Anderson Island Living - Vacation Rentals in Islamorada

Chesapeake Beach Resort From US $268
         

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9.2 (1742 Reviews)
Hotel
  • Air Conditioner
  • Pool
  • TV
5 bedroom - Deep Dockage & Heated Pool in Islamorada. From US $1,322
         

Serenity by the Sea! Anglers Reef with Boat Slip Available! From US $393
         

Luxury Places to Stay in Islamorada

Over 1576+ Luxury Places to Stay in or Near Islamorada
New
House
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10 Bedroom Private Ocean Front Estate From US $3,453
         

10.0 (1 Review)
Villa
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  • Pool

Top-Rated Vacation Rentals with a Pool in Islamorada

Over 1126+ Top-Rated Vacation Rentals with a Pool in or Near Islamorada
Now booking heavily for 2027! - Oceanfront - Heated Pool - Dock From US $1,359
         

Pet-Friendly Vacation Rentals in Islamorada

Over 512+ Pet-Friendly Vacation Rentals in or Near Islamorada
Hooked on Islamorada Oceanfront Townhome, Private Dock, Pool From US $764
         

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9.5 (2 Reviews)
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Luxe Beachfront Villa From US $1,680
         

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New
Villa
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  • Pet Friendly
Oceanfront Keys Escape | Private Beach & Pool | 3 Acres From US $1,595
         

10.0 (53 Reviews)
House
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  • Pet Friendly
Venetian Shores Waterfront with Ocean Access, Pool From US $1,099
         

10.0 (39 Reviews)
House
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  • Pet Friendly
Gated Keys Home | Dock, Heated Pool & 2 Pools | Pet-OK From US $1,015
         

10.0 (34 Reviews)
House
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  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Islamorada

Over 311+ Large Vacation Homes & Villas in or Near Islamorada
Pineapple Beach From US $2,500
         

10.0 (1 Review)
House
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  • Pool
The Islands of Islamorada From US $774
         

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9.6 (76 Reviews)
Villa
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Islamorada house with best location. Lic # 24-0055 From US $624
         

10.0 (21 Reviews)
Villa
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Isla Honeydew: 3 En-Suite Bedrooms, Pool, Dock From US $457
         

10.0 (8 Reviews)
Villa
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Wheelchair Accessible Vacation Homes in Islamorada

Over 441+ Wheelchair Accessible Vacation Homes in or Near Islamorada
Islander Resort From US $710
         

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8.9 (1338 Reviews)
Resort
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  • Pet Friendly
Cheeca Lodge & Spa From US $313
         

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9.2 (1325 Reviews)
Resort
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Egret House @ Tarpon Point From US $973
         

10.0 (22 Reviews)
House
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Islamorada Penthouse with Private Beach & Pool! From US $904
         

10.0 (21 Reviews)
Condo
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  • Pool

Islamorada Vacation Rentals and Airbnb Places to Stay Under $200

Over 116+ 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 $196
         

8.8 (700 Reviews)
Apartment
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  • Pool
Exec Bay w/heated Pool, Marina, Beach, Pets ok, Tennis/Pickleball From US $128
         

Instantly Bookable Vacation Homes in Islamorada

Over 826+ Instantly Bookable Vacation Homes in or Near Islamorada
Anglers Reef Islamorada - 2:2.5, Boat Slip, Pool & Beach From US $416
         

Sunset Access + Boat Basin | Walkable Islamorada From US $405
         

10.0 (47 Reviews)
Apartment
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  • Parking
  • TV
Peacock Shores Islamorada - Vacation On The Beach! From US $427
         

10.0 (46 Reviews)
House
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  • Pool
Islamorada's Anglers Reef- Extra special June rates From US $394
         

Elevated Retreat | Sunset Access + Boat Basin From US $388
         

10.0 (36 Reviews)
Apartment
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  • Parking
  • TV

About Islamorada Vacation Rentals

With more than 1585 Islamorada vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Andersonislandliving 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 Andersonislandliving 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 735.98 ft² on average, with prices averaging US $765 a night.

Andersonislandliving 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
Vacation Homes 895
Hotels 199
Holiday Apartments 131
Villas 104
Resorts 63
Others 15
Cottages 14

Use these Quick Filters to Find a Vacation Rental in Islamorada

Pro Tip: Andersonislandliving makes it easy to compare the best listings on Andersonislandliving homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Andersonislandliving 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 1585 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.