Monroe County Holiday Rentals

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Top Cities in Monroe County

Top Holiday Rentals Destinations in Monroe County

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (371)
"Great screened Patio, comfy bed, large 1 bedroom and livingroom. Highly recommend. Beautiful beach view and lots of loungers"
The price is AU$296
includes taxes & fees
10 Dec - 11 Dec
Breezy Palms Resort

Aqua Lodge Rentals At Coconut Cay

3.5 star property
9.6 out of 10, Exceptional, (124)
"Clean, quiet. Balcony to the sea was a big plus. Everything was excellent."
The price is AU$514
includes taxes & fees
1 Dec - 2 Dec
Aqua Lodge Rentals At Coconut Cay

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1133)
"Large rooms, clean, quiet."
The price is AU$272
includes taxes & fees
25 Nov - 26 Nov
Skipjack Resort & Marina

Yacht Haven Marina

3.5 star property
9.8 out of 10, Exceptional, (92)
"Spent most of a week in one of the houseboats, it was super clean and comfortable. It was a real nice alternative to a hotel room, fun to watch the fish and manatee from the balcony and the view was awesome too, we will return!"
Yacht Haven Marina

Old Wooden Bridge Resort and Marina

2.5 star property
8.4 out of 10, Very good, (161)
"The houseboat was a delight. Super comfortable and a full kitchen. Very dog-friendly. The woman who checked us in was super nice, and the salt-water pool felt great!"
The price is AU$377
includes taxes & fees
25 Nov - 26 Nov
Old Wooden Bridge Resort and Marina

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (104)
"Nice for affordable price "
The price is AU$448
includes taxes & fees
25 Nov - 26 Nov
Aqua Lodges at Hurricane Hole Marina

Knight's Key Suites

3.0 star property
9.0 out of 10, Wonderful, (1064)
"I liked full kitchen. Balcony door dos not close, but it’s not a big deal. Location is central to Fla Keys. "
The price is AU$196
includes taxes & fees
9 Dec - 10 Dec
Knight's Key Suites

Tropical Cottages

3.0 star property
8.4 out of 10, Very good, (745)
"Great place. Clean rooms and great staff. Thanks for the hospitality. Highly recommended "
The price is AU$147
includes taxes & fees
5 Dec - 6 Dec
Tropical Cottages

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (356)
"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 AU$371
includes taxes & fees
2 Dec - 3 Dec
Steps from Duval, Pool on Site & Bikes Included!

Poolside Cottage #411

10.0 out of 10, Exceptional, (30)
"Nice location very close to everything and close enough to Duval St. Unit itself was in good condition and the kitchen stocked pretty good but was missing dish cloths, dish towels and dishwasher detergent. None of the grills on the property were functional. Host was very responsive the entire process. Would stay there again"
The price is AU$592
includes taxes & fees
2 Dec - 3 Dec
Poolside Cottage #411

TIDES ON SIMONTON ~ Perfectly located just off Duval and all the fun!

9.2 out of 10, Wonderful, (165)
"We found the tides on Simonton online and booked it immediately. When we arrived, the check-in process was very easy and the location is very nice. We ate down the street at Duffys twice during our stay and it is an amazing place. I highly recommend their prime rib. we will definitely be back "
TIDES ON SIMONTON ~ Perfectly located just off Duval and all the fun!

Anchorage Resort & Yacht Club

3.0 star property
8.6 out of 10, Excellent, (266)
"Have stayed here many times and will continue to do so. Near my daughter and lots of other things to do. It is a two room suite overlooking Florida Bay. Got a boat? Dock it here. Rooms are big, spotless, comfortable and a kitchenette included. Five stars."
The price is AU$389
includes taxes & fees
25 Nov - 26 Nov
Anchorage Resort & Yacht Club

34’ Catamaran Sailboat

9.6 out of 10, Exceptional, (27)
"Overall it was a great experience."
34’ Catamaran Sailboat

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

9.4 out of 10, Exceptional, (43)
"This tiny home was AMAZING! We stayed here for a night on our way back from key west and it was the perfect place. The tiny home was super clean and had everything we needed. The beds were incredibly comfortable in both the loft upstairs and in the bedroom. Bathrooms were awesome as well. The campground was awesome and was very walkable, we didn’t use the pool or the beach access but both were close walking distance. Would definitely stay here again! There is a publix right outside of the...
The price is AU$593
includes taxes & fees
2 Dec - 3 Dec
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Cabins at Bonefish Bay

3.0 star property
10.0 out of 10, Exceptional, (22)
"Very quiet easy access,on the water free kayak and bike use will definitely stay here again only hour drive to key west but way more reasonable."
Cabins at Bonefish Bay

Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!

9.2 out of 10, Wonderful, (238)
"Place was very comfortable-great for couples who "
The price is AU$906
includes taxes & fees
27 Nov - 28 Nov
Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

9.0 out of 10, Wonderful, (184)
"Loved this ocean view property! Very nice location and very comfortable home!"
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

TA Beach, Pool, Marina, family friendly, Kitchen, Jacuzzi

9.4 out of 10, Exceptional, (184)
"Beautiful beach view. Turquoise blue water. Close to a lot of fun things to see, like the Dolphin Research Center and the Sea Turtle Hospital. "
TA Beach, Pool, Marina, family friendly, Kitchen, Jacuzzi

Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

9.4 out of 10, Exceptional, (214)
"Very clean. Could use some updating such as fresh paint. "
The price is AU$679
includes taxes & fees
26 Nov - 27 Nov
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC

9.0 out of 10, Wonderful, (202)
"Close to Duval Street and within walking distance to everything. Full kitchen is nice. Good for a Key West visit. "
The price is AU$428
includes taxes & fees
11 Dec - 12 Dec
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC
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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