Vacation Homes in Monroe County

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Top Cities in Monroe County

Our top choices for Monroe County holiday homes

The Hammocks at Marathon

The Hammocks at Marathon
2.5 star property
Marathon
9.0 out of 10, Wonderful, (127 reviews)
"The room was very spacious and clean. Front desk staff were very friendly and helpful."
United States
Michael
The Hammocks at Marathon

Hemingway Caribbean Townhome/Private Pool by Beach,Key West charm,free parking

Hemingway Caribbean Townhome/Private Pool by Beach,Key West charm,free parking
Old Town Key West
8.8 out of 10, Excellent, (6 reviews)
"So quaint and private. Close to everything and the private pool was absolutely lovely! Owners were accommodating and so friendly and nice!"
United States
Sandi H.
Hemingway Caribbean Townhome/Private Pool by Beach,Key West charm,free parking

Charming 3-bedroom house in Big Pine Key near Beach and Key West

Charming 3-bedroom house in Big Pine Key near Beach and Key West
Sands
8.8 out of 10, Excellent, (3 reviews)
"Great property, surrounded by key deer and wild roosters. "
United States
Scott B.
The price is HK$2,592
HK$5,805 total
includes taxes & fees
1 Mar - 2 Mar
Charming 3-bedroom house in Big Pine Key near Beach and Key West

Perla Blanca 4 Bed 5 Bath kayaks pool boat dock

Perla Blanca 4 Bed 5 Bath kayaks pool boat dock
Marathon
9.8 out of 10, Exceptional, (52 reviews)
"Beautiful house, wonderful location. "
United States
Melissa S.
Perla Blanca 4 Bed 5 Bath kayaks pool boat dock

Restful waterfront townhome with deck, great water views & washer/dryer

Restful waterfront townhome with deck, great water views & washer/dryer
Duck Key
9.2 out of 10, Wonderful, (93 reviews)
"Great place"
United States
Diego
Restful waterfront townhome with deck, great water views & washer/dryer

Outstanding pool and outdoor area 5 minute walk to beach!

Outstanding pool and outdoor area 5 minute walk to beach!
Marathon
10.0 out of 10, Exceptional, (79 reviews)
"Loved the location and this home was the perfect place to spend a week with the family!! "
United States
Diana W.
Outstanding pool and outdoor area 5 minute walk to beach!

Charming townhome with ocean views, an open porch & steps from the water

Charming townhome with ocean views, an open porch & steps from the water
Duck Key
9.4 out of 10, Exceptional, (14 reviews)
"great location and parkin"
United States
Henry J.
Charming townhome with ocean views, an open porch & steps from the water

Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval, Pool

Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval, Pool
Key West Historic District
10.0 out of 10, Exceptional, (48 reviews)
"Great location nice place"
United States
michelle s.
Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval, Pool

Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water

Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water
Coral Lagoon
9.6 out of 10, Exceptional, (107 reviews)
"Great place for the entire family! Will definitely book again. "
United States
Kyle C.
Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water

CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
Old Town Key West
9.6 out of 10, Exceptional, (200 reviews)
"Great quiet location!"
United States
Edward C.
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

Perfect Location, Private Heated Pool, Pristine Luxury Home!

Perfect Location, Private Heated Pool, Pristine Luxury Home!
Old Town Key West
10.0 out of 10, Exceptional, (201 reviews)
"Outstanding place to stay, centrally located!"
United States
Elizabeth Y.
The price is HK$11,728
HK$19,888 total
includes taxes & fees
16 Mar - 17 Mar
Perfect Location, Private Heated Pool, Pristine Luxury Home!

Waterfront 2BR w/ Dock, Hot Tub & Easy Ocean Access – Boaters Welcome!

Waterfront 2BR w/ Dock, Hot Tub & Easy Ocean Access – Boaters Welcome!
Marathon
9.0 out of 10, Wonderful, (14 reviews)
"We enjoyed our stay! The dock access was the best part. "
United States
Madison R.
Waterfront 2BR w/ Dock, Hot Tub & Easy Ocean Access – Boaters Welcome!

TROPICAL RETREAT ~ 3 Bedroom/3.5 Bath 1/2 Block from Duval w/ Heated Pool!

TROPICAL RETREAT ~ 3 Bedroom/3.5 Bath 1/2 Block from Duval w/ Heated Pool!
Old Town Key West
9.6 out of 10, Exceptional, (105 reviews)
"The house has a great location and the staff was very attentive. Would stay here again!! Thank you!! "
United States
Ellen M.
TROPICAL RETREAT ~ 3 Bedroom/3.5 Bath 1/2 Block from Duval w/ Heated Pool!

OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
Stock Island
9.8 out of 10, Exceptional, (104 reviews)
"Everything was great. The home was beautiful and comfortable. The Host was quick to respond and was very pleasant. "
United States
Crystal H.
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Key Largo
9.6 out of 10, Exceptional, (88 reviews)
"Great location! Super quiet and relaxing area! "
United States
Devin H.
The price is HK$1,816
HK$3,949 total
includes taxes & fees
26 Feb - 27 Feb
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

BEACHFRONT POOL HOME

BEACHFRONT POOL HOME
Silver Shores
9.6 out of 10, Exceptional, (111 reviews)
"Property was great. Everyone enjoyed their stay definitely would come back."
United States
Bradley P.
BEACHFRONT POOL HOME

Waterfront, dog-friendly home with beautiful canal view & 2 shaded porches

Waterfront, dog-friendly home with beautiful canal view & 2 shaded porches
Duck Key
9.8 out of 10, Exceptional, (28 reviews)
"Perfect for our needs"
United States
Jon E.
Waterfront, dog-friendly home with beautiful canal view & 2 shaded porches

Private Secluded Ocean View & Pool Near Key West

Private Secluded Ocean View & Pool Near Key West
Summerland Key
8.2 out of 10, Very good, (101 reviews)
"Great house far enough away from Key West to be quiet and peaceful, and close enough to enjoy the nightlife! "
United States
Paul K.
Private Secluded Ocean View & Pool Near Key West

~BOOK NOW~APRIL-MID MAY 2026~650/NT~ Fish, Swim, Relax! Pool & Dock–NEAR BEACH

~BOOK NOW~APRIL-MID MAY 2026~650/NT~ Fish, Swim, Relax! Pool & Dock–NEAR BEACH
Marathon
10.0 out of 10, Exceptional, (79 reviews)
"Beautiful house, great location, we had an amazing time as this was a last-minute change of plans we could not have been more pleased. Michelle was always responsive when we had questions. Would definitely go back there again"
United States
Michele P.
~BOOK NOW~APRIL-MID MAY 2026~650/NT~ Fish, Swim, Relax! Pool & Dock–NEAR BEACH

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (151 reviews)
"Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. "
United States
bryan c.
The price is HK$2,930
HK$5,696 total
includes taxes & fees
3 Mar - 4 Mar
Cudjoe Cottages, swimming pool, just 20 miles from Key West
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

Monroe County Vacation Homes information

Number of reviews
1,560
Accommodation
3855 Vacation Homes
Lowest Price
HK$3,949
Highest Price
HK$19,888

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