Holiday Rentals in Monroe County

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Top Cities in Monroe County

Holiday RentalsHoliday Rentals

Key West

Key West

Featured Holiday Rentals in Monroe County

Our top choices for Monroe County holiday rentals

Cabins at Bonefish Bay
Deluxe Bungalow | Terrace/patio

Cabins at Bonefish Bay

3.0 star property
9.8 out of 10, Exceptional, (67)
"I love this place definitely I will go back there soon, rooms clean staff friendly, ocean view amazing the Floating Aqua Lodge was more than amazing. Thank you for making my vacation so special "
Cabins at Bonefish Bay
Yacht Haven Marina
42-inch Smart TV with digital channels, Netflix, Hulu

Yacht Haven Marina

3.5 star property
9.8 out of 10, Exceptional, (209)
"We loved staying on the houseboat! "
Yacht Haven Marina
Treasure Harbor
25-inch flat-screen TV with digital channels, TV

Treasure Harbor

3.0 star property
8.8 out of 10, Excellent, (103)
"Unique House boat experience, friendly staff. "
The price is €206
includes taxes & fees
17 Sept - 18 Sept
Treasure Harbor
Breezy Palms Resort
Exterior

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (536)
"Spacious rooms and location was great for what we needed. "
The price is €118
includes taxes & fees
1 Oct - 2 Oct
Breezy Palms Resort
Tropical Cottages
Exterior

Tropical Cottages

3.0 star property
8.6 out of 10, Excellent, (866)
"Very friendly staff, nice area"
The price is €76
includes taxes & fees
17 Sept - 18 Sept
Tropical Cottages
Aqua Lodges at Hurricane Hole Marina
Restaurant

Aqua Lodges at Hurricane Hole Marina

2.0 star property
9.0 out of 10, Wonderful, (162)
"The stay was beautiful "
The price is €211
includes taxes & fees
17 Sept - 18 Sept
Aqua Lodges at Hurricane Hole Marina
Hyatt Vacation Club at Sunset Harbor, Key West
Exterior

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very good, (314)
"Great hotel with excellent location "
Hyatt Vacation Club at Sunset Harbor, Key West
Skipjack Resort & Marina
Marina

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1203)
"Had a great time in Marathon. Nice accommodations, very friendly staff."
Skipjack Resort & Marina
The Islands of Islamorada
2 outdoor pools, open 8:00 AM to 6:00 PM, pool loungers

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (66)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is €573
includes taxes & fees
28 Sept - 29 Sept
The Islands of Islamorada
Old Wooden Bridge Resort and Marina
2 Bedroom Aqua Lodge # 13 Barracuda | Living area

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (258)
"Really I have the best experience and soon I want to go again "
The price is €196
includes taxes & fees
14 Oct - 15 Oct
Old Wooden Bridge Resort and Marina
Waterfront home with dock, pool table & private pool - walk to Sombrero Beach
A heated pool

Waterfront home with dock, pool table & private pool - walk to Sombrero Beach

8.8 out of 10, Excellent, (29)
"So enjoyed our stay here with a couple friends. Place has everything you need, is immaculate, fantastic view, and so close to either the beach in one direction and grocery stores in the other. Also located in a very nice residential neighborhood. Plan on returning! Thanks for the lovely stay!! "
Waterfront home with dock, pool table & private pool - walk to Sombrero Beach
Knight's Key Suites
Premium bedding, soundproofing, iron/ironing board, free WiFi

Knight's Key Suites

3.0 star property
9.0 out of 10, Wonderful, (1145)
"Great place "
The price is €92
includes taxes & fees
21 Sept - 22 Sept
Knight's Key Suites
Aqua Lodge Rentals At Coconut Cay
BBQ/picnic Area

Aqua Lodge Rentals At Coconut Cay

3.5 star property
9.6 out of 10, Exceptional, (183)
"Very very nice place"
Aqua Lodge Rentals At Coconut Cay
Key Largo Cottages
Boating

Key Largo Cottages

2.5 star property
9.6 out of 10, Exceptional, (24)
"Beautiful and peaceful place "
Key Largo Cottages
Steps from Duval, Pool on Site & Bikes Included!
Exterior

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (401)
"Great location. The bike was an awesome way to get around. Pool was very clean and refreshing. "
The price is €239
includes taxes & fees
13 Oct - 14 Oct
Steps from Duval, Pool on Site & Bikes Included!
Anchorage Resort & Yacht Club
Exterior

Anchorage Resort & Yacht Club

3.0 star property
8.6 out of 10, Excellent, (296)
"Really good place to stay "
The price is €181
includes taxes & fees
24 Sept - 25 Sept
Anchorage Resort & Yacht Club
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
Exterior

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (181)
"Great location; excellent property management "
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
Heart of Downtown Key West Cottage With Off-Street Parking
Exterior

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (136)
"Great Location, Free Parking, comfortable beds"
Heart of Downtown Key West Cottage With Off-Street Parking
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
1 bedroom, free WiFi, bed sheets

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (21)
"We had a wonderful stay here with our kids. Can’t beat the location."
The price is €300
includes taxes & fees
19 Sept - 20 Sept
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!
Beach nearby

COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

9.6 out of 10, Exceptional, (141)
"This property was great, it had everything needed, extremely clean and walking distance to Davual st.The pool area is wonderful and it was the perfect temperature!Would highly recommend."
The price is €269
includes taxes & fees
15 Oct - 16 Oct
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!
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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"all good"
MAXIM 3-night trip
Posted 6 days ago
Cheeca Lodge & Spa

Find out more about Monroe County

Find out more about Monroe County

Holiday Homes in Monroe County

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