Vacation Homes in Monroe County

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Top Cities in Monroe County

Vacation HomesVacation Homes

Key West

Key West
Vacation HomesVacation Homes

Marathon

Marathon

Our top choices for Monroe County vacation homes

Outdoor pool

Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages
3.0 star property
Summerland Key
9.4 out of 10, Exceptional, (14 reviews)
"First time staying here it won’t be our last!"
United States
Thomas
Sugarloaf Key RV Resort & Cottages
Outdoor pool, pool umbrellas, sun loungers

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, (140 reviews)
"This was the perfect place, right on the ocean and a full kitchen so you can cook your own meals. The room was very clean, I loved that they had a laundry basket and laundry detergent in the room for you, came in handy seeing as we stayed for 7 days. Amazing place to watch the sunset from a hammock and we got lucky enough to see some nurse sharks at the docks right outside of our hotel."
United States
Andrew Jackson
The price is AED 757
AED 955 total
includes taxes & fees
6 Jul - 7 Jul
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
Fridge, microwave, oven, dishwasher

Sea Esta Suite | Located On Iconic Duval w/ Pool

Sea Esta Suite | Located On Iconic Duval w/ Pool
Old Town Key West
9.8 out of 10, Exceptional, (46 reviews)
"Great stay! "
United States
Colleen S.
The price is AED 929
AED 3,089 total
includes taxes & fees
28 Jun - 29 Jun
Sea Esta Suite | Located On Iconic Duval w/ Pool
Terrace/patio

ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!

ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!
Old Town Key West
9.6 out of 10, Exceptional, (97 reviews)
"The location was phenomenal. "
United States
David L.
ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!
Exterior

Waterfront 2BR Home w/ Dock + Golf Cart, Open Water Views in Venture Out

Waterfront 2BR Home w/ Dock + Golf Cart, Open Water Views in Venture Out
Cudjoe Key
10.0 out of 10, Exceptional, (16 reviews)
"Good facilities and nice location. Great value for money."
United States
Mark B.
Waterfront 2BR Home w/ Dock + Golf Cart, Open Water Views in Venture Out
Outdoor pool, a heated pool

Oceanfront, Pool, Tiki, Amazing Views, Near Vaca, Great Dockage, Kayaks, Bikes

Oceanfront, Pool, Tiki, Amazing Views, Near Vaca, Great Dockage, Kayaks, Bikes
Marathon Shores
10.0 out of 10, Exceptional, (107 reviews)
"House was amazing and location was perfect wish we could’ve stayed longer. "
United States
Michael G.
Oceanfront, Pool, Tiki, Amazing Views, Near Vaca, Great Dockage, Kayaks, Bikes
Outdoor pool, a heated pool

NEW! OCEANFRONT SHOWHOUSE CASA MAR • NO RESORT OR MANAGMENT FEES • 2 KING SUITES

NEW! OCEANFRONT SHOWHOUSE CASA MAR • NO RESORT OR MANAGMENT FEES • 2 KING SUITES
Rock Harbor
9.8 out of 10, Exceptional, (113 reviews)
"Nicely decorated and nice location. "
United States
Rob L.
NEW! OCEANFRONT SHOWHOUSE CASA MAR • NO RESORT OR MANAGMENT FEES • 2 KING SUITES
Property grounds

Water Front Home with Tiki Hut and 40 Ft Dock and Launch

Water Front Home with Tiki Hut and 40 Ft Dock and Launch
Key Largo
8.8 out of 10, Excellent, (13 reviews)
Water Front Home with Tiki Hut and 40 Ft Dock and Launch
A heated pool

LADY ADMIRAL ~Sweet cottage & guest house with private heated pool off Duval!

LADY ADMIRAL ~Sweet cottage & guest house with private heated pool off Duval!
Old Town Key West
9.8 out of 10, Exceptional, (246 reviews)
"Neat, comfortable, attractively decorated and perfectly located."
United States
Stanley S.
LADY ADMIRAL ~Sweet cottage & guest house with private heated pool off Duval!
Exterior

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
Matecumbe
9.8 out of 10, Exceptional, (50 reviews)
"Very clean Extremely well stocked Perfect for 2 couples!"
United States
Carol
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
Outdoor dining

LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool

LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
Old Town Key West
10.0 out of 10, Exceptional, (233 reviews)
"Location was perfect. Very clean and relaxing stay."
United States
Gina P.
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
Fridge, microwave, oven, stovetop

SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
Old Town Key West
9.8 out of 10, Exceptional, (215 reviews)
"Location was perfect! The home was just right for 3 couples. "
United States
Diane P. P.
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
A heated pool, sun loungers

MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!

MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
Old Town Key West
9.6 out of 10, Exceptional, (232 reviews)
"We had a nice stay. Good location. Listing was very accurate."
United States
Edward S.
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
Fridge, microwave, oven, stovetop

Luxurious Island Pearl - June 1st-July 15th 15% Off!-Private Pool - 2BD/2Bath

Luxurious Island Pearl - June 1st-July 15th 15% Off!-Private Pool - 2BD/2Bath
Key West Historic District
10.0 out of 10, Exceptional, (56 reviews)
"Amazing stay five star!! "
United States
Erica S.
The price is AED 1,634
AED 3,604 total
includes taxes & fees
25 Jun - 26 Jun
Luxurious Island Pearl - June 1st-July 15th 15% Off!-Private Pool - 2BD/2Bath
Exterior

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Key Largo
9.6 out of 10, Exceptional, (88 reviews)
"Great location with respect to attractions (snorkeling, etc), restaurants and groceries; great sunrise and sunset views; property is very quiet/serene; straightforward logistics for checking in and checking out."
United States
Jeffrey W.
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Terrace/patio

Road's End | Prime Old Town Location! Updated Home w/ Pool

Road's End | Prime Old Town Location! Updated Home w/ Pool
Old Town Key West
9.8 out of 10, Exceptional, (16 reviews)
"The property was very clean with an excellent location. "
United States
Mike T.
The price is AED 663
AED 1,856 total
includes taxes & fees
13 Jul - 14 Jul
Road's End | Prime Old Town Location! Updated Home w/ Pool
TV

ISLAND DAZE ~ Adorable 2 Bedroom, 2 Bathroom Cottage 1/2 block to Duval!

ISLAND DAZE ~ Adorable 2 Bedroom, 2 Bathroom Cottage 1/2 block to Duval!
Old Town Key West
9.8 out of 10, Exceptional, (168 reviews)
"You couldn’t get a better location. It was a great place good parking, it had everything we needed in the kitchen. Rooms were beautiful but we did have a bug problem the first day but the host did have it looked after. We would stay again thank you Dan"
Canada
Danny
ISLAND DAZE ~ Adorable 2 Bedroom, 2 Bathroom Cottage 1/2 block to Duval!
Marina

Open Water View from porch , golf cart, dock, bikes, kayaks, trailer parking

Open Water View from porch , golf cart, dock, bikes, kayaks, trailer parking
Cudjoe Key
9.8 out of 10, Exceptional, (141 reviews)
"Friendly community that was very safe and walkable. Had everything we needed. "
United States
Anna B.
Open Water View from porch , golf cart, dock, bikes, kayaks, trailer parking
Outdoor pool, a heated pool

Keys Oceanfront Oasis 4BR, 3.5 Bath Pool Home in Marathon. Amazing views

Keys Oceanfront Oasis 4BR, 3.5 Bath Pool Home in Marathon. Amazing views
Marathon Shores
10.0 out of 10, Exceptional, (1 review)
"This was our 3rd time staying at this property in Marathon. We always enjoyed our stay but this time the updates to the home were nice and the owners were very efficient at getting back with us on any questions we had!"
United States
Hannah M.
Keys Oceanfront Oasis 4BR, 3.5 Bath Pool Home in Marathon. Amazing views
A heated pool

CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!

CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!
Key West Historic District
9.8 out of 10, Exceptional, (235 reviews)
"It was our second stay here. The home is in a great location and the heated private plunge pool is a plus."
United States
David R.
CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!
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

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

8/10 Good
"The food was amazing! There was a language barrier for the maid staff, but most were very nice. The last three days the place was overrun by little league baseball players and their families. The lobby was packed with screaming, horseplay all hours and both pools were overcrowded with kids as well. The pool was not maintained well and was full of hair and bugs. Overall, fantastic experience."
Autumn 7-night trip
Posted 6 hours ago
Blue Flamingo Resort Key West