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

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  6.  Cutthroat Harbor Estates

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543 Best Vacation Rentals in Cutthroat Harbor Estates (Starting from $189)

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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Dock Holiday
Dock Holiday
House
Cudjoe Key, FL, USA
0.5k from Cutthroat Harbor Estates center

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

2 Bedrooms4 Guests
7.6

Good

5 reviews

$293
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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Mermaid Magic by Last Key Realty
Mermaid Magic by Last Key Realty
House
Cudjoe Key, FL, USA
0.6k from Cutthroat Harbor Estates center

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

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$875
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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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
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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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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
Check Availability
Tree Top Paradise
Tree Top Paradise
House
Cudjoe Key, FL, USA
0.7k from Cutthroat Harbor Estates center

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

2 Bedrooms6 Guests
8.8

Fabulous

30 reviews

$189
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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Tidewater Views by Last Key Realty
Tidewater Views by Last Key Realty
House
Cudjoe Key, FL, USA
0.7k from Cutthroat Harbor Estates center

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

2 Bedrooms6 Guests
New to Booking
$424
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
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
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
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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
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Cudjoe Key Home with a View
Cudjoe Key Home with a View
House
Cudjoe Key, FL, 33042, United States
0.4k from Cutthroat Harbor Estates center

Extra Bed, Hot Tub, Internet, No Smoking, Pool, Toys

2 Bedrooms6 Guests
9.0

Fabulous

2 reviews

$388
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 Vacation Rentals in Cutthroat Harbor Estates.

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Frequently Asked Questions

You can explore 543 verified vacation rentals in Cutthroat Harbor Estates. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Cutthroat Harbor Estates vary depending on the season, property size, and location. Rates typically start from around $189 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Cutthroat Harbor Estates include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Cutthroat Harbor Estates welcome pets. Currently, 36 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Cutthroat Harbor Estates often include amenities such as Wellness Facilities, View, and Ocean View. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.