Stay 30 - Vacation Rentals in Anne's Beach

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From US $513

         

10.0 (31 Reviews)

House

NEW POOL * Waterfront Paradise with Amazing Sunsets on Beach*

• 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 $517

         

9.8 (19 Reviews)

House

3200 square ft. Masterpiece Home, Fishing Paradise Waterfront, Beach Islamorada

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

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From US $1,388

         

New

Apartment

Ocean View Two Duplex Penthouses Retreat amenities: tennis court heated Pool Vista Key

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

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From US $141

         

8.8 (84 Reviews)

Resort

Matecumbe Resort

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

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From US $592

         

10.0 (1 Review)

House

ISLAMORADA BEACH HOUSE

• Air Conditioner
• Parking
• TV

• Florida
• Islamorada

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From US $1,283

         

|

New

House

Beach Residence Private overwater dock Heated Pool Mahi Key

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

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From US $445

         

10.0 (156 Reviews)

Condo

AQUAMARINE OCEANVIEW+”SPECIAL RATES”+nDOCK+POOL+GYM+SPA+”153”5 STAR REVIEWS!

• 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 $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 $426

         

10.0 (62 Reviews)

Condo

Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities

• Air Conditioner
• Parking
• Pool

• 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 $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 $987

         

10.0 (24 Reviews)

House

Islamorada Boaters Paradise with 70' Dock and private beach access.

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

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From US $579

         

10.0 (21 Reviews)

House

Waterfront beautifully renovated 6 Bedrooms 4 Bath , Gated Private Home

• Air Conditioner
• Parking
• Pet Friendly

• Islamorada
• Toll Gate Shores

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From US $336

         

10.0 (21 Reviews)

House

Water Front 3/3 Family and Boat Friendly Home, Great Views

• Air Conditioner
• Parking
• Pet Friendly

• Islamorada
• Toll Gate Shores

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From US $387

         

10.0 (15 Reviews)

Condo

Ocean View with protected dock on lagoon with private boat ramp

• Air Conditioner
• TV
• Security/Safety

• Florida
• Lower Matecumbe Key

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From US $368

         

10.0 (11 Reviews)

Condo

Gulf View Retreat @ Bay Harbor

• Air Conditioner
• Pool
• TV

• 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 $388

         

10.0 (9 Reviews)

House

Incredible Bayside Home in the Florida Keys!

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

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From US $448

         

10.0 (7 Reviews)

Condo

Florida Keys Spacious 1 BR with 2 Balconies Pool view

• Air Conditioner
• Parking
• Pool

• Florida
• Lower Matecumbe Beach

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From US $686

         

10.0 (6 Reviews)

House

Island pool home awaits in Islamorada's Port Antigua

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

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★ Pro Tip: Stay30 makes it easy to compare the best listings on Stay30 homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Stay30 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 Anne's Beach.