Search Vacation Homes in Rockland Key

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Vacation Homes in Rockland Key

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.
$390 nightly
The price is $433
Nov 17 - Nov 18
Total with taxes and fees
NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

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.
$487 nightly
The price is $541
Nov 20 - Nov 21
Total with taxes and fees
Kelly's Kabin - Adorable Private Summerland Key Cottage

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
$535 nightly
The price is $594
Nov 15 - Nov 16
Total with taxes and fees
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

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.
$472 nightly
The price is $524
Nov 16 - Nov 17
Total with taxes and fees
NOV. & DEC. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Waterfront Luxury Home - Tidelands House

2.0 star property
Raccoon Key
$2,689 nightly
The price is $3,025
Nov 19 - Nov 20
Total with taxes and fees
Waterfront Luxury Home - Tidelands House

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.
$555 nightly
The price is $616
Nov 17 - Nov 18
Total with taxes and fees
Island Time #110 Ocean Views - Cudjoe Key

Poolside Cottage #411

Key West
9.8 out of 10, Exceptional, (53)
"Clean and as advertised "
United States
John H.
$266 nightly
The price is $296
Nov 16 - Nov 17
Total with taxes and fees
Poolside Cottage #411

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.
$629 nightly
The price is $698
Nov 19 - Nov 20
Total with taxes and fees
Old Florida Style, wrap around porch, boat basin for dockage, open water

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.
$420 nightly
The price is $466
Nov 30 - Dec 1
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

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
$486 nightly
The price is $539
Nov 18 - Nov 19
Total with taxes and fees
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

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

2.0 star property
Cudjoe Key
$530 nightly
The price is $588
Nov 15 - Nov 16
Total with taxes and fees
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

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.
$558 nightly
The price is $619
Nov 15 - Nov 16
Total with taxes and fees
Reel Island Retreat #273 at Venture Out in the Florida Keys

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.
$266 nightly
The price is $296
Nov 16 - Nov 17
Total with taxes and fees
Poolside Cottage #412

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.
$1,439 nightly
The price is $1,579
Nov 19 - Nov 20
Total with taxes and fees
Palm - Beach Houses Key West

New Waterfront Home - Dreamside House

2.0 star property
Raccoon Key
$2,689 nightly
The price is $3,025
Nov 19 - Nov 20
Total with taxes and fees
New Waterfront Home - Dreamside House

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.
$612 nightly
The price is $680
Nov 17 - Nov 18
Total with taxes and fees
Spanish Queen @Venture Out, Cudjoe Key

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

2.0 star property
Cudjoe Key
$551 nightly
The price is $612
Nov 15 - Nov 16
Total with taxes and fees
Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape

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.
$667 nightly
The price is $740
Nov 18 - Nov 19
Total with taxes and fees
Paradise found

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.
$585 nightly
The price is $650
Nov 17 - Nov 18
Total with taxes and fees
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

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.
$315 nightly
The price is $349
Nov 17 - Nov 18
Total with taxes and fees
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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