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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Featured Cottages in Rockland Key

Heart of Downtown Key West Cottage With Off-Street Parking
Exterior

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (120)
"Perfect spot for small group or couple to stay one block over from Duval St. Highly recommend staying here!"
Heart of Downtown Key West Cottage With Off-Street Parking
Cottage with Pool and Boat Dockage just minutes to Key West!
Exterior

Cottage with Pool and Boat Dockage just minutes to Key West!

8.6 out of 10, Excellent, (134)
"Perfect location for us 23 miles to key west. Restaurants near by, pool, fishing pier. Can't wait to come back and do it all over again!"
Cottage with Pool and Boat Dockage just minutes to Key West!
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Outdoor pool

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

8.8 out of 10, Excellent, (155)
"Place was very clean. The property is in need of upkeep and updating. It was hit in the last hurricane. "
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
Terrace/patio

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

9.2 out of 10, Wonderful, (12)
"Great location. Walkable to everywhere we wanted to go. Comfortable beds"
The price is NZ$515
includes taxes & fees
29 Apr - 30 Apr
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
The Dancing Rooster: 2 Blocks from Duval in Old Town.
Beach nearby

The Dancing Rooster: 2 Blocks from Duval in Old Town.

10.0 out of 10, Exceptional, (118)
"3 relaxing days"
The price is NZ$1,261
includes taxes & fees
12 May - 13 May
The Dancing Rooster: 2 Blocks from Duval in Old Town.
Cottage with Pool and Dockage, just minutes to Key West
Pool

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (140)
"We had a wonderful time at your place. Thank you for having us, we loved the Keys!"
The price is NZ$584
includes taxes & fees
1 May - 2 May
Cottage with Pool and Dockage, just minutes to Key West
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Fridge, microwave, oven, stovetop

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

9.0 out of 10, Wonderful, (72)
"My family and I enjoyed our stay. It was very convenient to everything we wanted to do. Would definitely stay again."
The price is NZ$604
includes taxes & fees
29 Apr - 30 Apr
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!
Beach

SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!

9.4 out of 10, Exceptional, (23)
"Lovely, quiet property. I really enjoyed my stay. Pool was heated. Wonderful place to relax under the stars."
SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!
Direct Oceanfront Cottage-Sunrise View- #2,
On the beach

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (174)
"Very comfortable and clean place right by water, had a great stay "
Direct Oceanfront Cottage-Sunrise View- #2,
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Beach nearby

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

8.0 out of 10, Very good, (39)
"It's a good quiet place about 20 miles from Key West. The property itself has seen its best years-- it has aged now but functional. The entrance is a bit tricky to find, right off of the highway. Overall a good place if you don't mind driving back and forth between Key West attractions. "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Beach nearby

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

8.8 out of 10, Excellent, (68)
"Place was everything we needed, would definitely stay again "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
Terrace/patio

Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!

9.6 out of 10, Exceptional, (11)
"Was perfect tucked away spot on quiet end of Island but walking distance to everything. "
The price is NZ$588
includes taxes & fees
5 May - 6 May
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
Charming cottages, dockage, pool, just minutes to Key West
Fridge, microwave, oven, stovetop

Charming cottages, dockage, pool, just minutes to Key West

8.6 out of 10, Excellent, (114)
"Amazing place for a getaway. Very calm quiet area and close to 2 nice beaches. "
Charming cottages, dockage, pool, just minutes to Key West
Quaint cottage, pool, dockage just minutes to Key West!
Miscellaneous

Quaint cottage, pool, dockage just minutes to Key West!

9.0 out of 10, Wonderful, (135)
"It is what it is, only wish the furniture was not worn out. "
Quaint cottage, pool, dockage just minutes to Key West!
Canal front, dockage, 2 bedroom, 2 bath
Outdoor pool, a heated pool

Canal front, dockage, 2 bedroom, 2 bath

9.0 out of 10, Wonderful, (81)
"Excellent appearance, location, amenities and comfort. Bedrooms are a little tight but manageable. Host was very responsive and easy to work with. "
Canal front, dockage, 2 bedroom, 2 bath
HIDDEN OASIS 3 blocks from Duval
TV

HIDDEN OASIS 3 blocks from Duval

2.5 star property
9.4 out of 10, Exceptional, (86)
"Great location, loved the pool and outdoor patio"
The price is NZ$1,333
includes taxes & fees
8 May - 9 May
HIDDEN OASIS 3 blocks from Duval
Get your ISLAND STLYE on!
Exterior

Get your ISLAND STLYE on!

2.0 star property
9.6 out of 10, Exceptional, (79)
"My husband enjoyed the pool and locale"
The price is NZ$1,403
includes taxes & fees
24 May - 25 May
Get your ISLAND STLYE on!
Cottage with swimming pool and dockage, just minutes to Key West!
Miscellaneous

Cottage with swimming pool and dockage, just minutes to Key West!

9.0 out of 10, Wonderful, (145)
"We had a wonderful stay in a small cottage in Cudjoe Key. It was a fun little place stay. Location was great for visiting the other Keys. I would seriously look at staying in one of the bigger cottages if I brought my family down. Thank you very much!"
Cottage with swimming pool and dockage, just minutes to Key West!
STAR FISH COTTAGE, Sleeps 4 - Summer Vacation, Lobster & Fishing Season is Here!
Sun-loungers, beach towels

STAR FISH COTTAGE, Sleeps 4 - Summer Vacation, Lobster & Fishing Season is Here!

9.6 out of 10, Exceptional, (51)
"Clean, convenient, great host. Would definitely stay again! Especially enjoyed the daily pastries!!"
STAR FISH COTTAGE, Sleeps 4 - Summer Vacation, Lobster & Fishing Season is Here!
ISLE BE BACK To The Sunny Keys
Fridge, microwave, oven, stovetop

ISLE BE BACK To The Sunny Keys

9.6 out of 10, Exceptional, (30)
"Had a great time with family for mini season. Would definitely rent again. Beautiful place and plenty of room!"
ISLE BE BACK To The Sunny Keys
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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Other property types in Rockland Key

Aqua Lodges at Hurricane Hole Marina
Restaurant

Aqua Lodges at Hurricane Hole Marina

2.0 star property
9.0 out of 10, Wonderful, (133)
"Would definitely stay here again! "
The price is NZ$551
includes taxes & fees
5 May - 6 May
Aqua Lodges at Hurricane Hole Marina
Hyatt Vacation Club at Sunset Harbor, Key West
Outdoor pool

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very good, (294)
"We had a nice stay. The property was in a great location."
The price is NZ$668
includes taxes & fees
4 May - 5 May
Hyatt Vacation Club at Sunset Harbor, Key West
Coconut Mallory Resort And Marina By Kees Vacations
2 outdoor pools

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (808)
"Very tropical, on the water. Everything u need in amenities. Pools were great!"
Coconut Mallory Resort And Marina By Kees Vacations
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.