Cruise And Resorts - Vacation Rentals in Monroe County

Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures From US $424
         

BEAUTIFUL STAY ON THE WATER From US $270
         

1.0 (14 Reviews)
Boat Rental
  • Air Conditioner
  • Parking
  • View
Yacht Haven Marina From US $278
         

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9.8 (228 Reviews)
Boat Rental
  • Air Conditioner
  • Parking
  • View
Waterfront Sunset View in the Aqua Villa Sand Dollar @ Mangrove Resort LLC From US $354
         

Affordable luxury yacht charters. From US $1,174
         

10.0 (48 Reviews)
Boat Rental
  • Air Conditioner
  • Parking
  • TV
Ocean views! Luxury suites From US $638
         

10.0 (26 Reviews)
Boat Rental
  • Air Conditioner
  • Parking
  • TV
Aqua Lodge Houseboat "The Grey Lady" From US $506
         

10.0 (22 Reviews)
Boat Rental
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Monroe County

Over 10000+ Luxury Places to Stay in or Near Monroe County
Little Bay Compound From US $16,123
         

New
House
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  • Pet Friendly
The Greenmoor House at Lunara Bay From US $8,800
         

New
House
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  • Pet Friendly
The Dreamside House at Lunara Bay From US $8,800
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Monroe County

Over 9762+ Top-Rated Vacation Rentals with a Pool in or Near Monroe County
Almond Tree Inn Hotel - Adults Only From US $272
         

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10.0 (1003 Reviews)
Hotel
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  • Pool

Pet-Friendly Vacation Rentals in Monroe County

Over 4297+ Pet-Friendly Vacation Rentals in or Near Monroe County
Amsterdam's Curry Mansion Inn From US $563
         

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8.8 (139 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Capmar House by Brightwild Huge Home Pool From US $1,724
         

10.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • Balcony/Terrace
Luxury 3-Bedroom Waterfront Home with Pool AND Dock! From US $1,764
         

9.8 (132 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Monroe County

Over 2251+ Large Vacation Homes & Villas in or Near Monroe County
Pelico Paradise From US $304
         

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9.6 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Atlantic View Luxury Villa with Pool From US $983
         

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10.0 (1 Review)
Villa
  • Parking
  • Pet Friendly
  • Pool
5 bedroom - Deep Dockage & Heated Pool in Islamorada. From US $1,313
         

Wheelchair Accessible Vacation Homes in Monroe County

Over 2897+ Wheelchair Accessible Vacation Homes in or Near Monroe County
Sunshine Key King Travel Trailer 4 From US $238
         

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8.9 (20 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Islands of Islamorada From US $730
         

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9.8 (69 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Sea View Farm Style Ocean front Condo Views From US $449
         

10.0 (154 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Birds Eye Loft Perched Above the Marina 1BR 1BA 5413 From US $343
         

Top Floor unit with a ocean view! PRIVATELY OWNED From US $296
         

9.8 (127 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Monroe County Varoom and Airbnb Places to Stay Under $200

Over 1192+ Monroe County Varoom and Airbnb Places to Stay Under $200
Dolphin Retreat From US $162
         

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8.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxurious Tropical Retreat with Private Tiki Hut From US $129
         

9.8 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
@ KEY WEST DOWNTOWN STUDIO APT AMAZING PRICES FOR WINTER OF 2025 From US $122
         

Outdoor Resorts, Long Key, FL From US $114
         

7.4 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Instantly Bookable Vacation Homes in Monroe County

Over 8817+ Instantly Bookable Vacation Homes in or Near Monroe County

About Monroe County Vacation Rentals

With more than 173 Monroe County vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Cruiseandresorts and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Monroe County.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Cruiseandresorts Monroe County, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Monroe County. Places to stay near Monroe County are 199.15 ft² on average, with prices averaging $603 a night.

Cruiseandresorts makes it easy and safe to find and compare vacation rentals in Monroe County with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Monroe County

Type Count

Use these Quick Filters to Find a Vacation Rental in Monroe County

Pro Tip: Cruiseandresorts makes it easy to compare the best listings on Cruiseandresorts homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Cruiseandresorts homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Monroe County.

Weather in Monroe County

View the weather forecast for Monroe County before booking your Monroe County Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F