Best apartment offers in Islamorada, FL

1210 available apartment offers

7 nights
2
1
  • airbnb
  • booking
  • makemytrip
  • oyo
  • yatra
  • goibibo
  • travelguru
  • cleartrip
  • vrbo
  • expedia
  • hotelscom
  • tripcom
  • agoda
Islamorada, FL apartments
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

1210 Best apartments in Islamorada, FL

Best family friendly Islamorada, FL Holiday Apartments and Self Catering Accommodations

Among the 1210 accommodations in Islamorada, FL, here are the 4 best family friendly holiday apartments

Work Remote, Or Not At All, In Paradise At This Cozy, Beachy Condo! - Islamorada, FL
9.6 91 reviews

Work Remote, Or Not At All, In Paradise At This Cozy, Beachy Condo!

apartment, Islamorada, Village of Islands
This Islamorada seaside apartment, near Old Road Gallery and Founders Park (within 3km), offers stunning ocean views and easy beach access.
The 79 square metre property sleeps six, boasting two bedrooms, two bathrooms, a fully equipped kitchen, free Wi-Fi, a pool, jacuzzi, and tennis court, plus barbecue facilities and limited housekeeping.
Florida Keys Condo With Pool, Beach Access, Marina, Pickleball & More - Islamorada, FL
9.6 21 reviews

Florida Keys Condo With Pool, Beach Access, Marina, Pickleball & More

apartment, Tavernier
This Tavernier condo, situated between Islamorada and Key Largo, offers convenient proximity to the beach (a short walk), kayak and paddleboard rentals (0.8 km), and John Pennekamp Coral Reef State Park and Jacob's Aquatic Centre (distances unspecified).
Sleeping six guests, this two-bedroom, two-bathroom apartment boasts two balconies with ocean views, a swimming pool, hot tub, and access to tennis courts, pickleball courts, and a playground (all within 0.5 km), plus provision of equipment for various activities.
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.
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.

Best Holiday Apartments and Self Catering Accommodations in Islamorada, FL with a pool

Among the 1210 accommodations in Islamorada, FL, here are the 4 best apartments with a pool

Best Canal In Keys 4/3,heated Pool, Dock, 5* Rated - Islamorada, FL
10 6 reviews

Best Canal In Keys 4/3,heated Pool, Dock, 5* Rated

house, Islamorada, Village of Islands
This Islamorada waterfront property, near mile marker 90, offers direct ocean access via a deep-water canal, close proximity to Founders Park and its amenities, including pickleball courts, and is conveniently located near Islamorada's best restaurants and shops.
The four-bedroom, three-bathroom house sleeps eight guests and boasts a heated pool, hot tub, game room with a pool table, screened porch, and a fully equipped kitchen including a dishwasher, fridge and freezer.
Spectacular Ocean Front Home In Beautiful Islamorada!slip,com Pool, & Prv Bch - Islamorada, FL
10 59 reviews

Spectacular Ocean Front Home In Beautiful Islamorada!slip,com Pool, & Prv Bch

apartment, Islamorada, Village of Islands
This waterfront property is located just off the Overseas Highway in Islamorada, a short distance from Windley Key Fossil Reef Geological State Park, Founders Park, and Islamorada County Park, providing easy access to local attractions. The home has received excellent user ratings, highlighting its quality and appeal.
This two-bedroom, three-bathroom house can accommodate up to six guests. It features a fully equipped kitchen, a swimming pool, a terrace, and a barbecue grill, ensuring a comfortable and enjoyable stay. Guests can enjoy direct access to the water for fishing, kayaking, and other water activities, or relax on the balcony with stunning views of the ocean.
Relaxed Boho Vibes & Views [ Ocean Pointe 2315] - Islamorada, FL
9.8 1725 reviews

Relaxed Boho Vibes & Views [ Ocean Pointe 2315]

apartment, Tavernier
This beachside apartment building is located in Tavernier, Florida, just a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, offering a tranquil setting within easy reach of local attractions. The resort consistently receives excellent ratings for its location, cleanliness and overall experience.
The Keys Life At Ocean Pointe apartment offers two bedrooms, a sofa bed and a balcony, providing ample space for families or groups. Guests can enjoy a range of amenities including a swimming pool, Jacuzzi, tennis court, and a bar, as well as direct access to the beach.
Islamorada Paradise: Stunning Oceanview Condo Stay - Islamorada, FL
No reviews

Islamorada Paradise: Stunning Oceanview Condo Stay

apartment, Islamorada, Village of Islands
This Islamorada ocean view condominium offers direct Atlantic access from its prime location in the Village of Islands, placing you moments from notable restaurants, bars, and fishing charters.
This two-bedroom, one-bathroom property accommodates up to six guests and features a private balcony with ocean vistas, a fully equipped kitchen, on-site swimming pool, fitness centre, and private parking.

Frequently asked questions about apartment rentals in Islamorada, FL

  • What is Islamorada, FL best known for?

    Islamorada is often called the 'Sportfishing Capital of the World', so it's no surprise that fishing is a big draw. It's also a great place to enjoy the beautiful Florida Keys, with its stunning beaches, clear waters, and diverse marine life.
  • What are the best ways to relax in Islamorada, FL?

    Islamorada is all about slowing down and enjoying the laid-back atmosphere. Spend some time lounging on the beach, take a dip in the ocean, or enjoy a sunset cruise. You can also treat yourself to a massage at one of the many spas in the area.
  • What are the advantages of choosing an apartment for your stay in Islamorada, FL?

    Apartments offer more space and privacy than a hotel room, and you can often find great deals, especially if you're travelling with a family or group. Many apartments also come with kitchens, so you can save money by cooking some of your own meals.

Popular destinations

Best Islamorada, FL holiday apartments with air conditioning

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 flat is located in the centre of Islamorada, directly on a private beach with ocean views and within 1.5 kilometres of Islamorada Brewery & Distillery and Florida Keys Brewing Co.
This pet-friendly accommodation offers a heated outdoor swimming pool, complimentary Wi-Fi, and on-site bike, kayak, and paddleboard rentals, with a capacity for four guests.
Oceanside Retreat W/rooftop, Pool & Kayaks - Islamorada, FL
No reviews

Oceanside Retreat W/rooftop, Pool & Kayaks

apartment, Key Largo
This Key Largo flat, located within a secure gated community, is a short walk from Bluefin Rock Harbor Marina and offers convenient access to attractions such as John Pennekamp Coral Reef State Park and Harry Harris Park.
This three-bedroom, two-bathroom apartment accommodates up to eight guests and features a private rooftop, onsite kayaks, a communal pool and hot tub, air conditioning, a fully equipped kitchen with a microwave oven and dishwasher, and complimentary high-speed Wi-Fi and parking.
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.
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 pet-friendly Islamorada, FL holiday apartments

Among the 1210 accommodations in Islamorada, FL, here are the 4 best pet friendly holiday apartments

Canal Front, Paradise In Islamorada - Islamorada, FL
No reviews

Canal Front, Paradise In Islamorada

apartment, Islamorada, Village of Islands
This canal-front holiday home in Islamorada, Village of Islands, is situated at mile marker 90, offering 40 feet of private dockage and convenient access to local attractions.
Accommodating up to six guests, this property features two bedrooms and two bathrooms, along with a swimming pool, hot tub, and an outdoor kitchen, making it ideal for boaters and families seeking a Keys ambiance.
Relax And Unwind! Pet-friendly Property, Onsite Pool, Free Breakfast - Islamorada, FL
No reviews

Relax And Unwind! Pet-friendly Property, Onsite Pool, Free Breakfast

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 the Islamorada Brewery & Distillery and Florida Keys Brewing Co.
The 35 square metre (380 sq ft) self-catering flat sleeps four guests in two queen-size beds and includes a kitchenette, daily housekeeping, a heated pool with ocean views, and kayak/paddleboard rentals; complimentary continental breakfast is also provided.
Private 1 Bedroom Apartment With Kitchen, Keylargo Tavernier - Islamorada, FL
10 1 review

Private 1 Bedroom Apartment With Kitchen, Keylargo Tavernier

apartment, Tavernier
This private one-bedroom flat in Tavernier is located 5.15 kilometres from Pigeon Key and 11.10 kilometres from Windley Key, with John Pennekamp State Park and Dolphin Cove both 17.70 kilometres away.
This 38 square metre apartment accommodates up to three guests and features a kitchen with a fridge and microwave, air conditioning, a garden, and free Wi-Fi, with a patio and outdoor dining area for relaxation.
Two Balcony Rooms W/ Heated Pool Access + Free Breakfast| 1 Mile To Theater - Islamorada, FL
No reviews

Two Balcony Rooms W/ Heated Pool Access + Free Breakfast| 1 Mile To Theater

apartment, Islamorada, Village of Islands
This two-bedroom flat in Islamorada, Village of Islands, boasts an exceptional beachfront position within the village, offering direct access to the coast and situated just 270 metres from Windley Key Fossil Reef Geological State Park and 810 metres from Hog Heaven.
This accommodation for up to eight guests features air conditioning, Wi-Fi, a shared swimming pool, and a private balcony, with concierge services available and proximity to sailing, kayaking, mountain climbing, and hiking activities.
©2026 cozycozy.com