Vacation Rentals in Monroe County

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Top Cities in Monroe County

Top Vacation Rentals in Monroe County

Tropical Cottages

3.0 star property
8.4 out of 10, Very Good, (817)
"Cute place, convenient location"
The price is ¥15,992
¥17,991 total
includes taxes & fees
Jun 29 - Jun 30
Tropical Cottages

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (147)
"Would definitely stay here again! "
The price is ¥10,206
¥35,787 total
includes taxes & fees
Jun 22 - Jun 23
Aqua Lodges at Hurricane Hole Marina

Yacht Haven Marina

3.5 star property
9.8 out of 10, Exceptional, (159)
"Excellent place, beautiful, super relaxing"
Yacht Haven Marina

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (488)
"Laid back atmosphere with renovated rooms."
The price is ¥14,662
¥24,012 total
includes taxes & fees
Jun 22 - Jun 23
Breezy Palms Resort

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (239)
"price - clean and newly renovated boats - nice staff - easy check in/out."
Old Wooden Bridge Resort and Marina

Knight's Key Suites

3.0 star property
9.0 out of 10, Wonderful, (1120)
"It was reasonable and near where we were going."
The price is ¥13,637
¥18,459 total
includes taxes & fees
Jun 29 - Jun 30
Knight's Key Suites

Cabins at Bonefish Bay

3.0 star property
10.0 out of 10, Exceptional, (47)
"Property and staff were great and would stay there again. The only thing we weren’t fond of was the water pressure in faucets was very low for showering."
Cabins at Bonefish Bay

Treasure Harbor

3.0 star property
9.0 out of 10, Wonderful, (80)
"Very clean and great atmosphere "
The price is ¥22,054
¥45,201 total
includes taxes & fees
Jun 22 - Jun 23
Treasure Harbor

Aqua Lodges at 47th Street Gulfside

3.0 star property
8.4 out of 10, Very Good, (39)
"Loved the location! Had such a great time and watched beautiful sunsets every night from the local dock. "
The price is ¥21,297
¥44,350 total
includes taxes & fees
Jun 29 - Jun 30
Aqua Lodges at 47th Street Gulfside

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1190)
"Staff is very friendly, food was delicious! "
Skipjack Resort & Marina

VanGogh Studio | Updated, Old Town, Heated Pool

8.4 out of 10, Very Good, (20)
"We loved our stay. The room was great, small but all we needed. "
The price is ¥14,877
¥41,371 total
includes taxes & fees
Jul 1 - Jul 2
VanGogh Studio | Updated, Old Town, Heated Pool

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (61)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is ¥78,828
¥96,696 total
includes taxes & fees
Jun 25 - Jun 26
The Islands of Islamorada

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very Good, (814)
"Great place really nice rooms"
Coconut Mallory Resort And Marina By Kees Vacations

Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

8.0 out of 10, Very Good, (9)
"Kevin and Capt. Phil were great hosts. Would definitely stay there again. "
The price is ¥20,300
¥83,648 total
includes taxes & fees
Jul 10 - Jul 11
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

9.6 out of 10, Exceptional, (136)
"We had a great 2 night stay while in Key West. The property was as advertised.The FREE off-street parking was an excellent perk.The location was very good as it was within walking distance of the heart of Key West."
The price is ¥13,775
¥35,563 total
includes taxes & fees
Jun 22 - Jun 23
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (125)
"Perfect spot for small group or couple to stay one block over from Duval St. Highly recommend staying here!"
Heart of Downtown Key West Cottage With Off-Street Parking

Key Largo Cottages

2.5 star property
9.4 out of 10, Exceptional, (20)
"The stay was great and the property manager Jenn was amazing. Would stay again"
Key Largo Cottages

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (388)
"Beautiful place and weather "
The price is ¥13,434
¥33,564 total
includes taxes & fees
Jun 22 - Jun 23
Steps from Duval, Pool on Site & Bikes Included!

CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!

9.8 out of 10, Exceptional, (114)
"Excellent location, walkable to Duval Street. We were able to park on-site and walk to everything. We would definitely stay here again."
The price is ¥14,210
¥35,906 total
includes taxes & fees
Jun 24 - Jun 25
CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (176)
"We would definitely stay here again! Great location, exactly as described, overall great place."
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
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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