Holiday Homes in Rockland Key

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Check prices for these dates

Next weekend
7 Nov - 9 Nov
In two weeks
14 Nov - 16 Nov
In one month
28 Nov - 30 Nov
In two months
26 Dec - 28 Dec

Featured Holiday Homes in Rockland Key and around

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
9.6 out of 10, Exceptional, (84)
"The secluded dock is a nice feature. The driveway is tricky to exit. "
United States
drywall c.
The price is €614
includes taxes & fees
19 Nov - 20 Nov
Old Florida Style, wrap around porch, boat basin for dockage, open water
Outdoor pool, a heated pool
OCT. & NOV. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
OCT. & NOV. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
9.8 out of 10, Exceptional, (81)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is €462
includes taxes & fees
9 Nov - 10 Nov
OCT. & NOV. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Outdoor dining
OCT. & NOV. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
OCT. & NOV. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
9.6 out of 10, Exceptional, (98)
"Clean place with room for 2 couples. Everything you need."
United States
Jason W.
The price is €372
includes taxes & fees
30 Oct - 31 Oct
OCT. & NOV. 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
9.8 out of 10, Exceptional, (119)
"We enjoyed our stay! Great little house and location. "
United States
Lisa K.
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
9.2 out of 10, Wonderful, (7)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is €523
includes taxes & fees
30 Oct - 31 Oct
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
A heated pool
Island Time #110 Ocean Views - Cudjoe Key
Island Time #110 Ocean Views - Cudjoe Key
2.5 star property
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 €546
includes taxes & fees
30 Oct - 31 Oct
Island Time #110 Ocean Views - Cudjoe Key
Outdoor pool
One of the very few beach houses with a daily, rental license in the Keys.
One of the very few beach houses with a daily, rental license in the Keys.
8.8 out of 10, Excellent, (64)
"My family and I had an incredible stay. We utilized every available component of the home including the dock. Property manager provided us with 2 available free ramps to drop off our jet-skis. We settled on the ramp located on Blimp Road, which was a 10 minute drive and 15-20 minute ride on the skis. We were able to tie off our skis our whole stay with no issues. Home was exactly as disclosed and worked great for our family. Communication was great, with quick respond time. "
United States
Yissel W.
The price is €1,123
includes taxes & fees
11 Nov - 12 Nov
One of the very few beach houses with a daily, rental license in the Keys.
Outdoor pool, a heated pool
Spanish Queen @Venture Out, Cudjoe Key
Spanish Queen @Venture Out, Cudjoe Key
9.4 out of 10, Exceptional, (19)
"We enjoyed our stay at venture out at the Spanish main residence it was lovely and we are going to return again next year"
United States
susan l.
The price is €593
includes taxes & fees
11 Nov - 12 Nov
Spanish Queen @Venture Out, Cudjoe Key
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
The price is €517
includes taxes & fees
30 Oct - 31 Oct
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
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
The price is €547
includes taxes & fees
11 Nov - 12 Nov
Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape
Balcony
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
8.4 out of 10, Very good, (117)
"Deer in the front yard, perfect location, clean and friendly "
United States
Sara H.
The price is €475
includes taxes & fees
30 Oct - 31 Oct
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Beach nearby
Beach Getaway in the Florida Keys
Beach Getaway in the Florida Keys
8.4 out of 10, Very good, (7)
"Amazing property and views. Tom was great and very helpful with places to go and things to do. Will definitely recommend!!"
United States
Robyn M.
Beach Getaway in the Florida Keys
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
9.6 out of 10, Exceptional, (7)
"We really enjoyed our stay here. We really loved sitting on the back porch by the water and the closeness to the community pool and courts. "
United States
Lindsay C.
Reel Island Retreat #273 at Venture Out in the Florida Keys
On the beach, beach towels
Upscale Luxury House on Open Water Gated Community, Dock, Pool, Kayaks, Bikes
Upscale Luxury House on Open Water Gated Community, Dock, Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (238)
"Lovely property. Well equipped, nicely decorated, perfect for our stay."
United States
Karen M.
The price is €720
includes taxes & fees
30 Oct - 31 Oct
Upscale Luxury House on Open Water Gated Community, Dock, Pool, Kayaks, Bikes
A heated pool
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key
2.0 star property
9.0 out of 10, Wonderful, (7)
"Place was perfect for our trip. Staff was super nice and helpful as well. "
United States
Rebecca G.
The price is €576
includes taxes & fees
30 Oct - 31 Oct
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key
A heated pool
Mahi House #440 - 35' seawall
Mahi House #440 - 35' seawall
10.0 out of 10, Exceptional, (1)
"The house was just right. Nice community. Quiet and peaceful. Just what we needed. The host was kind and responsive. "
United States
Emily P.
The price is €541
includes taxes & fees
30 Oct - 31 Oct
Mahi House #440 - 35' seawall
A heated pool
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Property grounds
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
2.0 star property
The price is €604
includes taxes & fees
11 Nov - 12 Nov
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
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
9.4 out of 10, Exceptional, (27)
"Close to Key West and lots of great boating"
United States
Simon S.
The price is €624
includes taxes & fees
11 Nov - 12 Nov
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
Pool
Palm - Beach Houses Key West
Palm - Beach Houses Key West
10.0 out of 10, Exceptional, (14)
"We had a great time at this out-of-the-way spot. It was quiet, beautiful, and comfortable. Lots to do around the property. The pool area is especially beautiful. Highly recommend!"
United States
Crystal G.
Palm - Beach Houses Key West
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
"Clean room amazing beach"
Josh 4-night trip
Posted 8 hours ago
Casa Marina Key West, Curio Collection by Hilton

Find out more about Rockland Key

Rockland Key Holiday Homes information

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