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

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  5.  Islamorada

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250 Best Oceanfront 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
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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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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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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
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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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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
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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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Oceanfront Private Cottage!
Oceanfront Private Cottage!
Cottage
Islamorada, FL, 33036, United States
0.9k from Islamorada center

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

1 Bedroom4 Guests
10.0

Exceptional

113 reviews

$269
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
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Breathtaking ocean views for your Paradise vacations
Breathtaking ocean views for your Paradise vacations
Apartment
Islamorada, FL, 33036, United States
0.9k from Islamorada center

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

2 Bedrooms8 Guests
10.0

Exceptional

100 reviews

$464
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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Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
Apartment
Islamorada, FL, 33036, United States
1.0k from Islamorada center

AC, Barbecue, Breakfast Included, Elevator, Fireplace, Free Parking, Heater, Internet, Kitchen

2 Bedrooms4 Guests
8.4

Very Good

6 reviews

$424
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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Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking
Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking
Apartment
Islamorada, FL, 33036, United States
1.0k from Islamorada center

AC, Barbecue, Breakfast Included, Elevator, Free Parking, Heater, Internet, No Smoking, Pool

2 Bedrooms4 Guests
5.0

Review score

2 reviews

$424
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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Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast
Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast
Apartment
Islamorada, FL, 33036, United States
1.0k from Islamorada center

AC, Barbecue, Breakfast Included, Elevator, Fireplace, Free Parking, Heater, Internet, Kitchen

2 Bedrooms4 Guests
6.0

Review score

3 reviews

$424
Average price / night
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3‑Acre Oceanfront Estate w/ Pool ON the Atlantic, 2 Homes & Beach
3‑Acre Oceanfront Estate w/ Pool ON the Atlantic, 2 Homes & Beach
House
Islamorada, FL, 33036, United States
1.1k from Islamorada center

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

3 Bedrooms8 Guests
10.0

Exceptional

49 reviews

$1409
Average price / night
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Sprawling Bayfront Estate in Heart of Islamorada with Deep Dockage, Heated Pool, Kayaks and More!
Sprawling Bayfront Estate in Heart of Islamorada with Deep Dockage, Heated Pool, Kayaks and More!
House
Islamorada, FL, 33036, United States
1.2k from Islamorada center

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

8 Bedrooms22 Guests
New to Booking
$3309
Average price / night
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Spacious Bayfront Home with Heated Pool, Deep Dockage, Kayaks and More
Spacious Bayfront Home with Heated Pool, Deep Dockage, Kayaks and More
House
Islamorada, FL, 33036, United States
1.2k from Islamorada center

AC, Barbecue, Crib, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Microwave

4 Bedrooms10 Guests
10.0

Exceptional

11 reviews

$1302
Average price / night
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Charming Bayfront Cottage in Heart of Islamorada with Heated Pool, Deep Dockage, Kayaks & More
Charming Bayfront Cottage in Heart of Islamorada with Heated Pool, Deep Dockage, Kayaks & More
Cottage
Islamorada, FL, 33036, United States
1.2k from Islamorada center

AC, Barbecue, Crib, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Microwave

2 Bedrooms6 Guests
10.0

Exceptional

19 reviews

$878
Average price / night
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Private Cottage on Bayfront Estate with Heated Pool, Deep Dockage, Kayaks and More
Private Cottage on Bayfront Estate with Heated Pool, Deep Dockage, Kayaks and More
Cottage
Islamorada, FL, 33036, United States
1.2k from Islamorada center

AC, Barbecue, Crib, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Microwave

2 Bedrooms6 Guests
10.0

Exceptional

15 reviews

$674
Average price / night
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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 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

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 Oceanfront Rentals in Islamorada.

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Islamorada Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 250 verified oceanfront rentals in Islamorada. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Islamorada vary depending on the property size, exact beachfront location, and season. Rates typically start from around $183 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Islamorada offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Islamorada welcome pets. Currently, 31 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Islamorada often include features designed for a comfortable coastal stay, such as View, Wellness Facilities, and Oceanfront. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.