Family-Friendly Vacation Rentals in Long Key, FL: Compare 10+ Sites & Save

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53 Best Family Vacation Rentals in Long Key (Starting from $106)

Turtle Beach Retreat
Turtle Beach Retreat
House
Layton, FL, USA
3.7k from Long 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
Check Availability
Beautiful Pool Home Located in a Quiet Neighborhood
Beautiful Pool Home Located in a Quiet Neighborhood
House
Long Key, FL, 33001, United States
0.5k from Long Key center

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

2 Bedrooms6 Guests
New to Booking
$649
Average price / night
Check Availability
Florida Keys Getaway with Stunning Ocean Views
Florida Keys Getaway with Stunning Ocean Views
House
Layton, FL, USA
4.3k from Long 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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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
0.5k from Long Key center

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

3 Bedrooms8 Guests
New to Booking
$265
Average price / night
Check Availability
Walk to Beach Florida Keys Gem with Ocean Views
Walk to Beach Florida Keys Gem with Ocean Views
House
Layton, FL, USA
4.3k from Long 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
Check Availability
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
0.8k from Long 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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The Henry Flagler
The Henry Flagler
House
Layton, FL, USA
4.3k from Long 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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Fishing and Boating Paradise with 30 Foot Boat Slip and Swimming Pool
Fishing and Boating Paradise with 30 Foot Boat Slip and Swimming Pool
Condo
Long Key, FL, 33001, United States
2.1k from Long Key center

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

3 Bedrooms6 Guests
10.0

Exceptional

42 reviews

$426
Average price / night
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The Zane Grey
The Zane Grey
House
Layton, FL, USA
4.3k from Long 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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Outdoor Resorts, Long Key, FL
Outdoor Resorts, Long Key, FL
House
Layton, FL, 33001, United States
4.0k from Long Key center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Laundry, Microwave

2 Bedrooms8 Guests
6.8

Good

9 reviews

$106
Average price / night
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Beachfront Ocean Duplex
Beachfront Ocean Duplex
House
Layton, FL, USA
4.3k from Long 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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BRING YOUR BOAT! Perfect Florida Keys Family Getaway with Activities Galore!
BRING YOUR BOAT! Perfect Florida Keys Family Getaway with Activities Galore!
Cottage
Layton, FL, 33001, United States
4.0k from Long Key center

AC, Arcade, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$280
Average price / night
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Tollgate Tides
Tollgate Tides
House
Islamorada, FL, USA
8.0k from Long Key center

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

2 Bedrooms6 Guests
New to Booking
$154
Average price / night
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Long Key florida,Beachfront Paradise, two bedroom ,3.5 bath, on Ocean, with Pool
Long Key florida,Beachfront Paradise, two bedroom ,3.5 bath, on Ocean, with Pool
Condo
Layton, FL, 33001, United States
4.2k from Long Key center

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

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$394
Average price / night
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Paradise Beach
Paradise Beach
House
Islamorada, FL, USA
8.2k from Long 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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Atlantic Ocean Beachfront Duplex with Private Dock
Atlantic Ocean Beachfront Duplex with Private Dock
House
Long Key, FL, 33001, United States
4.3k from Long Key center

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

2 Bedrooms5 Guests
10.0

Exceptional

90 reviews

$588
Average price / night
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Fisherman's Retreat
Fisherman's Retreat
House
Conch Key, FL, USA
8.7k from Long Key center

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

2 Bedrooms8 Guests
New to Booking
$199
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
7.9k from Long 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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Ocean View Duplex Penthouse Retreat amenities: tennis court heated Pool Vista Key One
Ocean View Duplex Penthouse Retreat amenities: tennis court heated Pool Vista Key One
Apartment
Islamorada, FL, USA
9.0k from Long Key center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Hot tubs, Places to stay

1 Bedroom10 Guests
New to Booking
$880
Average price / night
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Water Front 3/3 Family and Boat Friendly Home, Great Views
Water Front 3/3 Family and Boat Friendly Home, Great Views
House
Islamorada, FL, 33036, United States
8.0k from Long Key center

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

3 Bedrooms8 Guests
10.0

Exceptional

21 reviews

$295
Average price / night
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Ocean View Penthouse Retreat amenities: tennis court heated Pool Vista Key Two
Ocean View Penthouse Retreat amenities: tennis court heated Pool Vista Key Two
Apartment
Islamorada, FL, USA
9.0k from Long Key center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$582
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
8.0k from Long 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
Check Availability
Ocean View Two Duplex Penthouses Retreat amenities: tennis court heated Pool Vista Key
Ocean View Two Duplex Penthouses Retreat amenities: tennis court heated Pool Vista Key
Apartment
Islamorada, FL, USA
9.1k from Long Key center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Hot tubs, Places to stay

1 Bedroom18 Guests
New to Booking
$1388
Average price / night
Check Availability
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
8.1k from Long Key center

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

6 Bedrooms12 Guests
10.0

Exceptional

21 reviews

$668
Average price / night
Check Availability
You will never want to leave
You will never want to leave
House
Islamorada, FL, 33036, United States
8.1k from Long Key center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1031
Average price / night
Check Availability
\"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
8.1k from Long Key center

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

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$495
Average price / night
Check Availability
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
8.3k from Long Key center

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

5 Bedrooms12 Guests
10.0

Exceptional

72 reviews

$1052
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 Long Key.

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Long Key Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 53 verified family-friendly vacation rentals in Long Key. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Long Key vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $106 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Long Key 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 Long Key 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 Long Key often include amenities such as Child Friendly, View, and Ocean View. 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.