqua Lodges at Hurricane Hole Marina
Aqua Lodges at Hurricane Hole Marina
2. Steps from Duval, Pool on Site & Bikes Included!
Steps from Duval, Pool on Site & Bikes Included!
3. Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
5. 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
6. Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
7. The Grand Cayman | Beautifully Remodeled Key West!
The Grand Cayman | Beautifully Remodeled Key West!
8. The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
10. Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
11. The Cat Island Suite | Charmingly Renovated w/ Pool
The Cat Island Suite | Charmingly Renovated w/ Pool
12. QUIET POUR ~ On Duval St, Adult Only, Adjoining Rum Bar and Near Beach!
QUIET POUR ~ On Duval St, Adult Only, Adjoining Rum Bar and Near Beach!
13. ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
14. Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
15. Ricky's Retreat - Truman @ Duval | Ideal Getaway!
Ricky's Retreat - Truman @ Duval | Ideal Getaway!
16. Duval Delight | Recently Remodeled Condo on Duval!
Duval Delight | Recently Remodeled Condo on Duval!
17. Kelly's Kabin - Adorable Private Summerland Key Cottage
Kelly's Kabin - Adorable Private Summerland Key Cottage
18. Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool
Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool
19. Duval Hideaway | Dog-Friendly w/ Shared Hot Tub
Duval Hideaway | Dog-Friendly w/ Shared Hot Tub
20. SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDSFind holiday rentals that suit your style
Top Rockland Key Hotel Reviews

The Southernmost Inn - Adults Only
Find out more about Rockland Key
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Rockland Key holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up Rockland Key. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Rockland Key. Seeing all the best attractions is bound to make you fall in love with Rockland Key. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Rockland Key short-term rentals, that won’t be hard to do.
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