830+ Vacation Rentals Near Theater of the Sea |
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  3. Islamorada
  4. Theater of the Sea

Floridarentalvacations - Vacation Rentals in Theater of the Sea

Property Image From $388
         

10.0 (196 Reviews)
House
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $966
         

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10.0 (2 Reviews)
House
Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water views!
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $462
         

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10.0 (19 Reviews)
House
372 m² House ∙ 4 bedrooms ∙ 10 guests
  • 4004 ft² House
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $674
         

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9.8 (66 Reviews)
Villa
The Islands of Islamorada
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $413
         

10.0 (185 Reviews)
House
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $400
         

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9.6 (19 Reviews)
House
Anglers Reef Paradise
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $325
         

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10.0 (14 Reviews)
Villa
62 m² Villa ∙ 2 bedrooms ∙ 4 guests
  • 667 ft² Villa
  • Air Conditioner
  • Parking
  • TV

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Property Image From $130
         

9.4 (192 Reviews)
House
Ragged Edge Resort & Marina
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $396
         

10.0 (180 Reviews)
House
Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $495
         

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9.5 (2 Reviews)
Villa
Anglers Reef Vacation Rental
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $133
         

10.0 (9 Reviews)
Condo
93 m² Condo ∙ 2 bedrooms ∙ 4 guests
  • 1001 ft² Condo
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $459
         

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9.0 (14 Reviews)
House
Angler's Reef Resort by KeysCaribbean
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $1,125
         

10.0 (118 Reviews)
House
5 bedroom - Deep Dockage & Heated Pool in Islamorada.
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $248
         

9.1 (157 Reviews)
Resort
Ragged Edge Resort & Marina
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $651
         

10.0 (114 Reviews)
House
Beautiful Ocean View in Angler's Reef with View of Sand Bar/Boat slip
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $348
         

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8.7 (1439 Reviews)
Resort
Islander Resort
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $433
         

10.0 (103 Reviews)
House
Single Family Home In Angler's Reef Gated Community,Beautiful Ground,Resort Pool
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $865
         

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8.6 (801 Reviews)
Resort
Cheeca Lodge & Spa
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $297
         

10.0 (91 Reviews)
Villa
Keys Kottage: Bayside villa W/free onsite boat ramp marina & trailer parking.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $649
         

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8.5 (33 Reviews)
Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $338
         

9.6 (8 Reviews)
House
Paradise @ Islamorada
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $180
         

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8.5 (2 Reviews)
House
EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $354
         

10.0 (116 Reviews)
Villa
Serenity by the Sea! Anglers Reef with Boat Slip Available!
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $919
         

10.0 (38 Reviews)
House
Paradise in Venetian Shores Pool/SPA - Heater/Chiller & Commercial Ice Maker
  • Air Conditioner
  • Parking
  • Pet Friendly

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★ Pro Tip: Floridarentalvacations makes it easy to compare the best listings on Floridarentalvacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Floridarentalvacations 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 Theater of the Sea.

Weather in Theater of the Sea

View the weather forecast for Theater of the Sea before booking your Theater of the Sea Vacation Rentals to confirm your best time to go.

December - February
High 81°F       Low 56°F
March - May
High 87°F       Low 59°F
June - August
High 91°F       Low 74°F
September - November
High 90°F       Low 64°F

Top Attractions Around Theater of the Sea, FL

Floridarentalvacations offers a large selection of top attractions around Theater of the Sea. Research things to do on your vacation before you visit Theater of the Sea.


Bud n' Mary's Dive Center Founders Park Anne's Beach Bluefin Rock Harbor Marina Florida Keys Dive Center Harry Harris Park Florida Keys Flats Fishing Islamorada County Park Hurricane Monument Windley Key Fossil Reef Geological State Park Kiki's Spa Laura Quinn Wild Bird Sanctuary History of Diving Museum Panhandle Key Matecumbe United Methodist Church PADDLE! the Florida Keys Pigeon Key AKA Dive Charter Florida Keys Brewing Co. Mariners Hospital