A waterfront promenade with multi-story buildings, palm trees, and a clear blue sky.

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Top Cities in Monroe County

Our top choices for Monroe County condo rentals

1. Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (19 reviews)
"Great location, we will return"
United States
Juan
Caloosa Cove Resort by CoolVacay

2. Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!

Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
Tavernier
10.0 out of 10, Exceptional, (207 reviews)
"Great host and property!"
United States
Paul T.
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!

3. NOV-DEC SELL-OFF!! OCEANFRONT Lux 1350sf, Great Views &All Amenities of Home!!

NOV-DEC SELL-OFF!! OCEANFRONT Lux 1350sf, Great Views &All Amenities of Home!!
Key Largo
9.6 out of 10, Exceptional, (320 reviews)
"Host was very accommodating! Very clean,everything you need. We would stay again. It was peaceful and relaxing. I would recommend this condo to anyone."
United States
annie s.
NOV-DEC SELL-OFF!! OCEANFRONT Lux 1350sf, Great Views &All Amenities of Home!!

4. Key West Paradise Found - Experience a premiere Key West Ocean Front Property

Key West Paradise Found - Experience a premiere Key West Ocean Front Property
Beachside
9.8 out of 10, Exceptional, (343 reviews)
"The smell in the building was like sewer but otherwise all was well."
United States
Sheryl
Key West Paradise Found - Experience a premiere Key West Ocean Front Property

5. Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.

Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.
Tavernier
9.6 out of 10, Exceptional, (93 reviews)
"Great spot that was conveniently located. Clean and well appointed."
United States
Franz H.
Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.

6. Luxury Waterfront at Galion Resort in Old Town

Luxury Waterfront at Galion Resort in Old Town
Key West Historic District
9.6 out of 10, Exceptional, (114 reviews)
"A great place for my family to stay on our trip! Lots of room and all the amenities you could need for a perfect trip to Key West."
United States
Katie C.
Luxury Waterfront at Galion Resort in Old Town

7. Indigo Reef Resort Villas & Marina by KeysCaribbean

Indigo Reef Resort Villas & Marina by KeysCaribbean
3.5 star property
Marathon Shores
9.2 out of 10, Wonderful, (49 reviews)
"A real gem. This property is clean and beautiful. Brand new dock, landscaping is perfect, location is within minutes of everything you would want while maintaining a “getting away from it all” vibe. We will be back. "
United States
Bradley
Indigo Reef Resort Villas & Marina by KeysCaribbean

8. Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Midtown
9.8 out of 10, Exceptional, (331 reviews)
"Condo was very comfortable and the location was great. Enjoyed having the bikes to ride."
United States
P R.
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

9. Treehouse Condo 2nd Floor Balcony sleeps 6 free parking

Treehouse Condo 2nd Floor Balcony sleeps 6 free parking
Old Town Key West
9.0 out of 10, Wonderful, (10 reviews)
"This was a great place for our group and Marc was a very accommodating host."
United States
Brendan A.
Treehouse Condo 2nd Floor Balcony sleeps 6 free parking

10. 4 bed & 4 bath Unit 906 @Mariners Club - Sleeps 10!! Ohana Cay

4 bed & 4 bath Unit 906 @Mariners Club - Sleeps 10!! Ohana Cay
Rock Harbor
9.6 out of 10, Exceptional, (71 reviews)
"Great place and location."
United States
Leeann A.
4 bed & 4 bath Unit 906 @Mariners Club - Sleeps 10!! Ohana Cay

11. Chic Coastal Retreat with Pool, Marina, Beach Access & Resort-Style Amenities

Chic Coastal Retreat with Pool, Marina, Beach Access & Resort-Style Amenities
Tavernier
9.8 out of 10, Exceptional, (103 reviews)
"Great location, clean property, love the views! "
United States
Katy H.
Chic Coastal Retreat with Pool, Marina, Beach Access & Resort-Style Amenities

12. 3 Bedroom 2 Bath Oceanfront Condo quiet and secluded adjacent to Hotel/Marina

3 Bedroom 2 Bath Oceanfront Condo quiet and secluded adjacent to Hotel/Marina
Stock Island
10.0 out of 10, Exceptional, (72 reviews)
"Great place! Would stay again!!"
United States
Jennifer O.
3 Bedroom 2 Bath Oceanfront Condo quiet and secluded adjacent to Hotel/Marina

13. OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST

OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
Old Town Key West
9.6 out of 10, Exceptional, (158 reviews)
"Excellent location for a week in the Keys. Was able to walk to all the Duval Street attractions. "
United States
Michael R.
$480 nightly
The price is $536
Nov 29 - Nov 30
Total with taxes and fees
OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST

14. JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!

JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!
Old Town Key West
9.6 out of 10, Exceptional, (199 reviews)
"Excellent location ..... condo was as described in listing. Definitely would consider staying again."
United States
Mike
JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!

15. 3-bedroom ocean view condo in delightful Key West with WiFi, AC

3-bedroom ocean view condo in delightful Key West with WiFi, AC
Stock Island
9.6 out of 10, Exceptional, (24 reviews)
"Great space and lovely views, perfect for our party of 5 adult guests."
United States
Randall V.
3-bedroom ocean view condo in delightful Key West with WiFi, AC

16. Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.

Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
Key West
9.2 out of 10, Wonderful, (115 reviews)
"I enjoyed my stay at the resort, highly recommend!"
United States
Michelaine a.
$435 nightly
The price is $488
Nov 9 - Nov 10
Total with taxes and fees
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.

17. Tropical Oasis on Sombrero Beach in the Heart of Marathon FL

Tropical Oasis on Sombrero Beach in the Heart of Marathon FL
Marathon
9.8 out of 10, Exceptional, (16 reviews)
"What a charming and beautiful property. Beautiful landscape and the room was clean and comfortable. (The only minor issue was the lack of electrical outlets , but we brought our own extension cords) We definitely recommend this place 👌"
United States
JOHN
$333 nightly
The price is $371
Nov 15 - Nov 16
Total with taxes and fees
Tropical Oasis on Sombrero Beach in the Heart of Marathon FL

18. 3 Bedroom 2 Bath Ocean view Condo with Full Kitchen, Covered Parking

3 Bedroom 2 Bath Ocean view Condo with Full Kitchen, Covered Parking
Stock Island
9.8 out of 10, Exceptional, (102 reviews)
"Great place to stay"
United States
Louie Q.
3 Bedroom 2 Bath Ocean view Condo with Full Kitchen, Covered Parking

19. Water Front Condo in Duck Key. FREE WIFI! Overlooking the Gulf of Mexico.

Water Front Condo in Duck Key. FREE WIFI! Overlooking the Gulf of Mexico.
Duck Key
9.6 out of 10, Exceptional, (107 reviews)
"Loved our stay!"
United States
Elesha G.
Water Front Condo in Duck Key. FREE WIFI! Overlooking the Gulf of Mexico.

20. The Cayo Coco | Key West Condo with Pool, Hot Tub!

The Cayo Coco | Key West Condo with Pool, Hot Tub!
Key West
9.6 out of 10, Exceptional, (17 reviews)
"Super clean place, location was perfect and quiet "
United States
Carlos R.
$420 nightly
The price is $470
Nov 9 - Nov 10
Total with taxes and fees
The Cayo Coco | Key West Condo with Pool, Hot Tub!
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

Price trends for hotels in Monroe County

Less expensive
More expensive
This month
Next month
September
February
$506
$534
Month
Price
January
$663
February
$802
March
$673
April
$532
May
$534
June
$406
July
$441
August
$396
September
$388
October
$420
November
$506
December
$534
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed Condo Rentals in Monroe County. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Monroe County

Monroe County Condo Rentals information

Number of reviews
1,993
Accommodation
1205 Condo Rentals
Lowest Price
$371
Highest Price
$536

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