
Holiday rentals near Theater of the Sea
We found 2,534 holiday rentals — enter your dates for availability
If you'd like to stay close to Theater of the Sea, take a look at private holiday rentals to find the perfect one for your trip. Whether you're staying in a holiday rental with friends, family or just with your pet, you'll find the amenities that you need and want, which might include Wi-Fi and a fireplace. What you'll find is a property to rent that has what everyone needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Theater of the Sea
Showing deals for:26 Sept - 3 Oct
Image gallery for VOTED BEST KEY LARGO VACATION RENTAL

1010 out of 10 rating
Exceptional
(77 reviews)
VOTED BEST KEY LARGO VACATION RENTAL
Key Largo, FL
8% off
Price is NZ$5,166
NZ$5,166
NZ$738 per night
includes taxes & fees
Image gallery for Historic Jewel of Key Largo With Two Houses on private two Acres

1010 out of 10 rating
Exceptional
(100 reviews)
Historic Jewel of Key Largo With Two Houses on private two Acres
Key Largo, FL
6% off
Price is NZ$15,017
NZ$15,017
NZ$2,145 per night
includes taxes & fees
Image gallery for Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, SUPs & Day Dock

1010 out of 10 rating
Exceptional
(69 reviews)
Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, SUPs & Day Dock
Islamorada, FL
8% off
Price is NZ$8,206
NZ$8,206
NZ$1,172 per night
includes taxes & fees
Image gallery for 2 bedroom & 25' Boat Dock ~ Waterfront Atlantic Side & PrivateTiki dining, bikes

1010 out of 10 rating
Exceptional
(76 reviews)
2 bedroom & 25' Boat Dock ~ Waterfront Atlantic Side & PrivateTiki dining, bikes
Key Largo, FL
13% off
Price is NZ$2,942
NZ$2,942
NZ$420 per night
includes taxes & fees
Image gallery for Angler’s Reef house. Paddle or Kayak to sandbar. Lic #24-0055

1010 out of 10 rating
Exceptional
(12 reviews)
Angler’s Reef house. Paddle or Kayak to sandbar. Lic #24-0055
Islamorada, FL
8% off
Price is NZ$6,326
NZ$6,326
NZ$904 per night
includes taxes & fees
Image gallery for Relaxing Spacious Vacation Home: Amazing Oceanside Pools, Jacuzzi, WiFi, & More

9.69.6 out of 10 rating
Exceptional
(71 reviews)
Relaxing Spacious Vacation Home: Amazing Oceanside Pools, Jacuzzi, WiFi, & More
Key Largo, FL
7% off
Price is NZ$5,631
NZ$5,631
NZ$804 per night
includes taxes & fees
Image gallery for Vacation Paradise-Relax-Enjoy the Sunshine & Sea Breeze

9.89.8 out of 10 rating
Exceptional
(71 reviews)
Vacation Paradise-Relax-Enjoy the Sunshine & Sea Breeze
Key Largo, FL
8% off
Price is NZ$6,499
NZ$6,499
NZ$928 per night
includes taxes & fees
Image gallery for Canal home in Islamorada. Views from 2nd fl pool, partial 65' of dock.

1010 out of 10 rating
Exceptional
(31 reviews)
Canal home in Islamorada. Views from 2nd fl pool, partial 65' of dock.
Tavernier, FL
7% off
Price is NZ$12,255
NZ$12,255
NZ$1,751 per night
includes taxes & fees
Image gallery for Key Largo, Paradise! Single family second floor home with gorgeous views.

1010 out of 10 rating
Exceptional
(32 reviews)
Key Largo, Paradise! Single family second floor home with gorgeous views.
Key Largo, FL
7% off
Price is NZ$3,199
NZ$3,199
NZ$457 per night
includes taxes & fees
Image gallery for Stylish & Secluded: Pool, Dock, Key Largo Living

9.89.8 out of 10 rating
Exceptional
(10 reviews)
Stylish & Secluded: Pool, Dock, Key Largo Living
Key Largo, FL
8% off
Price is NZ$4,222
NZ$4,222
NZ$603 per night
includes taxes & fees
Image gallery for Key Largo 'Shangri La' Experience

1010 out of 10 rating
Exceptional
(5 reviews)
Key Largo 'Shangri La' Experience
Key Largo, FL
8% off
Price is NZ$3,693
NZ$3,693
NZ$528 per night
includes taxes & fees
Image gallery for NEW! OCEANSIDE CASA LARGO TROPICAL GETAWAY! PICKLEB-BEACH-POOL-KAYAK-TENNI-FISH

1010 out of 10 rating
Exceptional
(7 reviews)
NEW! OCEANSIDE CASA LARGO TROPICAL GETAWAY! PICKLEB-BEACH-POOL-KAYAK-TENNI-FISH
Key Largo, FL
8% off
Price is NZ$5,657
NZ$5,657
NZ$808 per night
includes taxes & fees
Image gallery for Amazing Florida Keys Retreat!

1010 out of 10 rating
Exceptional
(69 reviews)
Amazing Florida Keys Retreat!
Key Largo, FL
8% off
Price is NZ$5,241
NZ$5,241
NZ$749 per night
includes taxes & fees
Image gallery for Islamorada Keys Waterfront Heated Pool Hottub Luxury Canal Home w Private Dock

1010 out of 10 rating
Exceptional
(6 reviews)
Islamorada Keys Waterfront Heated Pool Hottub Luxury Canal Home w Private Dock
Tavernier, FL
8% off
Price is NZ$10,409
NZ$10,409
NZ$1,487 per night
includes taxes & fees
Image gallery for Newly upgraded Key Largo Villa W/Boat Slip

1010 out of 10 rating
Exceptional
(81 reviews)
Newly upgraded Key Largo Villa W/Boat Slip
Key Largo, FL
8% off
Price is NZ$6,107
NZ$6,107
NZ$872 per night
includes taxes & fees
Image gallery for Paradise in the Florida Keys at our Moon Bay Condo

1010 out of 10 rating
Exceptional
(17 reviews)
Paradise in the Florida Keys at our Moon Bay Condo
Key Largo, FL
8% off
Price is NZ$4,183
NZ$4,183
NZ$598 per night
includes taxes & fees
Image gallery for Jaw-dropping Canal View Key Largo Boat Slip, Bay

1010 out of 10 rating
Exceptional
(16 reviews)
Jaw-dropping Canal View Key Largo Boat Slip, Bay
Key Largo, FL
8% off
Price is NZ$3,071
NZ$3,071
NZ$439 per night
includes taxes & fees
Image gallery for Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.

9.69.6 out of 10 rating
Exceptional
(51 reviews)
Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.
Tavernier, FL
8% off
Price is NZ$4,856
NZ$4,856
NZ$694 per night
includes taxes & fees
Image gallery for Beautiful Bay Front Two-Floor Condo with boat slip in Moonbay - Key Largo

9.89.8 out of 10 rating
Exceptional
(49 reviews)
Beautiful Bay Front Two-Floor Condo with boat slip in Moonbay - Key Largo
Key Largo, FL
8% off
Price is NZ$3,670
NZ$3,670
NZ$524 per night
includes taxes & fees
Image gallery for Stay 2 nights, 3rd night 10% thru June 30th, 2025

9.89.8 out of 10 rating
Exceptional
(6 reviews)
Stay 2 nights, 3rd night 10% thru June 30th, 2025
Key Largo, FL
14% off
Price is NZ$2,655
NZ$2,655
NZ$379 per night
includes taxes & fees
Image gallery for Your Island Home Away From Home!

9.69.6 out of 10 rating
Exceptional
(60 reviews)
Your Island Home Away From Home!
Key Largo, FL
8% off
Price is NZ$4,923
NZ$4,923
NZ$703 per night
includes taxes & fees
Image gallery for True Key Largo Luxury!

1010 out of 10 rating
Exceptional
(9 reviews)
True Key Largo Luxury!
Key Largo, FL
8% off
Price is NZ$7,588
NZ$7,588
NZ$1,084 per night
includes taxes & fees
Image gallery for Tropical Paradise at Moon Bay Key Largo, Florida

1010 out of 10 rating
Exceptional
(18 reviews)
Tropical Paradise at Moon Bay Key Largo, Florida
Key Largo, FL
8% off
Price is NZ$5,013
NZ$5,013
NZ$716 per night
includes taxes & fees
Image gallery for Florida Keys Paradise Awaits!

1010 out of 10 rating
Exceptional
(144 reviews)
Florida Keys Paradise Awaits!
Tavernier, FL
7% off
Price is NZ$3,066
NZ$3,066
NZ$438 per night
includes taxes & fees
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