Stay 30 - Vacation Rentals in Indian Key Historic State Park

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From US $1,872

         

10.0 (106 Reviews)

House

Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

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From US $308

         

|

9.5 (4 Reviews)

House

Key Lime Cottage in the heart of Islamorada

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

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From US $446

         

|

8.8 (62 Reviews)

Condo

Topsider Resort

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

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From US $701

         

10.0 (91 Reviews)

House

TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

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From US $282

         

|

9.0 (762 Reviews)

Resort

Pines & Palms Resort

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

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From US $279

         

|

9.2 (1000 Reviews)

Hotel

Pines & Palms Resort

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

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From US $1,263

         

10.0 (87 Reviews)

House

Only 3 weeks left in 2025 for a pre-Christmas getaway! Oceanfront/Pool/dock

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

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From US $346

         

|

8.7 (228 Reviews)

Resort

Bayside Villas by Islander Resort

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

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From US $233

         

|

8.8 (1269 Reviews)

Resort

Amara Cay Resort

• Air Conditioner
• Pool
• TV

• Florida
• Islamorada

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From US $1,424

         

10.0 (76 Reviews)

House

Sunset Reef - Bayside Gated Estate, Pool, Spa, Deep Water Dock, Kayaks & SUPs

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

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From US $663

         

10.0 (70 Reviews)

Condo

Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, SUPs & Day Dock

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

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From US $2,171

         

10.0 (57 Reviews)

House

Final open week of 2026 - Dec 13th - 20th Stunning Oceanfront Estate

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

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From US $544

         

10.0 (53 Reviews)

House

ISLAMORADA WATERFRONT HOME, SPECTACULAR VIEW-GREAT DOCKAGE-WiFi-CONTACT OWNER

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

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From US $905

         

10.0 (48 Reviews)

House

Beach Dream House, relax and enjoy the clear waters of Islamorada FL

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

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From US $327

         

10.0 (35 Reviews)

Condo

Ocean & Bay Views. Welcome To Paradise!

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

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From US $1,500

         

|

10.0 (29 Reviews)

House

Turtle Beach is an Oasis on the Atlantic Ocean

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

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From US $1,316

         

10.0 (19 Reviews)

House

Egret House @ Tarpon Point

• Air Conditioner
• Pool
• TV

• Florida
• Islamorada

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From US $456

         

10.0 (18 Reviews)

House

Islamorada retreat "Bungalow Blue" w/heated pool, Bikes, BBQ, amenities galore!

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

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From US $1,075

         

10.0 (11 Reviews)

House

The Bonefish House at Tarpon Point ~ 4 Bed/4 Bath Oceanfront Home

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

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From US $758

         

10.0 (10 Reviews)

House

Sandy Beach Cove🏝️🏖️ Gated Private Beach Home Plus Cottage Oasis , With Dock

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

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From US $385

         

10.0 (10 Reviews)

House

Tarpon Bend ocean view with boat lifts

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

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From US $1,124

         

10.0 (5 Reviews)

House

The Snook House at Tarpon Point ~ 4 Bed/4 Bath Oceanfront Home

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

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From US $532

         

10.0 (2 Reviews)

Villa

Studio w/2 Queen Beds, Kitchenette, Pool, Free Parking & Pet Friendly

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

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From US $2,452

         

10.0 (1 Review)

House

Private Beach/Private overwater dock/Heated Pool/Mahi Key

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

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