Villa Rentals in Plantation by the Sea, FL: Compare 10+ Sites & Save

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  3.  USA

  4.  Florida

  5.  Islamorada
  6.  Plantation by the Sea

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34 Best Villa Rentals in Plantation by the Sea (Starting from $129)

Anglers Reef Vacation Rental
Anglers Reef Vacation Rental
Villa
Islamorada, FL, USA
4.0k from Plantation by the Sea center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach

2 Bedrooms6 Guests
9.5

Superb

2 reviews

$495
Average price / night
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Exec Bay 3 Bedroom townhouse w/heated pool, marina, tennis & more
Exec Bay 3 Bedroom townhouse w/heated pool, marina, tennis & more
Villa
Islamorada, FL, 33036, United States
0.7k from Plantation by the Sea center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$189
Average price / night
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Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location
Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location
Villa
Islamorada, FL, USA
8.3k from Plantation by the Sea center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings

3 Bedrooms6 Guests
New to Booking
$802
Average price / night
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Exec Bay w/heated Pool, Marina, Beach, Pets ok, Tennis/Pickleball
Exec Bay w/heated Pool, Marina, Beach, Pets ok, Tennis/Pickleball
Villa
Islamorada, FL, 33036, United States
0.7k from Plantation by the Sea center

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

3 Bedrooms6 Guests
9.4

Superb

17 reviews

$129
Average price / night
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Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location
Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location
Villa
Islamorada, FL, USA
8.3k from Plantation by the Sea center

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

3 Bedrooms6 Guests
New to Booking
$737
Average price / night
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Executive Bay - Next to Beach and Pool!
Executive Bay - Next to Beach and Pool!
Villa
Islamorada, FL, 33036, United States
0.7k from Plantation by the Sea center

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

2 Bedrooms4 Guests
New to Booking
$200
Average price / night
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Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Villa
Islamorada, FL, USA
8.3k from Plantation by the Sea center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$627
Average price / night
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Charming Ocean Front Pool Home with dockage & pool
Charming Ocean Front Pool Home with dockage & pool
Villa
Islamorada, FL, 33036, United States
2.0k from Plantation by the Sea center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Free Parking, Internet, Kitchen, Laundry

5 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$2100
Average price / night
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Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location
Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location
Villa
Islamorada, FL, USA
8.3k from Plantation by the Sea center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$617
Average price / night
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NewListing Canal Home Snake Creek with Bay&Ocean Access Tiki&Pool 100ft Dockage
NewListing Canal Home Snake Creek with Bay&Ocean Access Tiki&Pool 100ft Dockage
Villa
Islamorada, FL, 33036, United States
3.0k from Plantation by the Sea center

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

5 Bedrooms14 Guests
10.0

Exceptional

1 reviews

$519
Average price / night
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Isla Honeydew - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Isla Honeydew - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Villa
Islamorada, FL, USA
8.3k from Plantation by the Sea center

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

3 Bedrooms6 Guests
New to Booking
$1281
Average price / night
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Oversized Islamorada Villa 110 in Gated Anglers Reef: Pool, Kayaks, Bikes, Beach
Oversized Islamorada Villa 110 in Gated Anglers Reef: Pool, Kayaks, Bikes, Beach
Villa
Islamorada, FL, 33036, United States
3.9k from Plantation by the Sea center

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

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$450
Average price / night
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Islamorada house with best location. Lic # 24-0055
Islamorada house with best location. Lic # 24-0055
Villa
Islamorada, FL, 33036, United States
3.9k from Plantation by the Sea center

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

2 Bedrooms6 Guests
10.0

Exceptional

19 reviews

$624
Average price / night
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Serenity by the Sea!!  Anglers Reef with Boat Slip Available!!
Serenity by the Sea!! Anglers Reef with Boat Slip Available!!
Villa
Islamorada, FL, 33036, United States
4.0k from Plantation by the Sea center

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

2 Bedrooms6 Guests
10.0

Exceptional

121 reviews

$392
Average price / night
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Island Time: Partial Ocean View, Ensuite bedrooms, Free Dockage, Htd Pool
Island Time: Partial Ocean View, Ensuite bedrooms, Free Dockage, Htd Pool
Villa
Islamorada, FL, 33036, United States
4.7k from Plantation by the Sea center

AC, Balcony, Dryer, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$613
Average price / night
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Ocean's Fourteen:Direct Ocean View-Balconies-Dock-Htd Pool
Ocean's Fourteen:Direct Ocean View-Balconies-Dock-Htd Pool
Villa
Islamorada, FL, 33036, United States
4.9k from Plantation by the Sea center

AC, Balcony, Dryer, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$617
Average price / night
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  Spectacular 4 bedroom 4 1/2 bath villa on Tavernier Creek in Florida Keys.
Spectacular 4 bedroom 4 1/2 bath villa on Tavernier Creek in Florida Keys.
Villa
Tavernier, FL, 33070, United States
5.3k from Plantation by the Sea center

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

4 Bedrooms8 Guests
New to Booking
$1125
Average price / night
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Oceanfront Charm Meets Bespoke Luxury- Brand New 9 Bedroom Estate & Sleeps 26
Oceanfront Charm Meets Bespoke Luxury- Brand New 9 Bedroom Estate & Sleeps 26
Villa
Tavernier, FL, 33070, United States
6.6k from Plantation by the Sea center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Elevator, Fitness Equipment, Free Parking, Hot Tub

9 Bedrooms18 Guests
New to Booking
$9138
Average price / night
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The Islands of Islamorada
The Islands of Islamorada
Villa
82779 Old Hwy, Islamorada, FL, 33036, United States
7.6k from Plantation by the Sea center

AC, Bar, Barbecue, Breakfast Available, Elevator, Fitness Equipment, Free Parking, Heater, Hot Tub

1 Bedroom4 Guests
9.8

Exceptional

73 reviews

$841
Average price / night
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Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Villa
Islamorada, FL, 33036, United States
8.2k from Plantation by the Sea center

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

3 Bedrooms6 Guests
9.6

Exceptional

4 reviews

$631
Average price / night
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Isla Mirabelle: Boutique Resort, FREE Boat Dockage Sep-Oct Only!
Isla Mirabelle: Boutique Resort, FREE Boat Dockage Sep-Oct Only!
Villa
Islamorada, FL, 33036, United States
8.2k from Plantation by the Sea center

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

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$635
Average price / night
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Keys Kottage: Bayside villa W/ free onsite boat ramp marina & trailer parking.
Keys Kottage: Bayside villa W/ free onsite boat ramp marina & trailer parking.
Villa
Islamorada, FL, 33036, United States
8.2k from Plantation by the Sea center

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

2 Bedrooms4 Guests
10.0

Exceptional

93 reviews

$358
Average price / night
Check Availability
Isla Lychee: Boutique Resort, FREE Boat Dockage Sep-Oct Only!
Isla Lychee: Boutique Resort, FREE Boat Dockage Sep-Oct Only!
Villa
Islamorada, FL, 33036, United States
8.3k from Plantation by the Sea center

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

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$638
Average price / night
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Bayside: Bayfront villa W/ free onsite boat ramp marina & trailer parking.
Bayside: Bayfront villa W/ free onsite boat ramp marina & trailer parking.
Villa
Islamorada, FL, 33036, United States
8.3k from Plantation by the Sea center

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

2 Bedrooms4 Guests
9.8

Exceptional

40 reviews

$358
Average price / night
Check Availability
The Nest Villa & Marina with boat ramp, sun terrace, water views. Pet friendly!
The Nest Villa & Marina with boat ramp, sun terrace, water views. Pet friendly!
Villa
Islamorada, FL, 33036, United States
8.3k from Plantation by the Sea center

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

2 Bedrooms4 Guests
10.0

Exceptional

16 reviews

$450
Average price / night
Check Availability
10 Bedroom Private Ocean Front Estate
10 Bedroom Private Ocean Front Estate
Villa
Islamorada, FL, 33036, United States
8.3k from Plantation by the Sea center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Elevator, Fitness Equipment, Free Parking, Heater

10 Bedrooms22 Guests
10.0

Exceptional

1 reviews

$3453
Average price / night
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Isla Honeydew: 3 En-Suite Bedrooms, Pool, Dock
Isla Honeydew: 3 En-Suite Bedrooms, Pool, Dock
Villa
Islamorada, FL, 33036, United States
8.4k from Plantation by the Sea center

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

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$615
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 Villa Rentals in Plantation by the Sea.

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Frequently Asked Questions

You can currently explore 34 verified villa rentals in Plantation by the Sea. Our listings are sourced from multiple leading booking platforms, giving you a broad and up-to-date selection of luxury and private villas in one place.

Villa prices in Plantation by the Sea vary depending on the season, location, and amenities. Rates typically start from around $129 per night, with premium properties costing more during peak travel periods. Comparing options across different platforms can help you find the best value for your dates.

Many villas in Plantation by the Sea are designed for privacy and comfort, and a large number of them feature private pools. You can easily filter your search to find villas with pools, helping you choose the perfect stay for relaxation or group travel in Plantation by the Sea.

Yes, Plantation by the Sea offers a wide range of villas ideal for group stays. Many properties include 3 or more bedrooms, making them well-suited for family gatherings, events, or trips with friends. You can filter by bedroom count to quickly find options that match your group size.

For popular travel periods, it’s generally recommended to book your Plantation by the Sea villa around 60 to 90 days in advance to secure the best selection. However, since we compare 10+ sites, it’s still possible to find great last-minute options even 2 to 4 weeks before your trip.

Villas in Plantation by the Sea often include highly sought-after amenities such as Wellness Facilities, View, and Pool. These features enhance comfort and convenience, making them especially popular among travelers visiting Plantation by the Sea.

To discover top-rated villas in Plantation by the Sea, you can sort listings by guest ratings and reviews. Our platform aggregates feedback from multiple trusted sources, helping you identify highly rated properties based on real guest experiences. Use the "Rating" filter above to start your search.