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

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Oceanfront Rentals
  3.  USA

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

Refine your search

Price per night

Amenity Filter

Rating

285 Best Oceanfront 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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
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
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
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
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
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
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
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
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
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
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
Check Availability
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
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
Discover Florida Keys! Seaside Villa w/ Patio! Marina, Pool, Parking, Breakfast
Discover Florida Keys! Seaside Villa w/ Patio! Marina, Pool, Parking, 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 Bedroom4 Guests
8.0

Good

4 reviews

$246
Average price / night
Check Availability
Kayak in Florida Keys! Seaside Villa w/ Patio! Marina, Pool, Kayak
Kayak in Florida Keys! Seaside Villa w/ Patio! Marina, Pool, Kayak
Apartment
Islamorada, FL, 33036, United States
0.4k from Theater of the Sea center

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

1 Bedroom4 Guests
2.0

Review score

1 reviews

$246
Average price / night
Check Availability
Sportfishing in Florida Keys! FREE Parking, Pets Allowed, Pool, Bike Rentals!
Sportfishing in Florida Keys! FREE Parking, Pets Allowed, Pool, Bike Rentals!
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 Bedroom4 Guests
10.0

Exceptional

1 reviews

$246
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 Oceanfront Rentals in Theater of the Sea.

Where to stay in Theater of the Sea? Best neighborhoods & areas

Theater of the Sea Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 285 verified oceanfront rentals in Theater of the Sea. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Theater of the Sea vary depending on the property size, exact beachfront location, and season. Rates typically start from around $183 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Theater of the Sea offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Theater of the Sea welcome pets. Currently, 53 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Theater of the Sea often include features designed for a comfortable coastal stay, such as Oceanfront, View, and Ocean View. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.