Holiday Homes in Rockland Key

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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Holiday Homes in Rockland Key

MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
Fridge, microwave, oven, stovetop

MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!

9.6 out of 10, Exceptional, (209)
"Outstanding property! Cannot recommend highly enough!"
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
TROPICAL RETREAT ~ 3 Bedroom/3.5 Bath 1/2 Block from Duval w/ Heated Pool!
Terrace/patio

TROPICAL RETREAT ~ 3 Bedroom/3.5 Bath 1/2 Block from Duval w/ Heated Pool!

9.6 out of 10, Exceptional, (89)
"Property was amazing, exactly what is shown in the listing, beds were extremely comfortable, will stay again"
TROPICAL RETREAT ~ 3 Bedroom/3.5 Bath 1/2 Block from Duval w/ Heated Pool!
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
A heated pool

BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!

9.6 out of 10, Exceptional, (81)
"This property is perfectly located near Duval street and within walking distance to the marina. A perfect location for those wanting to shop and enjoy the amenities the marina has to offer. We can’t wait to go back. "
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
Tropical Key West out of the way
Pool

Tropical Key West out of the way

9.4 out of 10, Exceptional, (172)
"Good spot for longer trips and never a problem parking. Easy trip to Old Town and the Lower Keys for other activities. We always stay at least a week and take our pup, so its great for us. Close to The Perry Hotel for both a great Happy Hour and fine diningDining"
The price is NZ$908
includes taxes & fees
2 Aug - 3 Aug
Tropical Key West out of the way
DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!
A heated pool

DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!

10.0 out of 10, Exceptional, (1)
"We absolutely loved our stay at the Delaney house. The pool and outdoor area were lovely and private, the location was excellent and walking distance from fun Key West spots but quiet and cozy, and the beds were all incredibly comfortable! Would definitely recommend this place to everyone!"
DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!
Harbor Walk Hideaways | Group Compound In Old Town!
Outdoor dining

Harbor Walk Hideaways | Group Compound In Old Town!

10.0 out of 10, Exceptional, (4)
"I come to Key West often. This is the best location and property I’ve stayed in. Everything was wonderful. I will book this every single time I come. it is perfect for big families, couples or a group of friends. "
The price is NZ$1,568
includes taxes & fees
27 July - 28 July
Harbor Walk Hideaways | Group Compound In Old Town!
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, (185)
"We had 3 couples and the location was great. The house was very nice. "
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
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, (188)
"We loved the house. From the location, to ambiance and heated pool- it was all amazing! We didn’t cook at all and spent most of our time out and about, but we used the pool day and night. We had 2 couples and 2 additional friends and it was the perfect amount of space and privacy! Would highly recommend this spot and nearby is a cute little bike shop to easily rent a bike cruiser or golf cart for your time! "
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!
Interior

ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!

9.8 out of 10, Exceptional, (137)
"The place was everything that was advertised! Great weather, location, cottage and friends - what could be better!!"
ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!
Waterfront luxury home with private pool
Dining

Waterfront luxury home with private pool

9.8 out of 10, Exceptional, (78)
"We had a wonderful stay at 3/4 time! It is a beautiful VRBO to use in Key West. We truly appreciated all the thoughtful touches that made the place feel like a home away from home.The location was perfect, and the space was clean, comfortable, and well-equipped for a relaxing getaway. We absolueltly loved the heated pool. It was the perfect base for exploring Key West, and we’re already looking forward to our next visit."
Waterfront luxury home with private pool
JUNE-SEPT. WEEKLY DISCOUNT!!! - BOTTOMS UP BUNGALOW 2 Bed/2 Bath PRIVATE POOL
Pool

JUNE-SEPT. WEEKLY DISCOUNT!!! - BOTTOMS UP BUNGALOW 2 Bed/2 Bath PRIVATE POOL

10.0 out of 10, Exceptional, (107)
"Great place to stay for our spring trip as a family of 3. "
The price is NZ$2,191
includes taxes & fees
5 Aug - 6 Aug
JUNE-SEPT. WEEKLY DISCOUNT!!! - BOTTOMS UP BUNGALOW 2 Bed/2 Bath PRIVATE POOL
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Pool

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

10.0 out of 10, Exceptional, (3)
"The place was just as pictured, very comfortable and private. Very clean and spacious. The only issue we had was trying to get the back door to lock. "
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Fridge, microwave, oven, stovetop

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

9.0 out of 10, Wonderful, (151)
"The place was spacious, very clean and beautiful!"
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
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

9.6 out of 10, Exceptional, (77)
"Very nice place to stay. Quick and efficient communication with host! Seemless check in and check out process. "
Old Florida Style, wrap around porch, boat basin for dockage, open water
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
TV

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

10.0 out of 10, Exceptional, (203)
"Wonderful stay!"
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town /Private Heated Pool!
A heated pool

A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town /Private Heated Pool!

9.8 out of 10, Exceptional, (87)
"Great location "
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town /Private Heated Pool!
CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
Dining

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

9.8 out of 10, Exceptional, (135)
"Property was clean and comfortable with everything we needed. Only complaint is the late check in time."
CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!
A heated pool

CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!

9.8 out of 10, Exceptional, (218)
"We had a great time and loved the property "
CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!
Luxury two floor apartment in prime location of famous Duval Street
Beach towels

Luxury two floor apartment in prime location of famous Duval Street

9.6 out of 10, Exceptional, (82)
"Perfect place to stay. Great location. "
The price is NZ$1,194
includes taxes & fees
11 Aug - 12 Aug
Luxury two floor apartment in prime location of famous Duval Street
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
Outdoor dining

Nassau Suite just steps to Duval Tropical oasis quiet location Downtown

9.0 out of 10, Wonderful, (237)
"We had a really great time in Key West and much of it was due to the accommodations, as it was clean, offered every amenity and then some but most importantly was the location! The Courtyard was serene and quiet, and you didn't feel like you were just steps away from the activity of Duval Street and could just about walk to everything! We were REALLY happy we stayed here!! "
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
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

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"Only issue was the $200 per night hold on card"
James 5-night trip
Posted 23 hours ago
Casa Marina Key West, Curio Collection by Hilton