1+ Vacation Rentals Near Indian Waterways |
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Luxury Home Villas - Vacation Rentals in Indian Waterways

Bay view villa in Islamorada, palm trees, shade trees and two private porches From US $440
         

New
Villa
Bay view villa in Islamorada, palm trees, shade trees and two private porches
  • Child Friendly

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Luxury Places to Stay in Indian Waterways

Over 50+ Luxury Places to Stay in or Near Indian Waterways
Waterfront Home With Swimming Pool From US $727
         

10.0 (4 Reviews)
House
Waterfront Home With Swimming Pool
  • Air Conditioner
  • Parking
  • Pet Friendly

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Morada Breeze ~ 6 Bedroom Plantation Key Home with Pool & Dockage From US $619
         

New
House
Morada Breeze ~ 6 Bedroom Plantation Key Home with Pool & Dockage
  • Air Conditioner
  • Parking
  • Pool

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Sunset Peninsula—a multi-family, original, Florida Keys waterfront retreat! From US $536
         

10.0 (4 Reviews)
House
Sunset Peninsula—a multi-family, original, Florida Keys waterfront retreat!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Islamorada Oasis, Luxurious 4 bedroom 3 bath home. Heated pool! Boat Lift option From US $523
         

10.0 (5 Reviews)
House
Islamorada Oasis, Luxurious 4 bedroom 3 bath home. Heated pool! Boat Lift option
  • Air Conditioner
  • Pool
  • TV

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Luxury Islamorada Oasis: Pool, Dock, Fire Pit, King Beds & Canal Views From US $516
         

10.0 (7 Reviews)
House
Luxury Islamorada Oasis: Pool, Dock, Fire Pit, King Beds & Canal Views
  • Air Conditioner
  • Parking
  • Pool

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Waterfront Home Indian Waterways Heart of Islamorada Pool and Dock, Dogs Welcome From US $468
         

10.0 (1 Review)
House
Waterfront Home Indian Waterways Heart of Islamorada Pool and Dock, Dogs Welcome
  • Air Conditioner
  • Parking
  • Pet Friendly

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Keys waterfront paradise From US $456
         

New
House
Keys waterfront paradise
  • Air Conditioner
  • Pool
  • Private Pool

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Mojito Breeze in the heart of Islamorada From US $452
         

New
House
Mojito Breeze in the heart of Islamorada
  • Air Conditioner
  • Pet Friendly
  • Pool

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Top-Rated Vacation Rentals with a Pool in Indian Waterways

Over 15+ Top-Rated Vacation Rentals with a Pool in or Near Indian Waterways
Sunsets on the bay at Villa Mia From US $363
         

10.0 (13 Reviews)
House
Sunsets on the bay at Villa Mia
  • Air Conditioner
  • Parking
  • Pet Friendly

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Get ready to dive into your Islamorada Retreat From US $408
         

10.0 (2 Reviews)
House
Get ready to dive into your Islamorada Retreat
  • Air Conditioner
  • Parking
  • Pool

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Islamorada, Indian Waterways, waterfront retreat - heated pool, 30’ dock From US $405
         

9.8 (6 Reviews)
House
Islamorada, Indian Waterways, waterfront retreat - heated pool, 30’ dock
  • Air Conditioner
  • Parking
  • Pool

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Canal front Oasis with Pool and Tiki Hut From US $279
         

9.0 (4 Reviews)
House
Canal front Oasis with Pool and Tiki Hut
  • Air Conditioner
  • Pet Friendly
  • Pool

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Manatee Manor ~ 3 Bedroom Island Home on Plantation Key with Pool & Dockage From US $347
         

New
House
Manatee Manor ~ 3 Bedroom Island Home on Plantation Key with Pool & Dockage
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  • Parking
  • Pool

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Private Tropical Oasis From US $180
         

9.6 (4 Reviews)
Apartment
Private Tropical Oasis
  • Air Conditioner
  • Pet Friendly
  • Pool

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Gorgeous Canal front home with a pool and Tiki hut From US $203
         

6.0 (1 Review)
House
Gorgeous Canal front home with a pool and Tiki hut
  • Air Conditioner
  • Parking
  • Pet Friendly

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Island Home ~ Brand New Construction ~ Luxury Living Meets Island Living From US $893
         

New
House
Island Home ~ Brand New Construction ~ Luxury Living Meets Island Living
  • Air Conditioner
  • Pool
  • Balcony/Terrace

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Pet-Friendly Vacation Rentals in Indian Waterways

Over 17+ Pet-Friendly Vacation Rentals in or Near Indian Waterways
Canalfront, Dog-Friendly Home with High-Speed WiFi, Private Boat Ramp, and Kayak From US $208
         

10.0 (8 Reviews)
House
Canalfront, Dog-Friendly Home with High-Speed WiFi, Private Boat Ramp, and Kayak
  • Air Conditioner
  • Parking
  • Pet Friendly

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Islamorada Haven From US $130
         

|
New
House
Islamorada Haven
  • Air Conditioner
  • Pet Friendly
  • View

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Spacious 3 bedroom home in Plantation key with 30 foot dock From US $266
         

10.0 (1 Review)
House
Spacious 3 bedroom home in Plantation key with 30 foot dock
  • Air Conditioner
  • Parking
  • Pet Friendly

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Spectacular Keys home-corner canal, hot tub, tiki From US $398
         

New
House
Spectacular Keys home-corner canal, hot tub, tiki
  • Air Conditioner
  • Parking
  • Pet Friendly

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Spacious Canal-Front Home: Florida Keys Gem From US $286
         

New
House
Spacious Canal-Front Home: Florida Keys Gem
  • Air Conditioner
  • Parking
  • Pet Friendly

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Islamorada Haven - FIshing, watersports, relaxation From US $152
         

10.0 (2 Reviews)
Cottage
Islamorada Haven - FIshing, watersports, relaxation
  • Air Conditioner
  • Parking
  • Pet Friendly

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Salty Suites, simply put, it's paradise 365 days a year. From US $289
         

New
House
Salty Suites, simply put, it's paradise 365 days a year.
  • Air Conditioner
  • Parking
  • Pet Friendly

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A great place to relax, fish, or even work from. 2/2 , 66 ft From US $206
         

10.0 (1 Review)
House
A great place to relax, fish, or even work from. 2/2 , 66 ft
  • Air Conditioner
  • Parking
  • Pet Friendly

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Large Vacation Homes & Villas in Indian Waterways

Over 7+ Large Vacation Homes & Villas in or Near Indian Waterways
Colorful Island-Style Canalfront Retreat in Islamorada with Dockage and Private Guest Suite From US $283
         

New
House
Colorful Island-Style Canalfront Retreat in Islamorada with Dockage and Private Guest Suite
  • Air Conditioner
  • Parking
  • TV

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Bay-front, family compound in Tavernier is the perfect Keys retreat.
New
From US $500
         

New
House
Bay-front, family compound in Tavernier is the perfect Keys retreat.
  • Child Friendly

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Mojito Breeze Getaway From US $485
         

New
House
Mojito Breeze Getaway
  • Air Conditioner
  • Parking
  • Pet Friendly

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Mojito Breeze Getaway by RedAwning From US $426
         

New
House
Mojito Breeze Getaway by RedAwning
  • Air Conditioner
  • Parking
  • Pet Friendly

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Manatee Harbor - Bayfront Home on Plantation Key From US $654
         

New
House
Manatee Harbor - Bayfront Home on Plantation Key
  • Air Conditioner
  • Pool
  • View

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Newly built 4-bedroom house in Tavernier with ample dock space and Kayak ramp. From US $632
         

New
House
Newly built 4-bedroom house in Tavernier with ample dock space and Kayak ramp.
  • Air Conditioner
  • Parking
  • Pet Friendly

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NEW! Canal-Front with Tropical Charm & Private Guest Apartment on Plantation Key From US $286
         

New
House
NEW! Canal-Front with Tropical Charm & Private Guest Apartment on Plantation Key
  • Air Conditioner
  • Parking
  • TV

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Indian Waterways Varoom and Airbnb Places to Stay Under $200

Over 3+ Indian Waterways Varoom and Airbnb Places to Stay Under $200
Tropical Oasis Anchor located on the bayside. Upcoming Pool ready by 2026 From US $189
         

10.0 (1 Review)
House
Tropical Oasis Anchor located on the bayside. Upcoming Pool ready by 2026
  • Air Conditioner
  • Parking
  • TV

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Trendy canal-front home with dock, full kitchen, central AC, & washer/dryer From US $147
         

6.0 (1 Review)
House
Trendy canal-front home with dock, full kitchen, central AC, & washer/dryer
  • Air Conditioner
  • Parking
  • TV

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Beautiful home in Islamorada From US $159
         

New
House
Beautiful home in Islamorada
  • Air Conditioner
  • Parking
  • TV

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Instantly Bookable Vacation Homes in Indian Waterways

Over 6+ Instantly Bookable Vacation Homes in or Near Indian Waterways
Modern Cozy Beachouse Gem From US $406
         

10.0 (2 Reviews)
House
Modern Cozy Beachouse Gem
  • Air Conditioner
  • Parking
  • TV

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Sunset Paradise in Islamorada, Florida Keys From US $256
         

5.0 (2 Reviews)
House
Sunset Paradise in Islamorada, Florida Keys
  • Air Conditioner
  • Balcony/Terrace
  • Bedding/Linens

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Spectacular Keys home on corner canal, hot tub, tiki hut + much more! From US $406
         

New
House
Spectacular Keys home on corner canal, hot tub, tiki hut + much more!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Casa Margarita Islamorada, Paradise awaits! From US $336
         

New
House
Casa Margarita Islamorada, Paradise awaits!
  • Air Conditioner
  • Parking
  • Pool

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Deep Water Canal Home with Private Pool and Dock From US $302
         

New
House
Deep Water Canal Home with Private Pool and Dock
  • Air Conditioner
  • Pet Friendly
  • Pool

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Waterfront paradise with fire pit, Washer/Dryer, and central AC From US $242
         

New
House
Waterfront paradise with fire pit, Washer/Dryer, and central AC
  • Air Conditioner
  • Parking
  • TV

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About Indian Waterways Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Luxuryhomevilla Indian Waterways, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Indian Waterways. Places to stay near Indian Waterways with prices averaging $440 a night.

Luxuryhomevilla makes it easy and safe to find and compare vacation rentals in Indian Waterways with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Indian Waterways

Type Count
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Use these Quick Filters to Find a Vacation Rental in Indian Waterways

★ Pro Tip: Luxuryhomevilla makes it easy to compare the best listings on Luxuryhomevilla homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Luxuryhomevilla homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Indian Waterways.

Weather in Indian Waterways

View the weather forecast for Indian Waterways before booking your Indian Waterways Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F