Tampa Apartments Across America Islamorada
Islamorada
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Islamorada

Oct 19 - Oct 20 ·
2 guests

Islamorada Vacation Rentals

Islamorada
2 guests

Adults:

2

Children:

0

Child’s age:

Over 100 stays assessed to highlight the standout picks

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1. Key Lime Cottage In The Heart Of Islamorada

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

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

4. Anglers Reef Vacation Rental

Cheap Islamorada Vacation Rentals

5. Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location

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

7. Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable

Pet Friendly Vacation Rentals Islamorada Florida

8. Ocean Views With Secret Speakeasy Bbq Patio Dock Pool 3Br With Private Bathrooms

9. Executive Bay Islamorada By Sofla Vacations

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

Best Islamorada Vacation Rentals

  • Guest favorite
Key Lime Cottage In The Heart Of Islamorada Key Lime Cottage In The Heart Of Islamorada

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
10
5 reviews
~ US$326 / 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

10
5 reviews
From US$ 326 / night
  • Beach access
Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views! Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views!

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
10
3 reviews
~ US$1093 / 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!

10
3 reviews
From US$ 1093 / night
  • Private beach
Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina

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
10
2 reviews
~ US$394 / 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

10
2 reviews
From US$ 394 / night

Cheap Islamorada Vacation Rentals

  • Private beach
Anglers Reef Vacation Rental Anglers Reef Vacation Rental

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
9.7
4 reviews
~ US$365 / 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

9.7
4 reviews
From US$ 365 / night
  • Beach access
Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location

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

84 Johnston Ave Unit #2
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
10
1 reviews
~ US$587 / night

Isla Key Kiwi - 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
  • Heated swimming pool

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

10
1 reviews
From US$ 587 / night
  • Beach access
Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable

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
10
1 reviews
~ US$590 / 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

10
1 reviews
From US$ 590 / night

Pet Friendly Vacation Rentals Islamorada Florida

  • Beach access
Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable

Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable

84 Johnston Ave Unit #7
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
10
2 reviews
~ US$722 / night

Isla Mirabelle - 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
  • Heated swimming pool

Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable

10
2 reviews
From US$ 722 / night
  • Beach access
Ocean Views With Secret Speakeasy Bbq Patio Dock Pool 3Br With Private Bathrooms Ocean Views With Secret Speakeasy Bbq Patio Dock Pool 3Br With Private Bathrooms

Ocean Views With Secret Speakeasy Bbq Patio Dock Pool 3Br With Private Bathrooms

A1, 84745 Old Highway
3.7 km (2.3 mi) from city center
223
  • BBQ facilities
  • Free parking
  • Security
  • Air conditioning
  • Entertainment
  • Outdoor swimming pool
10
3 reviews
~ US$723 / night

Ocean Views With Secret Speakeasy Bbq Patio Dock Pool 3Br With Private Bathrooms

3.7 km (2.3 mi) from city center
223
  • BBQ facilities
  • Free parking
  • Security
  • Air conditioning
  • Entertainment
  • Outdoor swimming pool

Ocean Views With Secret Speakeasy Bbq Patio Dock Pool 3Br With Private Bathrooms

10
3 reviews
From US$ 723 / night
  • Private beach
Executive Bay Islamorada By Sofla Vacations Executive Bay Islamorada By Sofla Vacations

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 centre
  • Outdoor swimming pool
8
3 reviews
~ US$150 / 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 centre
  • Outdoor swimming pool

Executive Bay Islamorada By Sofla Vacations

8
3 reviews
From US$ 150 / night

Islamorada Vacation Rentals Oceanfront

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

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
9.5
2 reviews
~ US$624 / 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

9.5
2 reviews
From US$ 624 / night
  • Top location
  • Beach access
Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location

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
9.5
2 reviews
~ US$1360 / 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

9.5
2 reviews
From US$ 1360 / night
  • Beach access
At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom

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
8
1 reviews
~ US$467 / 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

8
1 reviews
From US$ 467 / night

Islamorada Vacation Rentals with Private Pool

Pineapple Beach Pineapple Beach

Pineapple Beach

130 Aregood Lane
9.4 km (5.9 mi) from city center
1
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Heating
  • Golf centre
  • Garden area
10
1 reviews
~ US$2875 / night

Pineapple Beach

9.4 km (5.9 mi) from city center
1
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Heating
  • Golf centre
  • Garden area

Pineapple Beach

10
1 reviews
From US$ 2875 / night
  • Beach access
Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location

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
8
1 reviews
~ US$1071 / 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

8
1 reviews
From US$ 1071 / night
  • Great deal
  • Beach access
Islamorada Modern Penthouse With Private Beach Islamorada Modern Penthouse With Private Beach

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
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

9
1 reviews
La Dolce Vita Villa La Dolce Vita Villa

La Dolce Vita Villa

116 Stromboli Dr
5.7 km (3.5 mi) from city center
161
  • Free parking
~ US$333 / night

La Dolce Vita Villa

5.7 km (3.5 mi) from city center
161
  • Free parking

La Dolce Vita Villa

From US$ 333 / night
  • Beach access
Sunshine Place Sunshine Place

Sunshine Place

84371 Overseas Hwy
3.1 km (1.9 mi) from city center
  • Cookware/ Kitchen utensils
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Tea and coffee facilities
  • Fitness centre
~ US$384 / night

Sunshine Place

3.1 km (1.9 mi) from city center
  • Cookware/ Kitchen utensils
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Tea and coffee facilities
  • Fitness centre

Sunshine Place

From US$ 384 / night
Waterfront Ocean Access Canal Kamp Key Homes Waterfront Ocean Access Canal Kamp Key Homes

Waterfront Ocean Access Canal Kamp Key Homes

76412 Overseas Highway
9.5 km (5.9 mi) from city center
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Massage
~ US$450 / night

Waterfront Ocean Access Canal Kamp Key Homes

9.5 km (5.9 mi) from city center
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Massage

Waterfront Ocean Access Canal Kamp Key Homes

From US$ 450 / night
Little Bay Cottage Little Bay Cottage

Little Bay Cottage

82246 Overseas Hwy
0.2 km (0.1 mi) from city center
  • Cookware/ Kitchen utensils
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Tea and coffee facilities
  • Fitness centre
~ US$549 / night

Little Bay Cottage

0.2 km (0.1 mi) from city center
  • Cookware/ Kitchen utensils
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Tea and coffee facilities
  • Fitness centre

Little Bay Cottage

From US$ 549 / night

Are you in a hurry?

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

Name of hotel Accommodation Rating Price, $
Key Lime Cottage In The Heart Of Islamorada

10.0 / 10

(5 Reviews)

 From 326$
Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views!

10.0 / 10

(3 Reviews)

 From 1093$
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$
Anglers Reef Vacation Rental

9.7 / 10

(4 Reviews)

 From 365$
Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location

10.0 / 10

(1 Reviews)

 From 587$

Location