Short-Term Rentals in Theater of the Sea, FL: Compare 10+ Sites & Save

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  3.  USA

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

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545 Best Short-Term 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 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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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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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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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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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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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 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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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 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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Beacon Reef 501
Beacon Reef 501
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
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
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
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Beach View Unit in Islamorada! Pets Allowed, Parking, Pool!
Beach View Unit in Islamorada! Pets Allowed, Parking, Pool!
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

22 reviews

$223
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 Short-Term Rentals in Theater of the Sea.

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Frequently Asked Questions

You can explore 545 verified short-term rentals in Theater of the Sea, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Theater of the Sea vary depending on location, property size, and travel dates. Rates typically start from around $183 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Theater of the Sea include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Theater of the Sea, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Theater of the Sea often include amenities such as View, Internet, and Ocean View, providing a comfortable and convenient stay.

Short-term rentals in Theater of the Sea are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.