Key West Papa Islamorada
Islamorada
2 guests

Adults:

2

Children:

0

Child’s age:

Islamorada

Sep 20 - Sep 21 ·
2 guests

Islamorada Luxury Villas

Islamorada
2 guests

Adults:

2

Children:

0

Child’s age:

Over 95 stays assessed to highlight the standout picks

Navigation

1. Anglers Reef Paradise

2. Anglers Reef Vacation Rental

3. Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina

4. Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views!

5. Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable

6. Key Lime Cottage In The Heart Of Islamorada

7. Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool

8. Executive Bay Islamorada By Sofla Vacations

9. Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location

10. At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom

  • Guest favorite
  • Private beach
Hotel Image Hotel Image

Anglers Reef Paradise

110 Anglers Way 110
4.4 km (2.7 mi) from city center
144
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Heating
  • Pool with view
  • Heated swimming pool

Located about 5 minutes' walk from the Windley Key Fossil Reef Geological State Park, Anglers Reef Paradise Islamorada villa offers opportunities for snorkelling, diving, and cycling in the area.

9.6
19 reviews
~ €331 / night

Anglers Reef Paradise

4.4 km (2.7 mi) from city center
144
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Heating
  • Pool with view
  • Heated swimming pool

Anglers Reef Paradise

Located about 5 minutes' walk from the Windley Key Fossil Reef Geological State Park, Anglers Reef Paradise Islamorada villa offers opportunities for snorkelling, diving, and cycling in the area.

9.6
19 reviews
From € 331 / night
  • Private beach
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Anglers Reef Vacation Rental

109 Anglers Way
4.4 km (2.7 mi) from city center
121
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Pool with view

Anglers Reef Vacation Rental Islamorada villa offers proximity to nearby tourist spots, such as Windley Key Island, situated 6 minutes' walk away. Offering canoeing, cycling, and fishing, the 2-bedroom villa is suitable for 6 guests.

9.8
4 reviews
~ €316 / night

Anglers Reef Vacation Rental

4.4 km (2.7 mi) from city center
121
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Pool with view

Anglers Reef Vacation Rental

Anglers Reef Vacation Rental Islamorada villa offers proximity to nearby tourist spots, such as Windley Key Island, situated 6 minutes' walk away. Offering canoeing, cycling, and fishing, the 2-bedroom villa is suitable for 6 guests.

9.8
4 reviews
From € 316 / night
  • Private beach
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Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina

135 Anglers Way
4.3 km (2.7 mi) from city center
122
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Live entertainment
  • Pool with view

Situated only 0.6 km from the Windley Key Fossil Reef Geological State Park, the 2-bedroom Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina offers live performances to diversify guests' entertainment. Guests can enjoy diving, canoeing, and cycling at the holiday home, located about 10 minutes by car from the Islamorada.

10
2 reviews
~ €341 / night

Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina

4.3 km (2.7 mi) from city center
122
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Live entertainment
  • Pool with view

Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina

Situated only 0.6 km from the Windley Key Fossil Reef Geological State Park, the 2-bedroom Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina offers live performances to diversify guests' entertainment. Guests can enjoy diving, canoeing, and cycling at the holiday home, located about 10 minutes by car from the Islamorada.

10
2 reviews
From € 341 / night
  • Beach access
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Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views!

84 Johnston Ave Unit #9
0.0 km (0.0 mi) from city center
156
  • Cookware/ Kitchen utensils
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Heated swimming pool

Situated approximately 25 minutes' walk from the Indian Key State Historic Site, the 3-bedroom Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views! Islamorada villa offers guests to enjoy a wellness centre and a year-round outdoor swimming pool.

10
3 reviews
~ €946 / night

Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views!

0.0 km (0.0 mi) from city center
156
  • Cookware/ Kitchen utensils
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Heated swimming pool

Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views!

Situated approximately 25 minutes' walk from the Indian Key State Historic Site, the 3-bedroom Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views! Islamorada villa offers guests to enjoy a wellness centre and a year-round outdoor swimming pool.

10
3 reviews
From € 946 / night
  • Beach access
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Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable

84 Johnston Ave Unit #3
0.0 km (0.0 mi) from city center
156
  • Cookware/ Kitchen utensils
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Outdoor swimming pool

The 3-bedroom Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada villa accommodates up to 6 guests and offers proximity to the world-class museum "Florida Keys History and Discovery Center", located merely 6 minutes' walk away.

10
1 reviews
~ €511 / night

Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable

0.0 km (0.0 mi) from city center
156
  • Cookware/ Kitchen utensils
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Outdoor swimming pool

Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable

The 3-bedroom Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada villa accommodates up to 6 guests and offers proximity to the world-class museum "Florida Keys History and Discovery Center", located merely 6 minutes' walk away.

10
1 reviews
From € 511 / night
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Key Lime Cottage In The Heart Of Islamorada

76777 Overseas Highway
9.1 km (5.7 mi) from city center
49
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Heated swimming pool

Located just around the corner from the Lower Matecumbe Key, 2-bedroom Key Lime Cottage In The Heart Of Islamorada offers a heated swimming pool for guests to relax by. Providing guests with Wi-Fi and private parking, the property is 4.8 km from Anne's Beach.

10
5 reviews
~ €590 / night

Key Lime Cottage In The Heart Of Islamorada

9.1 km (5.7 mi) from city center
49
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Heated swimming pool

Key Lime Cottage In The Heart Of Islamorada

Located just around the corner from the Lower Matecumbe Key, 2-bedroom Key Lime Cottage In The Heart Of Islamorada offers a heated swimming pool for guests to relax by. Providing guests with Wi-Fi and private parking, the property is 4.8 km from Anne's Beach.

10
5 reviews
From € 590 / night
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Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool

84745 Old Hwy 11
3.7 km (2.3 mi) from city center
158
  • Free parking
  • Tours/Ticket assistance
  • Air conditioning
  • Flat-screen TV
  • Live entertainment
  • Pool with view

The 3-bedroom Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool villa enjoys a prime location only an 8-minute walk from the Windley Key Fossil Reef Geological State Park, and invites guests to spend time on a terrace.

9.5
2 reviews
~ €540 / night

Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool

3.7 km (2.3 mi) from city center
158
  • Free parking
  • Tours/Ticket assistance
  • Air conditioning
  • Flat-screen TV
  • Live entertainment
  • Pool with view

Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool

The 3-bedroom Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool villa enjoys a prime location only an 8-minute walk from the Windley Key Fossil Reef Geological State Park, and invites guests to spend time on a terrace.

9.5
2 reviews
From € 540 / night
  • Private beach
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Executive Bay Islamorada By Sofla Vacations

87200 Overseas Highway
7.6 km (4.7 mi) from city center
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Golf course
  • Outdoor swimming pool

The 8-room Executive Bay Islamorada By Sofla Vacations villa is located around a 15-minute walk from the Crossland Gallery and provides a swimming pool, ensuring a relaxing stay. Guests can enjoy snorkelling, diving, and fishing at this property, located about 7 km from the History of Diving Museum.

8
3 reviews
~ €130 / night

Executive Bay Islamorada By Sofla Vacations

7.6 km (4.7 mi) from city center
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Golf course
  • Outdoor swimming pool

Executive Bay Islamorada By Sofla Vacations

The 8-room Executive Bay Islamorada By Sofla Vacations villa is located around a 15-minute walk from the Crossland Gallery and provides a swimming pool, ensuring a relaxing stay. Guests can enjoy snorkelling, diving, and fishing at this property, located about 7 km from the History of Diving Museum.

8
3 reviews
From € 130 / night
  • Top location
  • Beach access
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Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location

84 Johnston Avenue Unit #4
0.0 km (0.0 mi) from city center
156
  • Cookware/ Kitchen utensils
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Outdoor swimming pool

Located about 15 minutes' walk from the Upper Matecumbe Key, the 3-bedroom Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa gives access to various tourist sites in the vicinity.

9.5
2 reviews
~ €1177 / night

Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location

0.0 km (0.0 mi) from city center
156
  • Cookware/ Kitchen utensils
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Outdoor swimming pool

Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location

Located about 15 minutes' walk from the Upper Matecumbe Key, the 3-bedroom Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa gives access to various tourist sites in the vicinity.

9.5
2 reviews
From € 1177 / night
  • Beach access
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At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom

84745 Old Hwy #6
3.7 km (2.3 mi) from city center
163
  • Cookware/ Kitchen utensils
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Heated swimming pool

At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom Islamorada villa accommodates up to 8 guests and offers proximity to the Windley Key Fossil Reef Geological State Park, located a mere 7 minutes' walk away. The holiday home features opportunities for snorkelling, ping-pong, and fishing in the area, 4.9 km from the Hurricane Monument.

8
1 reviews
~ €405 / night

At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom

3.7 km (2.3 mi) from city center
163
  • Cookware/ Kitchen utensils
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Fitness centre
  • Heated swimming pool

At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom

At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom Islamorada villa accommodates up to 8 guests and offers proximity to the Windley Key Fossil Reef Geological State Park, located a mere 7 minutes' walk away. The holiday home features opportunities for snorkelling, ping-pong, and fishing in the area, 4.9 km from the Hurricane Monument.

8
1 reviews
From € 405 / night
  • Beach access
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Pineapple Beach

130 Aregood Lane
9.4 km (5.9 mi) from city center
1
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Golf course
  • Garden area

Pineapple Beach Islamorada villa is located nearly 25 minutes' walk from the Islamorada and provides cycling and fishing for active guests. Offering a hot tub, this Islamorada holiday home is 2.5 km from the Rain Barrel Sculpture Gallery.

This accommodation provides a private swimming pool equipped with a hot tub for guests' additional relaxation.

10
1 reviews
~ €2488 / night

Pineapple Beach

9.4 km (5.9 mi) from city center
1
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Golf course
  • Garden area

Pineapple Beach

Pineapple Beach Islamorada villa is located nearly 25 minutes' walk from the Islamorada and provides cycling and fishing for active guests. Offering a hot tub, this Islamorada holiday home is 2.5 km from the Rain Barrel Sculpture Gallery.

This accommodation provides a private swimming pool equipped with a hot tub for guests' additional relaxation.

10
1 reviews
From € 2488 / night
  • Beach access
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Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location

84 Johnston Ave Unit #8
0.0 km (0.0 mi) from city center
156
  • Cookware/ Kitchen utensils
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Ironing facilities
  • Fitness centre

The 3-bedroom Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa accommodates up to 6 guests and offers proximity to the Lobster Trap Art Gift Shop and Gallery, located merely a 9-minute walk away.

8
1 reviews
~ €927 / night

Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location

0.0 km (0.0 mi) from city center
156
  • Cookware/ Kitchen utensils
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Ironing facilities
  • Fitness centre

Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location

The 3-bedroom Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa accommodates up to 6 guests and offers proximity to the Lobster Trap Art Gift Shop and Gallery, located merely a 9-minute walk away.

8
1 reviews
From € 927 / night
  • Great deal
  • Beach access
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Islamorada Modern Penthouse With Private Beach

80639 Old Highway
2.7 km (1.7 mi) from city center
279
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Jacuzzi
  • Outdoor swimming pool

Located a mere 600 metres from the Indian Key State Historic Site, the 3-bedroom Islamorada Modern Penthouse With Private Beach villa is suitable for 7 guests and offers a Jacuzzi to relax in. Boasting access to a terrace, this Islamorada holiday home invites guests to visit the History of Diving Museum, located about a 10-minute ride away.

9
1 reviews

Islamorada Modern Penthouse With Private Beach

2.7 km (1.7 mi) from city center
279
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Jacuzzi
  • Outdoor swimming pool

Islamorada Modern Penthouse With Private Beach

Located a mere 600 metres from the Indian Key State Historic Site, the 3-bedroom Islamorada Modern Penthouse With Private Beach villa is suitable for 7 guests and offers a Jacuzzi to relax in. Boasting access to a terrace, this Islamorada holiday home invites guests to visit the History of Diving Museum, located about a 10-minute ride away.

9
1 reviews
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Paradise Beach

13.6 km (8.5 mi) from city center
107
  • Cookware/ Kitchen utensils
  • Ironing facilities
  • Tea and coffee facilities
  • Patio

The beachfront Paradise Beach Islamorada villa is located around a 25-minute walk from the Craig Key and invites guests to enjoy a patio.

In the surroundings, you can enjoy cycling and fishing.

~ €178 / night

Paradise Beach

13.6 km (8.5 mi) from city center
107
  • Cookware/ Kitchen utensils
  • Ironing facilities
  • Tea and coffee facilities
  • Patio

Paradise Beach

The beachfront Paradise Beach Islamorada villa is located around a 25-minute walk from the Craig Key and invites guests to enjoy a patio.

In the surroundings, you can enjoy cycling and fishing.

From € 178 / night
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Tollgate Tides

205 Tollgate Blvd
13.7 km (8.5 mi) from city center
139
  • Cookware/ Kitchen utensils
  • Ironing facilities
  • Tea and coffee facilities
  • Patio

Tollgate Tides Villa Islamorada is located approximately a 10-minute ride from the Craig Key and provides windsurfing and fishing for active guests. Located a stone's throw from Anne's Beach, the Islamorada holiday home boasts a terrace with views of the garden.

~ €181 / night

Tollgate Tides

13.7 km (8.5 mi) from city center
139
  • Cookware/ Kitchen utensils
  • Ironing facilities
  • Tea and coffee facilities
  • Patio

Tollgate Tides

Tollgate Tides Villa Islamorada is located approximately a 10-minute ride from the Craig Key and provides windsurfing and fishing for active guests. Located a stone's throw from Anne's Beach, the Islamorada holiday home boasts a terrace with views of the garden.

From € 181 / night

Are you in a hurry?

Here is a quick list of hotels in Islamorada, selected based on their rating

Name of hotel Accommodation Rating Price, $
Anglers Reef Paradise

9.6 / 10

(19 Reviews)

From 382$
Anglers Reef Vacation Rental

9.8 / 10

(4 Reviews)

From 365$
Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina

10.0 / 10

(2 Reviews)

From 394$
Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views!

10.0 / 10

(3 Reviews)

From 1093$
Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable

10.0 / 10

(1 Reviews)

From 590$

Location