Vacation Rentals with Private Pool in MiLo Watersports, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
  5.  Summerland Key
  6.  MiLo Watersports

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121 Best Vacation Rentals with Private Pool in MiLo Watersports (Starting from $232)

Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Dockage & Dog-Friendly
Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Dockage & Dog-Friendly
House
Summerland Key, FL, 33042, United States
0.2k from MiLo Watersports center

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

3 Bedrooms10 Guests
8.0

Good

1 reviews

$374
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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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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Caribbean Cabana: Your Perfect 3BR Oceanfront Retreat with Dockage, Pool and Breathtaking Views!
Caribbean Cabana: Your Perfect 3BR Oceanfront Retreat with Dockage, Pool and Breathtaking Views!
House
Summerland Key, FL, 33042, United States
0.4k from MiLo Watersports center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$530
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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Mad Mahi Canal with pool.<br>This is a pet friendly home. A pet fee and approval of your pet is required.
Mad Mahi Canal with pool.<br>This is a pet friendly home. A pet fee and approval of your pet is required.
House
Summerland Key, FL, 33042, United States
0.4k from MiLo Watersports center

AC, Barbecue, Free Parking, Internet, Kitchen, Laundry, No Smoking, Pool, TV

4 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$514
Average price / night
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Summerland Key House Open Air Living
Summerland Key House Open Air Living
House
Summerland Key, FL, 33042, United States
0.6k from MiLo Watersports center

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

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$298
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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Blue Pearl of Summerland Key 4 Bedrooms, 3 Baths with Dock, Heated Pool and Spa
Blue Pearl of Summerland Key 4 Bedrooms, 3 Baths with Dock, Heated Pool and Spa
House
Summerland Key, FL, 33042, United States
1.0k from MiLo Watersports center

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

4 Bedrooms8 Guests
10.0

Exceptional

9 reviews

$579
Average price / night
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The Roost in Summerland Cove Isles
The Roost in Summerland Cove Isles
House
Summerland Key, FL, 33042, United States
1.1k from MiLo Watersports center

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

4 Bedrooms6 Guests
New to Booking
$787
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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Oceanfront  Home-Pool, Dock-Available Daily, Weekly or Monthly.
Oceanfront Home-Pool, Dock-Available Daily, Weekly or Monthly.
House
Summerland Key, FL, 33042, United States
1.1k from MiLo Watersports center

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

3 Bedrooms10 Guests
9.8

Exceptional

49 reviews

$1321
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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Beautiful Lagoon view on canal pool home Summerland
Beautiful Lagoon view on canal pool home Summerland
House
Summerland Key, FL, 33042, United States
1.3k from MiLo Watersports center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$274
Average price / night
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Solstice Seaside Waterfront House w/Pool & Spectacular Ocean Views/Min 28 Nights
Solstice Seaside Waterfront House w/Pool & Spectacular Ocean Views/Min 28 Nights
House
Summerland Key, FL, 33042, United States
1.4k from MiLo Watersports center

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

4 Bedrooms8 Guests
9.0

Fabulous

7 reviews

$501
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
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Summerland Nest - Ocean view with private beach and pool
Summerland Nest - Ocean view with private beach and pool
House
Summerland Key, FL, 33042, United States
1.5k from MiLo Watersports center

AC, Barbecue, Free Parking, Internet, Kitchen, Laundry, No Smoking, Pool, TV

7 Bedrooms14 Guests
9.4

Superb

3 reviews

$847
Average price / night
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Beautiful Oceanfront Villa with Pool and near Key West, Florida
Beautiful Oceanfront Villa with Pool and near Key West, Florida
Villa
Summerland Key, FL, 33042, United States
1.5k from MiLo Watersports center

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

2 Bedrooms5 Guests
New to Booking
$621
Average price / night
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Waterfront Sunrise & Sunset Full Views! Pool, dock, lift, Industerial Ice Maker
Waterfront Sunrise & Sunset Full Views! Pool, dock, lift, Industerial Ice Maker
House
Summerland Key, FL, 33042, United States
2.4k from MiLo Watersports center

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

5 Bedrooms8 Guests
New to Booking
$717
Average price / night
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ARTIST HOUSE ~ Canal Front 4 BR/3.5 Ba Home w/ Pool & Ocean and Gulf Access!
ARTIST HOUSE ~ Canal Front 4 BR/3.5 Ba Home w/ Pool & Ocean and Gulf Access!
House
Cudjoe Key, FL, 33042, United States
2.9k from MiLo Watersports center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$414
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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2 Bedroom Canal Home in Cudjoe Key, FL w/ Private Pool & Extra Loft Space
2 Bedroom Canal Home in Cudjoe Key, FL w/ Private Pool & Extra Loft Space
House
Cudjoe Key, FL, 33042, United States
3.0k from MiLo Watersports center

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

2 Bedrooms6 Guests
New to Booking
$368
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 Vacation Rentals with Private Pool in MiLo Watersports.

Where to stay in MiLo Watersports? Best neighborhoods & areas

MiLo Watersports Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 121 verified vacation rentals with a private pool in MiLo Watersports. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in MiLo Watersports vary depending on the property size, location, and travel season. Rates typically start from around $232 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in MiLo Watersports also welcome pets. Currently, 26 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in MiLo Watersports often include additional features such as Laundry, Pool, and Private Pool. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in MiLo Watersports include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.