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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar
Outdoor dining
NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cudjoe Key
9.6 out of 10, Exceptional, (98)
"This is a great place to stay, neighborhood is nice, very convenient with the marina and boat ramp on site. I would definitely stay here again. "
United States
Edward H.
The price is HK$1,158
HK$3,365 total
includes taxes & fees
17 Nov - 18 Nov
NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Fridge, microwave, oven, stovetop
Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage

Summerland Key
9.8 out of 10, Exceptional, (120)
"Great location for some much needed time away."
United States
Brad R.
The price is HK$1,748
HK$4,202 total
includes taxes & fees
20 Nov - 21 Nov
Kelly's Kabin - Adorable Private Summerland Key Cottage
A heated pool
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2.5 star property
Cudjoe Key
9.2 out of 10, Wonderful, (7)
"A cozy, clean, and great stay in Cudjoe! Only 30 mins from Key West."
United States
Javier
The price is HK$1,469
HK$4,613 total
includes taxes & fees
15 Nov - 16 Nov
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Outdoor pool, a heated pool
NOV. & DEC. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

NOV. & DEC. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cudjoe Key
9.8 out of 10, Exceptional, (82)
"Great property, owners were very helpful and we really enjoyed our stay!"
United States
Lee J.
The price is HK$1,702
HK$4,070 total
includes taxes & fees
16 Nov - 17 Nov
NOV. & DEC. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
8 bedrooms, Internet
Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House

2.0 star property
Raccoon Key
The price is HK$14,183
HK$23,509 total
includes taxes & fees
15 Dec - 16 Dec
Waterfront Luxury Home - Tidelands House
A heated pool
Island Time #110 Ocean Views - Cudjoe Key

Island Time #110 Ocean Views - Cudjoe Key

2.5 star property
Cudjoe Key
9.4 out of 10, Exceptional, (10)
"Greta property, really enjoyed the water view and the bbq grill "
United States
William B.
The price is HK$1,632
HK$4,789 total
includes taxes & fees
17 Nov - 18 Nov
Island Time #110 Ocean Views - Cudjoe Key
Outdoor dining
Poolside Cottage #411

Poolside Cottage #411

Key West
9.8 out of 10, Exceptional, (53)
"Clean and as advertised "
United States
John H.
The price is HK$1,294
HK$2,298 total
includes taxes & fees
16 Nov - 17 Nov
Poolside Cottage #411
Property grounds
Old Florida Style, wrap around porch, boat basin for dockage, open water

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

Little Torch Key
9.6 out of 10, Exceptional, (85)
"Just a beautiful location, paradise. Spent mornings in the covered porch, husband loved the lagoon for fishing. We brought kayaks and the kids loved it. The dogs enjoyed the large property as well. "
United States
Kendra K.
The price is HK$2,331
HK$5,422 total
includes taxes & fees
19 Nov - 20 Nov
Old Florida Style, wrap around porch, boat basin for dockage, open water
Exterior detail
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Cudjoe Key
10.0 out of 10, Exceptional, (2)
"Absolutely love it here… Randy is great to work with and always available. "
United States
Jeannine R.
The price is HK$1,842
HK$3,620 total
includes taxes & fees
30 Nov - 1 Dec
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Balcony
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Cutthroat Harbor Estates
8.4 out of 10, Very good, (117)
"The whole experience was decent until the last night. We met with a lot of termites and two cockroaches"
United States
Kiril
The price is HK$1,748
HK$4,189 total
includes taxes & fees
18 Nov - 19 Nov
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
A heated pool
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

2.0 star property
Cudjoe Key
The price is HK$1,428
HK$4,567 total
includes taxes & fees
19 Nov - 20 Nov
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
A heated pool
Reel Island Retreat #273 at Venture Out in the Florida Keys

Reel Island Retreat #273 at Venture Out in the Florida Keys

Cudjoe Key
9.6 out of 10, Exceptional, (7)
"Very clean place"
United States
Michael T.
The price is HK$1,632
HK$4,789 total
includes taxes & fees
23 Nov - 24 Nov
Reel Island Retreat #273 at Venture Out in the Florida Keys
Outdoor dining
Poolside Cottage #412

Poolside Cottage #412

Key West
9.2 out of 10, Wonderful, (27)
"very nice bungalow right in front of the pool. Well maintained and comfortable. Was a great place to stay."
United States
DONALD H.
The price is HK$1,294
HK$2,298 total
includes taxes & fees
16 Nov - 17 Nov
Poolside Cottage #412
Pool
Palm - Beach Houses Key West

Palm - Beach Houses Key West

Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14)
"Excellent place to stay if you are seeking a getaway off the beaten path. Well landscaped to give privacy to each bungalow. 2 amazing piers to fish/jet ski from. The pool and grill area is a PERFECT place to cool off and escape the heat with the swim up bar. The staff even gave us coconuts to enjoy fresh from their trees. Each day we saw amazing wildlife and even had key deer visit us. We are considering booking the whole place for a family reunion. Would also make for a great corporate...
United States
Robert K.
The price is HK$5,983
HK$12,270 total
includes taxes & fees
19 Nov - 20 Nov
Palm - Beach Houses Key West
8 bedrooms, Internet
New Waterfront Home - Dreamside House

New Waterfront Home - Dreamside House

2.0 star property
Raccoon Key
The price is HK$14,183
HK$23,509 total
includes taxes & fees
15 Dec - 16 Dec
New Waterfront Home - Dreamside House
Outdoor pool, a heated pool
Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key

Cudjoe Key
9.4 out of 10, Exceptional, (19)
"This home was perfect for our family of four to enjoy a few days in paradise. The amenities provided were amazing and the home was beautiful. The host was very easy to contact and attentive to any questions we had. We will definitely be back again and highly recommend this property."
United States
Mandy M.
The price is HK$2,720
HK$5,280 total
includes taxes & fees
17 Nov - 18 Nov
Spanish Queen @Venture Out, Cudjoe Key
A heated pool
Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape

Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape

2.0 star property
Cudjoe Key
The price is HK$1,632
HK$4,734 total
includes taxes & fees
23 Nov - 24 Nov
Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape
Outdoor dining
Paradise found

Paradise found

Stock Island
9.8 out of 10, Exceptional, (31)
"Nice stay and budget friendly. Hard to find a place to house 5 guys but this an accomplished that easily. Conveniently located to the airport and the restaurants in the area were great. If your trip in Key West involves the marina, the marina is just behind the hogfish grill. "
United States
Mike Q.
The price is HK$3,101
HK$5,750 total
includes taxes & fees
18 Nov - 19 Nov
Paradise found
A heated pool
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

Cudjoe Key
9.4 out of 10, Exceptional, (27)
"Lovely property by the water in Cudjoe Key. Very comfortable and well equipped. Host was very communicative and location was great for getting to Key West and other local attractions. Would definitely stay again! "
United Kingdom
Tom K.
The price is HK$1,836
HK$5,049 total
includes taxes & fees
17 Nov - 18 Nov
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
Property grounds
Shared Pool & Parking - The Cottage at James House

Shared Pool & Parking - The Cottage at James House

Key West Historic District
9.6 out of 10, Exceptional, (4)
"This cottage is just as pictured, really cute. It could use more storage in the bathroom, there is no counter space and nowhere to put shampoo in the shower. Also the tv is internet, no cable. The music from Duvall at night and trash trucks and street cleaning in the morning can be loud, but the AC blocks most of it.The host was very responsive and helpful on txt, and we had onsite off street parking which was great.We mostly loved this place and would be very happy to return "
United States
Lorraine C.
The price is HK$1,360
HK$2,715 total
includes taxes & fees
17 Nov - 18 Nov
Shared Pool & Parking - The Cottage at James House
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

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"Great setting and overall experience. Beautiful grounds!"
Michael 2-night trip
Posted 3 days ago
Winslow's Bungalows - Key West Historic Inns

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Rockland Key Vacation Homes information

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