Accommodations in Theater of the Sea, FL: Compare 10+ Sites & Save

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  2. Accommodations
  3.  USA

  4.  Florida
  5.  Islamorada
  6.  Theater of the Sea

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520 Best Accommodations in Theater of the Sea (Starting from $247)

Oceanfront Islamorada Townhome with Dock and Pool
Oceanfront Islamorada Townhome with Dock and Pool
House
Islamorada, FL, USA
0.2k from Theater of the Sea center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms7 Guests
New to Booking
$764
Average price / night
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NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony
NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony
House
Islamorada, FL, 33036, United States
0.1k from Theater of the Sea center

AC, Arcade, Balcony, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$756
Average price / night
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Drop Anchor Resort & Marina
Drop Anchor Resort & Marina
Resort
Islamorada, FL, USA
0.5k from Theater of the Sea center

Accommodations, Pools, Resorts, Parking, 3-star, Lodgings, Beach, Places to stay, Glamping

18 Bedrooms43 Guests
7.7

Good

341 reviews

$377
Average price / night
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“ The Ultimate redneck” boat experience
“ The Ultimate redneck” boat experience
Boat Rental
Islamorada, FL, 33036, United States
0.1k from Theater of the Sea center

Barbecue, Breakfast Included, Free Parking, Heater, Kitchen, Patio

1 Bedroom2 Guests
4.8

Review score

3 reviews

$247
Average price / night
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Sunshine Place
Sunshine Place
House
Islamorada, FL, USA
0.6k from Theater of the Sea center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Beach, Places to stay

1 Bedroom3 Guests
New to Booking
$302
Average price / night
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Oceanfront Panoramic Bliss • 3 Stories, Paddleboards, Gameroom & Boat Dockage
Oceanfront Panoramic Bliss • 3 Stories, Paddleboards, Gameroom & Boat Dockage
House
Islamorada, FL, 33036, United States
0.2k from Theater of the Sea center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet

3 Bedrooms8 Guests
10.0

Exceptional

10 reviews

$817
Average price / night
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Anglers Reef Vacation Rental
Anglers Reef Vacation Rental
Villa
Islamorada, FL, USA
0.7k from Theater of the Sea center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach

2 Bedrooms6 Guests
9.5

Superb

2 reviews

$495
Average price / night
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Oceanfront Islamorada Townhome- Private Dock, Pool & Pet-Friendly
Oceanfront Islamorada Townhome- Private Dock, Pool & Pet-Friendly
House
Islamorada, FL, 33036, United States
0.2k from Theater of the Sea center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

3 Bedrooms7 Guests
10.0

Exceptional

5 reviews

$757
Average price / night
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Anglers Reef Paradise
Anglers Reef Paradise
House
Islamorada, FL, USA
0.7k from Theater of the Sea center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach

2 Bedrooms6 Guests
9.6

Exceptional

19 reviews

$400
Average price / night
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At The Sandbar: Partial Ocean View, Htd Pool, Free Dockage, GameRoom, EV Charger
At The Sandbar: Partial Ocean View, Htd Pool, Free Dockage, GameRoom, EV Charger
House
Islamorada, FL, 33036, United States
0.3k from Theater of the Sea center

AC, Arcade, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

9 reviews

$628
Average price / night
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Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Resort
Islamorada, FL, USA
0.8k from Theater of the Sea center

Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, 3-star, Lodgings, Beach

26 Bedrooms69 Guests
8.4

Very Good

26 reviews

$649
Average price / night
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Discover Peaceful Palms 2 in Islamorada—spacious 3-bedroom condo with pool access!
Discover Peaceful Palms 2 in Islamorada—spacious 3-bedroom condo with pool access!
House
Islamorada, FL, 33036, United States
0.3k from Theater of the Sea center

AC, Balcony, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms8 Guests
6.0

Review score

1 reviews

$664
Average price / night
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Florida Keys Boat Trips Multi Activity
Florida Keys Boat Trips Multi Activity
Boat Rental
Islamorada, FL, USA
1.7k from Theater of the Sea center

Accommodations, Parking, Boats, Pet-friendly, Lodgings, Beach, Places to stay

1 Bedroom6 Guests
New to Booking
$342
Average price / night
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Off-Grid Islamorada Stay
Off-Grid Islamorada Stay
Boat Rental
Islamorada, FL, 33036, United States
0.3k from Theater of the Sea center

AC, No Smoking

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$455
Average price / night
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Florida Keys Boat Charters
Florida Keys Boat Charters
Boat Rental
Islamorada, FL, USA
1.7k from Theater of the Sea center

Parking, Child Friendly

1 Bedroom6 Guests
New to Booking
$324
Average price / night
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Oceanfront Paradise w/ Speakeasy, Karaoke, Pool & Dock for Endless Play
Oceanfront Paradise w/ Speakeasy, Karaoke, Pool & Dock for Endless Play
House
Islamorada, FL, 33036, United States
0.3k from Theater of the Sea center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

3 Bedrooms8 Guests
New to Booking
$766
Average price / night
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Chesapeake Beach Resort
Chesapeake Beach Resort
Resort
Islamorada, FL, USA
1.7k from Theater of the Sea center

Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, 3-star, Lodgings, Beach

45 Bedrooms75 Guests
8.0

Good

846 reviews

$536
Average price / night
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Island Time: Partial Ocean View, Ensuite bedrooms, Free Dockage, Htd Pool
Island Time: Partial Ocean View, Ensuite bedrooms, Free Dockage, Htd Pool
Villa
Islamorada, FL, 33036, United States
0.3k from Theater of the Sea center

AC, Balcony, Dryer, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$613
Average price / night
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Harbor House
Harbor House
House
Islamorada, FL, USA
2.1k from Theater of the Sea center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Places to stay, Family

4 Bedrooms8 Guests
New to Booking
$366
Average price / night
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Spectacular Ocean Front Home In Beautiful Islamorada!Slip,Com Pool, & Prv Bch
Spectacular Ocean Front Home In Beautiful Islamorada!Slip,Com Pool, & Prv Bch
House
Islamorada, FL, 33036, United States
0.4k from Theater of the Sea center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

48 reviews

$450
Average price / night
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Beacon Reef 222
Beacon Reef 222
House
Islamorada, FL, USA
2.5k from Theater of the Sea center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

2 Bedrooms4 Guests
New to Booking
$252
Average price / night
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Convenient Stay in Florida! Free Parking, Free Breakfast, Pool, Pets Allowed
Convenient Stay in Florida! Free Parking, Free Breakfast, Pool, Pets Allowed
Apartment
Islamorada, FL, 33036, United States
0.4k from Theater of the Sea center

AC, Barbecue, Breakfast Included, Elevator, Free Parking, Heater, Internet, Kitchen, Microwave

1 Bedroom4 Guests
6.0

Review score

1 reviews

$296
Average price / night
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Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast
Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast
Apartment
Islamorada, FL, 33036, United States
0.4k from Theater of the Sea center

AC, Barbecue, Breakfast Included, Elevator, Free Parking, Heater, Internet, Kitchen, Microwave

1 Bedroom4 Guests
New to Booking
$296
Average price / night
Check Availability
Just What You Were Looking For! Free Breakfast, Onsite Pool, Free Parking
Just What You Were Looking For! Free Breakfast, Onsite Pool, Free Parking
Apartment
Islamorada, FL, 33036, United States
0.4k from Theater of the Sea center

AC, Barbecue, Breakfast Included, Elevator, Free Parking, Heater, Internet, Kitchen, Microwave

1 Bedroom4 Guests
8.0

Good

1 reviews

$296
Average price / night
Check Availability
Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking
Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking
Apartment
Islamorada, FL, 33036, United States
0.4k from Theater of the Sea center

AC, Barbecue, Breakfast Included, Elevator, Free Parking, Heater, Internet, Microwave, No Smoking

1 Bedroom2 Guests
New to Booking
$295
Average price / night
Check Availability
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
Apartment
Islamorada, FL, 33036, United States
0.4k from Theater of the Sea center

AC, Barbecue, Breakfast Included, Elevator, Free Parking, Heater, Internet, Kitchen, Microwave

1 Bedroom2 Guests
New to Booking
$295
Average price / night
Check Availability
Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast
Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast
Apartment
Islamorada, FL, 33036, United States
0.4k from Theater of the Sea center

AC, Barbecue, Breakfast Included, Elevator, Free Parking, Heater, Internet, Microwave, No Smoking

1 Bedroom2 Guests
New to Booking
$295
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Accommodations in Theater of the Sea.

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Frequently Asked Questions

You can explore 520 verified accommodations in Theater of the Sea, including hotels, vacation rentals, resorts, and boutique stays. This variety makes it easier to choose the option that best fits your travel style and budget.

Accommodation prices in Theater of the Sea vary based on property type, location, and travel dates. Rates typically start from around $247 per night, with higher prices for premium properties and peak travel periods.

Hotels are ideal for convenience and short stays, while vacation rentals offer more space and privacy. Resorts are suitable for all-inclusive experiences, and boutique properties provide a more unique and personalized stay in Theater of the Sea.

Yes, Theater of the Sea offers many family-friendly options, including large vacation rentals and hotels with suites or connecting rooms. Currently, 51 listings in Theater of the Sea are well-suited for families and group travel.

Booking 30 to 60 days in advance is generally recommended for the best availability and pricing. For peak travel seasons or major events in Theater of the Sea, booking several months ahead can help secure your preferred property.

Accommodations in Theater of the Sea commonly include amenities such as View, Ocean View, and Internet. Availability may vary depending on the type of property you choose.

Yes, some accommodations in Theater of the Sea focus on sustainable practices such as energy efficiency and reduced environmental impact. You can filter listings to find options that align with your preferences in Theater of the Sea.