Search Vacation Homes in Rockland Key

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 689 Vacation Homes in Rockland Key with updated reviews, rates, and availability.

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Terrace/patio

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

9.0 out of 10, Wonderful, (31)
"Peaceful and paradise!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
Fridge, microwave, oven, stovetop

SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

9.8 out of 10, Exceptional, (171)
"Accommodations were great. Loft bedroom was a little noisy if people got up early. Noise came straight upstairs. Otherwise accommodations were great. Kitchen well stocked and washer and dryer!! "
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
Property grounds

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

9.6 out of 10, Exceptional, (30)
"This was a very smooth, perfect 5 night visit. The property offered us everything that we could need. It was a short drive to Duval St and all of the activities in Key West yet the property was very peaceful with a wonderful waterfront patio that we sat out on and enjoyed. The hot tub was a nice treat as well. I have to mention the incredible responsiveness of the property manager. Every question that I had they responded to within minutes which was very much appreciated. "
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
A heated pool

OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

9.6 out of 10, Exceptional, (75)
"This was our first time staying in an air b&b. We absolutely loved our stay! We wish we would have booked for longer. We highly recommend this place as it was super clean, spacious, and relaxing! We will be back! "
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
Beachside @ Torchview Waterfront Retreat
On the beach, beach towels

Beachside @ Torchview Waterfront Retreat

9.8 out of 10, Exceptional, (37)
"I had a wonderful 3 weeks stay at Beachside@Torchview. I loved the privacy of the house, the gorgeous sunset views, and the peaceful mornings sitting out on the deck while drinking my morning coffee. I would highly recommend this house for anyone looking for a quiet getaway in the busy Florida Keys. It was everything I had hoped for, and I will definitely be staying here again if I decide to return to the Keys next year. The house was very clean and suited my needs perfectly, and the host...
Beachside @ Torchview Waterfront Retreat
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
Beach

LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool

10.0 out of 10, Exceptional, (186)
"Another fabulous stay at the Lost Shaker of Salt. Great location on Key West. Accommodations met our needs. The pool is delightful. Can’t wait to stay here again when we come back to Key West. "
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
A heated pool

EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

9.8 out of 10, Exceptional, (87)
"Loved the house it was awesome for our group plenty of space for our large group. The beds were very comfortable and every thing was clean and looked new. "
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!
Terrace/patio

~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!

9.8 out of 10, Exceptional, (162)
"Loved this light filled little cottage with a huge back porch and yard. It was a great launching pad for our visit to the area. "
~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!
Poolside Cottage #411
Outdoor dining

Poolside Cottage #411

10.0 out of 10, Exceptional, (33)
"Really nice place to stay. We had a pleasant stay and the property was great "
The price is ￥53,127
￥82,304 total
includes taxes & fees
Jan 8 - Jan 9, 2025
Poolside Cottage #411
Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!
A heated pool

Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!

9.8 out of 10, Exceptional, (98)
"Great place to stay very kid friendly and a short golfcart ride to everything "
Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!
Old Florida Style, wrap around porch, boat basin for dockage, open water
Property grounds

Old Florida Style, wrap around porch, boat basin for dockage, open water

9.8 out of 10, Exceptional, (58)
"Our family of five adults and a dog had a fantastic week at this beautiful house! We had plenty of space, it was super clean and well kept. The countertop ice maker was definitely appreciated! We didn’t cook but all the tools you could need are there. We did place an Instacart order from Publix for a few things and delivery was no problem. Lots of restaurants are within a short drive and Kiki’s right down the road was a plus and had great food. We spent most mornings and evenings hanging out on...
Old Florida Style, wrap around porch, boat basin for dockage, open water
CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
A heated pool

CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!

9.8 out of 10, Exceptional, (111)
"Ok location. 10 minutes to key west. Nice pool"
CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
Pool & Parking, Near Duval - Poolside Paradise
Pool

Pool & Parking, Near Duval - Poolside Paradise

9.2 out of 10, Wonderful, (11)
"Great location 1/2 block from Duval. Lots of great towels, and pillows! I didn’t know this is two units connected but no connecting door, you access back unit via the pool. We needed both sofa beds but one had broken springs and was unusable. The floors hadn’t been mopped and all of my kids had black feet from walking around barefoot. If you are planning to cook you might want to bring a decent frying pan and a sharp knife. They have plenty of knives but none sharp. The grill didn’t work and...
The price is ￥118,985
￥225,004 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Pool & Parking, Near Duval - Poolside Paradise
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
On the beach, sun loungers, beach towels

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (219)
"Perfect location with sunset views and kayaking "
The price is ￥46,893
￥116,256 total
includes taxes & fees
Jan 8 - Jan 9, 2025
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Dec. Spec Only dates 12 (2-5) 12 (8-11) & 12 (14-19) Near beach full kitch
Exterior detail

Dec. Spec Only dates 12 (2-5) 12 (8-11) & 12 (14-19) Near beach full kitch

9.6 out of 10, Exceptional, (204)
"Cute, older place in good location, with nice front porch. You can walk, but we rented bikes, and glad we did. Because you have to park on street and only in designated areas, it's hard to find a spot. Place did not seem that clean. Floors were really dirty. Walked 10 steps after getting out of shower and our feet were black!"
Dec. Spec Only dates 12 (2-5) 12 (8-11) & 12 (14-19) Near beach full kitch
Poolside Cottage #412
Outdoor dining

Poolside Cottage #412

9.8 out of 10, Exceptional, (16)
"Quiet area of the key west neighbors quiet, nice bike ride to key west and grocery store was close by. Would recommend renting from the resort"
The price is ￥53,127
￥81,833 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Poolside Cottage #412
3 night minimum! Spectacular Ocean Views!
A heated pool

3 night minimum! Spectacular Ocean Views!

8.4 out of 10, Very Good, (18)
"Venture out is a great location for being on the water. This rental was reasonable, spacious and clean! We had an amazing stay with no issues!"
3 night minimum! Spectacular Ocean Views!
NEWLY REMODELED KITCHEN!! PET FRIENDLY! 3 Bedroom 3 bathroom home. Sleeps 8
Outdoor pool, a heated pool

NEWLY REMODELED KITCHEN!! PET FRIENDLY! 3 Bedroom 3 bathroom home. Sleeps 8

9.6 out of 10, Exceptional, (196)
"Exactly as advertised with an incredible host. We had a great time in Key West! "
NEWLY REMODELED KITCHEN!! PET FRIENDLY! 3 Bedroom 3 bathroom home. Sleeps 8
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
A heated pool

SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!

9.8 out of 10, Exceptional, (171)
"Beautiful, well appointed home in a great neighborhood. Great communication and lovely experience!"
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
A heated pool

CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

9.6 out of 10, Exceptional, (173)
"Captains Quarters is a beautiful house, great location, walking distance to Duval, clean, heated pool and plenty of amenities to make your stay enjoyable. Would def stay there again. "
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
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.
Don't see what you're looking for?
See all available properties in Rockland Key
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Rockland Key

Aqua Lodges at Hurricane Hole Marina
Restaurant

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (106)
"Nice for affordable price "
The price is ￥32,395
￥58,548 total
includes taxes & fees
Jan 7 - Jan 8, 2025
Aqua Lodges at Hurricane Hole Marina
Steps from Duval, Pool on Site & Bikes Included!
Beach towels

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (358)
"very clean, was able to park the car and walk to where we wanted to go. I would stay again."
The price is ￥24,992
￥49,690 total
includes taxes & fees
Jan 9 - Jan 10, 2025
Steps from Duval, Pool on Site & Bikes Included!
Poolside Cottage #411
Outdoor dining

Poolside Cottage #411

10.0 out of 10, Exceptional, (33)
"Really nice place to stay. We had a pleasant stay and the property was great "
The price is ￥53,127
￥82,304 total
includes taxes & fees
Jan 8 - Jan 9, 2025
Poolside Cottage #411
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.