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 Pointe - Pool, Hot Tub, View, Beach, Parking - Islamorada, FL
10 3 reviews

Ocean Pointe - Pool, Hot Tub, View, Beach, Parking

apartment, Tavernier
This Ocean Pointe beach condo in Tavernier offers magnificent ocean and pool views, situated just 5 minutes from downtown Tavernier and a 15-minute drive from John Pennekamp Coral Reef State Park.
This family-friendly apartment sleeps five and boasts two bedrooms and two bathrooms, featuring a fully equipped kitchen, air conditioning, a private beach with sunloungers and floaties, resort amenities including a pool and hot tub, and a balcony with ocean views.
Condo ∙ 3 Bedrooms ∙ 8 Guests - Islamorada, FL
No reviews

Condo ∙ 3 Bedrooms ∙ 8 Guests

apartment, Islamorada, Village of Islands
This bayfront flat, located at Mile Marker 83 in Islamorada, Village of Islands, offers direct water access and sunset views, placing you near the 'Sportfishing Capital of the World' for exceptional fishing and boating.
Accommodating up to eight guests, this three-bedroom property boasts a private pool, a well-equipped kitchen with stainless steel appliances, a master balcony, and an outdoor kitchen, ideal for enjoying the Florida climate and water activities.
Best Location In The Keys Waterfront 3/3 Home, Boat Dock, Great Layout! - Islamorada, FL
10 2 reviews

Best Location In The Keys Waterfront 3/3 Home, Boat Dock, Great Layout!

apartment, Islamorada, Village of Islands
This waterfront property is situated in Indian Waterways, a neighbourhood in Tavernier, just a short distance from Founders Park and the beach. The area offers a peaceful and relaxing atmosphere, perfect for enjoying the natural beauty of the Florida Keys.
The house is ideal for families or groups of up to four people, with two bedrooms and two bathrooms. Enjoy the convenience of a fully equipped kitchen, a screened-in porch, and a large enclosed garage, as well as the option to bring your own boat or rent one on-site.
Charming Waterfront Oceanside Canal Home-large Protected Dockage-wifi-smart Tvs. - Islamorada, FL
9.6 92 reviews

Charming Waterfront Oceanside Canal Home-large Protected Dockage-wifi-smart Tvs.

apartment, Islamorada, Village of Islands
This waterfront apartment is situated in Lower Matecumbe, on the Atlantic side canal in Islamorada, at mile marker 76.5, just a short distance from Robbie's Marina, Bud and Mary's Marina, and World Wide Sportsman. This property has received excellent reviews from previous guests.
The apartment is spacious, covering 130 square metres and accommodating up to six guests, with three bedrooms and three bathrooms. You'll enjoy the convenience of a fully equipped kitchen, air conditioning, a terrace, a garden, a spa, parking, and access to high-speed internet.

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.

Condo ∙ 2 Bedrooms ∙ 6 Guests - Islamorada, FL
9.0 1 review

Condo ∙ 2 Bedrooms ∙ 6 Guests

apartment, Islamorada, Village of Islands
This Islamorada condo, part of the Topsider Resort, offers oceanfront private beach access and is situated 2km from Lazy Days South, 8.7km from Alligator Reef Lighthouse, and 6.6km from Robbie's of Islamorada.
The two-bedroom, two-bathroom apartment sleeps six, features a fully equipped kitchen, private balcony with tropical views, and access to resort amenities including a heated pool, Jacuzzi, and tennis courts, plus complimentary boat docking (up to 7m).
Best Place To Stay In Florida! 3 Pet-friendly Units, Free Breakfast, Parking - Islamorada, FL
10 1 review

Best Place To Stay In Florida! 3 Pet-friendly Units, Free Breakfast, Parking

apartment, Islamorada, Village of Islands
This Islamorada beachfront apartment, part of a pet-friendly resort, offers direct beach access and is centrally located, providing easy access to local breweries and proximity to Indian Key Historic State Park and San Pedro Underwater Archaeological Preserve State Park (distances unspecified).
The 75 square metre property comprises three uniquely decorated bedrooms, each with two queen-size beds, accommodating up to twelve guests, and includes a private kitchen, three bathrooms, a swimming pool, concierge service, parking, and daily continental breakfast.
Single Family Home In Angler's Reef Gated Community, Beaches,marina,heated Pool - Islamorada, FL
9.8 103 reviews

Single Family Home In Angler's Reef Gated Community, Beaches,marina,heated Pool

apartment, Islamorada, Village of Islands
This beachfront property is located in Islamorada, just under 5 kilometres from Windley Key Fossil Reef Geological State Park, Founders Park, and Islamorada County Park, and 3.5 kilometres from the History of Diving Museum. The home has received excellent ratings for location, cleanliness and user experience.
The house is spread over 149 square metres and can accommodate up to 6 guests. It features 2 bedrooms, 3 bathrooms, a fully equipped kitchen, a spacious balcony, a swimming pool, a jacuzzi, a garden, a spa and parking.
Anglers Reef Islamorada 2br 3ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina - Islamorada, FL
10 2 reviews

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

house, Islamorada, Village of Islands
This ocean-view property is located within the gated Anglers Reef community in Islamorada, Village of Islands, a 1km walk from Windley Key and 1.6km from Windley Key Fossil Reef Geological State Park.
This three-bedroom, three-bathroom house offers 122 square metres of living space, accommodating up to nine guests and boasting a fully equipped kitchen, private pool, and free Wi-Fi, all within easy reach of Islamorada's attractions.

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.

Cheeca Lodge & Spa - Islamorada, FL
9.0 1983 reviews

Cheeca Lodge & Spa

resort, Islamorada, Village of Islands
Cheeca Lodge & Spa is situated on a 27-acre stretch of waterfront in Islamorada, just a 20-minute drive from downtown Key Largo and 13.7 miles from Long Key State Park. The resort has received very good user ratings, with excellent scores for location and cleanliness.
The property features spacious rooms with balconies and resort views. Guests can enjoy a range of amenities, including a 9-hole golf course, spa, fishing pier, swimming pools, fitness centre, tennis courts, and watersports facilities.
Spring & Summer Dates Available Licensed Rental Vr #25-0235  No Boats - Islamorada, FL
10 62 reviews

Spring & Summer Dates Available Licensed Rental Vr #25-0235 No Boats

apartment, Islamorada, Village of Islands
This family-friendly apartment is located on the beach in Islamorada, within a short distance of Islamorada County Park, Founders Park, and the Florida Keys Dive Center. It has received excellent user ratings, making it a popular choice for travellers.
The apartment is spacious, covering 74 square metres and comfortably accommodating up to six guests. It comes with a range of amenities, including a swimming pool, a tennis court, and a fitness centre, ensuring a comfortable and enjoyable stay.
Condo ∙ 2 Bedrooms ∙ 6 Guests - Islamorada, FL
No reviews

Condo ∙ 2 Bedrooms ∙ 6 Guests

apartment, Islamorada, Village of Islands
This two-bedroom flat is located in Angler's Reef, a secure oceanfront community in Islamorada, offering direct beach access and a heated oceanfront swimming pool.
This family-friendly accommodation sleeps up to six guests and features a kitchen with a fridge, microwave, and dishwasher, along with air conditioning, a terrace/balcony, garden, and parking.
The Snook House At Tarpon Point  ~ 4 Bed/4 Bath Oceanfront Home - Islamorada, FL
10 8 reviews

The Snook House At Tarpon Point ~ 4 Bed/4 Bath Oceanfront Home

apartment, Islamorada, Village of Islands
This property is located on Lower Matecumbe Key, just 6.4km south of downtown Islamorada and directly across the road from Robbie's, a popular spot for fishing, dining, and exploring. It has received excellent reviews from previous guests.
This four-bedroom, four-bathroom house spans 271 square meters and can accommodate up to eight guests. The property offers a range of amenities including a private pool, direct beach access, a fully-equipped kitchen, a terrace, a garden, parking, and internet access.

Best Islamorada, FL holiday rentals with parking

Anglers Reef Is Oceanfront, Yellowtail Hse. 2/2.5 - Islamorada, FL
9.4 27 reviews

Anglers Reef Is Oceanfront, Yellowtail Hse. 2/2.5

apartment, Islamorada, Village of Islands
This holiday home in Anglers Reef, a gated resort community in Islamorada, is just a short distance from local shops, bars, and restaurants, and a boat ride from the famous Islamorada "sandbar" and Alligator Reef. The property has received excellent ratings for its location, cleanliness, and overall experience.
The two-bedroom, two-bathroom home can comfortably accommodate up to six guests and features a spacious open layout with three flat-screen TVs, granite countertops, and updated appliances. Guests can enjoy private beaches, a heated pool, outdoor bathrooms, and complimentary use of paddleboards, kayaks, and bicycles.
Aquamarine Oceanview+special Rates+ Dock+pool+gym+spa+1535 Star Reviews!!! - Islamorada, FL
10 159 reviews

Aquamarine Oceanview+special Rates+ Dock+pool+gym+spa+1535 Star Reviews!!!

apartment, Islamorada, Village of Islands
This waterfront apartment is situated in Islamorada's Matecumbe district, just a short distance from Bud n' Mary's Dive Center and Florida Keys Brewing Co., offering stunning views of the ocean and marina. The apartment has received excellent user ratings, indicating a high level of satisfaction among previous guests.
The apartment is spacious, measuring 158 square metres and accommodating up to 6 guests. It features a range of amenities and activities, including a private dock, a heated pool, a hot tub, a fitness centre, lighted tennis courts, a clubhouse, and a well-equipped equipment closet.
Best Location For Your Best Vacation! - Islamorada, FL
9.6 24 reviews

Best Location For Your Best Vacation!

apartment, Islamorada, Village of Islands
This Islamorada waterfront property, situated in Tavernier in the Florida Keys, offers direct bay and ocean access via a private 75-foot dock, conveniently located near the Florida Keys Dive Center and John Pennekamp Coral Reef State Park.
This three-bedroom, two-bathroom holiday home boasts 344 square metres of living space, accommodating up to ten guests and featuring a fenced tropical backyard with a gazebo, fire pit, and Tiki bar by the pool, plus a fully equipped kitchen and all linens provided.
Port Antigua New Lux Apart - Islamorada, FL
10 1 review

Port Antigua New Lux Apart

apartment, Islamorada, Village of Islands
This luxurious apartment in Islamorada's Port Antigua district is situated minutes from Alligator Reef Lighthouse, offering easy access to pristine waters ideal for swimming, fishing and boating.
The first-floor, one-bedroom, two-bathroom flat sleeps two guests and boasts a private pool, Jacuzzi, sauna, and private beach access, perfect for a romantic getaway.

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.

Prime Location Islamorada Anglers Reef Oceanview Private Beaches, Pool & Marina - Islamorada, FL
10 8 reviews

Prime Location Islamorada Anglers Reef Oceanview Private Beaches, Pool & Marina

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.

Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable - Islamorada, FL
10 2 reviews

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

house, 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
Villa ∙ 3 Bedrooms ∙ 6 Guests - Islamorada, FL
10 2 reviews

Villa ∙ 3 Bedrooms ∙ 6 Guests

house, Islamorada, Village of Islands
Isla Mirabelle: Free Boat Dockage Sep-oct Only! - Islamorada, FL
9.7 7 reviews

Isla Mirabelle: Free Boat Dockage Sep-oct Only!

house, 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.

Waterfront Sunset View Aqua Villa At Conch Shell @ Mangrove Resort Llc - Islamorada, FL
9.3 42 reviews

Waterfront Sunset View Aqua Villa At Conch Shell @ Mangrove Resort Llc

house, Tavernier
Family Escape In Islamorada! Seaside Unit, Balcony! Breakfast Included! - Islamorada, FL
No reviews

Family Escape In Islamorada! Seaside Unit, Balcony! Breakfast Included!

apartment, Islamorada, Village of Islands
Anchor Here: Oceanfront 1br Condo With Marina Access - Islamorada, FL
9.6 18 reviews

Anchor Here: Oceanfront 1br Condo With Marina Access

apartment, Islamorada, Village of Islands
Florida Keys Tour! Private Beach Access W/ Marina! Pets Allowed, Free Breakfast - Islamorada, FL
No reviews

Florida Keys Tour! Private Beach Access W/ Marina! Pets Allowed, Free Breakfast

apartment, 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.

Outstanding Ocean View W/heated Pool Beach Marina - Islamorada, FL
No reviews

Outstanding Ocean View W/heated Pool Beach Marina

apartment, Tavernier
Modern And Coastal 3212 Is Across From Pool - Islamorada, FL
9.0 3 reviews

Modern And Coastal 3212 Is Across From Pool

house, Tavernier
4409 Ocean Pointe Suites - Islamorada, FL
9.6 112 reviews

4409 Ocean Pointe Suites

apartment, Tavernier
Spacious End Suite With Atlantic Views - Islamorada, FL
9.9 119 reviews

Spacious End Suite With Atlantic Views

apartment, Tavernier
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