Oceanfront Rentals in Cutthroat Harbor Estates, FL: Compare 10+ Sites & Save

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  3.  USA

  4.  Florida
  5.  Cudjoe Key
  6.  Cutthroat Harbor Estates

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232 Best Oceanfront Rentals in Cutthroat Harbor Estates (Starting from $190)

Dolphin Daydreams by Last Key Realty
Dolphin Daydreams by Last Key Realty
House
Cudjoe Key, FL, USA
0.4k from Cutthroat Harbor Estates center

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

1 Bedroom4 Guests
New to Booking
$351
Average price / night
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Gasparilla Villa - Your Ocean View Oasis on Cudjoe Key - Sunset Views!
Gasparilla Villa - Your Ocean View Oasis on Cudjoe Key - Sunset Views!
House
Cudjoe Key, FL, 33042, United States
0.3k from Cutthroat Harbor Estates center

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

3 Bedrooms6 Guests
New to Booking
$275
Average price / night
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Pelican's Roost, Waterfront comfort at Venture Out
Pelican's Roost, Waterfront comfort at Venture Out
House
Cudjoe Key, FL, USA
0.5k from Cutthroat Harbor Estates center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

2 Bedrooms5 Guests
9.2

Superb

15 reviews

$303
Average price / night
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Ocean view home -Private launch & breath taking sunset views-min 28 day rentals
Ocean view home -Private launch & breath taking sunset views-min 28 day rentals
Cottage
Cudjoe Key, FL, 33042, United States
0.3k from Cutthroat Harbor Estates center

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

2 Bedrooms4 Guests
9.8

Exceptional

24 reviews

$215
Average price / night
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Turtle Cove Views by Last Key Realty
Turtle Cove Views by Last Key Realty
House
Cudjoe Key, FL, USA
0.6k from Cutthroat Harbor Estates center

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

2 Bedrooms6 Guests
7.0

Good

1 reviews

$513
Average price / night
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Canal front, dockage, 2 bedroom,  2 bath
Canal front, dockage, 2 bedroom, 2 bath
Cottage
Cudjoe Key, FL, 33042, United States
0.3k from Cutthroat Harbor Estates center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
8.8

Fabulous

96 reviews

$351
Average price / night
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Island Oasis ~ YOUR Paradise Awaits!
Island Oasis ~ YOUR Paradise Awaits!
House
Cutthroat Harbor Estates, Cudjoe Key, Florida, USA
0.6k from Cutthroat Harbor Estates center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

2 Bedrooms6 Guests
7.4

Good

5 reviews

$386
Average price / night
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Waterfront Keys Sunset Spectacular
Waterfront Keys Sunset Spectacular
House
Cudjoe Key, FL, 33042, United States
0.3k from Cutthroat Harbor Estates center

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

3 Bedrooms8 Guests
New to Booking
$460
Average price / night
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OCEANIA. water front cottage retreat ~
OCEANIA. water front cottage retreat ~
Villa
Cudjoe Key, FL, USA
0.6k from Cutthroat Harbor Estates center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

2 Bedrooms6 Guests
9.4

Superb

16 reviews

$826
Average price / night
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Paradise Palms in Cudjoe Key #635
Paradise Palms in Cudjoe Key #635
House
Cudjoe Key, FL, 33042, United States
0.4k from Cutthroat Harbor Estates center

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

2 Bedrooms5 Guests
10.0

Exceptional

2 reviews

$385
Average price / night
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NAUTILUS.ocean front cottage retreat ~
NAUTILUS.ocean front cottage retreat ~
Villa
Cudjoe Key, FL, USA
0.6k from Cutthroat Harbor Estates center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

2 Bedrooms6 Guests
9.2

Superb

16 reviews

$908
Average price / night
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Island Home in Paradise #624 - OCEANFRONT Community!
Island Home in Paradise #624 - OCEANFRONT Community!
House
Cudjoe Key, FL, 33042, United States
0.4k from Cutthroat Harbor Estates center

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

2 Bedrooms4 Guests
New to Booking
$300
Average price / night
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Serenity Now Seaside Escape - Brand New Build!
Serenity Now Seaside Escape - Brand New Build!
House
Cudjoe Key, FL, USA
0.7k from Cutthroat Harbor Estates center

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

1 Bedroom6 Guests
New to Booking
$469
Average price / night
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**DOLPHIN DAYDREAMS @ VENTURE OUT** New Home & Golf Cart + LAST KEY SERVICES…
**DOLPHIN DAYDREAMS @ VENTURE OUT** New Home & Golf Cart + LAST KEY SERVICES…
House
Cudjoe Key, FL, 33042, United States
0.4k from Cutthroat Harbor Estates center

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

2 Bedrooms4 Guests
10.0

Exceptional

5 reviews

$457
Average price / night
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Oceanview Retreat with 60ft Seawall
Oceanview Retreat with 60ft Seawall
House
Cudjoe Key, FL, USA
0.8k from Cutthroat Harbor Estates center

Ocean View, Hot Tub, Pool, Barbecue/Outdoor Cooking, Security/Safety, Air Conditioner, Balcony/Terrace

2 Bedrooms4 Guests
New to Booking
$608
Average price / night
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Canal-Front Gem w/ Peekaboo Views in Cudjoe Key!
Canal-Front Gem w/ Peekaboo Views in Cudjoe Key!
House
Cudjoe Key, FL, 33042, United States
0.4k from Cutthroat Harbor Estates center

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

2 Bedrooms6 Guests
New to Booking
$190
Average price / night
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Parrotfish Pointe
Parrotfish Pointe
House
Cudjoe Key, FL, USA
1.0k from Cutthroat Harbor Estates center

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

3 Bedrooms6 Guests
New to Booking
$301
Average price / night
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Beautiful, 2100 sq ft 3/2 w/ocean views & easy ocean & gulf access.
Beautiful, 2100 sq ft 3/2 w/ocean views & easy ocean & gulf access.
House
Cudjoe Key, FL, 33042, United States
0.4k from Cutthroat Harbor Estates center

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

3 Bedrooms8 Guests
10.0

Exceptional

12 reviews

$337
Average price / night
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Ocean View with Pool, 4 bedroom Vila Near Key West
Ocean View with Pool, 4 bedroom Vila Near Key West
Villa
Cudjoe Key, FL, USA
2.4k from Cutthroat Harbor Estates center

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

4 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$810
Average price / night
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A slice of paradise
A slice of paradise
Cottage
Cudjoe Key, FL, 33042, United States
0.4k from Cutthroat Harbor Estates center

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

3 Bedrooms6 Guests
9.0

Fabulous

98 reviews

$270
Average price / night
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Newly built home in Cudjoe Key
Newly built home in Cudjoe Key
House
Cudjoe Key, FL, USA
2.6k from Cutthroat Harbor Estates center

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

3 Bedrooms7 Guests
New to Booking
$583
Average price / night
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**CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES…
**CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES…
House
Cudjoe Key, FL, 33042, United States
0.4k from Cutthroat Harbor Estates center

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

3 Bedrooms9 Guests
8.8

Fabulous

3 reviews

$483
Average price / night
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Sea La Vie Your Oceanfront Escape in Cudjoe Key, Florida  3BD, 3BA
Sea La Vie Your Oceanfront Escape in Cudjoe Key, Florida 3BD, 3BA
House
Cudjoe Key, FL, 33042, United States
0.4k from Cutthroat Harbor Estates center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$532
Average price / night
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Emerald Seas - Florida Keys Ocean Front Paradise!
Emerald Seas - Florida Keys Ocean Front Paradise!
Villa
Cudjoe Key, FL, 33042, United States
0.4k from Cutthroat Harbor Estates center

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

2 Bedrooms4 Guests
10.0

Exceptional

23 reviews

$663
Average price / night
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Shangri-la in the Keys! Enjoy the water views and a 45' dock space!
Shangri-la in the Keys! Enjoy the water views and a 45' dock space!
House
Cudjoe Key, FL, 33042, United States
0.4k from Cutthroat Harbor Estates center

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

2 Bedrooms6 Guests
9.4

Superb

42 reviews

$422
Average price / night
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Bimini Breeze - VO 313
Bimini Breeze - VO 313
House
Cudjoe key, FL, 33042, United States
0.5k from Cutthroat Harbor Estates center

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

2 Bedrooms6 Guests
9.4

Superb

3 reviews

$345
Average price / night
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Sunny Gens - Venture Out #606
Sunny Gens - Venture Out #606
House
Cudjoe Key, FL, 33042, United States
0.5k from Cutthroat Harbor Estates center

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

2 Bedrooms6 Guests
8.0

Good

2 reviews

$333
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 Cutthroat Harbor Estates.

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Frequently Asked Questions

You can explore 232 verified oceanfront rentals in Cutthroat Harbor Estates. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Cutthroat Harbor Estates vary depending on the property size, exact beachfront location, and season. Rates typically start from around $190 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 Cutthroat Harbor Estates 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 Cutthroat Harbor Estates welcome pets. Currently, 22 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 Cutthroat Harbor Estates 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.