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

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  2. Oceanfront Rentals
  3.  USA

  4.  Florida
  5.  Fiesta Key

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102 Best Oceanfront Rentals in Fiesta Key (Starting from $161)

Lime Tree Bay Resort
Lime Tree Bay Resort
Resort
Islamorada, FL, USA
2.7k from Fiesta Key center

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

61 Bedrooms54 Guests
8.6

Fabulous

2082 reviews

$247
Average price / night
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Stay where you play, On the water w/Boat dock & Trailer parking. Pet friendly!
Stay where you play, On the water w/Boat dock & Trailer parking. Pet friendly!
Apartment
Layton, FL, 33001, United States
0.8k from Fiesta Key center

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

2 Bedrooms6 Guests
9.8

Exceptional

71 reviews

$388
Average price / night
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Paradise Beach
Paradise Beach
House
Islamorada, FL, USA
5.8k from Fiesta Key center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay, Accessible hotels

3 Bedrooms7 Guests
New to Booking
$242
Average price / night
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Spectacular Open-Water Sunset Views w/Boat Slip & Trailer Parking. Pet Friendly!
Spectacular Open-Water Sunset Views w/Boat Slip & Trailer Parking. Pet Friendly!
Apartment
Layton, FL, 33001, United States
0.8k from Fiesta Key center

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

2 Bedrooms6 Guests
10.0

Exceptional

63 reviews

$375
Average price / night
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Turtle Beach Retreat
Turtle Beach Retreat
House
Layton, FL, USA
6.4k from Fiesta Key center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay, Family

2 Bedrooms4 Guests
New to Booking
$161
Average price / night
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Spectacular Views of Ocean with Pool and Boat Slip.
Spectacular Views of Ocean with Pool and Boat Slip.
House
Long Key, FL, 33001, United States
1.2k from Fiesta Key center

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

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$543
Average price / night
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Florida Keys Getaway with Stunning Ocean Views
Florida Keys Getaway with Stunning Ocean Views
House
Layton, FL, USA
7.0k from Fiesta Key center

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

3 Bedrooms10 Guests
New to Booking
$909
Average price / night
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Private Waterfront Home, Heated Pool, Beach, Tiki w/Grill, Dock, Kayaks, Sunset
Private Waterfront Home, Heated Pool, Beach, Tiki w/Grill, Dock, Kayaks, Sunset
House
Long Key, FL, 33001, United States
2.7k from Fiesta Key center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Extra Bed, Fireplace, Free Parking, Heater

3 Bedrooms10 Guests
10.0

Exceptional

103 reviews

$1473
Average price / night
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Walk to Beach Florida Keys Gem with Ocean Views
Walk to Beach Florida Keys Gem with Ocean Views
House
Layton, FL, USA
7.0k from Fiesta Key center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach, Places to stay

2 Bedrooms10 Guests
New to Booking
$588
Average price / night
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Home w/ 2nd Story Pool & Spa w/ Open Water Views
Home w/ 2nd Story Pool & Spa w/ Open Water Views
House
Layton, FL, 33001, United States
2.7k from Fiesta Key center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Hot Tub, Internet, Kitchen

4 Bedrooms10 Guests
10.0

Exceptional

76 reviews

$1480
Average price / night
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The Henry Flagler
The Henry Flagler
House
Layton, FL, USA
7.1k from Fiesta Key center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Beach, Places to stay

2 Bedrooms6 Guests
9.5

Superb

2 reviews

$430
Average price / night
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Beautiful Pool Home Located in a Quiet Neighborhood
Beautiful Pool Home Located in a Quiet Neighborhood
House
Long Key, FL, 33001, United States
3.0k from Fiesta Key center

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

2 Bedrooms6 Guests
New to Booking
$649
Average price / night
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The Zane Grey
The Zane Grey
House
Layton, FL, USA
7.1k from Fiesta Key center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Beach, Places to stay

2 Bedrooms5 Guests
8.0

Good

1 reviews

$431
Average price / night
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Sand 'N Sea ~ 3 Bedroom Canal Front Home w/ Pool in Layton
Sand 'N Sea ~ 3 Bedroom Canal Front Home w/ Pool in Layton
House
Layton, FL, 33001, United States
3.0k from Fiesta Key center

AC, Balcony, Barbecue, Dryer, Elevator, Extra Bed, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
New to Booking
$265
Average price / night
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Beachfront Ocean Duplex
Beachfront Ocean Duplex
House
Layton, FL, USA
7.1k from Fiesta Key center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Beach, Places to stay

4 Bedrooms8 Guests
New to Booking
$708
Average price / night
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3 Bedroom / 2.5 Bathroom Layton Home with Pool & Dockage
3 Bedroom / 2.5 Bathroom Layton Home with Pool & Dockage
House
Layton, FL, 33001, United States
3.2k from Fiesta Key center

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

3 Bedrooms6 Guests
New to Booking
$428
Average price / night
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Sandglass 4
Sandglass 4
House
Islamorada, FL, USA
7.4k from Fiesta Key center

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

5 Bedrooms12 Guests
New to Booking
$640
Average price / night
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\"Islamorada Waterside Getaway: Prime Fishing, Sunset Views, Beachside Bliss!\"
\"Islamorada Waterside Getaway: Prime Fishing, Sunset Views, Beachside Bliss!\"
House
Islamorada, FL, 33036, United States
5.4k from Fiesta Key center

AC, Balcony, Barbecue, Dryer, Heater, Internet, Kitchen, Laundry, Microwave

5 Bedrooms12 Guests
10.0

Exceptional

20 reviews

$407
Average price / night
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Beachfront Villa at Islamorada BY THE GLAMHOMES
Beachfront Villa at Islamorada BY THE GLAMHOMES
Villa
Islamorada, FL, USA
8.7k from Fiesta Key center

Internet, View, Private Beach, Oceanfront, Sports/Activities, Ocean View, Fireplace/Heating

4 Bedrooms6 Guests
1.0

Review score

1 reviews

$7615
Average price / night
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Beautiful 2/2 Islamorada Home Directly on Florida Bay (28 Day Minimum Rental)
Beautiful 2/2 Islamorada Home Directly on Florida Bay (28 Day Minimum Rental)
House
Islamorada, FL, 33036, United States
5.5k from Fiesta Key center

AC, Arcade, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet

2 Bedrooms4 Guests
10.0

Exceptional

7 reviews

$253
Average price / night
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A Piece of Paradise Islamorada, Fl. On the water 3/2, 90 Ft of dock New Pool
A Piece of Paradise Islamorada, Fl. On the water 3/2, 90 Ft of dock New Pool
House
Islamorada, FL, 33036, United States
5.5k from Fiesta Key center

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

3 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$571
Average price / night
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Waterfront beautifully renovated 6 Bedrooms 4 Bath , Gated Private Home
Waterfront beautifully renovated 6 Bedrooms 4 Bath , Gated Private Home
House
Islamorada, FL, 33036, United States
5.6k from Fiesta Key center

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

6 Bedrooms12 Guests
10.0

Exceptional

21 reviews

$668
Average price / night
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\"Our Happy Place\" Paradise in Islamorada with Heated Pool and 90 ft Dock
\"Our Happy Place\" Paradise in Islamorada with Heated Pool and 90 ft Dock
House
Islamorada, FL, 33036, United States
5.6k from Fiesta Key center

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

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$495
Average price / night
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Beautiful Home in a Great Neighborhood with Ocean Access and Boat Ramp on Property
Beautiful Home in a Great Neighborhood with Ocean Access and Boat Ramp on Property
House
Islamorada, FL, 33036, United States
5.8k from Fiesta Key center

AC, Barbecue, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
New to Booking
$277
Average price / night
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Waterfront Oasis 2Mins2BeachTons dockage VERY Private Immediate ocean/bay access
Waterfront Oasis 2Mins2BeachTons dockage VERY Private Immediate ocean/bay access
House
Islamorada, FL, 33036, United States
5.8k from Fiesta Key center

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

5 Bedrooms12 Guests
10.0

Exceptional

72 reviews

$1052
Average price / night
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Work from home in this slice of Islamorada paradise!
Work from home in this slice of Islamorada paradise!
Cottage
Islamorada, FL, 33036, United States
5.9k from Fiesta Key center

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

2 Bedrooms5 Guests
9.8

Exceptional

14 reviews

$291
Average price / night
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Boater's Paradise
Boater's Paradise
House
Islamorada, FL, 33036, United States
5.9k from Fiesta Key center

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

4 Bedrooms9 Guests
10.0

Exceptional

2 reviews

$404
Average price / night
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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 Fiesta Key.

Where to stay in Fiesta Key? Best neighborhoods & areas

Fiesta Key Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 102 verified oceanfront rentals in Fiesta Key. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Fiesta Key vary depending on the property size, exact beachfront location, and season. Rates typically start from around $161 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 Fiesta Key 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 Fiesta Key welcome pets. Currently, 33 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 Fiesta Key often include features designed for a comfortable coastal stay, such as View, Oceanfront, and Ocean View. 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.