The Islands Advisors - Vacation Rentals in Islamorada

The Islands of Islamorada From US $954
         

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9.8 (72 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
5 bedroom - Deep Dockage & Heated Pool in Islamorada. From US $1,350
         

Paradise @ Islamorada From US $388
         

9.6 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Islamorada

Over 1533+ Luxury Places to Stay in or Near Islamorada
Little Bay Compound From US $16,123
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Beachfront Villa at Islamorada BY THE GLAMHOMES From US $7,615
         

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1.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Private Beach/Private overwater dock/Heated Pool/Mahi Key From US $4,538
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
10 Bedroom Private Ocean Front Estate From US $3,453
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in Islamorada

Over 1075+ Top-Rated Vacation Rentals with a Pool in or Near Islamorada
The Caribbean Resort From US $639
         

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10.0 (166 Reviews)
Hotel
  • Air Conditioner
  • Pool
  • Designated Smoking Area
5 Star Modern Oceanfront Islamorada Townhome on the Beach! From US $387
         

Pet-Friendly Vacation Rentals in Islamorada

Over 499+ Pet-Friendly Vacation Rentals in or Near Islamorada
Islander Resort From US $710
         

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8.7 (1439 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
Oceanfront Private Cottage! From US $269
         

10.0 (113 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Fisher Inn Resort & Marina From US $274
         

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8.2 (1009 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Breathtaking ocean views for your Paradise vacations From US $465
         

10.0 (100 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
May 2nd - 9th available Oceanfront - Heated Pool - Dock From US $1,474
         

10.0 (94 Reviews)
House
  • Air Conditioner
  • Parking
  • 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)
House
  • Air Conditioner
  • Parking
  • Pool
ISLAMORADA BEACH HOUSE From US $592
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • TV
Islamorada house with best location. Lic # 24-0055 From US $624
         

10.0 (19 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Isla Honeydew: 3 En-Suite Bedrooms, Pool, Dock From US $616
         

Wheelchair Accessible Vacation Homes in Islamorada

Over 409+ Wheelchair Accessible Vacation Homes in or Near Islamorada
Chesapeake Beach Resort From US $349
         

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8.6 (862 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
Cheeca Lodge & Spa From US $437
         

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9.2 (1307 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Ocean & Bay Views. Welcome To Paradise! From US $325
         

10.0 (36 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Islamorada Penthouse with Private Beach & Pool! From US $1,212
         

10.0 (21 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Egret House @ Tarpon Point From US $1,057
         

10.0 (21 Reviews)
House
  • Air Conditioner
  • Pool
  • TV

Islamorada Vacation Rentals and Airbnb Places to Stay Under $200

Over 112+ Islamorada Vacation Rentals and Airbnb Places to Stay Under $200
Islamorada Paradise Overlooking the Fabulous Florida Bay. From US $189
         

Matecumbe Resort From US $192
         

8.8 (99 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Ocean front property From US $132
         

9.6 (7 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Exec Bay w/heated Pool, Marina, Beach, Pets ok, Tennis/Pickleball From US $161
         

Instantly Bookable Vacation Homes in Islamorada

Over 781+ Instantly Bookable Vacation Homes in or Near Islamorada
Anglers Reef Islamorada - 2:2.5, Boat Slip, Pool & Beach From US $458
         

3‑Acre Oceanfront Estate w/Pool ON the Atlantic, 2 Homes & Beach From US $1,409
         

About Islamorada Vacation Rentals

With more than 1542 Islamorada vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Theislandsadvisors 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 Theislandsadvisors 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 753.92 ft² on average, with prices averaging $785 a night.

Theislandsadvisors 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 899
Hotels with Suites 156
Holiday Apartments 126
Villas 101
Resorts 62
Cottages 15
Others 15

Use these Quick Filters to Find a Vacation Rental in Islamorada

Pro Tip: Theislandsadvisors makes it easy to compare the best listings on Theislandsadvisors homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Theislandsadvisors 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 1542 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.