Holiday Homes in Monroe County

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Top Cities in Monroe County

Featured Holiday Homes in Monroe County

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$484
includes taxes & fees
2 Dec - 3 Dec
Aqua Lodge Rentals At Coconut Cay

Conch Cove - 3br/3ba with private heated pool and private parking

The price is AU$1,822
includes taxes & fees
10 Dec - 11 Dec
Conch Cove - 3br/3ba with private heated pool and private parking

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$586
includes taxes & fees
1 Dec - 2 Dec
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

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

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

9.6 out of 10, Exceptional, (99)
"It's a little house, you could almost say a tiny house, but it's super cute, really well maintained, very clean, very well stocked, it sleeps 6 people comfortably, and it's right by the water. Perfect if you have a boat, and they have three kayaks that you can use in the beautiful mangrove chanbels by the house."
The price is AU$740
includes taxes & fees
11 Dec - 12 Dec
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

Key Colony Beach Paradise

9.4 out of 10, Exceptional, (37)
"Everything was great with our stay and the property.😊"
Key Colony Beach Paradise

Spacious home with pool & balcony - 1 block from Duval Street

9.2 out of 10, Wonderful, (72)
"Great pool and location. "
The price is AU$1,765
includes taxes & fees
1 Dec - 2 Dec
Spacious home with pool & balcony - 1 block from Duval Street

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 AU$2,258
includes taxes & fees
2 Dec - 3 Dec
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL

DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!

9.2 out of 10, Wonderful, (177)
"The location was great. Close to everything but still quiet. The condo is more dated and worn than we expected. There was a strong musty smell as soon as we opened the door and adjusting the a/c didn't help. Maybe it's typical of the area but it really bothered my allergies. "
DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!

P22 - Updated 3 bedroom 2 bath duplex with private pool and deep water dockage.

9.4 out of 10, Exceptional, (16)
"It was a nice place to stay. The best about this house other than the location that it has 3 bedrooms with King/King/Queen which works perfectly for adults. House was clean, check in easy, great location, close to Key Colony Club. Enough parking for 3 cars. Nice pool"
P22 - Updated 3 bedroom 2 bath duplex with private pool and deep water dockage.

STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST.

10.0 out of 10, Exceptional, (150)
"Perfect location, perfect house, and perfect place for a 60th birthday celebration. Words cannot describe how much the owner has made this property a little piece of paradise. Our first time in Key West and we had a beyond fantastic week, even on my husband’s birthday that was on the day Hurricane Helene happened. My husband was surprised with a birthday gift on arrival. We definitely give this place and owners a 10 out of 10. "
STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST.

Golfside Tropical Retreat With Pool

10.0 out of 10, Exceptional, (13)
"We have visited the Keys multiple times for family vacations. This property by far makes the top of the list. Very clean and setup perfectly. The house is conveniently located for anything you want to do in Marathon. Nice size pool and dock amenities for a very memorable Florida Keys experience. Will be booking this property for future vacations. Thank you Guy for letting us rent your beautiful home."
Golfside Tropical Retreat With Pool

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
3 Dec - 4 Dec
Poolside Cottage #411

Feb 3-10 $245 off the rates close beach full kitchen & patio

9.6 out of 10, Exceptional, (200)
"Very walkable. Cozy comfortable place. Cute and safe neighborhood. Setup well for cooking. AC pumps some good cold air. "
Feb 3-10 $245 off the rates close beach full kitchen & patio

Nassau Suite just steps to Duval Tropical oasis quiet location Downtown

9.0 out of 10, Wonderful, (222)
"Nice place ,great ammenties very close to duval street, cuban place right on the corner by it is great "
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown

Villa Largo Island Retreat

9.6 out of 10, Exceptional, (29)
"This house was perfect for our families (4 adults and 3 toddlers). It was very relaxing, tons of space, and in a great location within walking distance to the shoreline. There was a playground, swimming pool, and a lagoon right outside our back door! Everything was beautiful and the host was very quick to respond to any questions we had. Definitely would recommend this property! "
Villa Largo Island Retreat

Kelly's Kabin - Adorable Private Summerland Key Cottage

9.8 out of 10, Exceptional, (104)
"The property is as described. Good location. We would stay there again."
The price is AU$948
includes taxes & fees
12 Dec - 13 Dec
Kelly's Kabin - Adorable Private Summerland Key Cottage

Poolside Paradise | Private Oasis, 1 Block to Duval!

9.2 out of 10, Wonderful, (11)
"Great location 1/2 block from Duval. Lots of great towels, and pillows! I didn’t know this is two units connected but no connecting door, you access back unit via the pool. We needed both sofa beds but one had broken springs and was unusable. The floors hadn’t been mopped and all of my kids had black feet from walking around barefoot. If you are planning to cook you might want to bring a decent frying pan and a sharp knife. They have plenty of knives but none sharp. The grill didn’t work and...
The price is AU$1,519
includes taxes & fees
1 Dec - 2 Dec
Poolside Paradise | Private Oasis, 1 Block to Duval!

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!

The Flower Power House - Boho Beautiful

2.5 star property
8.6 out of 10, Excellent, (22)
"Great space for us to gather away from the craziness but close enough."
The Flower Power House - Boho Beautiful
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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