Accommodations in Islamorada, FL: Compare 10+ Sites & Save

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461 Best Accommodations 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
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
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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 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
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Chesapeake Beach Resort
Chesapeake Beach Resort
Resort
Islamorada, FL, USA
0.5k from Islamorada center

Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, 3-star, Lodgings, Beach

45 Bedrooms75 Guests
8.0

Good

846 reviews

$536
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 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 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 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
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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
Check Availability
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 Accommodations in Islamorada.

Where to stay in Islamorada? Best neighborhoods & areas

Stay Near Islamorada's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Islamorada Accommodations on the Map

Frequently Asked Questions

You can explore 461 verified accommodations in Islamorada, including hotels, vacation rentals, resorts, and boutique stays. This variety makes it easier to choose the option that best fits your travel style and budget.

Accommodation prices in Islamorada vary based on property type, location, and travel dates. Rates typically start from around $183 per night, with higher prices for premium properties and peak travel periods.

Hotels are ideal for convenience and short stays, while vacation rentals offer more space and privacy. Resorts are suitable for all-inclusive experiences, and boutique properties provide a more unique and personalized stay in Islamorada.

Yes, Islamorada offers many family-friendly options, including large vacation rentals and hotels with suites or connecting rooms. Currently, 62 listings in Islamorada are well-suited for families and group travel.

Booking 30 to 60 days in advance is generally recommended for the best availability and pricing. For peak travel seasons or major events in Islamorada, booking several months ahead can help secure your preferred property.

Accommodations in Islamorada commonly include amenities such as Internet, Wellness Facilities, and Fireplace/Heating. Availability may vary depending on the type of property you choose.

Yes, some accommodations in Islamorada focus on sustainable practices such as energy efficiency and reduced environmental impact. You can filter listings to find options that align with your preferences in Islamorada.