Holiday Homes in Monroe County

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Check prices for these dates

In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov

Top Cities in Monroe County

Holiday HomesHoliday Homes

Key West

Key West

Featured Holiday Homes in Monroe County

Our top choices for Monroe County holiday homes

The Hammocks at Marathon
Outdoor pool, pool umbrellas, pool loungers

The Hammocks at Marathon

2.5 star property
9.0 out of 10, Wonderful, (98)
"Very nice and clean nice pool area nice tity bar an restant easy to get in and out good gym area"
The Hammocks at Marathon
Seaside Retreat: Waterfront Home with private heated pool & lush landscaping
Terrace/patio

Seaside Retreat: Waterfront Home with private heated pool & lush landscaping

9.6 out of 10, Exceptional, (75)
"Beautiful house "
Seaside Retreat: Waterfront Home with private heated pool & lush landscaping
Perla Blanca 4 Bed 5 Bath kayaks pool boat dock
Exterior

Perla Blanca 4 Bed 5 Bath kayaks pool boat dock

9.8 out of 10, Exceptional, (49)
"House was spotless, very bright and open! We really enjoyed the pool and even saw a few manatees in the canal! Great location, will be returning next time we’re in the Florida Keys!"
Perla Blanca 4 Bed 5 Bath kayaks pool boat dock
Manatee Bay , Pool table, Jacuzzi, Pool, Kayaks, REDUCED RATES AVAIL NOW<br>
Outdoor pool, a heated pool

Manatee Bay , Pool table, Jacuzzi, Pool, Kayaks, REDUCED RATES AVAIL NOW<br>

8.4 out of 10, Very good, (91)
"We loved staying her so much! I had everything we needed and some. Loved the location also! Was so great!"
Manatee Bay , Pool table, Jacuzzi, Pool, Kayaks, REDUCED RATES AVAIL NOW<br>
Vacation with attitude!
Fridge, microwave, oven, stovetop

Vacation with attitude!

10.0 out of 10, Exceptional, (8)
"Good location, family friendly, very nice pool and outdoors. "
Vacation with attitude!
Piece of Paradise located at Hawks Cay in Duck Key
Pool

Piece of Paradise located at Hawks Cay in Duck Key

9.4 out of 10, Exceptional, (3)
"Amazing place. "
Piece of Paradise located at Hawks Cay in Duck Key
DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!
A heated pool

DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!

10.0 out of 10, Exceptional, (3)
"Beautiful property, perfectly located, and one of the best VRBO experiences we have ever had."
DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Property grounds

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

8.8 out of 10, Excellent, (55)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: great place, great location! we'll be back year after year!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Exterior

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

9.8 out of 10, Exceptional, (67)
"Such a great, gated location with access to a variety of amenities. "
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Amelia's Hideaway - Hidden Key West Courtyard - Steps off Duval w Private Pool
A heated pool

Amelia's Hideaway - Hidden Key West Courtyard - Steps off Duval w Private Pool

9.0 out of 10, Wonderful, (57)
"We had a wonderful stay. The layout of the property was perfect for our group of 8. The pool and the rooftop patio were perfect. The property manager was also very responsive to any questions we had."
Amelia's Hideaway - Hidden Key West Courtyard - Steps off Duval w Private Pool
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, (218)
"We had a great time and loved the property "
CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!
Spec @107.lodg+ Aug & sept. 10 min walk beach, close to all + full kitch& patio
Terrace/patio

Spec @107.lodg+ Aug & sept. 10 min walk beach, close to all + full kitch& patio

9.0 out of 10, Wonderful, (170)
"This was a great location and easy place to stay. We were able to walk to many locations in Old Town. The new updates are a nice addition to this location. Fresh paint, refrigerator, A/C and the patio is a great place to relax. "
Spec @107.lodg+ Aug & sept. 10 min walk beach, close to all + full kitch& patio
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Outdoor pool, a heated pool

Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

9.6 out of 10, Exceptional, (19)
"Clean , beautiful location and pools . "
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
Property grounds

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

9.4 out of 10, Exceptional, (49)
"Clean, home included everything you could need. Best of all, communication was clear, friendly, professional and a binder was left with activities, restaurants, etc. Parking spot was clear and easy. Beautiful stay"
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
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

8.8 out of 10, Excellent, (87)
"Property was adequate but could use a few updates. The location was great. Easy to get to Key West near good local restaurants and beaches. Would stay again. "
The price is AU$1,072
includes taxes & fees
26 Aug - 27 Aug
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Snappers - King Room w/ Ocean View Wifi
Terrace/patio

Snappers - King Room w/ Ocean View Wifi

The price is AU$159
includes taxes & fees
26 Aug - 27 Aug
Snappers - King Room w/ Ocean View Wifi
Old Florida Style, wrap around porch, boat basin for dockage, open water
Property grounds

Old Florida Style, wrap around porch, boat basin for dockage, open water

9.6 out of 10, Exceptional, (78)
"Took the team down to the keys for a little R&R"
Old Florida Style, wrap around porch, boat basin for dockage, open water
KATE'S KRAWL OFF DUVAL ~ 1 BR/1 BA Private Home/Outdoor Deck/Steps to Duval!
Outdoor dining

KATE'S KRAWL OFF DUVAL ~ 1 BR/1 BA Private Home/Outdoor Deck/Steps to Duval!

9.8 out of 10, Exceptional, (78)
"We were so happy with our stay! It was clean, easy and in a great spot! Highly recommend this place. "
KATE'S KRAWL OFF DUVAL ~ 1 BR/1 BA Private Home/Outdoor Deck/Steps to Duval!
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
Outdoor pool, a heated pool

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

9.6 out of 10, Exceptional, (31)
"Nice property . Well kept. Good management "
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets
Beach towels

🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets

9.2 out of 10, Wonderful, (45)
"Great sunsets; quiet street; fantastic marine life. Frank was very responsive. The property is not brand new but delivered on what we needed: pool, great dock for fishing and keeping boat during day. Booked again for next year. "
🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets
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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Top Monroe County Hotel Reviews

Find out more about Monroe County

Find out more about Monroe County

Monroe County Holiday Homes information

Number of reviews
Accommodation
3915 Holiday Homes
Lowest Price
AU$159
Highest Price
AU$1,072