Rockland Key Vacation Rentals from $227: Search Short-Term Rentals

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Our top choices for Rockland Key vacation rentals

1. Grand Marina Suite by Brightwild Waterfront

Stock Island

Pawel

$461 nightly

Aug 27 - Aug 28

Total with taxes and fees

2. Aqua Lodges at Hurricane Hole Marina

Stock Island

Kagni

$248 nightly

Aug 26 - Aug 27

Total with taxes and fees

3. Capmar House at Lunara Bay

Raccoon Key

Wilbert C.

$1,307 nightly

Aug 26 - Aug 27

Total with taxes and fees

4. 47ft Viking Yacht · 2 Pools · Perry Marina · Key West

Stock Island

Benjamin

$361 nightly

Aug 26 - Aug 27

Total with taxes and fees

5. Aquaria House at Lunara Bay

Raccoon Key

james f.

$1,307 nightly

Aug 26 - Aug 27

Total with taxes and fees

6. Grand Marina Suite - Poolside & Waterfront Condo

Stock Island

Brent H.

$483 nightly

Aug 27 - Aug 28

Total with taxes and fees

7. Sunny Condo with WiFi, Hot Tub, Pool & Tennis

Key West

Aneesah D.

$640 nightly

Aug 27 - Aug 28

Total with taxes and fees

8. Evershore Estate at Lunara Bay | Wellness Home

Raccoon Key

John F.

$1,309 nightly

Aug 30 - Aug 31

Total with taxes and fees

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Top Rockland Key Hotel Reviews

Havana Cabana at Key West

10/10 Excellent

"I enjoyed every minute of our stay. From when our plane arrived, we only had to wait about 20 minutes for the van to pick us up. The driver was very helpful and got us to the property and checked in quickly with no issues. We even got into our room over an hour early. Once we got situated we spoke with the concierge and set up a couple of activities for the week. We then took the free shuttle to Duval St. All of the drivers were a wealth of knowledge and helped us plan our stay. This was our first time to Key West but it definitely won’t be our last. I loved everything about the island and all the people seemed to be enjoying themselves. What little stress I brought with me was definitely gone within the first full day on island time. What a great time we had. All the staff was always friendly and welcoming and would go out of their way to assist you when they could. I will definitely stay at this location again. It’s perfectly set where you have access to anywhere on the island with the shuttle vans never far away. The porters definitely made me feel at home and they always had some stories of knowledge about the island. I wish I could give each of the porters an individual gift I would. They all deserve every bit of praise they get. Great job Havana Cabana. We will definitely be back !!!"

Casa Marina Key West, Curio Collection by Hilton

8/10 Good

"This place is beautiful and well maintained. Our room had a window that you could see the ocean. Staff was helpful and friendly. The beach was nice but during August the seagrass made it unusable. Only one pool was open due to construction (which we were not notified of) and it was packed. Only flaw for us was the food and drink prices ($11 draft beer or $24 margaritas). But we made the best of it and eat / drank downtown. The spa was amazing."

Pier House Resort & Spa

10/10 Excellent

"We thoroughly enjoyed our stay at Pier House. The location can't be beat--walking distance to most attractions, and golf carts are available onsite for going farther, such as Fort Zachary Taylor. We were treated with complete attention to any of our requests and questions. We typically select a resort with at least a guest laundry, if no in-room washer/dryer, but the laundry service was efficient and reasonably priced. The daily refreshing of linens was nice--seems like that has to be requested at many resorts now or is only after a few nights. They did a good job keeping the sargassum out of the Pier House swimming area and off the beach. Several of the ice machines didn't work, minor inconvenience. We would absolutely stay there again."

DoubleTree Resort by Hilton Grand Key - Key West

8/10 Good

"Joe at the front desk was very helpful. We did have a few issues with housekeeping and being able to get into our room. On four separate occasions, we had to come and have someone readjust the lock on our door because our keys did not work. We did enjoy the complementary coffee each morning."

Find out more about Rockland Key

Everything you need to know about Rockland Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Rockland Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Rockland Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Rockland Key vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Rockland Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Rockland Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $227 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Rockland Key rentals

At Expedia, we put the best Rockland Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Rockland Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Rockland Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Rockland Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Check prices for these dates

Our top choices for Rockland Key vacation rentals

1. Grand Marina Suite by Brightwild Waterfront

2. Aqua Lodges at Hurricane Hole Marina

3. Capmar House at Lunara Bay

4. 47ft Viking Yacht · 2 Pools · Perry Marina · Key West

5. Aquaria House at Lunara Bay

6. Grand Marina Suite - Poolside & Waterfront Condo

7. Sunny Condo with WiFi, Hot Tub, Pool & Tennis

8. Evershore Estate at Lunara Bay | Wellness Home

9. Sunrise Suites Condo with Balcony - Shared Pool, Hot Tub, Tennis, Free Parking

10. Springtide House at Lunara Bay

11. Two Bedroom Residence With Balcony

12. Newly Furnished Suite with Pool, Hot Tub, Tennis, Balcony, Parking - Dog OK

13. Suncoast House at Lunara Bay

14. Mastway House at Lunara Bay - Wellness Home

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

16. The Butterfly Nest | Newly Updated w/ Shared Pool

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

18. Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family

19. Spindrift House at Lunara Bay

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

Find vacation rentals that suit your style

Top Rockland Key Hotel Reviews

Havana Cabana at Key West

Find out more about Rockland Key

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