Search Islamorada, FL villas and holiday homes

522 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Islamorada, FL villas
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

522 Villa rentals in Islamorada, FL

Best Islamorada, FL villas and holiday homes with a pool

Among the 522 accommodations in Islamorada, FL, here are the 4 best villas and holiday homes with a pool

Ocean View Treehouse Double King Suite 3403 - Islamorada, FL
9.7 9 reviews
Islamorada, FL
30/07 – 06/08
A$535/nighttotal: A$3745 (7 )

Ocean View Treehouse Double King Suite 3403

2 2
house , Tavernier
Ocean View Treehouse Double King Suite 3403 is a Tavernier property, a 2-kilometre walk from Harry Harris Park Beach and a short drive from attractions including Pigeon Key (5 km), Windley Key (13 km), and the Theatre of the Sea (14 km).
This 76-square-metre self-catering house features two bedrooms, one bathroom, sleeps seven guests, and includes a fully equipped kitchen with fridge, microwave, and dishwasher, plus a swimming pool and garden.
Isla Kiwi: Free Boat Dockage Sep-oct Only! - Islamorada, FL
9.8 8 reviews
Islamorada, FL
07/08 – 23/08
A$720/nighttotal: A$11520 (16 )

Isla Kiwi: Free Boat Dockage Sep-oct Only!

1 4
house , Islamorada, Village of Islands
Isla Kiwi Villa #2, a three-bedroom upscale villa, is located in Islamorada's Art District, within walking distance of shops and restaurants, and a short drive (approximately 1.3 km) from Robbie's Marina and the Theatre of the Sea.
This luxury holiday home sleeps six guests, boasting three ensuite bathrooms, a private deck with partial water views, access to a heated communal pool and BBQ area, and is fully equipped with top-of-the-line appliances.
Isla Key Lychee - Waterfront Boutique Resort, Island Paradise, Prime Location - Islamorada, FL
Islamorada, FL
17/10 – 26/10
A$790/nighttotal: A$7110 (9 )

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

3 6
house , Islamorada, Village of Islands
Isla Key Lychee, a waterfront villa in Islamorada, offers easy access to Upper Matecumbe Key (a 2km walk) and Windley Key (4km), with Pigeon Key and John Pennekamp Coral Reef State Park further away.
This three-bedroom, three-bathroom property boasts 156 square metres of living space, comfortably accommodating nine guests and featuring a fully equipped kitchen, private balcony, swimming pool, fitness centre, free Wi-Fi, and on-site parking.
Deactivated Due To Bad Review And Low Productivity Compared To Other Listings. - Islamorada, FL
Islamorada, FL
18/07 – 22/07
A$1981/nighttotal: A$7924 (4 )

Deactivated Due To Bad Review And Low Productivity Compared To Other Listings.

4 4
house , Islamorada, Village of Islands
This beachfront property in Matecumbe, Islamorada, is situated near the Morada Way Arts & Cultural District and the Keys History & Discovery Centre, offering easy access to attractions within a 2.4km radius.
The 194 square metre property comprises two villas, each with two king-size beds and a sofa bed, accommodating up to 12 guests, and boasts private patios with bayside views, access to a swimming pool, BBQ facilities, and water sports rentals, plus a 50% discount on admission to the Keys History & Discovery Centre as part of the resort fee.

Best Islamorada, FL villas and holiday homes with a kitchen

62 M² Villa ∙ 2 Bedrooms ∙ 4 Guests - Islamorada, FL
10 14 reviews
Islamorada, FL
09/10 – 12/10
A$462/nighttotal: A$1386 (3 )

62 M² Villa ∙ 2 Bedrooms ∙ 4 Guests

2 2
house , Islamorada, Village of Islands
This secluded villa in Islamorada, Village of Islands, is situated on a 1-acre lot overlooking Florida Bay, offering water views and sunsets, with a private marina and boat launch, and is within walking distance of local amenities including the Islamorada Brewery & Distillery.
This 62-square-meter holiday home accommodates up to 4 guests across 2 bedrooms and 2 bathrooms, featuring air conditioning, Wi-Fi, a fully equipped kitchen, and a spacious 1200 sq ft roof terrace with a gas grill, plus complimentary dockage for one boat up to 26 feet.
Paradise Palms Ocean Pointe 1206 - Islamorada, FL
9.5 13 reviews
Islamorada, FL
18/07 – 22/07
A$454/nighttotal: A$1816 (4 )

Paradise Palms Ocean Pointe 1206

2 4
house , Tavernier
Paradise Palms Ocean Pointe 1206, a Key Largo property, is situated a short 1.9km walk from Harry Harris Park Beach and within easy driving distance of Pigeon Key, Windley Key, and John Pennekamp Coral Reef State Park.
This two-bedroom, two-bathroom house offers 77 square metres of living space, sleeping up to eight guests and boasting a private pool, garden, free Wi-Fi, and a fully equipped kitchen including a dishwasher; nearby attractions include the beaches of Key Largo.
Key Largo Baha Penthouse Ocean Pointe 1416 - Islamorada, FL
9.6 6 reviews
Islamorada, FL
18/07 – 22/07
A$488/nighttotal: A$1952 (4 )

Key Largo Baha Penthouse Ocean Pointe 1416

1 4
house , Tavernier
Key Largo Baha Penthouse Ocean Pointe 1416, situated in Key Largo, Florida, offers a 77 square metre, two-bedroom, two-bathroom apartment approximately 1.6km from Harry Harris Park Beach and conveniently located for exploring Pigeon Key, Windley Key, and John Pennekamp Coral Reef State Park.
This self-catering property sleeps seven guests and boasts a fully equipped kitchen, private patio with ocean views, swimming pool, jacuzzi, free Wi-Fi, and access to a washing machine.
Beacon Reef 301 - Islamorada, FL
Islamorada, FL
08/09 – 06/10
A$334/nighttotal: A$9352 (28 )

Beacon Reef 301

2 2
house , Islamorada, Village of Islands
Beacon Reef 301 is a beachfront property situated in Islamorada, Village of Islands, located 2.1 kilometres from the Theater of the Sea and 2.4 kilometres from Upper Matecumbe Key.
This holiday home offers accommodation for up to seven guests, featuring two bedrooms and two bathrooms, with amenities including a Jacuzzi, spa, fitness centre, water park, garden, and complimentary WiFi.

Frequently asked questions about villa rentals in Islamorada, FL

Destinations nearby

Best Islamorada, FL villas and holiday homes with air conditioning

Isla Lychee: Boutique Resort, Free Boat Dockage Sep-oct Only! - Islamorada, FL
10 7 reviews
Islamorada, FL
17/10 – 26/10
A$802/nighttotal: A$7218 (9 )

Isla Lychee: Boutique Resort, Free Boat Dockage Sep-oct Only!

3 6
house , Islamorada, Village of Islands
Isla Lychee: Little Basin Villas, a waterfront boutique resort in Matecumbe, Islamorada, is within walking distance of the Islamorada Brewery & Distillery and Keys History & Discovery Centre, and less than 2.4km from the History of Diving Museum.
This 156 square metre, three-bedroom villa sleeps six, offering four bathrooms, a fully equipped kitchen, free Wi-Fi, a private balcony, and access to on-site barbecue grills.
Heavenly Hideaway Ocean Pointe 3306 - Islamorada, FL
10 1 review
Islamorada, FL
28/06 – 01/07
A$473/nighttotal: A$1419 (3 )

Heavenly Hideaway Ocean Pointe 3306

2 5
house , Tavernier
Heavenly Hideaway Ocean Pointe 3306, a two-bedroom house in Tavernier, Florida, offers ocean views and is a short walk (less than 2km) from Harry Harris Park Beach, with Pigeon Key (4.5km), Windley Key Fossil Reef Geological State Park (14.3km), and John Pennekamp Coral Reef State Park (17.7km) also within easy reach.
This 80 square metre property sleeps eight guests and boasts a fully equipped kitchen, air conditioning, a swimming pool, jacuzzi, garden, parking, and in-unit laundry facilities; perfect for a self-catering holiday.
Isla Mamey: Boutique Resort, Free Boat Dockage Sept-oct Only! - Islamorada, FL
9.8 8 reviews
Islamorada, FL
30/07 – 06/08
A$931/nighttotal: A$6517 (7 )

Isla Mamey: Boutique Resort, Free Boat Dockage Sept-oct Only!

3 2
house , Islamorada, Village of Islands
Isla Mamey: Waterfront Boutique Resort, in Matecumbe, Islamorada, offers a three-bedroom villa a short walk from Matecumbe United Methodist Church and Florida Keys Brewing Co., and within 1.6km of the Morada Way Arts & Cultural District and Hurricane Monument.
This 156 square metre, smoke-free property sleeps six, boasting a private pool, fully equipped kitchen, free Wi-Fi, and outdoor amenities including a garden and barbecue grills.
House ∙ 3 Bedrooms ∙ 5 Guests - Islamorada, FL
Islamorada, FL
08/09 – 06/10
A$341/nighttotal: A$9548 (28 )

House ∙ 3 Bedrooms ∙ 5 Guests

3 2
house , Islamorada, Village of Islands
This bayside villa in Islamorada, Village of Islands, offers a private retreat within 1 kilometre of the Publix Shopping Centre and downtown amenities, ideal for those seeking a tranquil escape with convenient access to local attractions. This three-bedroom, two-bathroom holiday home accommodates up to five guests and features a private heated and chilled swimming pool, a spacious garden with mature trees, and ample parking, including space for a boat trailer, making it perfect for fishing and boating enthusiasts.

Best Islamorada, FL villas and holiday homes with jacuzzi

Beacon Reef 503 - Islamorada, FL
Islamorada, FL
08/09 – 06/10
A$356/nighttotal: A$9968 (28 )

Beacon Reef 503

2 2
house , Islamorada, Village of Islands
Beacon Reef 503, a beachfront property in Islamorada, Village of Islands, is a short walk from the History of Diving Museum and within 2 km of Windley Key Fossil Reef Geological State Park and Upper Matecumbe Key.
This two-bedroom, two-bathroom apartment sleeps seven guests and boasts a fully equipped kitchen, Jacuzzi, private balcony with sea views, fitness centre, and on-site parking, plus free Wi-Fi and access to a spa.
Sunrise Penthouse 3316 Ocean Pointe 1br 2ba - Islamorada, FL
Islamorada, FL
09/10 – 12/10
A$379/nighttotal: A$1137 (3 )

Sunrise Penthouse 3316 Ocean Pointe 1br 2ba

1 2
house , Tavernier
This holiday cottage in Tavernier is a 13-minute walk from Harry Harris Park Beach, 5 kilometres from Pigeon Key, and 14.5 kilometres from the Theatre of the Sea.
This 85 square metre holiday home accommodates up to 7 guests and features air conditioning, a hot tub, a garden, parking, and a fully equipped kitchen with a dishwasher and microwave.
Beacon Reef 501 - Islamorada, FL
Islamorada, FL
08/09 – 06/10
A$327/nighttotal: A$9156 (28 )

Beacon Reef 501

2 2
house , Islamorada, Village of Islands
Beacon Reef 501 is a beachfront villa in Islamorada, Village of Islands, situated 2.1 kilometres from the Theater of the Sea and 2.4 kilometres from Upper Matecumbe Key.
This two-bedroom villa accommodates up to seven guests and features a jacuzzi, spa, fitness centre, water park access, and complimentary WiFi, with sea views from the terrace.
Islamorada | Maison Residences - Islamorada, FL
10 9 reviews
Islamorada, FL
17/10 – 26/10
A$1723/nighttotal: A$15507 (9 )

Islamorada | Maison Residences

1 6
house , Islamorada, Village of Islands
This luxurious four-bedroom Maison Residences apartment in Islamorada, Florida Keys, boasts direct access to a private beach and is conveniently located near various local attractions.
The 290 square metre property features an open-plan layout, accommodating up to ten guests, and includes a private pool, jacuzzi, and access to a 107-metre dock, perfect for water activities.
©2026 cozycozy.com