Holiday Rentals in Monroe County

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Top Cities in Monroe County

Featured Holiday Rentals in Monroe County

Old Wooden Bridge Resort and Marina

2.5 star property
8.4 out of 10, Very good, (189)
"Nice quiet area Everyone is so friendly and the little deer , are just adorable "
The price is €314
includes taxes & fees
11 Feb - 12 Feb
Old Wooden Bridge Resort and Marina

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1152)
"The staff at the front desk and the restaurant were great! "
The price is €528
includes taxes & fees
20 Feb - 21 Feb
Skipjack Resort & Marina

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (404)
"nice warm pool, nice ocean views."
The price is €235
includes taxes & fees
10 Mar - 11 Mar
Breezy Palms Resort

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (114)
"Great getaway, yet very close to Key West. It is about a 5-10 minute drive from property to Duval Street."
The price is €439
includes taxes & fees
23 Feb - 24 Feb
Aqua Lodges at Hurricane Hole Marina

Yacht Haven Marina

3.5 star property
9.8 out of 10, Exceptional, (111)
"There was issues with air conditioning. Staff did fix it. We would stay there again. "
Yacht Haven Marina

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (49)
"Lovely room with friendly staff. "
The price is €887
includes taxes & fees
6 Mar - 7 Mar
The Islands of Islamorada

Tropical Cottages

3.0 star property
8.4 out of 10, Very good, (779)
"We enjoyed our stay in Cottage 4. Everything was clean and the bed was very comfortable. It was quiet in the neighborhood of the cottages and the Taco truck had good food. Very nice stay! Thank you!"
The price is €217
includes taxes & fees
11 Feb - 12 Feb
Tropical Cottages

Knight's Key Suites

3.0 star property
9.0 out of 10, Wonderful, (1084)
"What you should expect on the Keys"
The price is €238
includes taxes & fees
14 Feb - 15 Feb
Knight's Key Suites

Aqua Lodge Rentals At Coconut Cay

3.5 star property
9.6 out of 10, Exceptional, (136)
"To be fair, its the first time we stay at a houseboat so we didn't know what to expect. We just needed a place to sleep because we planned our two days to be out and about doing activities. Overall the place fitted our needs: we had the 3 beds we needed to sleep all of us & the mattresses were comfortable to have a goodnight of sleep. It was clean, we had the extra blankets I requested due to the temperature was going to get colder for the weekend and it was dog friendly. What we didn't expect...
The price is €476
includes taxes & fees
11 Feb - 12 Feb
Aqua Lodge Rentals At Coconut Cay

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (803)
"Great location, clean, and good customer service. wish they had fishing rods and more to do around the property, and the AC didn't keep the upstairs cool, very hot up there at night. overall, happy about the stay."
Coconut Mallory Resort And Marina By Kees Vacations

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very good, (289)
"I had a great experience with my family!"
The price is €609
includes taxes & fees
13 Mar - 14 Mar
Hyatt Vacation Club at Sunset Harbor, Key West

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (367)
"Nice, clean and roomy studio. Very customer-oriented management. Perfect location for attending all the various festival venues. "
The price is €334
includes taxes & fees
6 Mar - 7 Mar
Steps from Duval, Pool on Site & Bikes Included!

Poolside Cottage #411

9.8 out of 10, Exceptional, (38)
"Quiet area close to everything we were looking for. "
The price is €518
includes taxes & fees
12 Feb - 13 Feb
Poolside Cottage #411

Key Largo Cottages

2.5 star property
9.4 out of 10, Exceptional, (20)
"Love this place! Very friendly and secluded. Not your typical resort-look elsewhere if that’s what you want. But if you want a friendly private sailing camp where you hang out with other fun people and like to sail and kayak, this is absolutely it! The use of the sailboat alone more than pays for the room."
The price is €493
includes taxes & fees
12 Feb - 13 Feb
Key Largo Cottages

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

10.0 out of 10, Exceptional, (4)
"Was just a teaser initial trip to Key West but staying on the water was awesome! Beautiful views and great amenities. Kevin and Captain Philip were great throughout the whole process including great local recommendations! One thing to note, if you are 6’ plus, will need to watch your head and the steps downstairs require concentration. As a shorter person (barely 5’!) it all worked perfectly for me! Look forward to staying again and taking the boat out next time! "
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

Aqua Lodges at 47th Street Gulfside

3.0 star property
8.6 out of 10, Excellent, (19)
"Had a wonderful time. So much to do in the area. We enjoyed the Cabana Club beach only a short drive away and included in the fee. We were there for the coldest week of the year. The maintenance gentleman, Scott and his assistant were kind enough to bring a hard to find space heater that kept us toasty warm as well a giving spot on recommendations for great places to eat. Some construction in the area but tolerable. Hope to return someday. "
The price is €404
includes taxes & fees
7 Mar - 8 Mar
Aqua Lodges at 47th Street Gulfside

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

9.4 out of 10, Exceptional, (49)
"We stayed here while attending a wedding at a nearby venue. We had 3 adults and an infant and realized that 3 adults is really difficult for this space as we had to crawl on our hands and knees on the upper level to not hit our head on the ceiling. We were a bit surprised by lack of some kitchen utensils (pot holders, pizza cutter etc) and the really small shower towels. But overall this space had really comfy beds and a great location in the Florida keys! I do think it’s best for 2 adults and...
The price is €483
includes taxes & fees
2 Mar - 3 Mar
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Anchorage Resort & Yacht Club

3.0 star property
8.6 out of 10, Excellent, (274)
"We loved our stay and the central / gated location was perfect! The view from all of the rooms balconies face the water to enjoy the sunset and it’s small enough to feel very private. Loved the bar restaurant, The Black Siren, next door! The service, food and drinks were perfect! Yes, it a bit dated but we knew that and it added to the fishing village vibe. We would definitely stay again! "
The price is €245
includes taxes & fees
11 Feb - 12 Feb
Anchorage Resort & Yacht Club

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

9.8 out of 10, Exceptional, (45)
"We spent a week uch enjoyed our visit. It's a little dated but very clean and comfortable. "
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!

9.8 out of 10, Exceptional, (17)
"Rented this nice boat for 2 nights for a two 60-somethings and three 20-somethings. From "A to Z" it meet or exceeded our expectations. Boat was a bit old, the carpets, etc. were more that a bit "dingy", and 5 adults certainly "maxed out" the space.... but we didn't care much. It was such a unique experience for our 3 younger guests who had NEVER been on a boat before. The harbor is very nice with good restaurants. etc. Jim our "check-in /out" guy was great. Jeff our captain for our 4 hour boat...
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
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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