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In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Rockland Key condo rentals

A swimming pool with lounge chairs, palm trees, and a view of the sunset over the water.

1. Pool View Suite | Beachside Resort

Pool View Suite | Beachside Resort
Key West
8.0 out of 10, Very good, (3 reviews)
"It was a holiday weekend. Key West in general all lodging was expensive. The room was very comfortable and clean. More than enough room. I was on the water which was amazing. The pool area was very awesome. Love that they have a bar and restaurant available. All the available excursions. I took advantage of the Sunset Tour. Property manager was available for any questions. Beachside staff was also very helpful. Would definitely visit again. Great Experience!! Thank you."
United States
Christie Y.
$249 nightly
The price is $276
Sep 20 - Sep 21
Total with taxes and fees
Pool View Suite | Beachside Resort
A brick pathway leading to a white staircase with a covered area above.

2. BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!

BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
Old Town Key West
10.0 out of 10, Exceptional, (6 reviews)
"The room was so perfect! Perfectly nestled just down a brick sidewalk right on Duval st. Closer to Southern most point, nice walking distance to Mallory square. The room was perfect for us."
United States
Sarah
$234 nightly
The price is $260
Sep 17 - Sep 18
Total with taxes and fees
BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
A wooden boardwalk leading to a building with a green roof, surrounded by lush greenery and palm trees.

3. 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.
$434 nightly
The price is $482
Sep 17 - Sep 18
Total with taxes and fees
The Cat Island Suite | Charmingly Renovated w/ Pool
A wooden boardwalk leading to a hotel with a green roof, surrounded by lush greenery and palm trees.

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

The Butterfly Nest | Newly Updated w/ Shared Pool
Key West
9.8 out of 10, Exceptional, (48 reviews)
"Had a great time place is lovely "
United States
Sarah P.
$446 nightly
The price is $496
Sep 17 - Sep 18
Total with taxes and fees
The Butterfly Nest | Newly Updated w/ Shared Pool
A wooden boardwalk leading to a hotel with a green roof, surrounded by palm trees and a water feature.

5. 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.
$434 nightly
The price is $482
Sep 17 - Sep 18
Total with taxes and fees
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
A gym with treadmills, elliptical machines, free weights, and exercise balls.

6. Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.2 out of 10, Wonderful, (24 reviews)
"Great stay"
United States
Dustin H.
$507 nightly
The price is $563
Sep 17 - Sep 18
Total with taxes and fees
Grand Marina Suite - Poolside & Waterfront Condo
A swimming pool area with multiple pools, palm trees, lounge chairs, and a clear blue sky.

7. Atlantic Parrot | Oceanfront Condo w/ Pool

Atlantic Parrot | Oceanfront Condo w/ Pool
Beachside
9.8 out of 10, Exceptional, (9 reviews)
"Absolutely beautiful property as well as room I loved it everything about it was beautiful "
United States
Misty C.
$668 nightly
The price is $742
Sep 17 - Sep 18
Total with taxes and fees
Atlantic Parrot | Oceanfront Condo w/ Pool
A tropical garden pathway leading to a building with a yellow facade and green shutters.

8. 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, (137 reviews)
"Great place to stay"
United States
walter l.
$271 nightly
The price is $301
Sep 18 - Sep 19
Total with taxes and fees
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
A wooden pathway leading to a beach with palm trees and a clear blue sky.

9. Island Time | Luxury Beach Condo w/ Pool & Hot Tub

Island Time | Luxury Beach Condo w/ Pool & Hot Tub
Key West
10.0 out of 10, Exceptional, (9 reviews)
"Neat and clean, spacious, easy walking access to the beach, nice amenities on the property with pool and hot tub."
United States
Stacey P.
$504 nightly
The price is $562
Sep 29 - Sep 30
Total with taxes and fees
Island Time | Luxury Beach Condo w/ Pool & Hot Tub
A spacious living room with a large flat-screen TV, a teal sofa, a coffee table, and a view of the ocean through large windows.

10. Waterfront Dock Pool Condo Near Duval St Pet OK

Waterfront Dock Pool Condo Near Duval St Pet OK
Meadows
9.4 out of 10, Exceptional, (48 reviews)
"Hosts are super responsive and helpful. Perfect location. Would absolutely stay here again! "
United States
Amber G.
$309 nightly
The price is $344
Sep 22 - Sep 23
Total with taxes and fees
Waterfront Dock Pool Condo Near Duval St Pet OK
A small, single-story building with a green roof and white walls, featuring a covered outdoor seating area with a trash bin and a small air conditioning unit.

11. The Tahiti Suite | Updated Key West Condo w/ Pool, Hot Tub, & Balcony!

The Tahiti Suite | Updated Key West Condo w/ Pool, Hot Tub, & Balcony!
Key West
$425 nightly
The price is $471
Sep 17 - Sep 18
Total with taxes and fees
The Tahiti Suite | Updated Key West Condo w/ Pool, Hot Tub, & Balcony!
A wooden boardwalk leading to a hotel with a pool and palm trees.

12. The Grenada at Sunrise Suites - Shared Pool

The Grenada at Sunrise Suites - Shared Pool
Naval Air Station Key West
8.8 out of 10, Excellent, (13 reviews)
"We had a lovely time- thank you"
United States
Jackie Y.
$460 nightly
The price is $512
Sep 17 - Sep 18
Total with taxes and fees
The Grenada at Sunrise Suites - Shared Pool
A tropical garden pathway leading to a building with a yellow facade and green shutters.

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!
Old Town Key West
9.6 out of 10, Exceptional, (111 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The studio and surroundings matched photos posted and provided a Key West atmosphere and experience. Walking to Key West activities and sites was feasible. Very happy with and positive addition to our Key West visit."
United States
Ken L.
$271 nightly
The price is $301
Sep 18 - Sep 19
Total with taxes and fees
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
A wide sandy beach with palm trees and a clear sky.

14. 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.
$354 nightly
The price is $395
Sep 20 - Sep 21
Total with taxes and fees
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
A hotel room with a bed, a television on a dresser, a chair, and a window with curtains.

15. The Tortuga at Sunrise Suites - Balcony & Pool

The Tortuga at Sunrise Suites - Balcony & Pool
Key West
8.6 out of 10, Excellent, (30 reviews)
"We were very impressed with the grounds. Loved the pool area. Was extremely clean"
United States
Margaret G.
$431 nightly
The price is $480
Sep 23 - Sep 24
Total with taxes and fees
The Tortuga at Sunrise Suites - Balcony & Pool
A narrow stone pathway flanked by a yellow building with a white fence and a wall-mounted electrical box.

16. Hidden Key West Cottage - Walk to Duval !!!

Hidden Key West Cottage - Walk to Duval !!!
Old Town Key West
10.0 out of 10, Exceptional, (3 reviews)
"Host was great! Fast response and easy to work with. Very, very, very clean! Quiet area A"
United States
Regina E.
$204 nightly
The price is $227
Sep 23 - Sep 24
Total with taxes and fees
Hidden Key West Cottage - Walk to Duval !!!
A wide sandy beach with palm trees and a clear sky.

17. 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
9.2 out of 10, Wonderful, (47 reviews)
"Great place for our 1 night in key west "
United States
Thadd W.
$369 nightly
The price is $410
Sep 20 - Sep 21
Total with taxes and fees
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
An outdoor patio area with tables and chairs, surrounded by palm trees and potted plants.

18. Key West 2BR | Pool, Hot Tub, Balcony & Parking

Key West 2BR | Pool, Hot Tub, Balcony & Parking
KEY WEST
9.2 out of 10, Wonderful, (5 reviews)
"Beautiful, clean condo . Just as listed.Scott has been a pleasure to work with. Beds could use mattress pads for comfort, but everything else is perfect. We will be returning. "
United States
Joe B.
$510 nightly
The price is $569
Sep 23 - Sep 24
Total with taxes and fees
Key West 2BR | Pool, Hot Tub, Balcony & Parking
A marina with boats docked, a clear sky, and a rainbow.

19. Waterfront Condo Dock Pool Near Duval St

Waterfront Condo Dock Pool Near Duval St
Meadows
9.8 out of 10, Exceptional, (29 reviews)
"Great stay! Beautiful view. No complaints. Easy check in and great communication with owner. Thanks for a great trip!"
United States
Haley P.
$360 nightly
The price is $400
Sep 21 - Sep 22
Total with taxes and fees
Waterfront Condo Dock Pool Near Duval St
A covered balcony with wicker chairs, a view of palm trees, and multiple flags.

20. AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!

AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
Old Town Key West
9.8 out of 10, Exceptional, (11 reviews)
"Friendly and clean place, love the look and location will be back"
United States
Amanda G.
$246 nightly
The price is $273
Sep 17 - Sep 18
Total with taxes and fees
AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
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

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

8/10 Good
"The property should have advertised that it was off season and there were amenities closed. The beach was closed the pool was closed. Those were two reasons we chose this resort. We also had a noise issue with the room and the front desk staff tried to give us ear plugs instead of trying to find another room."
Robert 4-night trip
Posted less than an hour ago
Southernmost Beach Resort and Guesthouses

Find out more about Rockland Key

Rockland Key Condo Rentals information

Number of reviews
280
Accommodation
339 Condo Rentals
Lowest Price
$227
Highest Price
$742

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