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

Vacation Rentals in Monroe County

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Top Cities in Monroe County

A beach with palm trees, people sunbathing, and a resort in the background.
Vacation RentalsVacation Rentals

Key West

Key West

Our top choices for Monroe County vacation rentals

A covered outdoor area with a wooden deck, palm trees, and a view of the beach.

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (780 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is ￥10,945
￥20,522 total
includes taxes & fees
Nov 10 - Nov 11
Breezy Palms Resort
A neatly made bed with a grey and white duvet, a wooden headboard, and a bedside table with a lamp and remote control.

2. Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,245 reviews)
"We had the pool view..Excellent!"
United States
Brandy
The price is ￥14,093
￥19,260 total
includes taxes & fees
Nov 29 - Nov 30
Knight's Key Suites
A row of floating houses with balconies, connected by walkways, on calm water.

3. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (202 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is ￥19,425
￥49,052 total
includes taxes & fees
Nov 9 - Nov 10
Aqua Lodges at Hurricane Hole Marina
An outdoor seating area with wicker furniture and cushions, a thatched-roof structure, and lush greenery.

4. Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,013 reviews)
"The family running the food truck and tiki hut were great. Felt like we were guests in their home."
United States
Douglas
The price is ￥18,844
￥21,200 total
includes taxes & fees
Nov 10 - Nov 11
Tropical Cottages
A spacious living room with a large window, a white sofa, a coffee table, and a painting of a tropical scene.

5. Anchorage Resort & Yacht Club

Anchorage Resort & Yacht Club
3.0 star property
Key Largo
8.8 out of 10, Excellent, (352 reviews)
"Very clean Nice staff"
United States
Doris
The price is ￥25,041
￥28,172 total
includes taxes & fees
Nov 11 - Nov 12
Anchorage Resort & Yacht Club
A spacious living area with a gray sectional sofa, wooden beams, and a ceiling fan.

6. Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (239 reviews)
"Never stayed in a houseboat before. It was a novel experience!"
United States
Susan
The price is ￥15,227
￥40,990 total
includes taxes & fees
Nov 15 - Nov 16
Aqua Lodge Rentals At Coconut Cay
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

7. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (181 reviews)
"Had a very enjoyable stay at Hemingway House. The place was spotless! All staff were very friendly and helpful. Would highly recommend staying here!"
United States
Diane
The price is ￥16,867
￥41,122 total
includes taxes & fees
Nov 8 - Nov 9
Treasure Harbor
A cozy room with a brown leather sofa, a white table, and a ceiling fan.

8. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (380 reviews)
"Great view , clean room and excellent staff ( Mr. shaggy )"
United States
Jordan
The price is ￥11,007
￥34,529 total
includes taxes & fees
Dec 4 - Dec 5
Old Wooden Bridge Resort and Marina
A nighttime pool area with a clear view of the pool, surrounding palm trees, and a building with a sign.

9. Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,296 reviews)
"Great spot"
Canada
Justin
The price is ￥25,073
￥34,585 total
includes taxes & fees
Nov 8 - Nov 9
Skipjack Resort & Marina
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

10. Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.6 out of 10, Exceptional, (380 reviews)
"Loved staying in the aqua lodges, such a relaxing place."
United States
Lauren
The price is ￥15,029
￥39,053 total
includes taxes & fees
Nov 8 - Nov 9
Yacht Haven Marina
A beachfront hotel with two palm trees, a flag, and a pool area with lounge chairs.

11. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (43 reviews)
"great stay and value! glad we went with this place for our trip, everyone loved it! beautiful, clean and the pool was great too!"
Canada
Nick
The price is ￥21,523
￥59,050 total
includes taxes & fees
Nov 16 - Nov 17
Florida Keys Getaway - Slps 4 - Ocean View
A white building with a covered porch and a palm tree.

12. Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!
Old Town Key West
9.6 out of 10, Exceptional, (463 reviews)
"This studio is in a wonderful location and comes with bikes and a pool spa. It is a fabulous place to stay for a relaxing get-away island-style."
United States
Laura D.
The price is ￥18,384
￥41,467 total
includes taxes & fees
Nov 18 - Nov 19
Steps from Duval, Pool on Site & Bikes Included!
A resort with a swimming pool, lounge chairs, and a view of the ocean.

13. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
2.5 star property
Marathon
9.2 out of 10, Wonderful, (147 reviews)
"It is an excellent place."
United States
Arianna
The price is ￥30,823
￥39,130 total
includes taxes & fees
Nov 30 - Dec 1
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
Exterior

14. Piece of Paradise

Piece of Paradise
2.0 star property
Key largo
The price is ￥27,078
￥59,757 total
includes taxes & fees
Dec 1 - Dec 2
Piece of Paradise
A wooden deck with a large tree, outdoor seating, and a marina in the background.

15. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Wonderful stay. Thank you."
United States
shannon b.
The price is ￥29,136
￥47,641 total
includes taxes & fees
Nov 29 - Nov 30
Poolside Cottage #412
A small, private entrance to a house with a brick pathway leading to a door.

16. Ricky's Retreat - Truman @ Duval | Ideal Getaway!

Ricky's Retreat - Truman @ Duval | Ideal Getaway!
Old Town Key West
9.8 out of 10, Exceptional, (40 reviews)
"Ricky’s Retreat is in a fantastic location. The room was all you need in Key West. Highly recommend it and will definitely stay there again."
United States
Brian R.
The price is ￥21,488
￥60,263 total
includes taxes & fees
Nov 16 - Nov 17
Ricky's Retreat - Truman @ Duval | Ideal Getaway!
A tropical garden pathway leading to a building with a yellow facade and green shutters.

17. SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (139 reviews)
"Great place to stay"
United States
walter l.
The price is ￥26,128
￥57,087 total
includes taxes & fees
Nov 10 - Nov 11
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Exterior

18. Aqua Lodges at 47th Street Gulfside

Aqua Lodges at 47th Street Gulfside
3.0 star property
Marathon
8.8 out of 10, Excellent, (61 reviews)
"Loved our stay at the aqua lodges 10/10 would do it again"
United States
Lauren
The price is ￥22,660
￥47,762 total
includes taxes & fees
Nov 8 - Nov 9
Aqua Lodges at 47th Street Gulfside
A tropical garden pathway leading to a building with a yellow facade and green shutters.

19. 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, (115 reviews)
"Absolutely perfect! Great location, great property and great unit. Beautiful pool area with ice machine and filtered water dispenser was a highlight for the very hot and humid time we visited. Would return immediately and stay in the same spot. Thank you for a very enjoyable time in Key West!"
United States
Justin D.
The price is ￥26,920
￥58,136 total
includes taxes & fees
Dec 1 - Dec 2
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
A wooden deck with a thatched roof, wooden chairs, and tables, overlooking a clear blue sea.

20. Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (116 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is ￥20,586
￥58,313 total
includes taxes & fees
Nov 19 - Nov 20
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
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

Lime Tree Bay Resort

Lime Tree Bay Resort

10/10 Excellent
"My husband and I had a wonderful stay! Our room had a small private balcony overlooking the pool, and the water - it was very peaceful. The restaurant next door was excellent and laid back - great place to eat after a day out exploring. the pool is zero entry - so can walk in from the side. they have a cute little sitting area downstairs that would be great to sit and play games - and fun hammocks and chairs by the water to sit and read, rest, or lay out in the sun. The resort is located about half way down the Keys - and was a great spot to use as a base to go out and explore during the day. I would stay here again in a heartbeat!"
Sara 2-night trip
Posted 1 hour ago
Lime Tree Bay Resort

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Vacation Apartments in Monroe County

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