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

Condo Rentals in Monroe County

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Monroe County condo rentals

Exterior

1. Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay
3.0 star property
Matecumbe
9.0 out of 10, Wonderful, (11 reviews)
"Great location, we will return"
United States
Juan
Caloosa Cove Resort by CoolVacay
On the beach, sun loungers, beach towels

2. Oceanfront Key Largo Paradise - Private Beach + Pool, Hot Tub & Marina

Oceanfront Key Largo Paradise - Private Beach + Pool, Hot Tub & Marina
Tavernier
10.0 out of 10, Exceptional, (306 reviews)
"Thoroughly enjoyed our stay!"
United States
Anonymous traveler
Oceanfront Key Largo Paradise - Private Beach + Pool, Hot Tub & Marina
Beach nearby

3. Charming Condo w/ Entertainment & Private Parking - Great In-Town Location

Charming Condo w/ Entertainment & Private Parking - Great In-Town Location
Old Town Key West
9.4 out of 10, Exceptional, (110 reviews)
"We had such a lovely stay, walked everywhere. The location couldnā€™t be better. The house was comfortable and roomy!"
United States
Madeline M.
The price is SARĀ 2,723
SARĀ 3,447 total
includes taxes & fees
26 Aug - 27 Aug
Charming Condo w/ Entertainment & Private Parking - Great In-Town Location
Exterior detail

4. ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (110 reviews)
"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: The property was just as listed. Very clean, quiet, the pool was very refreshing! Great location, walkable to almost anything. Would highly recommend!"
United States
Chris & Sarah F.
The price is SARĀ 409
SARĀ 1,083 total
includes taxes & fees
26 Aug - 27 Aug
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
On the beach, sun loungers, beach towels

5. Fall Special! 5 Star Resort Lagoon Pool Tennis GolfCart Kayaks Amenities

Fall Special! 5 Star Resort Lagoon Pool Tennis GolfCart Kayaks Amenities
Key Largo
10.0 out of 10, Exceptional, (51 reviews)
"Great place to stay!! Had everything we needed and was very comfortable!"
United States
Wendy
Fall Special! 5 Star Resort Lagoon Pool Tennis GolfCart Kayaks Amenities
Exterior

6. 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, (90 reviews)
"The place was clean, neat, well decorated, and very pleasant. The kitchen was very nice, well organized, well stocked with necessary items, and neat. The bedroom and bathroom were also spotless and tastefully decorated. The balcony although small provided some breathtaking views of the horizon! The grounds were clean and well maintained. The staff was pleasant and helpful. Overall, it was a very pleasant experience and I would recommend it to everyone!"
United States
Marie
Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.
Property grounds

7. Galleon Resort beach hotel luxury in Old Town Key West

Galleon Resort beach hotel luxury in Old Town Key West
Key West Historic District
9.8 out of 10, Exceptional, (158 reviews)
"Another great stay. Great view and amenities. "
United States
Jeff L.
Galleon Resort beach hotel luxury in Old Town Key West
Beach

8. Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View

Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View
Beachside
9.0 out of 10, Wonderful, (132 reviews)
"Wonderful location - the condo was beautifully appointed. We had everything we needed for our stay, and enjoyed the coastal view. It was paradise!"
United States
Barbra J.
Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View
Premium Townhome | Balcony view

9. 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 ā€œgetting away from it allā€ vibe. We will be back. "
United States
Bradley
Indigo Reef Resort Villas & Marina by KeysCaribbean
Property grounds

10. Dog-friendly condo with pool, hot tub, balcony, central AC, W/D, & fitness room

Dog-friendly condo with pool, hot tub, balcony, central AC, W/D, & fitness room
Key West
8.8 out of 10, Excellent, (125 reviews)
"We had the best time! Every things was so easy and any information we needed was clearly shared. Very clean, parking was great. Easy and quick to get anywhere on the island from our condo. Definitely recommend."
United States
Penney C.
The price is SARĀ 1,390
SARĀ 1,762 total
includes taxes & fees
24 Sep - 25 Sep
Dog-friendly condo with pool, hot tub, balcony, central AC, W/D, & fitness room
On the beach, sun loungers

11. Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Tavernier
9.8 out of 10, Exceptional, (249 reviews)
"This was a perfect spot for me, mom and my daughters. We came for a family wedding and the location was wonderful. The amenities were enjoyed and the view canā€™t be beat!"
United States
Maria C.
The price is SARĀ 676
SARĀ 1,570 total
includes taxes & fees
7 Sep - 8 Sep
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Beach towels

12. OLD TOWN STEPS TO DUVAL! LA DOLCE VITA #6, SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST

OLD TOWN STEPS TO DUVAL! LA DOLCE VITA #6, SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
Old Town Key West
9.6 out of 10, Exceptional, (157 reviews)
"Excellent location for a week in the Keys. Was able to walk to all the Duval Street attractions. "
United States
Michael R.
OLD TOWN STEPS TO DUVAL! LA DOLCE VITA #6, SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
Property grounds

13. 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, (195 reviews)
"We loved the location of this property."
United States
Victoria T.
JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!
A heated pool

14. COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!

COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!
Old Town Key West
9.4 out of 10, Exceptional, (118 reviews)
"Excellent stay, great location! "
United States
Dr. Christopher S.
COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!
Marina

15. 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, (99 reviews)
"Great place to stay!!"
United States
Jamie T.
Water Front Condo in Duck Key. FREE WIFI! Overlooking the Gulf of Mexico.
Outdoor dining

16. Oceanfront Views From Every Room! SEPT. DISCOUNT! RESERVE QUICKLY! Lic #26-0403

Oceanfront Views From Every Room! SEPT. DISCOUNT! RESERVE QUICKLY! Lic #26-0403
Tavernier
9.6 out of 10, Exceptional, (202 reviews)
"We loved our stay here! Close to everything but tucked away so it felt very private. Pool, sand and kayak were great too. Highly recommend!!"
United States
Diane D.
Oceanfront Views From Every Room! SEPT. DISCOUNT! RESERVE QUICKLY! Lic #26-0403
Terrace/patio

17. STARS ~ 4 bedroom, 2 Bath Condo, Shared Heated Pool, Downtown Location!

STARS ~ 4 bedroom, 2 Bath Condo, Shared Heated Pool, Downtown Location!
Key West Historic District
9.4 out of 10, Exceptional, (101 reviews)
"The house was within easy walking distance to shops and restaurants. "
United States
Tj S.
STARS ~ 4 bedroom, 2 Bath Condo, Shared Heated Pool, Downtown Location!
Beach

18. Top floor amazing view Toms Chicken Coop awaits your next stay. Best value

Top floor amazing view Toms Chicken Coop awaits your next stay. Best value
Beachside
9.8 out of 10, Exceptional, (169 reviews)
"Loved our stay! "
United States
Schwartz F.
Top floor amazing view Toms Chicken Coop awaits your next stay. Best value
On the beach, sun loungers, beach towels

19. Key Largo Oceanfront Escape: Pools, Beach, Fishing Pier, No Steps ! šŸļø

Key Largo Oceanfront Escape: Pools, Beach, Fishing Pier, No Steps ! šŸļø
Key Largo
10.0 out of 10, Exceptional, (216 reviews)
"Beautiful place. Would definitely stay here again."
United States
Stacey
Key Largo Oceanfront Escape: Pools, Beach, Fishing Pier, No Steps ! šŸļø
Beach

20. Botanical Island Delight Key West fantastic discounts for Summer & Fall

Botanical Island Delight Key West fantastic discounts for Summer & Fall
Beachside
9.0 out of 10, Wonderful, (155 reviews)
"Our first trip to Key West was made that much better by having a clean and easy to navigate VRBO home to rest in. The pool area was wonderful. We thoroughly enjoyed our visit!"
United States
Kathleen H.
Botanical Island Delight Key West fantastic discounts for Summer & Fall
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

Havana Cabana at Key West

Havana Cabana at Key West

10/10 Excellent
"I enjoyed every minute of our stay. From when our plane arrived, we only had to wait about 20 minutes for the van to pick us up. The driver was very helpful and got us to the property and checked in quickly with no issues. We even got into our room over an hour early. Once we got situated we spoke with the concierge and set up a couple of activities for the week. We then took the free shuttle to Duval St. All of the drivers were a wealth of knowledge and helped us plan our stay. This was our first time to Key West but it definitely wonā€™t be our last. I loved everything about the island and all the people seemed to be enjoying themselves. What little stress I brought with me was definitely gone within the first full day on island time. What a great time we had. All the staff was always friendly and welcoming and would go out of their way to assist you when they could. I will definitely stay at this location again. Itā€™s perfectly set where you have access to anywhere on the island with the shuttle vans never far away. The porters definitely made me feel at home and they always had some stories of knowledge about the island. I wish I could give each of the porters an individual gift I would. They all deserve every bit of praise they get. Great job Havana Cabana. We will definitely be back !!!"
Chance 6-night trip
Posted 5 hours ago
Havana Cabana at Key West