779+ Vacation Rentals Near Theater of the Sea |
  1. USA
  2. Florida
  3. Islamorada
  4. Theater of the Sea

Bigpineresortcottages - Vacation Rentals in Theater of the Sea

Property Image From $419
         

10.0 (198 Reviews)
House
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
  • Air Conditioner
  • Parking
  • Pool

View Availability
Property Image From $966
         

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

View Availability
Property Image From $674
         

|
9.8 (67 Reviews)
Villa
The Islands of Islamorada
  • Air Conditioner
  • Parking
  • Pool

View Availability
Property Image From $413
         

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

View Availability
Property Image From $400
         

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

View Availability
Property Image From $134
         

9.4 (196 Reviews)
House
Ragged Edge Resort & Marina
  • Air Conditioner
  • Parking
  • Pool

View Availability
Property Image From $429
         

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

View Availability
Property Image From $495
         

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

View Availability
Property Image From $459
         

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

View Availability
Property Image From $1,178
         

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

View Availability
Property Image From $647
         

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

View Availability
Property Image From $450
         

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

View Availability
Property Image From $313
         

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

View Availability
Property Image From $264
         

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

View Availability
Property Image From $375
         

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

View Availability
Property Image From $935
         

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

View Availability
Property Image From $211
         

9.2 (11 Reviews)
House
SPECTACULAR SUNSETS AND FRESH OCEAN BREEZE AWAIT YOU IN ISLAMORADA, FLORIDA!
  • Air Conditioner
  • Parking
  • Pool

View Availability
Property Image From $432
         

10.0 (165 Reviews)
House
Oceanside Getaway: Renovated Home with Boat Slip, Pool & Beach - Gated community
  • Air Conditioner
  • Parking
  • Pool

View Availability
Property Image From $363
         

10.0 (141 Reviews)
House
Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip.
  • Air Conditioner
  • Parking
  • Pool

View Availability
Property Image From $736
         

10.0 (115 Reviews)
House
4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL
  • Air Conditioner
  • Parking
  • Pool

View Availability
Property Image From $1,020
         

10.0 (114 Reviews)
House
Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.
  • Air Conditioner
  • Parking
  • Pool

View Availability
Property Image From $269
         

10.0 (110 Reviews)
Cottage
Oceanfront Private Cottage!
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Property Image From $664
         

10.0 (96 Reviews)
House
Islamorada Oceanfront Home with Ocean View, Dock, Comm Pool & Beach
  • Air Conditioner
  • Parking
  • Pool

View Availability
Property Image From $465
         

10.0 (91 Reviews)
House
Breathtaking ocean views for your Paradise vacations
  • Air Conditioner
  • Parking
  • Pet Friendly

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

Bigpineresortcottages 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