Family-Friendly Vacation Rentals in MiLo Watersports, FL: Compare 10+ Sites & Save

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119 Best Family Vacation Rentals in MiLo Watersports (Starting from $150)

Skyway Living
Skyway Living
House
Summerland Key, FL, USA
0.3k from MiLo Watersports center

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

2 Bedrooms6 Guests
New to Booking
$237
Average price / night
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Mariners Cove - The Kraken House
Mariners Cove - The Kraken House
House
Summerland Key, FL, 33042, United States
0.3k from MiLo Watersports center

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

5 Bedrooms10 Guests
9.8

Exceptional

9 reviews

$698
Average price / night
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Summerland Canal
Summerland Canal
House
Summerland Key, FL, USA
0.4k from MiLo Watersports center

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

2 Bedrooms5 Guests
New to Booking
$160
Average price / night
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Summer Month's Just Opened Up!!! Canal Front Pool Home in Summerland Key
Summer Month's Just Opened Up!!! Canal Front Pool Home in Summerland Key
House
Summerland Key, FL, 33042, United States
0.7k from MiLo Watersports center

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

3 Bedrooms6 Guests
10.0

Exceptional

12 reviews

$354
Average price / night
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Love Shack
Love Shack
House
Summerland Key, FL, USA
1.2k from MiLo Watersports center

Barbecue/Outdoor Cooking, Internet, Security/Safety, Laundry, Child Friendly

2 Bedrooms4 Guests
New to Booking
$150
Average price / night
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Sea Glass House of Summerland Key!\nPool, 70 feet of Seawall, deep water canal!
Sea Glass House of Summerland Key!\nPool, 70 feet of Seawall, deep water canal!
House
Summerland Key, FL, 33042, United States
0.8k from MiLo Watersports center

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

3 Bedrooms9 Guests
10.0

Exceptional

1 reviews

$476
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
2.9k from MiLo Watersports 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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REEL ESCAPE - 4 Bedroom / 2 Bathroom w/ Pool, Boat Dock & Sleeps 8!
REEL ESCAPE - 4 Bedroom / 2 Bathroom w/ Pool, Boat Dock & Sleeps 8!
House
Summerland Key, FL, 33042, United States
0.8k from MiLo Watersports center

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

4 Bedrooms8 Guests
9.8

Exceptional

6 reviews

$544
Average price / night
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Tidewater Views by Last Key Realty
Tidewater Views by Last Key Realty
House
Cudjoe Key, FL, USA
2.9k from MiLo Watersports 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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PALM COTTAGE - Sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED!
PALM COTTAGE - Sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED!
Cottage
Summerland Key, FL, 33042, United States
0.8k from MiLo Watersports center

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

1 Bedroom4 Guests
9.8

Exceptional

53 reviews

$267
Average price / night
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Island Oasis ~ YOUR Paradise Awaits!
Island Oasis ~ YOUR Paradise Awaits!
House
MiLo Watersports, Summerland Key, Florida, USA
2.9k from MiLo Watersports 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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One of the very few beach houses with a daily, rental license in the Keys.
One of the very few beach houses with a daily, rental license in the Keys.
House
Summerland Key, FL, 33042, United States
1.1k from MiLo Watersports center

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

4 Bedrooms12 Guests
8.8

Fabulous

67 reviews

$1296
Average price / night
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NAUTILUS.ocean front cottage retreat ~
NAUTILUS.ocean front cottage retreat ~
Villa
Cudjoe Key, FL, USA
2.9k from MiLo Watersports 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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Rise And Shine On The Water
Rise And Shine On The Water
House
Cudjoe Key, FL, 33042, United States
2.9k from MiLo Watersports 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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Pelican's Roost, Waterfront comfort at Venture Out
Pelican's Roost, Waterfront comfort at Venture Out
House
Cudjoe Key, FL, USA
3.0k from MiLo Watersports 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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Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock
Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock
House
Cudjoe Key, FL, 33042, United States
2.9k from MiLo Watersports center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$555
Average price / night
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Mermaid Magic by Last Key Realty
Mermaid Magic by Last Key Realty
House
Cudjoe Key, FL, USA
3.0k from MiLo Watersports 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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WATERFRONT HOME 35' SEAWALL & DOCK 2 Bedroom 2 Bath Vacation Rental
WATERFRONT HOME 35' SEAWALL & DOCK 2 Bedroom 2 Bath Vacation Rental
House
Cudjoe Key, FL, 33042, United States
2.9k from MiLo Watersports center

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

2 Bedrooms6 Guests
9.4

Superb

20 reviews

$379
Average price / night
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OCEANIA. water front cottage retreat ~
OCEANIA. water front cottage retreat ~
Villa
Cudjoe Key, FL, USA
3.0k from MiLo Watersports 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 2BR Home w/ Dock + Golf Cart, Open Water Views in Venture Out
Waterfront 2BR Home w/ Dock + Golf Cart, Open Water Views in Venture Out
House
Cudjoe Key, FL, 33042, United States
3.0k from MiLo Watersports center

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

2 Bedrooms6 Guests
10.0

Exceptional

9 reviews

$587
Average price / night
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Dock Holiday
Dock Holiday
House
Cudjoe Key, FL, USA
3.1k from MiLo Watersports 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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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
3.0k from MiLo Watersports 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
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2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Cottage
Cudjoe Key, FL, 33042, United States
3.0k from MiLo Watersports center

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

3 Bedrooms6 Guests
9.8

Exceptional

28 reviews

$648
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
3.1k from MiLo Watersports 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
3.1k from MiLo Watersports 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
3.1k from MiLo Watersports center

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

2 Bedrooms4 Guests
9.6

Exceptional

53 reviews

$958
Average price / night
Check Availability
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
3.1k from MiLo Watersports 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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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 MiLo Watersports.

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Frequently Asked Questions

You can explore 119 verified family-friendly vacation rentals in MiLo Watersports. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in MiLo Watersports vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $150 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in MiLo Watersports 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 MiLo Watersports 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 MiLo Watersports often include amenities such as Child Friendly, Pool, and Fireplace/Heating. 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.