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Theater of the Sea, Islamorada, Florida, United States of America

Theater of the Sea vacation rentals

We found 2,091 vacation rentals — enter your dates for availability

Discover a selection of 2,000 vacation rentals near Theater of the Sea, Islamorada that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $140 per night, and houses and condos are popular options for a stay near Theater of the Sea. Either way, you'll find a rental for everyone's needs.
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Houses

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Condos/Apartments

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Villas

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Studios

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Townhouses

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Cabins

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Cottages

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Bungalows

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Caravans

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Boats

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Hotels

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Resorts

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Find the best place to stay — Theater of the Sea

Waterfront Cozy Islamorada Paradise

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
$380 avg/night
(10)

Executive Bay Club U2 | 3 bed / 3 bath + Loft Townhouse in Islamorada

Sleeps 8 · 3 Bedrooms · 3 Bathrooms
$227 avg/night

Islamorada Spectacular Vacation At Executive Bay Club

Sleeps 6 · 2 Bedrooms · 3 Bathrooms
$175 avg/night
(1)

Keys Life Cottage | Islamorada Cottage with 30' Boat Slip & Pool Access!

Sleeps 6 · 2 Bedrooms · 1 Bathroom
$221 avg/night

Manatee Harbor - Bayfront Home on Plantation Key

Sleeps 12 · 4 Bedrooms · 3 Bathrooms
$625 avg/night

Stunning Ocean Harbour Corner Unit - Panoramic ocean views!

3 Bedrooms · 2 Bathrooms
$250 avg/night

Search 2,091 vacation rentals

Top rated rentals — Theater of the Sea
Stayed Jan 2023

New Years Vacation

It was a very nice condo. We really enjoyed the views from the patios. We saw some dolphins jumping in the ocean. We enjoyed the pool area and the beach was nice too, but not a good swimming area. The only thing we were bummed about was that Ocean Po...

Marcia V.
Marcia V.
Stayed Dec 2022

Keys vacation

Windley Cottage was a perfect escape from winter for our family. Nice house and community with plenty of amenities. Great pool, kayaks and paddle boards onsite...plenty to do. Tons of restaurants nearby and a good central location to explore all of t...

Dave D.
Dave D.
Stayed Dec 2022

Perfect!!

Our family thoroughly enjoyed our stay. I saw a review that mentioned a few issues but when we arrived, the unit was clean and well lit. The master bed had a new mattress. And new lamps. The townhouse has a backyard which was great for us. The facili...

Nicole M.
Nicole M.

New York

Stayed Dec 2022

Perfect for Solo or Couple

Treehouse is perfect for a solo traveler or couple. Has everything you need and plenty of space. Brought my own paddle board and easy access to the ocean on-site. Pool is lovely. Great location to explore & do day trips. Owners and staff are very a...

Jennifer G.
Jennifer G.
Stayed Dec 2022

Great VRBO

Loved the property. Very comfortable and ver clean property. You can tell the owners take pride in their place by offering great beds, towels and sheets were great. Kitchen was pleasantly stocked with great cookware and knifes. Only thing missing wer...

Karen D.
Karen D.

Raleigh, USA

Stayed Dec 2022

Pros Outweigh the Cons

We stayed at this property for a week and for the very reasonable price, it was suitable for our needs. The location was perfect to explore the Keys with everything you could want to do within an easy drive. The condo was located in a community with ...

janet c.
janet c.
Stayed Nov 2022

Amazing Stay

My husband and I came to this property on our baby moon and everything was perfect! The pictures are exactly the same and depict a very nice picture of what you are getting. The communication between the owners was quick when I had questions and they...

Hope E.
Hope E.
Stayed Nov 2022

Quiet and Convenient

My husband and I stayed here with another couple for a friends trip and it was the first time visiting the keys for all of us. The location is nice and feels tucked away from the highway, and it was not crowded at the resort which was a plus. Very co...

Melissa S.
Melissa S.
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How many vacation rentals are available around Theater of the Sea, Islamorada?

Our 2023 property listings offer a large selection of 2,091 vacation rentals around Theater of the Sea. From 1,071 house rentals to 603 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses near Theater of the Sea?

Yes, of course. Vrbo has 1,071 Houses near Theater of the Sea. Our other popular types of vacation rentals near Theater of the Sea include:

  • Condos/Apartments: 603 rentals available
  • Villas: 36 rentals available
  • Studios: 133 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Townhouses and more.

Can I find a vacation rental with pool near Theater of the Sea?

Yes, you can select your preferred vacation rental with pool among our 1,583 vacation rentals with pool available near Theater of the Sea. Please use our search bar to access the selection of vacation rentals available.