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Monroe County Villas

Escape to Paradise: Discover stunning Monroe County villas, perfect for beach lovers. Enjoy crystal-clear waters, scenic views & luxurious amenities.

Villas in Monroe County

Get Ready for Blissful Getaway, Near Islamorada Brewery & Distillery wGet Ready for Blissful Getaway, Near Islamorada Brewery & Distillery w/ Parking/ Parking
£213  night
4
1
1
Details View Offers
Villa IKI -Private Dock & Pool - Oceanfront 8 guests
5.0/5
£1093  night
10
4
2
Details View Offers
Harbor Walk Hideaways - The Pilar's Cottage | Pool
4.7/5
£182  night
4
1
1
Details View Offers
BG Beach Front villa Pool Beach Dock Ocean Sleeps 6 W&D Kitchen Parking WiFi BBQ
4.7/5
£339  night
6
2
2
Details View Offers
8BR Spacious Miami Shores Mansion w8BR Spacious Miami Shores Mansion w/Private Pool, Billiards, Cinema & PingPong!/Private Pool, Billiards, Cinema & PingPong!
£3761  night
20
9
6
Details View Offers
LUXURY VILLA
£452  night
10
5
3
Details View Offers
Stunning Key Biscayne Waterfront Villa with Heated Pool - 12mins to Miami
4.0/5
£3224  night
16
6
6
Details View Offers
Brickell Miami Villa Spacious 4BR\/4BA or 5BR\/5BA
£707  night
10
4
4
Details View Offers
LUXURY OCEAN FRONT ❤️ You won’t want to leave this Key Largo Property
5.0/5
£335  night
10
3
3
Details View Offers
OceanGaze Poolside Villa
4.7/5
£331  night
8
3
3
Details View Offers
Sunny Escape! Spacious Oceanfront Suite with Balcony! Beachfront Resort wSunny Escape! Spacious Oceanfront Suite with Balcony! Beachfront Resort w/ Pool!/ Pool!
£412  night
4
1
1
Details View Offers
LUXE HOME: Private Pool, BBQ & Games - 10Min Airport
5.0/5
£354  night
10
4
3
Details View Offers
Islamorada Getaway | 2 Family Ready Bayfront Villa wIslamorada Getaway | 2 Family Ready Bayfront Villa w/ Spacious Living Area/ Spacious Living Area
£1385  night
12
4
4
Details View Offers
Excellent Choice for Families! Full Kitchen, Pool, Pet-friendly, Free Parking!
£1043  night
8
3
2
Details View Offers
Seaside Escape - Waterfront Villa
4.8/5
£267  night
8
4
3
Details View Offers
Gull's Nest with Resort Privileges
4.8/5
£574  night
8
4
5
Details View Offers
Your Majestic View in Islamorada! Swimming Pool, Kitchenette, Pets Allowed!
£786  night
8
2
2
Details View Offers
Luxurious Oceanside Villa in the Florida Keys with Stunning Views
2.8/5
£234  night
6
2
3
Details View Offers
Isla Marlin 28: Palm lined luxury villa wIsla Marlin 28: Palm lined luxury villa w/dockage and sunset views/dockage and sunset views
4.9/5
£277  night
8
3
3
Details View Offers
Heavenly Escape: poolside heaven, King bed ,perfect location
5.0/5
£207  night
1
3
2
Details View Offers

Why a holiday villa in Monroe County

Escape to the breathtaking beauty of Monroe County, where pristine beaches and crystal-clear waters await your arrival. Imagine waking up each morning in a luxurious villa, surrounded by lush tropical gardens and just steps from the shore. Whether you're looking for a romantic getaway, a family vacation, or simply a chance to unwind and recharge, Monroe County villas offer the perfect blend of relaxation and adventure.

From snorkeling and diving among vibrant coral reefs to exploring the charming towns and villages that dot the coastline, there's no shortage of exciting experiences to be had in Monroe County. And with your villa serving as a comfortable and stylish base from which to explore, you'll have all the freedom and flexibility you need to create unforgettable memories with friends and family. So why settle for just any ordinary holiday when you can have an extraordinary one in this stunning Florida county?

When to rent a villa in Monroe County

Monroe County's subtropical climate offers a pleasant getaway throughout the year, but some periods are more suitable than others. If you're looking for warm weather without the peak-season crowds, consider visiting during the spring (April-May) or fall (September-October), when temperatures range from 70°F to 85°F (21°C to 30°C). These shoulder seasons offer ideal conditions for outdoor activities like snorkeling, diving, and beachcombing, with smaller crowds at popular spots. The weather is also less prone to extreme conditions, making it a great time for exploring the area.

If you're looking for the warmest weather possible, the summer months (June-August) are the best bet, with average highs in the mid-80s to low 90s Fahrenheit (30°C to 32°C). However, this is also peak tourist season, and prices for villas tend to be higher. If you're on a budget or prefer milder temperatures, the winter months (December-February) might not be the best choice, as they can bring cooler temperatures, averaging around 70°F to 75°F (21°C to 24°C). But if you're looking for a more relaxed atmosphere and don't mind cooler evenings, this could still be a great time for a villa holiday in Monroe County.

Where to go in Monroe County

With its stunning coastline stretching across 66 miles of oceanfront, Monroe County offers a diverse range of experiences and landscapes to explore from your villa base. For a taste of vibrant island life, head to Key West, the southernmost tip of the county, where colorful buildings, lively nightlife, and world-class seafood restaurants await. Alternatively, for a more relaxed pace, consider Islamorada or Marathon, which offer quieter walks along secluded beaches, tranquil sunsets, and an array of laid-back cafes and eateries.

Or perhaps you'll prefer the tranquility of the Upper Keys, where upscale communities like Tavernier and Key Largo offer villas with breathtaking ocean views, golf courses, and gourmet dining options. If you're looking for a mix of beach time and outdoor adventures, consider the lower Keys, where Calusa Beach, Sugarloaf Key, and Windley Key are just a few spots to enjoy snorkeling, diving, or simply soaking up the sun on some of Florida's most beautiful beaches.

Picture of two young girls swimming in a pool with their floatation rings
Family friendly villas
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Picture of a Titleist golf ball on the edge of the hole on a golfing green
Villas near golf course
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Image of a woman swimming in a pool at a holiday home
Private pool villas
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Discover regions within Monroe County

Islamorada
Islamorada
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Marathon
Marathon
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Key West
Key West
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Villas in Monroe County

Get Ready for Blissful Getaway, Near Islamorada Brewery & Distillery wGet Ready for Blissful Getaway, Near Islamorada Brewery & Distillery w/ Parking/ Parking
£213  night
4
1
1
Details View Offers
Villa IKI -Private Dock & Pool - Oceanfront 8 guests
5.0/5
£1093  night
10
4
2
Details View Offers
Harbor Walk Hideaways - The Pilar's Cottage | Pool
4.7/5
£182  night
4
1
1
Details View Offers
BG Beach Front villa Pool Beach Dock Ocean Sleeps 6 W&D Kitchen Parking WiFi BBQ
4.7/5
£339  night
6
2
2
Details View Offers
8BR Spacious Miami Shores Mansion w8BR Spacious Miami Shores Mansion w/Private Pool, Billiards, Cinema & PingPong!/Private Pool, Billiards, Cinema & PingPong!
£3761  night
20
9
6
Details View Offers
LUXURY VILLA
£452  night
10
5
3
Details View Offers
Stunning Key Biscayne Waterfront Villa with Heated Pool - 12mins to Miami
4.0/5
£3224  night
16
6
6
Details View Offers
Brickell Miami Villa Spacious 4BR\/4BA or 5BR\/5BA
£707  night
10
4
4
Details View Offers
LUXURY OCEAN FRONT ❤️ You won’t want to leave this Key Largo Property
5.0/5
£335  night
10
3
3
Details View Offers
OceanGaze Poolside Villa
4.7/5
£331  night
8
3
3
Details View Offers
Sunny Escape! Spacious Oceanfront Suite with Balcony! Beachfront Resort wSunny Escape! Spacious Oceanfront Suite with Balcony! Beachfront Resort w/ Pool!/ Pool!
£412  night
4
1
1
Details View Offers
LUXE HOME: Private Pool, BBQ & Games - 10Min Airport
5.0/5
£354  night
10
4
3
Details View Offers
Islamorada Getaway | 2 Family Ready Bayfront Villa wIslamorada Getaway | 2 Family Ready Bayfront Villa w/ Spacious Living Area/ Spacious Living Area
£1385  night
12
4
4
Details View Offers
Excellent Choice for Families! Full Kitchen, Pool, Pet-friendly, Free Parking!
£1043  night
8
3
2
Details View Offers
Seaside Escape - Waterfront Villa
4.8/5
£267  night
8
4
3
Details View Offers
Gull's Nest with Resort Privileges
4.8/5
£574  night
8
4
5
Details View Offers
Your Majestic View in Islamorada! Swimming Pool, Kitchenette, Pets Allowed!
£786  night
8
2
2
Details View Offers
Luxurious Oceanside Villa in the Florida Keys with Stunning Views
2.8/5
£234  night
6
2
3
Details View Offers
Isla Marlin 28: Palm lined luxury villa wIsla Marlin 28: Palm lined luxury villa w/dockage and sunset views/dockage and sunset views
4.9/5
£277  night
8
3
3
Details View Offers
Heavenly Escape: poolside heaven, King bed ,perfect location
5.0/5
£207  night
1
3
2
Details View Offers