Beach Home Rentals in MiLo Watersports, FL: Compare 10+ Sites & Save

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69 Beach Home Rentals in MiLo Watersports (Starting from $232)

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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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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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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Relax at the flying hogfish
Relax at the flying hogfish
House
Summerland Key, FL, 33042, United States
0.3k from MiLo Watersports center

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

3 Bedrooms6 Guests
9.6

Exceptional

14 reviews

$232
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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  Summerland Airport Hangar Home with Pool, Private Runway and deep wide Canal
Summerland Airport Hangar Home with Pool, Private Runway and deep wide Canal
House
Summerland Key, FL, 33042, United States
0.4k from MiLo Watersports center

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

2 Bedrooms6 Guests
New to Booking
$359
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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Ocean Front Modern Home
Ocean Front Modern Home
House
Summerland Key, FL, 33042, United States
0.4k from MiLo Watersports center

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

4 Bedrooms9 Guests
10.0

Exceptional

18 reviews

$497
Average price / night
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Oceanfront Sunsets in the Florida Keys
Oceanfront Sunsets in the Florida Keys
House
Summerland Key, FL, 33042, United States
0.4k from MiLo Watersports center

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

4 Bedrooms8 Guests
10.0

Exceptional

17 reviews

$472
Average price / night
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 Starfish Cottage - Sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED!
Starfish Cottage - Sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED!
Cottage
Summerland Key, FL, 33042, United States
0.4k from MiLo Watersports center

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

1 Bedroom4 Guests
9.8

Exceptional

60 reviews

$243
Average price / night
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FLAMINGO COTTAGE sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED!
FLAMINGO COTTAGE sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED!
Cottage
Summerland Key, FL, 33042, United States
0.6k from MiLo Watersports center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, Outdoor Grill

1 Bedroom4 Guests
9.8

Exceptional

47 reviews

$242
Average price / night
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Amazing 2 BR Home in Summerland w/ Great Boating Access & Private Heated Pool!
Amazing 2 BR Home in Summerland w/ Great Boating Access & Private Heated Pool!
House
Summerland Key, FL, 33042, United States
0.7k from MiLo Watersports center

AC, Barbecue, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
New to Booking
$367
Average price / night
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Summerland Serenity  Elevated Waterfront Luxury with Private Elevator & Pool
Summerland Serenity Elevated Waterfront Luxury with Private Elevator & Pool
House
Summerland Key, FL, 33042, United States
0.7k from MiLo Watersports center

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

5 Bedrooms12 Guests
New to Booking
$508
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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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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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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Views Views!  Direct Oceanfront, Beautiful Inside!
Views Views! Direct Oceanfront, Beautiful Inside!
House
Summerland Key, FL, 33042, United States
1.0k from MiLo Watersports center

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

2 Bedrooms4 Guests
10.0

Exceptional

13 reviews

$355
Average price / night
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Florida Keys Paradise!
Florida Keys Paradise!
House
Summerland Key, FL, 33042, United States
1.0k from MiLo Watersports center

Barbecue, Dryer, Heater, Hot Tub, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$383
Average price / night
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Kelly's Kabin - Adorable Private Summerland Key Cottage
Kelly's Kabin - Adorable Private Summerland Key Cottage
House
Summerland Key, FL, 33042, United States
1.0k from MiLo Watersports center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms5 Guests
9.8

Exceptional

123 reviews

$531
Average price / night
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PEACEFUL PARADISE DEEP WATER CANAL! MINUTES TO OCEAN \nFishing and Lobster season
PEACEFUL PARADISE DEEP WATER CANAL! MINUTES TO OCEAN \nFishing and Lobster season
House
Summerland Key, FL, 33042, United States
1.1k from MiLo Watersports center

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

3 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$480
Average price / night
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Deep/Wide/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise
Deep/Wide/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise
House
Summerland Key, FL, 33042, United States
1.1k from MiLo Watersports center

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

3 Bedrooms8 Guests
9.6

Exceptional

58 reviews

$319
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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Florida keys Waterfront,Forever Summer
Florida keys Waterfront,Forever Summer
House
Summerland Key, FL, 33042, United States
1.1k from MiLo Watersports center

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

4 Bedrooms8 Guests
9.4

Superb

6 reviews

$365
Average price / night
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3/2 on the Water in Paradise Monthly Rental 28 Day min.
3/2 on the Water in Paradise Monthly Rental 28 Day min.
House
Summerland Key, FL, 33042, United States
1.2k from MiLo Watersports center

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

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$289
Average price / night
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Windswept Beach
Windswept Beach
House
Summerland Key, FL, 33042, United States
1.3k from MiLo Watersports center

AC, Balcony, Dryer, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

3 Bedrooms8 Guests
New to Booking
$571
Average price / night
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Peaceful ocean front cottage.
Peaceful ocean front cottage.
Cottage
Summerland Key, FL, 33042, United States
1.3k from MiLo Watersports center

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

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$411
Average price / night
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Sirena Key | Luxury Oceanfront Estate, Pool, Guest Cottage, Dock, 30min to Key West
Sirena Key | Luxury Oceanfront Estate, Pool, Guest Cottage, Dock, 30min to Key West
House
Summerland Key, FL, 33042, United States
1.5k from MiLo Watersports center

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

5 Bedrooms14 Guests
New to Booking
$536
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 MiLo Watersports.

Where to stay in MiLo Watersports? Best neighborhoods & areas

MiLo Watersports Beach Rentals on the Map

Frequently Asked Questions

You can explore 69 verified beach rentals in MiLo Watersports. 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 MiLo Watersports vary depending on the season, property size, and distance from the shoreline. Rates typically start from around $232 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 MiLo Watersports 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 MiLo Watersports welcome pets. Currently, 27 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 MiLo Watersports often include amenities designed for coastal living, such as Ocean View, 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.