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

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  2. Vacation Rentals
  3.  USA

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

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488 Best Vacation Rentals in Theater of the Sea (Starting from $183)

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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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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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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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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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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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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Beacon Reef 301
Beacon Reef 301
House
Islamorada, FL, USA
2.5k from Theater of the Sea center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Beach, Jacuzzis

2 Bedrooms4 Guests
New to Booking
$183
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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Beacon Reef 306
Beacon Reef 306
House
Islamorada, FL, USA
2.5k from Theater of the Sea center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Beach, Jacuzzis

2 Bedrooms4 Guests
New to Booking
$192
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 307
Beacon Reef 307
House
Islamorada, FL, USA
2.5k from Theater of the Sea center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Beach, Jacuzzis

2 Bedrooms4 Guests
New to Booking
$197
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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Beacon Reef 310
Beacon Reef 310
House
Islamorada, FL, USA
2.5k from Theater of the Sea center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Beach, Jacuzzis

2 Bedrooms4 Guests
New to Booking
$206
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
Beacon Reef 406
Beacon Reef 406
House
Islamorada, FL, USA
2.5k from Theater of the Sea center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Beach, Jacuzzis

2 Bedrooms4 Guests
New to Booking
$188
Average price / night
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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
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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
Swim with Dolphins in the Florida Keys! FREE Breakfast & Parking, Marina, Pool!
Swim with Dolphins in the Florida Keys! FREE Breakfast & Parking, Marina, Pool!
Apartment
Islamorada, FL, 33036, United States
0.4k from Theater of the Sea center

AC, Balcony, Barbecue, Breakfast Included, Elevator, Free Parking, Heater, Housekeeping, Internet

1 Bedroom4 Guests
8.4

Very Good

5 reviews

$222
Average price / night
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Snorkeling & Kayaking Beach Resort! Seaside Villa w/Patio! Marina, Pool, Parking
Snorkeling & Kayaking Beach Resort! Seaside Villa w/Patio! Marina, Pool, Parking
Apartment
Islamorada, FL, 33036, United States
0.4k from Theater of the Sea center

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

1 Bedroom4 Guests
8.6

Fabulous

7 reviews

$222
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 Vacation Rentals in Theater of the Sea.

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Frequently Asked Questions

You can explore 488 verified vacation rentals in Theater of the Sea. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Theater of the Sea vary depending on the season, property size, and location. Rates typically start from around $183 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Theater of the Sea include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Theater of the Sea welcome pets. Currently, 49 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Theater of the Sea often include amenities such as View, Internet, and Ocean View. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.