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

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  6.  Cutthroat Harbor Estates

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202 Beach Home 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
Check Availability
Beautifully Renovated with Stunning Sunset Views and Dockage!
Beautifully Renovated with Stunning Sunset Views and Dockage!
House
Cudjoe Key, FL, 33042, United States
0.3k from Cutthroat Harbor Estates center

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

3 Bedrooms8 Guests
New to Booking
$350
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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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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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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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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Hawkins Lookout
Hawkins Lookout
House
Cudjoe Key, FL, USA
0.6k from Cutthroat Harbor Estates center

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

3 Bedrooms6 Guests
New to Booking
$304
Average price / night
Check Availability
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
Check Availability
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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Cudjoe Bay Getaway In Paradise
Cudjoe Bay Getaway In Paradise
House
Cudjoe Key, FL, 33042, United States
0.3k from Cutthroat Harbor Estates center

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

3 Bedrooms6 Guests
9.4

Superb

8 reviews

$234
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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Oceanfront Gated Corner lot Amazing Sunsets. 90” BoatDock & 12 person Swim Spa!
Oceanfront Gated Corner lot Amazing Sunsets. 90” BoatDock & 12 person Swim Spa!
House
Summerland Key, FL, 33042, United States
0.3k from Cutthroat Harbor Estates center

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

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$773
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 PARADISE
ISLAND PARADISE
Resort
Cudjoe Key, FL, 33042, United States
0.3k from Cutthroat Harbor Estates center

AC, Arcade, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet

1 Bedroom4 Guests
10.0

Exceptional

32 reviews

$262
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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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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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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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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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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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
Check Availability
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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**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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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
Check Availability
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
Check Availability
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
Check Availability
Oceanfront Home With Large Private Deck with boat dockage
Oceanfront Home With Large Private Deck with boat dockage
House
Summerland Key, FL, 33042, United States
0.4k from Cutthroat Harbor Estates center

AC, Balcony, Barbecue, Dryer, Elevator, Extra Bed, Free Parking, Heater, Internet

3 Bedrooms6 Guests
10.0

Exceptional

12 reviews

$444
Average price / night
Check Availability
**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
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 Beach Rentals in Cutthroat Harbor Estates.

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Frequently Asked Questions

You can explore 202 verified beach rentals in Cutthroat Harbor Estates. Our listings are sourced from trusted booking providers, giving you access to a wide selection of oceanfront homes, seaside condos, and coastal stays—all in one place.

Beach rental prices in Cutthroat Harbor Estates vary depending on the season, property size, and distance from the shoreline. Rates typically start from around $190 per night, with beachfront properties and peak summer dates often priced higher. Comparing available options can help you find the best fit for your budget.

Many beach rentals in Cutthroat Harbor Estates offer direct access to the sand or are located within a short walking distance of the shoreline. You can use filters to find properties with beachfront locations, private walkways, or unobstructed ocean views.

Yes, many beach rentals in Cutthroat Harbor Estates welcome pets. Currently, 26 listings allow pets, although policies may vary by property. It’s also a good idea to check local beach regulations for any restrictions on pets during your stay.

For peak travel periods such as summer holidays or spring break, it’s recommended to book your beach rental 90 to 120 days in advance to secure the best options. During off-peak seasons, you may find more flexibility and availability closer to your travel dates.

Beach rentals in Cutthroat Harbor Estates often include amenities designed for coastal living, such as View, Ocean View, and Balcony/Terrace. These features help enhance comfort and make it easier to enjoy time by the water.

Some beach rentals provide extras like chairs, umbrellas, or beach gear, but this can vary by property. It’s best to review the amenities section of each listing to confirm what is included and plan accordingly.