Monroe County Rentals By Owner

There are a lot of options in Monroe County. If you plan on staying in the Monroe County area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Monroe County:

• 5% Off Any Booking through Jan 31, 2026! Canal Front/Private Pool/Hot Tub/Dock!
• Absolutely Perfect! Reel Vacation Villa w/Pool, Dock, Close to Beach w/Extras!
• Sunset Villas - Affordable Open Waterfront Accommodations with Dockage & Ramp
• Two Bedroom Two Bath Balcony Villa Steps from Duval!
• Admirals Gold Key West - Truman Annex Villa - Close to Beach and Duval w Parking and Pool Access
• ISLAND PARADISE
• 4 BR 4 BA, Private Pool, Paddleboards, Bikes, Lots of Great Amenities!
• Tropical Retreat Villa on Lush Acre
• Sunset Villas: Bayfront Beach Compound *28 Night Min*
• Poolside Studio Villa Steps from Duval!

There are many large, family-friendly vacation homes available in Monroe County; however, here are the most popular family rentals listed on our site:

• Life in Paradise at #1 Rated Resort in Marathon - Coral Lagoon - Boat Slip Avail
• Old Town Garden Villas
• Marlin Bay Resort & Marina
• Keys Kottage: Bayside villa W/free onsite boat ramp marina & trailer parking.

Yes, there are 948 self-catering vacation homes in Monroe County that have hot tubs, swimming pools, & other amenities.

There are more than 948 luxury villas and vacation homes in or near Monroe County. Filter by price to compare find the most expensive places to stay on Castleinhawaii.

Yes, there are 948 pet friendly vacation homes and places to stays that are available in or near Monroe County that you may consider.