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Compare 689 Vacation Homes in Rockland Key with updated reviews, rates, and availability.

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
Property grounds
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
9.6 out of 10, Exceptional, (29)
"Beautiful property, amazing outdoor space on the water, clean and comfortable Given the cleaning fees are 50% of the cost I was little annoyed at how much check out chores are required of the guests. "
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w/ Private Pool!
A heated pool
BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w/ Private Pool!
9.8 out of 10, Exceptional, (59)
"Excellent location, clean, roomy, wonderful!"
BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w/ Private Pool!
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
A heated pool
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
9.6 out of 10, Exceptional, (74)
"My brother and I hadn’t seen each other for quite a while. This place offered us so much comfort and convenience. GREAT place to stay. We will be back. Thank you. "
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
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, (114)
"The cottage was perfect for two couples. Both bedrooms had attached bathrooms. Just a few houses down from Duval Street and a few blocks from the beach."
ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Beach nearby
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
9.0 out of 10, Wonderful, (67)
"Very quiet, clean, and overall great experience. I’ve been staying at properties in the Keys for over 20 years and this is one of the best experiences I have had."
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Terrace/patio
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
9.0 out of 10, Wonderful, (30)
"Peaceful and paradise!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
Fridge, microwave, oven, stovetop
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
9.8 out of 10, Exceptional, (10)
"Property was clean with everything we needed, including linens and beach towels. Kitchen was fully equipped. The upstairs was a little too warm at night, but it was in the 90's every day during our stay, so we could understand this. One of the twin beds has a mattress that was very uncomfortable, and needs replaced. We have a vacation rental of our own and we were well pleased with this property. We would recommend! Thank you for the little longer checkout time, as the hurricane changed...
The price is ￥92,580
￥223,909 total
includes taxes & fees
Nov 17 - Nov 18
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK
Fridge, microwave, oven, stovetop
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK
9.0 out of 10, Wonderful, (183)
"Had a great time. Great location. Doesn’t provide more than one trash bag which was an issue we ran into. "
The price is ￥49,993
￥109,585 total
includes taxes & fees
Nov 24 - Nov 25
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK
Poolside Cottage #411
Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (27)
"Nice STAY"
The price is ￥27,157
￥48,972 total
includes taxes & fees
Nov 18 - Nov 19
Poolside Cottage #411
Poolside Cottage #412
Outdoor dining
Poolside Cottage #412
10.0 out of 10, Exceptional, (13)
"Nice place right by the pool."
The price is ￥27,157
￥48,972 total
includes taxes & fees
Nov 18 - Nov 19
Poolside Cottage #412
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
Terrace/patio
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
9.8 out of 10, Exceptional, (21)
"Clean, cozy and cute "
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
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, (201)
"The house was clean and conveniently located. We walked to everything!"
CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!
Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location
Fridge, microwave, coffee/tea maker, toaster
Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location
9.0 out of 10, Wonderful, (169)
"My sister and I rented the place for ourselves and our 4 young adult kids (ranging from 18-21), and we had a very nice time. The AC is not really "central", has free-standing units in 2 of the bedrooms that vent outside, but they are well installed and do the trick, if a bit tricky to regulate the temperature correctly initially. The place is a typical Key West bungalow that feels like some shoeboxes were nailed together, and the back yard is even smaller than expected. Location is great, we did...
The price is ￥35,335
￥88,126 total
includes taxes & fees
Nov 21 - Nov 22
Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location
Kelly's Kabin - Adorable Private Summerland Key Cottage
Fridge, microwave, oven, stovetop
Kelly's Kabin - Adorable Private Summerland Key Cottage
9.8 out of 10, Exceptional, (104)
"Check in was super easy.Over all was a very comfortable place.Air condition was nice and cold..Everything worked properly.Located just South of Boondocks Bar&Grille which os one of our favorite spots.Easy to get back and forth to Key West.Would definately stay here again."
The price is ￥42,433
￥93,352 total
includes taxes & fees
Dec 1 - Dec 2
Kelly's Kabin - Adorable Private Summerland Key Cottage
20 MINUTES TO KEY WEST , BOATERS PARADISE
Exterior
20 MINUTES TO KEY WEST , BOATERS PARADISE
9.6 out of 10, Exceptional, (43)
"We enjoyed our stay. The resort area itself was nice and convenient for our needs. Communication with host was excellent. Any questions were promptly answered, as well as additional info to help us in the area. The property description is accurate. We'd be pleased to stay there again."
20 MINUTES TO KEY WEST , BOATERS PARADISE
Year Rd. w.7 night stay get 10% Off!. Full kitchen & outside area 1/2 mile beach
Terrace/patio
Year Rd. w.7 night stay get 10% Off!. Full kitchen & outside area 1/2 mile beach
9.0 out of 10, Wonderful, (153)
"A lovely, typical property located in Old Town area of Key West. Very comfortable stay, quiet ensuring good sleep. Great location and I did everything either by walking or on the bicycle I hired. Excellent communication with host who replied within a couple of hours if not sooner!!"
Year Rd. w.7 night stay get 10% Off!. Full kitchen & outside area 1/2 mile beach
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, (168)
"Lively house accommodating the 6 of us very well, with a cozy pool in the backyard. Speedy response for any questions. Clean, comfortable and within a short walk of the Duval St. attractions."
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
Outdoor dining
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
9.6 out of 10, Exceptional, (79)
"The stay was good. It was close enough to wedding venue. Few things wrong when we got there. My husband fixed the closet door because it would not open n shut also a door knob was about to fall off so he tightened it."
The price is ￥30,706
￥76,726 total
includes taxes & fees
Nov 17 - Nov 18
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Outdoor dining
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
9.4 out of 10, Exceptional, (25)
"The property is nicely decorated just as the pictures posted in the listing. Fully equipped with everything you need in the kitchen. All very cleaned. Location is great! It is also within a reasonable driving distance to Key West. "
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
12% Off Wk.stay Feb,March & April 1/2 mile 2 beach, full kitchen & front porch
Exterior detail
12% Off Wk.stay Feb,March & April 1/2 mile 2 beach, full kitchen & front porch
9.6 out of 10, Exceptional, (199)
"Very walkable. Cozy comfortable place. Cute and safe neighborhood. Setup well for cooking. AC pumps some good cold air. "
12% Off Wk.stay Feb,March & April 1/2 mile 2 beach, full kitchen & front porch
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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Other property types in Rockland Key

Aqua Lodges at Hurricane Hole Marina
Restaurant
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (104)
"Nice for affordable price "
The price is ￥17,915
￥41,851 total
includes taxes & fees
Nov 18 - Nov 19
Aqua Lodges at Hurricane Hole Marina
Steps from Duval, Pool on Site & Bikes Included!
Beach towels
Steps from Duval, Pool on Site & Bikes Included!
9.6 out of 10, Exceptional, (355)
"We walked most everywhere and loved the Southernmost Beach Bar! Eating at Moon Dog Cafe was so spectacular that we ate there 3 times in 2 days! This place is all it says it is. Simply perfect. "
The price is ￥15,276
￥36,821 total
includes taxes & fees
Dec 2 - Dec 3
Steps from Duval, Pool on Site & Bikes Included!
Poolside Cottage #411
Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (27)
"Nice STAY"
The price is ￥27,157
￥48,972 total
includes taxes & fees
Nov 18 - Nov 19
Poolside Cottage #411
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.