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Our Top 6

(Sorted by rating & number of reviews)

1. Anglers Reef Paradise
2. Little Bay Upper Apartment
3. Direct Oceanfront With Private Staircase To Beach Prestigious Islamorada Condocomplex Condo
4. Anglers Reef Getaway Villa
5. Exceptional Condo With Panoramic Views Of The Atlantic Ocean, Condo
6. 180 Degrees Of Ocean Views, Sitting On A Large Lagoon That Opens To Florida Bay Condo

Best Islamorada Vacation Rentals

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Islamorada
Dec 31, 2025 - Jan 01, 2026

Anglers Reef Paradise

9.6

Good

(20 Reviews)

+ 16 photos

Anglers Reef Paradise Villa is located in a residential area and is within walking distance from Windley Key Fossil Reef Geological State Park. The venue is composed of 2 bedrooms, a fully-equipped kitchen with a microwave, a refrigerator, and kitchenware and 2 bathrooms.

At this accommodation, you'll be 3.8 km from History of Diving Museum and 6 km from Michelle Nicole Lowe Art Gallery. There is an own beach in the neighbourhood. This villa is also set close to Windley Key. You can get to Indian Key State Historic Site in a few minutes by car.

Address: 110 Anglers Way 110
Rating: Good 9.6 (20 Reviews)
Price: From 382$

Little Bay Upper Apartment

+ 28 photos

Situated 1.4 km from Upper Matecumbe Key Island, Little Bay Upper Apartment provides accommodation with Wi-Fi throughout the venue. The property offers rooms with a balcony, tea and coffee-making facilities, and a multi-channel TV together with a fully equipped kitchen.

The apartment lies within a 17-minute walk of Hurricane Monument. Guests can dine in the restaurant Great Wall Taki Outi, which is about 350 metres away. You can get to Indian Key State Historic Site in a couple of minutes by car.

Address: 82246 Overseas Hwy

Direct Oceanfront With Private Staircase To Beach Prestigious Islamorada Condocomplex Condo

+ 15 photos

Guests at this beachfront venue can benefit from a heated pool and a fully-fitted kitchen while being close to History of Diving Museum.

The accommodation is a 25-minute walk to Upper Matecumbe Key Island and 2.2 km from Anne s Beach. Serving American specialities, Keys Grill is about 500 metres away. Lobster Trap Art Gift Shop and Gallery is within a short car ride and Island Community Church is close too.

Anglers Reef Getaway Villa

9.0

Good

(14 Reviews)

+ 15 photos

Anglers Reef Getaway Villa is located in a residential area within a 5-minute drive of Rain Barrel Village and offers a heated swimming pool. The venue has 2 bedrooms, an adjoining terrace, a dressing room, and a multi-channel television and an equipped kitchen that provides guests with a microwave oven, a refrigerator, and kitchenware.

The accommodation is a beachfront property in Islamorada, not far from Windley Key. The class museum "Florida Keys History and Discovery Center" is within 6 km away. Such major Islamorada sights including Windley Key Fossil Reef Geological State Park are also located nearby. You can get to Lobster Trap Art Gift Shop and Gallery in a few minutes by car.

Address: 135 Anglers Way
Rating: Good 9.0 (14 Reviews)
Price: From 450$

Exceptional Condo With Panoramic Views Of The Atlantic Ocean, Condo

+ 18 photos

This beachfront venue also includes a kitchen with a microwave, a refrigerator, and kitchenware.

The apartment is placed 2.1 km from Indian Key State Historic Site and about 2.2 km from Lignumvitae Key Botanical State Park. Lazy Days Restaurant as a dining choice is 350 metres away. Take a few minutes' cab ride to see Lobster Trap Art Gift Shop and Gallery.

Price: From 188$

180 Degrees Of Ocean Views, Sitting On A Large Lagoon That Opens To Florida Bay Condo

+ 49 photos

The venue is within 4.6 km of Craig Key Island and about 1.2 km from Lower Matecumbe Key Island.

The accommodation is nestled within a short taxi ride from Indian Key Historic State Park.

Address: 74980 Overseas Hwy 4
Price: From 727$