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

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Summerland Key
  6.  MiLo Watersports

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335 Best Vacation Rentals with Pool in MiLo Watersports (Starting from $160)

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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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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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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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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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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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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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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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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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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  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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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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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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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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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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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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 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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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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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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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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Summerland Cove..MM25 Summerland Key, Fl..Canal front-one street from open water
Summerland Cove..MM25 Summerland Key, Fl..Canal front-one street from open water
House
Summerland Key, FL, 33042, United States
0.4k from MiLo Watersports center

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

2 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$291
Average price / night
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Serenity Now Seaside Escape - Brand New Build!
Serenity Now Seaside Escape - Brand New Build!
House
Cudjoe Key, FL, USA
3.1k from MiLo Watersports center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay

1 Bedroom6 Guests
New to Booking
$469
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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Fishermans Paradise@The Pointe on Summerland Key 2Bed/2Bath, Pool, 120' of Dock
Fishermans Paradise@The Pointe on Summerland Key 2Bed/2Bath, Pool, 120' of Dock
House
Summerland Key, FL, 33042, United States
0.7k from MiLo Watersports center

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

2 Bedrooms4 Guests
New to Booking
$442
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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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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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 Pool in MiLo Watersports.

Where to stay in MiLo Watersports? Best neighborhoods & areas

MiLo Watersports Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 335 verified vacation rentals with a pool in MiLo Watersports. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in MiLo Watersports vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $160 per night, with private pool homes and peak travel periods often costing more.

Many rentals in MiLo Watersports offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in MiLo Watersports welcome pets. Currently, 28 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in MiLo Watersports often include additional outdoor features such as Pool, Wellness Facilities, and Fireplace/Heating. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in MiLo Watersports offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.