Vacation Rentals By Owner In Islamorada, FL

Showing 764 Of 764 Vacation Rentals

$401.6

Ocean View Guest Room, 1 King, Balcony | Pool

Islamorada, Florida, United States

Set on 15 oceanfront acres in Islamorada, Three Waters Resort & Marina features island-inspired rooms. Guests enjoy three pools, beach and marina access, on-site dining, a water taxi to sister properties, and guided fishing or water sports for a full Keys experience.brbrThis listing is for a room within a hotel.brbr✦ Your room is 352 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Outdoor pool available all year.brbr✦ Free parking lot – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $59.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. $150 USD non-refundable pet fee per room per staybrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Please note that a fee will apply for smoking in guest rooms.br✦ Pack and Play subject to availability at time or request, free.br✦ Get 10% off + $40 daily breakfast credit (2 guests) on 4+ night stays. Stay: Apr 7–Dec 23, 2026. Book by Jun 30, 2026.

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Bath

Sleeps

Exceptional(1)

$533.27

/ Nightly

Hotel

The Cove, Age 21 Plus, Junior Suite, 1 King, Ocean view, Balcony

Islamorada, Florida, United States

Set on 15 oceanfront acres in Islamorada, Three Waters Resort & Marina features island-inspired rooms. Guests enjoy three pools, beach and marina access, on-site dining, a water taxi to sister properties, and guided fishing or watersports for a full Keys experience.brbrThis listing is for a room within a hotel.brbr✦ Your room is 510 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Outdoor pool available all year.brbr✦ Free parking lot – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $59.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. $150 USD non-refundable pet fee per room per staybrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Please note that a fee will apply for smoking in guest rooms.br✦ Pack and Play subject to availability at time or request, free.br✦ Get 10% off + $40 daily breakfast credit (2 guests) on 4+ night stays. Stay: Apr 7–Dec 23, 2026. Book by Jun 30, 2026.

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Bath

Sleeps

Exceptional(11)

$372.4

/ Nightly

Hotel

Guest Room, 2 Queens, Balcony, Free Parking & 3 Outdoor Pools

Islamorada, Florida, United States

Set on 15 oceanfront acres in Islamorada, Three Waters Resort & Marina features island-inspired rooms. Guests enjoy three pools, beach and marina access, on-site dining, a water taxi to sister properties, and guided fishing or water sports for a full Keys experience.brbrThis listing is for a room within a hotel.brbr✦ Your room is 338 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Outdoor pool available all year.brbr✦ Free parking lot – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $59.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. $150 USD non-refundable pet fee per room per staybrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Please note that a fee will apply for smoking in guest rooms.br✦ Pack and Play subject to availability at time or request, free.br✦ Get 10% off + $40 daily breakfast credit (2 guests) on 4+ night stays. Stay: Apr 7–Dec 23, 2026. Book by Jun 30, 2026.

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Bath

Sleeps

$744.8

/ Nightly

Hotel

2 Guest Room, 2 Queens, Balcony, Free Parking, 3 Pools & Pet Friendly

Islamorada, Florida, United States

Set on 15 oceanfront acres in Islamorada, Three Waters Resort & Marina features island-inspired rooms. Guests enjoy three pools, beach and marina access, on-site dining, a water taxi to sister properties, and guided fishing or water sports for a full Keys experience.brbrThis listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 338 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Outdoor pool available all year.brbr✦ Free parking lot – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $200 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $59.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. $150 USD non-refundable pet fee per room per staybrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Please note that a fee will apply for smoking in guest rooms.br✦ Pack and Play subject to availability at time or request, free.br✦ Get 10% off + $40 daily breakfast credit (2 guests) on 4+ night stays. Stay: Apr 7–Dec 23, 2026. Book by Jun 30, 2026.

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Sleeps

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Condo

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Hotel resort

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Private vacation home

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Villa

View 78 Villa

Most popular vacation rentals in Islamorada

$1588.39

/ Nightly

Cottage

Oceanfront Cottage With Stunning Pool & Dockage in Islamorada

Islamorada, Florida, United States

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$1719.90

/ Nightly

Private vacation home

Private Beach / Private overwater dock / Heated Pool / Mahi Key

Islamorada, Florida, United States

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Sleeps

$1716.73

/ Nightly

Private vacation home

Royal Palm South 3 Bedrooms, 3 Baths, Ocean Front, Marina

Islamorada, Florida, United States

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Sleeps

$1606.37

/ Nightly

Private vacation home

Oceanfront Keys Escape | Private Beach & Pool | 3 Acres

Islamorada, Florida, United States

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Sleeps

$1600.73

/ Nightly

Private vacation home

Discover Sea Ranch in Islamorada: spacious 4BR home with private pool and stunning views.

Islamorada, Florida, United States

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Bath

Sleeps

$1595.07

/ Nightly

Private vacation home

Experience luxury at Little Bay Compound in Islamorada with stunning views.

Islamorada, Florida, United States

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Sleeps

$1510.57

/ Nightly

Private vacation home

Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!

Islamorada, Florida, United States

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Bath

Sleeps

$1409.53

/ Nightly

Private vacation home

Experience luxury at The Sapodilla House, a stunning 5-bedroom waterfront retreat in Islamorada.

Islamorada, Florida, United States

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Bath

Sleeps

$1433.51

/ Nightly

Condo

Experience luxury at Coastal Cove Villa, a 4-bedroom retreat in beautiful Islamorada!

Islamorada, Florida, United States

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Bath

Sleeps

$1948.66

/ Nightly

Private vacation home

New - Oceanfront Estate - Private Beach - Heated Pool - Stunning

Islamorada, Florida, United States

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Bath

Sleeps

Vacation Rentals By Owner In Islamorada, FL

$401.6

$533.27

$372.4

$744.8

Rent a place that suits your needs

Most popular vacation rentals in Islamorada

$1588.39

$1719.90

$1716.73

$1606.37

$1600.73

$1595.07

$1510.57

$1409.53

$1433.51

$1948.66

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