Short-Term Rentals in Islamorada, FL: Compare 10+ Sites & Save

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475 Best Short-Term 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
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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
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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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BOOK YOUR DREAM VACATION at  BEACON REEF - SPECIAL MAY DEAL
BOOK YOUR DREAM VACATION at BEACON REEF - SPECIAL MAY DEAL
Condo
Islamorada, FL, 33036, United States
0.2k from Islamorada center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Heater

2 Bedrooms4 Guests
9.4

Superb

9 reviews

$321
Average price / night
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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
Check Availability
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
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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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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 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
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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
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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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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 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
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 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
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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
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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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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
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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
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 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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This condo is located in one of Islamorada's most prestigious condo complexes.
This condo is located in one of Islamorada's most prestigious condo complexes.
Condo
Islamorada, FL, 33036, United States
0.6k from Islamorada center

AC, Balcony, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Hot Tub

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$226
Average price / night
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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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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

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 Short-Term Rentals in Islamorada.

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Islamorada Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 475 verified short-term rentals in Islamorada, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Islamorada vary depending on location, property size, and travel dates. Rates typically start from around $183 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Islamorada include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Islamorada, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Islamorada often include amenities such as Internet, Wellness Facilities, and Fireplace/Heating, providing a comfortable and convenient stay.

Short-term rentals in Islamorada are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.