Top Condo Rentals in Monroe County in 2026

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

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Our top choices for Monroe County condo rentals

An aerial view of a resort with a swimming pool, beach, and marina.

An aerial view of a coastal resort with a marina, multiple buildings, and a large hotel labeled "CAYMAN COAST."

A pool area with lounge chairs and umbrellas, overlooking the ocean.

A modern kitchen with white cabinets, a dining area with a round table and chairs, and a large window providing a view of the outdoors.

1. Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay

3.0 star property

Matecumbe

9.0 out of 10, Wonderful, (16 reviews)

9.0/10

Wonderful

(16 reviews)

"Great location, we will return"

Juan

Caloosa Cove Resort by CoolVacay

A wooden deck with two Adirondack chairs facing a view of the ocean and palm trees.

A resort with multiple buildings along a waterfront, connected by a dock.

A room with a view of the ocean, a wooden table, a sofa with floral cushions, and a lamp.

A room with a view of the ocean, a door leading outside, a table with a lamp, and two wicker chairs.

2. 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)

9.2/10

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. "

Bradley

Indigo Reef Resort Villas & Marina by KeysCaribbean

3. The Reef at Marathon

The Reef at Marathon

3.0 star property

Marathon

9.2 out of 10, Wonderful, (129 reviews)

9.2/10

Wonderful

(129 reviews)

"Amazing place as advertised."

Edgardo

The Reef at Marathon

A serene lakeside scene with palm trees and a building with a light-colored facade.

A wooden table with a vase of flowers, surrounded by wicker chairs, set against a backdrop of trees and a wooden structure.

A dock with boats, a wooden walkway, and a water body with palm trees in the background.

A waterfront property with a building labeled "Coconut Mallory," docked boats, and a tree-lined dock area.

4. Coconut Mallory Resort And Marina By Kees Vacations

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property

Key West

8.2 out of 10, Very good, (835 reviews)

8.2/10

Very good

(835 reviews)

"Great place to stay in key west!"

Waseem

Coconut Mallory Resort And Marina By Kees Vacations

A covered outdoor area with a wooden deck, white railings, and a view of the ocean.

A resort with multiple buildings, a large central pool, and a view of the ocean.

A poolside area with lounge chairs and palm trees.

A spacious dining area with a long table, wicker chairs, and hanging wicker lamps.

5. Waterfront Luxury Villa

Waterfront Luxury Villa

4.0 star property

Marathon Shores

Waterfront Luxury Villa

A wooden pier leading to a beach with two houses on either side.

A beach with blue umbrellas and striped lounge chairs facing the ocean.

A modern kitchen with white cabinetry, a microwave, and a coffee maker. There is a dining table with four chairs and a bowl of fruit on the counter.

A spacious living area with a white sofa, a patterned armchair, and a white coffee table.

6. Topsider Resort

Topsider Resort

3.5 star property

Matecumbe

8.8 out of 10, Excellent, (65 reviews)

8.8/10

Excellent

(65 reviews)

"We stay at Topsider every year, sometimes more than once a year. Definitely the best place to stay in this area. Most places don’t have a dock, a pool, and a beach. This place has all 3. It’s the perfect place!"

Zack

Topsider Resort

A waterfront property with a paved walkway leading to a dock, surrounded by lush greenery and palm trees.

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with seating.

A swimming pool with a 5 ft depth marker, surrounded by a white fence and palm trees.

A spacious living area with a dining table, a sofa, and a coffee table. There are ceiling fans, a large window, and a plant.

7. Upper Sunset North

Upper Sunset North

3.5 star property

Meadows

Upper Sunset North

A wooden dock leading to a marina with boats and a cityscape in the background.

A spacious living room with a sectional sofa, a dining area with a table and chairs, and large windows offering a view of the outdoors.

8. Sunset North

Sunset North

4.0 star property

Key West Historic District

Sunset North

A dining area with a wooden table and teal chairs, a sofa with blue cushions, and a painting of a beach scene.

A multi-story building with balconies, a parking garage, and a sign that reads "Coconut Mall".

A living room with a teal sofa, a wooden coffee table, a television, and a painting of a boat on the wall.

A multi-story building with a swimming pool, outdoor seating, and a fenced area with plants.

9. Coconut Mallory Marina and Resort Condo

Coconut Mallory Marina and Resort Condo

3.0 star property

Key West

2.0 out of 10, (1 review)

2.0/10

(1 review)

"They did not have a room for me when i arrived. Said there was nothing they could do. I was left stranded and ended up paying twice the price for a worst room which was all I could find."

Paris

Coconut Mallory Marina and Resort Condo

A covered outdoor seating area with white furniture, a view of the sea, and a white railing.

A waterfront hotel with a pool, palm trees, and a sunset.

A sign for Bayfront Suites Resort & Marina with a pathway lined by palm trees and a white fence.

10. Bayview South 801 Eisenhower Dr. #6

Bayview South 801 Eisenhower Dr. #6

3.5 star property

Meadows

Bayview South 801 Eisenhower Dr. #6

A resort with multiple buildings, a swimming pool, and a view of the ocean.

A row of two-story townhouses with a white picket fence, a paved walkway, and lush greenery.

A clear blue pool with white lounge chairs and umbrellas, surrounded by palm trees and greenery.

A dining area with a round table, chairs, and a ceiling fan.

11. A Siesta Bay by Avantstay Key West Walkable Gated Community, Shared Pool Month-long Stays

A Siesta Bay by Avantstay Key West Walkable Gated Community, Shared Pool Month-long Stays

3.5 star property

Old Town Key West

9.0 out of 10, Wonderful, (2 reviews)

9.0/10

Wonderful

(2 reviews)

"Excellent place to stay, close to everything!"

Donna

A Siesta Bay by Avantstay Key West Walkable Gated Community, Shared Pool Month-long Stays

A beach with palm trees and a clear blue sky.

A multi-story building with balconies, surrounded by lush greenery and a white picket fence.

A white picket fence, a pathway, and a bench in a lush garden with tall trees.

A covered outdoor area with a white picket fence, a black table, and a potted plant.

12. Southard Getaway by Avantstay w/ Covered Patio, Great Location & Shared Pool! Month Long Stays

Southard Getaway by Avantstay w/ Covered Patio, Great Location & Shared Pool! Month Long Stays

3.5 star property

Old Town Key West

Southard Getaway by Avantstay w/ Covered Patio, Great Location & Shared Pool! Month Long Stays

A covered outdoor area with a view of the ocean, wooden chairs, and a palm tree.

A resort with a pool, palm trees, and a view of the ocean.

A beachfront hotel with multiple-story buildings, a well-maintained lawn, and palm trees.

A pool area with lounge chairs and a view of the water.

13. Indigo Reef Resort Villas and Marina

Indigo Reef Resort Villas and Marina

3.0 star property

Marathon Shores

Indigo Reef Resort Villas and Marina

14. Key West Vacation Properties & Realty

Key West Vacation Properties & Realty

3.0 star property

Meadows

Key West Vacation Properties & Realty

A large, white, multi-story hotel with balconies, a swimming pool, and a landscaped garden.

A person taking a photo by a pool with a white fence and trees in the background.

A marina at dusk with boats docked, wooden piers, and a distant cityscape.

A kitchen with a double sink, a wine bottle, and a dining area with a view.

15. Bayview Retreat

Bayview Retreat

3.0 star property

Meadows

Bayview Retreat

A marina with boats docked, a wooden pier, and lush greenery.

A wooden dock extending into calm water, surrounded by lush greenery and palm trees.

16. Sunset South

Sunset South

3.5 star property

Meadows

Sunset South

A covered outdoor area with white railings, a wooden deck, and a view of the marina and water.

A wooden dock extending into calm water with a boat docked at the end.

A modern living room with a sofa, armchairs, a coffee table, and a large window offering a view of the outdoors.

17. Bayview Middle

Bayview Middle

3.5 star property

Meadows

Bayview Middle

18. Tarpon Flats Inn & Marina

Tarpon Flats Inn & Marina

3.0 star property

Key Largo

8.6 out of 10, Excellent, (47 reviews)

8.6/10

Excellent

(47 reviews)

"We stayed here for 3 nights and thoroughly enjoyed our stay. The room was comfortable with enough amenities to prepare basic food. The staff were very friendly and helpful and always on hand with good advice and recommendations. The setting of the Inn is truly amazing and very peaceful. I personally enjoyed watching the squirrels and lizards in the garden and on the beach every day and the kayaks are a nice little extra too. We will be back!"

Clair

Tarpon Flats Inn & Marina

A covered balcony with a view of a marina and water.

A modern kitchen with white cabinetry, a built-in dishwasher, and a central island. There is a dining area with a white table and chairs, and a living room with a sofa and a coffee table.

19. Upper Bayview North

Upper Bayview North

3.5 star property

Meadows

Upper Bayview North

20. Indigo Reef Marina Homes Close to Boat Slip by Pack and Relax

Indigo Reef Marina Homes Close to Boat Slip by Pack and Relax

4.0 star property

Marathon Shores

Indigo Reef Marina Homes Close to Boat Slip by Pack and Relax

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

Chesapeake Beach Resort

10/10 Excellent

"10/10 recommend!"

Jessica 3-night trip

Posted 1 hour ago

Chesapeake Beach Resort

Beachside Resort & Residences

10/10 Excellent

"Enjoyed our stay. The resort was very nice and we had the best time on the sandbar tour with Captain John!"

Mollie 3-night trip

Posted 1 hour ago

Beachside Resort & Residences

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent

"Loved complimentary transportation!"

Robert 2-night trip

Posted 2 hours ago

DoubleTree Resort by Hilton Grand Key - Key West

Southernmost Beach Resort and Guesthouses

10/10 Excellent

"The breakfast should be a little bit less greasy"

Monica 1-night trip

Posted 2 hours ago

Southernmost Beach Resort and Guesthouses

Isla Bella Beach Resort & Spa

10/10 Excellent

"Resort is beautiful, not too big or too small. Room was spectacular. Dinner was great, breakfast was ok. Will definetly be back."

Cristian 1-night trip

Posted 17 hours ago

Isla Bella Beach Resort & Spa

Hawks Cay Resort

8/10 Good

"Loved every moment"

Telena 3-night trip

Posted 21 hours ago

Hawks Cay Resort

Lime Tree Bay Resort

10/10 Excellent

"We will definitely stay here again! Beautiful property that was always clean and peaceful."

Katie 4-night trip

Posted 23 hours ago

Lime Tree Bay Resort

Parrot Key Hotel & Villas

10/10 Excellent

"We loved this resort! We will definitely be returning here in the future. Great location- not far from Duvall St but close enough that it’s only a 10 minute drive."

Vernon 4-night trip

Posted 1 day ago

Parrot Key Hotel & Villas

Waterside Suites & Marina

10/10 Excellent

"Easy checkin. Good pool. Balconies overlook an inlet with docked boats. Saw a lot of fish swimming, as well as divers taking lessons."

Charles 1-night trip

Posted 1 day ago

Waterside Suites & Marina

Find out more about Monroe County

Monroe County Condo Rentals information

Number of reviews	1,095
Accommodation	32 Condo Rentals
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Romantic Hotels in Duck Key
Key West Historic District Hotels
All Inclusive Resorts in Key West
Beach Resorts in Key West
Budget Hotels in Key West
Gay friendly Hotels in Key West
Luxury Hotels in Key West
Key West Hotels
Resorts in Little Torch Key
Marathon Hotels
Summerland Key Hotels

Flights to Big Pine Key
Flights to Duck Key
Flights to Key West
Flights from Florida Keys Marathon
Flights from Melody Key
Flights from Allentown (ABE) to Key West (EYW)
Flights from Denver (DEN) to Key West (EYW)
Flights from Dallas (DFW) to Marathon (MTH)
Flights from Indianapolis (IND) to Marathon (MTH)
Flights from Islip (ISP) to Marathon (MTH)
Flights from Lexington (LEX) to Marathon (MTH)
Flights from Melbourne (MEL) to Marathon (MTH)
Flights from Rochester (ROC) to Marathon (MTH)

Boca Chica Nude Beach
Clarence S. Higgs Memorial Beach Park
Coupon Bight Aquatic Preserve
Visit Cow Key
Visit Duck Key
Fort East Martello Museum and Gallery
Harry S. Truman Little White House
Key Colony Beach Holidays
Visit White Street Gallery District
Key West Holidays
Visit Little Venice
Mel Fisher Maritime Museum
Visit Melody Key
Robbie's
Smathers Beach
Southernmost Point

Things to do in Big Pine Key
Things to do in Cudjoe Key
Things to do in Key Colony Beach

Condo Rentals in Monroe County

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Monroe County condo rentals

1. Caloosa Cove Resort by CoolVacay

2. Indigo Reef Resort Villas & Marina by KeysCaribbean

3. The Reef at Marathon

4. Coconut Mallory Resort And Marina By Kees Vacations

5. Waterfront Luxury Villa

6. Topsider Resort

7. Upper Sunset North

8. Sunset North

9. Coconut Mallory Marina and Resort Condo

10. Bayview South 801 Eisenhower Dr. #6

11. A Siesta Bay by Avantstay Key West Walkable Gated Community, Shared Pool Month-long Stays

12. Southard Getaway by Avantstay w/ Covered Patio, Great Location & Shared Pool! Month Long Stays

13. Indigo Reef Resort Villas and Marina

14. Key West Vacation Properties & Realty

15. Bayview Retreat

16. Sunset South

17. Bayview Middle

18. Tarpon Flats Inn & Marina

19. Upper Bayview North

20. Indigo Reef Marina Homes Close to Boat Slip by Pack and Relax

Find holiday rentals that suit your style

Top Monroe County Hotel Reviews

Chesapeake Beach Resort

Find out more about Monroe County

Monroe County Condo Rentals information

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