Rockland Key Holiday Rentals

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Our top choices for Rockland Key holiday rentals

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (1)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is S$1,188
includes taxes & fees
18 Dec - 19 Dec
Atlantic View Luxury Villa with Pool

Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (2)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
The price is S$542
includes taxes & fees
15 Dec - 16 Dec
Island View 1BR Residence With Balcony

Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West
3.5 star property
Old Town Key West
8.4 out of 10, Very good, (319)
"Place was great bed was comfy and the water was HOT!!! "
United States
Angela
The price is S$394
includes taxes & fees
16 Dec - 17 Dec
Hyatt Vacation Club at Sunset Harbor, Key West

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (170)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is S$397
includes taxes & fees
14 Dec - 15 Dec
Aqua Lodges at Hurricane Hole Marina

Coconut Mallory Marina and Resort Condo

Coconut Mallory Marina and Resort Condo
3.0 star property
Key West
The price is S$1,696
includes taxes & fees
20 Dec - 21 Dec
Coconut Mallory Marina and Resort Condo

Contra House Key West

Contra House Key West
3.0 star property
Old Town Key West
The price is S$1,686
includes taxes & fees
14 Dec - 15 Dec
Contra House Key West

The Grenada Suite Pool View Private Balcony

The Grenada Suite Pool View Private Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (1)
The price is S$739
includes taxes & fees
15 Dec - 16 Dec
The Grenada Suite Pool View Private Balcony

The Trinidad by Brightwild Pool View Parking

The Trinidad by Brightwild Pool View Parking
2.0 star property
Key West
10.0 out of 10, Exceptional, (1)
"Our family spent one night at Key West and we fully enjoyed our stay here. Room is very clean, stylish and spacious. Beds are comfortable."
United States
Xiulin
The price is S$741
includes taxes & fees
15 Dec - 16 Dec
The Trinidad by Brightwild Pool View Parking

Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
2.0 star property
Stock Island
10.0 out of 10, Exceptional, (3)
"Nice place "
United States
Pawel
Grand Marina Suite by Brightwild Waterfront

The Bartlum Luxury Studio In Prime Location

The Bartlum Luxury Studio In Prime Location
2.0 star property
Key West Historic District
The price is S$588
includes taxes & fees
15 Dec - 16 Dec
The Bartlum Luxury Studio In Prime Location

Duval Dream Loft by Brightwild Right on Duval

Duval Dream Loft by Brightwild Right on Duval
2.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (1)
Duval Dream Loft by Brightwild Right on Duval

Sunnyside Up by Brightwild Pool Parking

Sunnyside Up by Brightwild Pool Parking
3.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (1)
The price is S$1,082
includes taxes & fees
15 Dec - 16 Dec
Sunnyside Up by Brightwild Pool Parking

Mesa House Uno by Brightwild Perfect Location

Mesa House Uno by Brightwild Perfect Location
2.0 star property
Key West Historic District
The price is S$1,262
includes taxes & fees
11 Jan - 12 Jan, 2026
Mesa House Uno by Brightwild Perfect Location

New The Cottage at James House

New The Cottage at James House
2.0 star property
Key West Historic District
8.0 out of 10, Very good, (2)
"The best thing about this property is location. Short walk to everything - short walk to Sloppy Joes. It is overpriced for the accommodations but you pay for location. "
United States
Pamela
The price is S$1,081
includes taxes & fees
11 Jan - 12 Jan, 2026
New The Cottage at James House

New Coastal Rose - Bright Loft With High Ceilings

New Coastal Rose - Bright Loft With High Ceilings
2.0 star property
Key West Historic District
New Coastal Rose - Bright Loft With High Ceilings

Ocean Front 1BR Suite With Direct Beach Access

Ocean Front 1BR Suite With Direct Beach Access
2.0 star property
Key West
10.0 out of 10, Exceptional, (2)
"Clean and spacious. Great view from room!"
United States
Jacqueline
The price is S$712
includes taxes & fees
15 Dec - 16 Dec
Ocean Front 1BR Suite With Direct Beach Access

Two Bedroom Residence With Balcony

Two Bedroom Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (1)
"The roosters crowing early morning was irritating "
United States
Catherine
The price is S$871
includes taxes & fees
16 Dec - 17 Dec
Two Bedroom Residence With Balcony

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is S$844
includes taxes & fees
16 Dec - 17 Dec
Starlight Serenity - Hideaway w Stunning Views

Poolside Suite by Brightwild Pvt Pool Parking

Poolside Suite by Brightwild Pvt Pool Parking
2.0 star property
Old Town Key West
Poolside Suite by Brightwild Pvt Pool Parking

Sky Suite on Duval by Brightwild Condo w Balcony

Sky Suite on Duval by Brightwild Condo w Balcony
2.0 star property
Old Town Key West
Sky Suite on Duval by Brightwild Condo w Balcony
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