Luxury Home Villas - Vacation Rentals in Islamorada

Anglers Reef Vacation Rental From US $495
         

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9.5 (2 Reviews)
Villa
  • Air Conditioner
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  • Pool
The Islands of Islamorada From US $810
         

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9.6 (76 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Serenity by the Sea! Anglers Reef with Boat Slip Available! From US $393
         

Islamorada house with best location. Lic # 24-0055 From US $624
         

10.0 (20 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Isla Honeydew: 3 En-Suite Bedrooms, Pool, Dock From US $499
         

10.0 (8 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Islamorada

Over 1586+ Luxury Places to Stay in or Near Islamorada
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10 Bedroom Private Ocean Front Estate From US $3,453
         

10.0 (1 Review)
Villa
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Oceanfront 4BR Villa | Resort Access + Bunks From US $2,945
         

10.0 (1 Review)
Condo
  • Air Conditioner
  • Parking
  • TV

Top-Rated Vacation Rentals with a Pool in Islamorada

Over 1131+ Top-Rated Vacation Rentals with a Pool in or Near Islamorada
The Caribbean Resort From US $639
         

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10.0 (172 Reviews)
Hotel
  • Air Conditioner
  • Pool
  • Designated Smoking Area
5 bedroom - Deep Dockage & Heated Pool in Islamorada. From US $1,322
         

Pet-Friendly Vacation Rentals in Islamorada

Over 508+ Pet-Friendly Vacation Rentals in or Near Islamorada
Islander Resort From US $710
         

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8.9 (1338 Reviews)
Resort
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  • Pet Friendly
Fisher Inn Resort & Marina From US $206
         

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8.2 (1010 Reviews)
Hotel
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  • Pet Friendly
Oceanfront Private Cottage! From US $269
         

10.0 (116 Reviews)
Cottage
  • Air Conditioner
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  • Pet Friendly
Breathtaking ocean views for your Paradise vacations From US $465
         

10.0 (104 Reviews)
Apartment
  • Air Conditioner
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  • Pet Friendly
Next available - August 2026 - Oceanfront - Heated Pool - Dock From US $1,373
         

10.0 (97 Reviews)
House
  • Air Conditioner
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  • Pet Friendly

Large Vacation Homes & Villas in Islamorada

Over 309+ Large Vacation Homes & Villas in or Near Islamorada
Pineapple Beach From US $2,500
         

10.0 (1 Review)
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Luxe Beachfront Villa From US $1,680
         

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New
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Isla Key Lime: Boutique Resort, FREE Boat Dockage Sept-Oct Only! From US $533
         

Private Beach/Private overwater dock/Heated Pool/Mahi Key From US $1,800
         

10.0 (2 Reviews)
House
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  • Pet Friendly

Wheelchair Accessible Vacation Homes in Islamorada

Over 432+ Wheelchair Accessible Vacation Homes in or Near Islamorada
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort From US $649
         

Cheeca Lodge & Spa From US $378
         

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9.2 (1318 Reviews)
Resort
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Ocean & Bay Views. Welcome To Paradise! From US $358
         

10.0 (36 Reviews)
Condo
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Egret House @ Tarpon Point From US $992
         

10.0 (22 Reviews)
House
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  • Pool
  • TV
Islamorada Penthouse with Private Beach & Pool! From US $979
         

10.0 (21 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Islamorada Vacation Rentals and Airbnb Places to Stay Under $200

Over 117+ Islamorada Vacation Rentals and Airbnb Places to Stay Under $200
Islamorada Paradise Overlooking the Fabulous Florida Bay. From US $189
         

Breezy Palms Resort From US $195
         

8.8 (687 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Exec Bay w/heated Pool, Marina, Beach, Pets ok, Tennis/Pickleball From US $129
         

Beach View Unit in Islamorada! Pets Allowed, Parking, Pool! From US $195
         

8.6 (25 Reviews)
Apartment
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  • Pet Friendly
Keys Cottage Downtown Islamorada — walk From US $197
         

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Instantly Bookable Vacation Homes in Islamorada

Over 823+ Instantly Bookable Vacation Homes in or Near Islamorada

About Islamorada Vacation Rentals

With more than 109 Islamorada vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Luxuryhomevilla 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 Islamorada.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Luxuryhomevilla Islamorada, 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 Islamorada. Places to stay near Islamorada are 1377.61 ft² on average, with prices averaging US $971 a night.

Luxuryhomevilla makes it easy and safe to find and compare vacation rentals in Islamorada 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 Islamorada

Type Count
Villas 105
Vacation Homes 2
Hotels 1
Resorts 1

Use these Quick Filters to Find a Vacation Rental in Islamorada

Pro Tip: Luxuryhomevilla makes it easy to compare the best listings on Luxuryhomevilla homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Luxuryhomevilla 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 Islamorada.

Weather in Islamorada

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

December - February
High 81°F       Low 56°F
March - May
High 87°F       Low 59°F
June - August
High 91°F       Low 74°F
September - November
High 90°F       Low 64°F

Islamorada Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Islamorada?
How many vacation rentals are available in Islamorada?

Currently, the total number of properties listed in 2026 is over 109 in the Islamorada area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Islamorada.