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

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105 Best Family 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
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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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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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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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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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SOUTHERN SUNSET - As seen on House Hunters-S228 E6 - Family Time in the FL Keys
SOUTHERN SUNSET - As seen on House Hunters-S228 E6 - Family Time in the FL Keys
House
Cudjoe Key, FL, 33042, United States
0.4k from Cutthroat Harbor Estates center

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

4 Bedrooms14 Guests
10.0

Exceptional

1 reviews

$497
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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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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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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Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
House
Cudjoe Key, FL, 33042, United States
0.5k from Cutthroat Harbor Estates center

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

2 Bedrooms6 Guests
9.8

Exceptional

262 reviews

$285
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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Night jasmine oceanfront vacation house
Night jasmine oceanfront vacation house
House
Cudjoe Key, FL, 33042, United States
0.5k from Cutthroat Harbor Estates center

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

4 Bedrooms10 Guests
10.0

Exceptional

27 reviews

$426
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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Open Water View from porch , golf cart, dock, bikes, kayaks, trailer parking
Open Water View from porch , golf cart, dock, bikes, kayaks, trailer parking
House
Cudjoe Key, FL, 33042, United States
0.5k from Cutthroat Harbor Estates center

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

3 Bedrooms6 Guests
9.8

Exceptional

131 reviews

$468
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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Waterfront Cottage with Stunning Views & Resort Amenities Near Key West!
Waterfront Cottage with Stunning Views & Resort Amenities Near Key West!
House
Cudjoe Key, FL, 33042, United States
0.5k from Cutthroat Harbor Estates center

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

3 Bedrooms4 Guests
9.8

Exceptional

129 reviews

$352
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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Canal front home @ Venture Out Resort in the Florida Keys!
Canal front home @ Venture Out Resort in the Florida Keys!
House
Cudjoe Key, FL, 33042, United States
0.5k from Cutthroat Harbor Estates center

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

2 Bedrooms6 Guests
9.2

Superb

50 reviews

$438
Average price / night
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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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Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
House
Cudjoe Key, FL, 33042, United States
0.5k from Cutthroat Harbor Estates center

AC, Barbecue, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
8.0

Good

16 reviews

$477
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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Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
Cottage
Cudjoe Key, FL, 33042, United States
0.5k from Cutthroat Harbor Estates center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Microwave

1 Bedroom4 Guests
10.0

Exceptional

37 reviews

$255
Average price / night
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Rise And Shine On The Water
Rise And Shine On The Water
House
Cudjoe Key, FL, 33042, United States
0.6k from Cutthroat Harbor Estates center

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

2 Bedrooms6 Guests
10.0

Exceptional

39 reviews

$686
Average price / night
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Waterfront 2BR in Venture Out with 35' Dock, Pool & Marina Basin Views
Waterfront 2BR in Venture Out with 35' Dock, Pool & Marina Basin Views
House
Cudjoe Key, FL, 33042, United States
0.6k from Cutthroat Harbor Estates center

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

2 Bedrooms6 Guests
New to Booking
$409
Average price / night
Check Availability
Waterfront 2BR Marina Basin Home with 35' Dock, Balcony & Pool
Waterfront 2BR Marina Basin Home with 35' Dock, Balcony & Pool
House
Cudjoe Key, FL, 33042, United States
0.6k from Cutthroat Harbor Estates center

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

2 Bedrooms6 Guests
New to Booking
$421
Average price / night
Check Availability
Oceanfront 2BR Retreat | 35' Dock, Open Views, Boater's Paradise
Oceanfront 2BR Retreat | 35' Dock, Open Views, Boater's Paradise
House
Cudjoe Key, FL, 33042, United States
0.6k from Cutthroat Harbor Estates center

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

2 Bedrooms4 Guests
9.6

Exceptional

53 reviews

$958
Average price / night
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Relax by Florida Keys Beaches, just a 7-min drive away
Relax by Florida Keys Beaches, just a 7-min drive away
House
Cudjoe Key, FL, 33042, United States
0.6k from Cutthroat Harbor Estates center

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

2 Bedrooms5 Guests
9.8

Exceptional

206 reviews

$356
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 Family Vacation Rentals in Cutthroat Harbor Estates.

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Frequently Asked Questions

You can explore 105 verified family-friendly vacation rentals in Cutthroat Harbor Estates. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Cutthroat Harbor Estates vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $189 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Cutthroat Harbor Estates offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Cutthroat Harbor Estates are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Cutthroat Harbor Estates often include amenities such as Child Friendly, Pool, and Wellness Facilities. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.