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

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431 Best Vacation Rentals in Islamorada (Starting from $183)

Beacon Reef 222
Beacon Reef 222
House
Islamorada, FL, USA
0.3k from Islamorada center

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

2 Bedrooms4 Guests
New to Booking
$252
Average price / night
Check Availability
Cozy Islamorada retreat!
Cozy Islamorada retreat!
House
Islamorada, FL, 33036, United States
0.1k from Islamorada center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms8 Guests
New to Booking
$461
Average price / night
Check Availability
Beacon Reef 301
Beacon Reef 301
House
Islamorada, FL, USA
0.3k from Islamorada center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Beach, Jacuzzis

2 Bedrooms4 Guests
New to Booking
$183
Average price / night
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Your Oceanfront Islamorada Retreat with Pool & Private Boat Basin!
Your Oceanfront Islamorada Retreat with Pool & Private Boat Basin!
House
Islamorada, FL, 33036, United States
0.2k from Islamorada center

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

2 Bedrooms3 Guests
New to Booking
$318
Average price / night
Check Availability
Beacon Reef 306
Beacon Reef 306
House
Islamorada, FL, USA
0.3k from Islamorada center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Beach, Jacuzzis

2 Bedrooms4 Guests
New to Booking
$192
Average price / night
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Charming 3BR retreat in Islamorada, perfect for family getaways!
Charming 3BR retreat in Islamorada, perfect for family getaways!
House
Islamorada, FL, 33036, United States
0.2k from Islamorada center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
New to Booking
$567
Average price / night
Check Availability
Beacon Reef 307
Beacon Reef 307
House
Islamorada, FL, USA
0.3k from Islamorada center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Beach, Jacuzzis

2 Bedrooms4 Guests
New to Booking
$197
Average price / night
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Spacious 4BR home in Islamorada with a heated pool, perfect for family getaways!
Spacious 4BR home in Islamorada with a heated pool, perfect for family getaways!
House
Islamorada, FL, 33036, United States
0.3k from Islamorada center

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

4 Bedrooms8 Guests
New to Booking
$515
Average price / night
Check Availability
Beacon Reef 310
Beacon Reef 310
House
Islamorada, FL, USA
0.3k from Islamorada center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Beach, Jacuzzis

2 Bedrooms4 Guests
New to Booking
$206
Average price / night
Check Availability
Experience comfort at Mini Ray's of Sunshine in Islamorada, perfect for families!
Experience comfort at Mini Ray's of Sunshine in Islamorada, perfect for families!
House
Islamorada, FL, 33036, United States
0.3k from Islamorada center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
New to Booking
$517
Average price / night
Check Availability
Beacon Reef 406
Beacon Reef 406
House
Islamorada, FL, USA
0.3k from Islamorada center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Beach, Jacuzzis

2 Bedrooms4 Guests
New to Booking
$188
Average price / night
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Islamorada Beach Beachfront, Fire Pit & Pool
Islamorada Beach Beachfront, Fire Pit & Pool
House
Islamorada, FL, 33036, United States
0.4k from Islamorada center

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

6 Bedrooms12 Guests
8.0

Good

1 reviews

$2804
Average price / night
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Beacon Reef 501
Beacon Reef 501
House
Islamorada, FL, USA
0.3k from Islamorada center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Beach, Jacuzzis

2 Bedrooms4 Guests
New to Booking
$206
Average price / night
Check Availability
Beautiful Pool home in Islamorada
Beautiful Pool home in Islamorada
House
Islamorada, FL, 33036, United States
0.4k from Islamorada center

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

3 Bedrooms6 Guests
New to Booking
$316
Average price / night
Check Availability
Beacon Reef 503
Beacon Reef 503
House
Islamorada, FL, USA
0.3k from Islamorada center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Beach, Jacuzzis

2 Bedrooms4 Guests
New to Booking
$256
Average price / night
Check Availability
Discover One Too Mini, a cozy 3-bedroom getaway in Islamorada, perfect for 8!
Discover One Too Mini, a cozy 3-bedroom getaway in Islamorada, perfect for 8!
House
Islamorada, FL, 33036, United States
0.5k from Islamorada center

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

3 Bedrooms8 Guests
New to Booking
$497
Average price / night
Check Availability
Little Bay Compound
Little Bay Compound
House
Islamorada, FL, USA
1.4k from Islamorada center

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

6 Bedrooms18 Guests
New to Booking
$16123
Average price / night
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Southern Diversion Estate  Islamorada
Southern Diversion Estate Islamorada
House
Islamorada, FL, 33036, United States
0.6k from Islamorada center

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

5 Bedrooms16 Guests
9.8

Exceptional

84 reviews

$2096
Average price / night
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Little Bay Prime
Little Bay Prime
Apartment
Islamorada, FL, USA
1.4k from Islamorada center

Apartments, Accommodations, Parking, Spa, Lodgings, Beach, Places to stay, Family

4 Bedrooms12 Guests
New to Booking
$1099
Average price / night
Check Availability
Discover Sea Ranch in Islamorada: spacious 4BR home with private pool and stunning views.
Discover Sea Ranch in Islamorada: spacious 4BR home with private pool and stunning views.
House
Islamorada, FL, 33036, United States
0.7k from Islamorada center

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

4 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$1600
Average price / night
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Little Bay Cottage
Little Bay Cottage
House
Islamorada, FL, USA
1.4k from Islamorada center

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

2 Bedrooms4 Guests
New to Booking
$550
Average price / night
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Beautiful Islamorada Home in he heart of the keys, boat-slip, pool, and gated.
Beautiful Islamorada Home in he heart of the keys, boat-slip, pool, and gated.
House
Islamorada, FL, 33036, United States
0.8k from Islamorada center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

4 Bedrooms8 Guests
New to Booking
$795
Average price / night
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Infinity Bay Islamorada ~ Luxury 9-bed, 10-bath Bayfront Estate in Islamorada
Infinity Bay Islamorada ~ Luxury 9-bed, 10-bath Bayfront Estate in Islamorada
House
Islamorada, FL, 33036, United States
0.8k from Islamorada center

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

9 Bedrooms18 Guests
New to Booking
$2378
Average price / night
Check Availability
4 BR Oceanview Villa | Accessible + Resort Perks
4 BR Oceanview Villa | Accessible + Resort Perks
House
Islamorada, FL, 33036, United States
0.8k from Islamorada center

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

4 Bedrooms8 Guests
New to Booking
$2515
Average price / night
Check Availability
Oceanview Living + Resort Perks | 4BR Villa
Oceanview Living + Resort Perks | 4BR Villa
House
Islamorada, FL, 33036, United States
0.8k from Islamorada center

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

4 Bedrooms8 Guests
New to Booking
$2534
Average price / night
Check Availability
Oceanview 4BR Villa + Resort Perks | Bunks | Sleeps 10
Oceanview 4BR Villa + Resort Perks | Bunks | Sleeps 10
House
Islamorada, FL, 33036, United States
0.8k from Islamorada center

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

4 Bedrooms10 Guests
New to Booking
$2630
Average price / night
Check Availability
Oceanfront + Resort Perks | 4BR Villa (Sleeps 8)
Oceanfront + Resort Perks | 4BR Villa (Sleeps 8)
House
Islamorada, FL, 33036, United States
0.8k from Islamorada center

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

4 Bedrooms8 Guests
New to Booking
$2753
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 Vacation Rentals in Islamorada.

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Frequently Asked Questions

You can explore 431 verified vacation rentals in Islamorada. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Islamorada vary depending on the season, property size, and location. Rates typically start from around $183 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Islamorada include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Islamorada welcome pets. Currently, 28 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Islamorada often include amenities such as Internet, Wellness Facilities, and Fireplace/Heating. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.