Villa Rentals in Islamorada, FL: Compare 10+ Sites & Save

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34 Best Villa Rentals in Islamorada (Starting from $358)

Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location
Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location
Villa
Islamorada, FL, USA
1.5k from Islamorada center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings

3 Bedrooms6 Guests
New to Booking
$802
Average price / night
Check Availability
The Islands of Islamorada
The Islands of Islamorada
Villa
82779 Old Hwy, Islamorada, FL, 33036, United States
0.8k from Islamorada center

AC, Bar, Barbecue, Breakfast Available, Elevator, Fitness Equipment, Free Parking, Heater, Hot Tub

1 Bedroom4 Guests
9.8

Exceptional

73 reviews

$841
Average price / night
Check Availability
Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location
Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location
Villa
Islamorada, FL, USA
1.5k from Islamorada center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$737
Average price / night
Check Availability
Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Villa
Islamorada, FL, 33036, United States
1.3k from Islamorada center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
9.6

Exceptional

4 reviews

$631
Average price / night
Check Availability
Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Villa
Islamorada, FL, USA
1.5k from Islamorada center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$627
Average price / night
Check Availability
Isla Lychee: Boutique Resort, FREE Boat Dockage Sep-Oct Only!
Isla Lychee: Boutique Resort, FREE Boat Dockage Sep-Oct Only!
Villa
Islamorada, FL, 33036, United States
1.4k from Islamorada center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$638
Average price / night
Check Availability
Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location
Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location
Villa
Islamorada, FL, USA
1.5k from Islamorada center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$617
Average price / night
Check Availability
Isla Mirabelle: Boutique Resort, FREE Boat Dockage Sep-Oct Only!
Isla Mirabelle: Boutique Resort, FREE Boat Dockage Sep-Oct Only!
Villa
Islamorada, FL, 33036, United States
1.4k from Islamorada center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$635
Average price / night
Check Availability
Isla Honeydew - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Isla Honeydew - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Villa
Islamorada, FL, USA
1.5k from Islamorada center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$1281
Average price / night
Check Availability
Bayside: Bayfront villa W/ free onsite boat ramp marina & trailer parking.
Bayside: Bayfront villa W/ free onsite boat ramp marina & trailer parking.
Villa
Islamorada, FL, 33036, United States
1.4k from Islamorada center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
9.8

Exceptional

40 reviews

$358
Average price / night
Check Availability
Anglers Reef Vacation Rental
Anglers Reef Vacation Rental
Villa
Islamorada, FL, USA
2.9k from Islamorada center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach

2 Bedrooms6 Guests
9.5

Superb

2 reviews

$495
Average price / night
Check Availability
Keys Kottage: Bayside villa W/ free onsite boat ramp marina & trailer parking.
Keys Kottage: Bayside villa W/ free onsite boat ramp marina & trailer parking.
Villa
Islamorada, FL, 33036, United States
1.4k from Islamorada center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

93 reviews

$358
Average price / night
Check Availability
10 Bedroom Private Ocean Front Estate
10 Bedroom Private Ocean Front Estate
Villa
Islamorada, FL, 33036, United States
1.4k from Islamorada center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Elevator, Fitness Equipment, Free Parking, Heater

10 Bedrooms22 Guests
10.0

Exceptional

1 reviews

$3453
Average price / night
Check Availability
The Nest Villa & Marina with boat ramp, sun terrace, water views. Pet friendly!
The Nest Villa & Marina with boat ramp, sun terrace, water views. Pet friendly!
Villa
Islamorada, FL, 33036, United States
1.5k from Islamorada center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

16 reviews

$450
Average price / night
Check Availability
Bayberry Key: Waterfront Htd Pool, FREE Boat Dockage Sep-Oct Only!
Bayberry Key: Waterfront Htd Pool, FREE Boat Dockage Sep-Oct Only!
Villa
Islamorada, FL, 33036, United States
1.7k from Islamorada center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
9.8

Exceptional

6 reviews

$645
Average price / night
Check Availability
Isla Honeydew: 3 En-Suite Bedrooms, Pool, Dock
Isla Honeydew: 3 En-Suite Bedrooms, Pool, Dock
Villa
Islamorada, FL, 33036, United States
1.7k from Islamorada center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$615
Average price / night
Check Availability
Isla Key Acaí: Waterfront Boutique Resort, FREE Boat Dockage Sep-Oct Only!
Isla Key Acaí: Waterfront Boutique Resort, FREE Boat Dockage Sep-Oct Only!
Villa
Islamorada, FL, 33036, United States
1.8k from Islamorada center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$673
Average price / night
Check Availability
Isla Kiwi: Waterfront Boutique Resort, FREE Boat Dockage Sept-Oct Only
Isla Kiwi: Waterfront Boutique Resort, FREE Boat Dockage Sept-Oct Only
Villa
Islamorada, FL, 33036, United States
1.9k from Islamorada center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$652
Average price / night
Check Availability
Ocean's Fourteen:Direct Ocean View-Balconies-Dock-Htd Pool
Ocean's Fourteen:Direct Ocean View-Balconies-Dock-Htd Pool
Villa
Islamorada, FL, 33036, United States
2.0k from Islamorada center

AC, Balcony, Dryer, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$617
Average price / night
Check Availability
Island Time: Partial Ocean View, Ensuite bedrooms, Free Dockage, Htd Pool
Island Time: Partial Ocean View, Ensuite bedrooms, Free Dockage, Htd Pool
Villa
Islamorada, FL, 33036, United States
2.2k from Islamorada center

AC, Balcony, Dryer, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$613
Average price / night
Check Availability
Isla Mamey: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Isla Mamey: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Villa
Islamorada, FL, 33036, United States
2.3k from Islamorada center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$654
Average price / night
Check Availability
Villa with private plunge pool, boat dock, & amazing sunsets in Islamorada Fl
Villa with private plunge pool, boat dock, & amazing sunsets in Islamorada Fl
Villa
Islamorada, FL, 33036, United States
2.3k from Islamorada center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$979
Average price / night
Check Availability
Islamorada Florida Bay Villa  Plunge Pool, Boat Dock, Amazing Sunset Views
Islamorada Florida Bay Villa Plunge Pool, Boat Dock, Amazing Sunset Views
Villa
Islamorada, FL, 33036, United States
2.3k from Islamorada center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
9.4

Superb

3 reviews

$1074
Average price / night
Check Availability
Isla Key Lime: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Isla Key Lime: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Villa
Islamorada, FL, 33036, United States
2.5k from Islamorada center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$683
Average price / night
Check Availability
Oversized Islamorada Villa 110 in Gated Anglers Reef: Pool, Kayaks, Bikes, Beach
Oversized Islamorada Villa 110 in Gated Anglers Reef: Pool, Kayaks, Bikes, Beach
Villa
Islamorada, FL, 33036, United States
2.9k from Islamorada center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$450
Average price / night
Check Availability
Serenity by the Sea!!  Anglers Reef with Boat Slip Available!!
Serenity by the Sea!! Anglers Reef with Boat Slip Available!!
Villa
Islamorada, FL, 33036, United States
2.9k from Islamorada center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

2 Bedrooms6 Guests
10.0

Exceptional

121 reviews

$392
Average price / night
Check Availability
Islamorada house with best location. Lic # 24-0055
Islamorada house with best location. Lic # 24-0055
Villa
Islamorada, FL, 33036, United States
3.0k from Islamorada center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

19 reviews

$624
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Villa Rentals in Islamorada.

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Islamorada Villa Rentals on the Map

Frequently Asked Questions

You can currently explore 34 verified villa rentals in Islamorada. Our listings are sourced from multiple leading booking platforms, giving you a broad and up-to-date selection of luxury and private villas in one place.

Villa prices in Islamorada vary depending on the season, location, and amenities. Rates typically start from around $358 per night, with premium properties costing more during peak travel periods. Comparing options across different platforms can help you find the best value for your dates.

Many villas in Islamorada are designed for privacy and comfort, and a large number of them feature private pools. You can easily filter your search to find villas with pools, helping you choose the perfect stay for relaxation or group travel in Islamorada.

Yes, Islamorada offers a wide range of villas ideal for group stays. Many properties include 5 or more bedrooms, making them well-suited for family gatherings, events, or trips with friends. You can filter by bedroom count to quickly find options that match your group size.

For popular travel periods, it’s generally recommended to book your Islamorada villa around 60 to 90 days in advance to secure the best selection. However, since we compare 10+ sites, it’s still possible to find great last-minute options even 2 to 4 weeks before your trip.

Villas in Islamorada often include highly sought-after amenities such as Internet, Wellness Facilities, and View. These features enhance comfort and convenience, making them especially popular among travelers visiting Islamorada.

To discover top-rated villas in Islamorada, you can sort listings by guest ratings and reviews. Our platform aggregates feedback from multiple trusted sources, helping you identify highly rated properties based on real guest experiences. Use the "Rating" filter above to start your search.