Vacation Rentals in Islamorada, FL

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Islamorada, FL holiday rentals
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1696 Holiday rentals and Airbnb in Islamorada, FL

Guests’ Top-Picked Family Holiday Rentals in Islamorada, FL, United States

Browse family holiday rentals in Islamorada, FL, United States with space for everyone to relax.

Ocean View Gem Ocean Pointe 3406 2ba/2br King/queen - Islamorada, FL
9.8 9 reviews

Ocean View Gem Ocean Pointe 3406 2ba/2br King/queen

apartment, Tavernier
This oceanfront apartment in Tavernier, Florida, is situated 1 kilometre from Harry Harris Park and within 5 kilometres of Mariners Hospital and the Florida Keys Dive Centre.
The 77-square-metre property boasts two bedrooms, two bathrooms, sleeps five guests, and includes a fully equipped kitchen, private balcony, swimming pool, jacuzzi, and in-unit laundry facilities.
Tiki Time Top Floor King 1 Br 1ba 1413 - Islamorada, FL
10 2 reviews

Tiki Time Top Floor King 1 Br 1ba 1413

apartment, Tavernier
This Tavernier condo, situated within the Ocean Pointe resort midway between Key Largo and Islamorada, offers easy access to John Pennekamp Coral Reef State Park and the History of Diving Museum.
The 54-square-metre (581-square-foot) one-bedroom, one-bathroom apartment sleeps four, features a fully equipped kitchen, in-unit laundry, a terrace with ocean and mangrove views, and access to resort amenities including a pool, tennis courts, and private beach.
Aqua Vista Ocean Pointe 3307 - Islamorada, FL
9.6 4 reviews

Aqua Vista Ocean Pointe 3307

apartment, Tavernier
This Tavernier seaside apartment, located 1.1 km from Harry Harris Park and within 5 km of Mariners Hospital and the Florida Keys Dive Centre, offers stunning ocean views.
The 77 square metre property features two bedrooms, two bathrooms, a sofa bed sleeping up to five guests, a fully equipped kitchen, private balcony, swimming pool, hot tub, and on-site barbecue facilities.
Reel Key Largo Escape Ocean Pointe 5209 - Islamorada, FL
9.6 10 reviews

Reel Key Largo Escape Ocean Pointe 5209

apartment, Tavernier
This Tavernier waterfront apartment is situated a 2.4km walk from Baker's Cay Resort Beach and Harry Harris Park, and within 5km of Mariners Hospital and the Florida Keys Dive Centre.
The 79-square-metre property offers two bedrooms, two bathrooms, a sofa bed, and sleeps four, boasting a private pool, balcony, fully equipped kitchen, and access to shared amenities including an indoor pool and barbecue grills.

Top-Rated Holiday Rentals with a Pool in Islamorada, FL, United States

Walk right out of your kitchen and jump into a crystal-clear swimming pool at island holiday rentals in Islamorada, FL, United States.

Amazing Sandy Beach Sunsets + New Pool + Best Location W/ Park - Bikes & Kayaks - Islamorada, FL
9.8 40 reviews

Amazing Sandy Beach Sunsets + New Pool + Best Location W/ Park - Bikes & Kayaks

apartment, Islamorada, Village of Islands
This Islamorada beachfront holiday home, located near Founders Park, offers easy access to Jimmy Johnson's Big Chill and the Florida Keys Dive Centre, all within a short driving distance.
The 130 square metre (1,400 square feet) property boasts three bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen with BBQ, a private beach, swimming pool, spa, and free Wi-Fi.
Casa Del Mar - Islamorada, FL
10 1 review

Casa Del Mar

apartment, Key Largo
This four-bedroom, four-bathroom apartment is located in Key Largo's Silver Shores district, offering convenient access to cultural sites such as the Old Road Gallery and History of Diving Museum, as well as landmarks like the Caribbean Club Bar and Christ of the Abyss, with John Pennekamp Coral Reef State Park just a short distance away.
This accommodation provides air conditioning, a swimming pool, a jacuzzi, a terrace, a garden, and parking, making it suitable for groups or families seeking a relaxing stay with comfortable year-round climate control and ensuite bathrooms featuring showers and hair dryers.
Your Home Away From Home! 4 Units, Free Parking, Onsite Pool & Breakfast! - Islamorada, FL
No reviews

Your Home Away From Home! 4 Units, Free Parking, Onsite Pool & Breakfast!

apartment, Islamorada, Village of Islands
This four-bedroom, four-bathroom apartment in Islamorada, Village of Islands, offers direct access to a private beach resort and is situated within 1 kilometre of the History of Diving Museum and the Keys History & Discovery Centre.
This pet-friendly residence accommodates up to 16 guests, featuring a heated swimming pool with ocean views, on-site bike and kayak rentals, and outdoor BBQ facilities, with complimentary continental breakfast and Wi-Fi included.
138 M² Condo ∙ 2 Bedrooms ∙ 4 Guests - Islamorada, FL
10 3 reviews

138 M² Condo ∙ 2 Bedrooms ∙ 4 Guests

apartment, Islamorada, Village of Islands
This penthouse apartment is located in Islamorada, approximately 13 kilometres from the town centre and within walking distance of Sunset Drive Beach and Anne's Beach, offering a peaceful retreat near the beautiful coastline. The property enjoys an excellent user rating, indicating its high standard of accommodation and amenities.
The apartment is spacious, with 138 square metres of floor area, comfortably accommodating a large group of travellers. It features a fully equipped kitchen, air conditioning, a swimming pool, a terrace, a fitness centre, a tennis court, and parking, providing a wide range of amenities for a relaxing and enjoyable stay.

Frequently asked questions about holiday rentals in Islamorada, FL

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Top-Rated Holiday Rentals with a Balcony in Islamorada, FL, United States

Wake up to the soothing sight of the blue horizon right from your private rental balcony in Islamorada, FL, United States.

Stay & Play; Enjoy Scenic Views  Ocean Pointe 5312 - Islamorada, FL
9.8 53 reviews

Stay & Play; Enjoy Scenic Views Ocean Pointe 5312

apartment, Tavernier
This waterfront apartment is situated in Tavernier, within easy walking distance of Baker's Cay Resort Beach and Harry Harris Park, and just a short drive from Mariners Hospital and Florida Keys Dive Center. It enjoys a peaceful location, perfect for a relaxing getaway. The apartment has received excellent guest reviews and is rated highly for its amenities and service.
The apartment has two bedrooms, two bathrooms, and can comfortably accommodate up to six guests. It has a fully equipped kitchen, a terrace or balcony, a swimming pool, a spa, a tennis court, and free parking, providing everything you need for a comfortable and enjoyable stay.
Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included. - Islamorada, FL
10 125 reviews

Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.

apartment, Islamorada, Village of Islands
This luxury waterfront villa, situated at mile marker 85 in Islamorada, offers convenient access to Indian Key Historic State Park and the San Pedro Underwater Archaeological Preserve State Park.
The 188 square metre property boasts four bedrooms, three bathrooms, sleeps eight guests, and includes a private boat slip (up to 31ft), a fully equipped chef's kitchen, and family-friendly amenities such as a highchair and children's toys.
Condo ∙ 3 Bedrooms ∙ 6 Guests - Islamorada, FL
10 3 reviews

Condo ∙ 3 Bedrooms ∙ 6 Guests

apartment, Islamorada, Village of Islands
This 3-bedroom, 2-bathroom flat offers direct Florida Bay views from its 5th-floor balcony within the private, gated Futura Yacht Club in Islamorada, Village of Islands.
This family-friendly condominium sleeps six and boasts a heated swimming pool, BBQ grills, tennis courts, and marina access for boats up to 36 feet, with easy ocean access via Snake Creek or Tavernier Creek.
Sunrise Breeze On The Marina [Ocean Pointe 5302] - Islamorada, FL
9.8 176 reviews

Sunrise Breeze On The Marina [Ocean Pointe 5302]

apartment, Tavernier
This Tavernier beach apartment is conveniently located within a 10-minute walk of Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the area's attractions. The property consistently receives excellent ratings for location, cleanliness, and overall user experience.
The apartment offers 85 square metres of space, comfortably accommodating up to 6 guests in its two bedrooms and two bathrooms. This family-friendly apartment includes a range of amenities such as a swimming pool, Jacuzzi, tennis court, and a garden, ensuring a comfortable and enjoyable stay.

Best Islamorada, FL holiday rentals with parking

Isla Honeydew: 3 En-suite Bedrooms, Pool, Dock - Islamorada, FL
10 9 reviews

Isla Honeydew: 3 En-suite Bedrooms, Pool, Dock

house, Islamorada, Village of Islands
Isla Honeydew, a three-bedroom waterfront villa in Matecumbe, Islamorada, is located within 1.6km of the Islamorada Brewery & Distillery and Keys History & Discovery Centre, and under 2.4km from the History of Diving Museum.
This 156 square metre property offers a fully equipped kitchen, private balcony, swimming pool, garden, and parking, accommodating up to six guests.
Ocean Pointe 2br Retreat Ocean View, Pool, Marina & Resort Amenities - Islamorada, FL
9.5 81 reviews

Ocean Pointe 2br Retreat Ocean View, Pool, Marina & Resort Amenities

apartment, Tavernier
This apartment is located in Blue Waters, a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, with Mariners Hospital and Florida Keys Dive Center within 5 kilometres. The accommodation has received excellent ratings for location, cleanliness and overall user experience.
The apartment has a floor area of 77 square metres and can accommodate up to 6 guests. It comes with a private pool, a spa tub, barbecue grills, a washing machine, a sofa bed, and a fully equipped kitchen, ensuring a comfortable stay for families and groups.
Swim With Dolphins In The Florida Keys! Free Breakfast & Parking, Marina, Pool! - Islamorada, FL
No reviews

Swim With Dolphins In The Florida Keys! Free Breakfast & Parking, Marina, Pool!

apartment, Islamorada, Village of Islands
This beachfront flat in downtown Islamorada, Village of Islands, is a short walk from Windley Key Fossil Reef Geological State Park and 9 minutes by car from Hog Heaven.
This one-bedroom flat accommodates two guests and offers air conditioning, Wi-Fi, a swimming pool, and parking, with easy access to water sports and cultural sites like the History of Diving Museum.
Classic Villa W/ Ocean View & Balcony! Beach Access, Free Parking & Breakfast - Islamorada, FL
No reviews

Classic Villa W/ Ocean View & Balcony! Beach Access, Free Parking & Breakfast

apartment, Islamorada, Village of Islands
This one-bedroom apartment in Islamorada's city centre offers direct beach access and is situated within easy reach of the History of Diving Museum and the Keys History & Discovery Center.
This pet-friendly accommodation for four guests features complimentary Wi-Fi, air conditioning, a heated outdoor pool with ocean views, and on-site bike, kayak, and paddleboard rentals, with daily continental breakfast and BBQ facilities also provided.

Top-Rated Luxury Holiday Rentals in Islamorada, FL, United States

Bask in absolute tropical privacy with upscale coastal design at luxury holiday rentals in Islamorada, FL, United States.

Snorkeling & Kayaking Resort! Seaside Villa, Patio, Breakfast, Pool, Parking! - Islamorada, FL
8.8 8 reviews

Snorkeling & Kayaking Resort! Seaside Villa, Patio, Breakfast, Pool, Parking!

apartment, Islamorada, Village of Islands

Top-Rated Downtown Holiday Rentals in Islamorada, FL, United States

Find holiday rentals in the heart of Islamorada, FL, United States close to shops and beaches.

Flakey's - Islamorada, FL
9.9 217 reviews

Flakey's

apartment, Islamorada, Village of Islands
Malayan Palm East 1 Bedroom, 1 Bath Garden View - Islamorada, FL
10 177 reviews

Malayan Palm East 1 Bedroom, 1 Bath Garden View

apartment, Islamorada, Village of Islands
Bayside: Bayfront Villa W/ Free Onsite Boat Ramp Marina & Trailer Parking. - Islamorada, FL
9.9 64 reviews

Bayside: Bayfront Villa W/ Free Onsite Boat Ramp Marina & Trailer Parking.

house, Islamorada, Village of Islands
Off The Charts-waterfront Tiki Bar & Private Dock - Islamorada, FL
10 14 reviews

Off The Charts-waterfront Tiki Bar & Private Dock

apartment, Islamorada, Village of Islands

Top-Rated Holiday Rentals near the Ocean in Islamorada, FL, United States

Open your glass doors and step directly from your living space onto the warm, powdery sand at seashore holiday rentals in Islamorada, FL, United States.

Starfish -1 Bedroom 1 Bath Apartment With Full Kitchen In Islamorada, Florida. - Islamorada, FL
9.4 3 reviews

Starfish -1 Bedroom 1 Bath Apartment With Full Kitchen In Islamorada, Florida.

apartment, Islamorada, Village of Islands
Snorkel Legendary Reefs - Relax Poolside | Op 2315 - Islamorada, FL
9.8 1818 reviews

Snorkel Legendary Reefs - Relax Poolside | Op 2315

apartment, Tavernier
Waterfront Home In The Heart Of The Fishing Capital Of The World. - Islamorada, FL
10 88 reviews

Waterfront Home In The Heart Of The Fishing Capital Of The World.

apartment, Islamorada, Village of Islands
Casa Dos Hondos Ii - Islamorada, FL
9.0 2 reviews

Casa Dos Hondos Ii

house, Islamorada, Village of Islands

Top-Rated Holiday Rentals with a Hot Tub in Islamorada, FL, United States

Watch the sun set over the water while soaking in a steaming outdoor hot tub at island holiday rentals in Islamorada, FL, United States.

Ocean Pointe Ocean View W/heated Pool Beach Marina - Islamorada, FL
8.6 13 reviews

Ocean Pointe Ocean View W/heated Pool Beach Marina

apartment, Tavernier
Bright 2br Condo With Breathtaking Ocean View - Islamorada, FL
9.4 10 reviews

Bright 2br Condo With Breathtaking Ocean View

apartment, Tavernier
Capt Craig's 1 Bedroom /1 Bath Apartment In Islamorada, Florida Keys - Islamorada, FL
9.8 22 reviews

Capt Craig's 1 Bedroom /1 Bath Apartment In Islamorada, Florida Keys

apartment, Islamorada, Village of Islands
Islamorada Luxury Waterfront Condo With Boat Slip - Islamorada, FL
9.8 29 reviews

Islamorada Luxury Waterfront Condo With Boat Slip

apartment, Islamorada, Village of Islands
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