Holiday Rentals in Islamorada, FL

1414 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Islamorada, FL holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

1414 Holiday rentals and Airbnb in Islamorada, FL

Best family friendly Islamorada, FL holiday rentals

Among the 1414 accommodations in Islamorada, FL, here are the 4 best family friendly rentals

Starfish -1 Bedroom 1 Bath Apartment With Full Kitchen In Islamorada, Florida. - Islamorada, FL
9.4 3 reviews
Islamorada, FL
01/01 – 31/05
121 €/nighttotal: 18150 € (150 )

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

1 2
apartment , Islamorada, Village of Islands
This one-bedroom apartment is located in Plantation Key Colony, a neighbourhood in Tavernier, just 160 kilometres from Miami International Airport and a short distance from the attractions of the Upper Keys. It has received excellent user ratings, making it a popular choice for travellers.
The apartment has a modern and comfortable interior, ideal for families of up to four people. It offers a range of amenities including internet access, a kitchen with a fridge and microwave, air conditioning, a terrace or balcony, and a spa. Guests can enjoy a peaceful retreat while having easy access to a variety of activities such as fishing, diving, exploring museums, shopping, and beaches.
Single Family Home In Angler's Reef Gated Community, Beaches,marina,heated Pool - Islamorada, FL
9.8 100 reviews
Islamorada, FL
27/06 – 04/07
385 €/nighttotal: 2695 € (7 )

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

2 2
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.
Key Largo-islamorada Area-1 Br, 1 Bath -Privately Owned Condo -Fab Reviews! - Islamorada, FL
10 193 reviews
Islamorada, FL
19/08 – 21/08
249 €/nighttotal: 498 € (2 )

Key Largo-islamorada Area-1 Br, 1 Bath -Privately Owned Condo -Fab Reviews!

1 4
apartment , Tavernier
This Tavernier apartment is situated just 3 kilometres from Mariners Hospital and Florida Keys Dive Center, with Baker's Cay Resort Beach and Harry Harris Park within a 1.5 kilometre walk. It has received excellent user ratings and is perfect for those looking for a comfortable and convenient base to explore Tavernier.
This one-bedroom, one-bathroom apartment is 56 square metres in size and can comfortably accommodate up to four guests. The apartment offers a range of amenities including a fully equipped kitchen, a private balcony, a swimming pool, a jacuzzi, a tennis court, and free Wi-Fi, all within a smoke-free environment.
House ∙ 2 Bedrooms ∙ 4 Guests - Islamorada, FL
Islamorada, FL
27/06 – 04/07
346 €/nighttotal: 2422 € (7 )

House ∙ 2 Bedrooms ∙ 4 Guests

2 2
house , Islamorada, Village of Islands
This oceanfront dwelling is located within the secure Anglers Reef community in Islamorada, offering direct access to the Florida Keys' celebrated sport-fishing and marine life, with world-class snorkelling, scuba diving, dining, and shopping opportunities approximately 1.6 kilometres away.
This family-friendly villa accommodates up to four guests, featuring two bedrooms and two bathrooms, a well-equipped kitchen with modern appliances, air conditioning, a swimming pool, a terrace, garden, and parking, with optional dock space available for rent for vessels up to 9.45 metres.

Best Islamorada, FL holiday rentals with a pool

Among the 1414 accommodations in Islamorada, FL, here are the 4 best rentals with a pool

Ocean Oasis At Ocean Pointe - Islamorada, FL
8.3 5658 reviews
Islamorada, FL
19/08 – 21/08
211 €/nighttotal: 422 € (2 )

Ocean Oasis At Ocean Pointe

1 4
house , Tavernier
Ocean Oasis at Ocean Pointe is situated in Tavernier, a short walk from Harry Harris Park Beach and a short drive from Pigeon Key, offering a tranquil escape in a beautiful location. The property has received very good ratings for its location, cleanliness and overall experience.
This holiday home features a well-equipped kitchen, a private balcony with sea views and a private beach for your enjoyment. Guests can also relax in the hot tub, swim in the pool, or enjoy the garden and outdoor play equipment.
Get Ready For Blissful Getaway! 2 Relaxing Units, Onsite Pool, Free Breakfast - Islamorada, FL
Islamorada, FL
03/08 – 05/08
431 €/nighttotal: 862 € (2 )

Get Ready For Blissful Getaway! 2 Relaxing Units, Onsite Pool, Free Breakfast

2 5
apartment , Islamorada, Village of Islands
This Islamorada apartment complex offers direct beach access in the centre of Islamorada, conveniently located near the History of Diving Museum and Keys History & Discovery Centre.
The self-catering property boasts two bedrooms, two bathrooms, and sleeps up to eight guests across a 54 square metre floor area, featuring a heated pool, barbecue facilities, and kayak/paddleboard hire.
1br Condo W/ Pool, Beach, Near Coral Reef Park - Islamorada, FL
Islamorada, FL
19/08 – 21/08
211 €/nighttotal: 422 € (2 )

1br Condo W/ Pool, Beach, Near Coral Reef Park

1 4
apartment , Tavernier
This two-bedroom holiday flat is situated in Tavernier, offering direct oceanfront access and being just a short drive to attractions in Key Largo and Islamorada, including the renowned John Pennekamp Coral Reef State Park.
This 56 square meter residence accommodates up to four guests, featuring a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a swimming pool, and on-site parking, with access to resort amenities such as a Jr. Olympic pool, hot tub, and tennis courts.
Ocean Pointe 2309 - Islamorada, FL
8.8 10 reviews
Islamorada, FL
03/08 – 05/08
317 €/nighttotal: 634 € (2 )

Ocean Pointe 2309

2 5
house , Tavernier
Ocean Pointe 2309, a beachfront property in Tavernier, Florida, offers ocean views and is a 14-minute walk from Harry Harris Park Beach and 4.8km from Pigeon Key.
This two-bedroom, two-bathroom house boasts 85 square metres of floor space, sleeps up to 11 guests, and includes a private pool, bar, free Wi-Fi, and parking.

Frequently asked questions about holiday rentals in Islamorada, FL

Destinations nearby

Best Islamorada, FL holiday rentals with a balcony

Updated Ocean-view Condo With 2 Balconies, Pool, Hot Tub, W/d, & Ac - Islamorada, FL
9.8 46 reviews
Islamorada, FL
03/08 – 05/08
322 €/nighttotal: 644 € (2 )

Updated Ocean-view Condo With 2 Balconies, Pool, Hot Tub, W/d, & Ac

2 5
apartment , Tavernier
This oceanfront condominium in Tavernier offers direct sea views from two private balconies and is a short walk to Ocean Point's private beach, with John Pennekamp Coral Reef State Park located 16 kilometres away.
This 78 square metre apartment, accommodating up to six guests, features a well-equipped kitchen, air conditioning, a private washer/dryer, and access to resort amenities including a swimming pool and hot tub, with nearby activities such as deep-sea fishing and water sports.
Spacious Newly Renovated 3 Bedroom, 2 Bath Home On The Canal In Islamorada, Fl - Islamorada, FL
Islamorada, FL
01/01 – 28/02
288 €/nighttotal: 16704 € (58 )

Spacious Newly Renovated 3 Bedroom, 2 Bath Home On The Canal In Islamorada, Fl

3 2
apartment , Islamorada, Village of Islands
This three-bedroom property in Tavernier, Islamorada, Village of Islands, is situated within 1 kilometre of the Florida Keys Dive Centre and Mangrove Marina, with John Pennekamp Coral Reef State Park and the Morada Way Arts & Cultural District also close by.
This apartment accommodates six guests and features air conditioning, a terrace, parking, and two bathrooms, offering comfortable sleeping arrangements with a king, queen, and full bed for your stay.
Charming & Tranquil Condo At Ocean Pointe-sleeps 6 - Islamorada, FL
10 81 reviews
Islamorada, FL
26/06 – 30/06
397 €/nighttotal: 1588 € (4 )

Charming & Tranquil Condo At Ocean Pointe-sleeps 6

2 3
apartment , Tavernier
This family-friendly apartment is located in Tavernier, a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the area's attractions. It has received excellent user ratings, making it a popular choice for travellers.
This 88 square metre apartment comfortably accommodates up to six guests in its two bedrooms and two bathrooms. You can enjoy a range of amenities, including a private pool, a tennis court, a garden, and a terrace, perfect for relaxing and enjoying the Florida sunshine.
Island Time | Ocean Pointe 1207 | Oceanfront 2br Condo In Key Largo - Islamorada, FL
9.0 98 reviews
Islamorada, FL
17/07 – 24/07
257 €/nighttotal: 1799 € (7 )

Island Time | Ocean Pointe 1207 | Oceanfront 2br Condo In Key Largo

2 3
apartment , Tavernier
This two-bedroom apartment in Tavernier is conveniently located within a 15-minute walk of Baker's Cay Resort Beach and Harry Harris Park, offering easy access to Tavernier's laid-back charm. The apartment has received excellent user and location ratings and a very good cleanliness rating.
The apartment comfortably accommodates up to six guests and features a fully equipped kitchen, two bathrooms, a washing machine, and a coffee/tea maker. Enjoy relaxing amenities like a TV, internet access, and a terrace/balcony, as well as the convenience of parking and an elevator.

Best Islamorada, FL holiday rentals with parking

Clean, Comfortable, & Centrally Located 1/1 - Islamorada, FL
10 1 review
Islamorada, FL
01/01 – 28/02
162 €/nighttotal: 9396 € (58 )

Clean, Comfortable, & Centrally Located 1/1

1 2
apartment , Islamorada, Village of Islands
This canal-side flat in Tavernier, Islamorada, is less than 500 metres from waterfront dining, shops, and attractions such as the Florida Keys Wild Bird Centre.
This one-bedroom, one-bathroom flat accommodates up to four guests and features a king-size bed, a large shower, a terrace, a garden with a grill and sunset views, a 50-foot dock, a dockside Tiki Hut, and an eight-person hot tub.
Friends' Getaway 2br W/ Ocean View, Pool & Beach - Islamorada, FL
Islamorada, FL
19/08 – 21/08
257 €/nighttotal: 514 € (2 )

Friends' Getaway 2br W/ Ocean View, Pool & Beach

2 4
apartment , Tavernier
This Tavernier oceanfront apartment, near Key Largo and Islamorada, offers private beach access and proximity to attractions such as Jimmy Johnson's Big Chill.
The 79-square-metre (850 sq ft) property sleeps six, featuring three bedrooms, two bathrooms, a fully equipped kitchen (fridge, microwave, dishwasher), a terrace, swimming pool access, and parking; resort amenities include a junior Olympic-sized pool, hot tub, and tennis courts.
Fish, Dive, Snorkel & Unwind-coral Reefs, Pool, Pickleball & Onsite Bar - Islamorada, FL
9.7 127 reviews
Islamorada, FL
03/08 – 05/08
358 €/nighttotal: 716 € (2 )

Fish, Dive, Snorkel & Unwind-coral Reefs, Pool, Pickleball & Onsite Bar

2 5
apartment , Tavernier
This waterfront apartment is situated in Tavernier, just a 2.4km walk from Baker's Cay Resort Beach and Harry Harris Park, offering a peaceful and scenic location close to the area's attractions. The property has consistently received excellent ratings for its cleanliness, location, and overall experience.
The apartment spans 87 square metres and comfortably accommodates up to six guests in its two bedrooms and two bathrooms. It features a range of amenities, including a swimming pool, jacuzzi, tennis court, and a fully equipped kitchen, making it ideal for families or groups seeking a relaxing and enjoyable stay.
Lovely 2-bedroom House In Ocean Front Resort. - Islamorada, FL
Islamorada, FL
01/01 – 31/05
319 €/nighttotal: 47850 € (150 )

Lovely 2-bedroom House In Ocean Front Resort.

2 2
apartment , Islamorada, Village of Islands
This Islamorada holiday home, part of the Sun Outdoors resort in the Seabreeze Trailer Park neighbourhood, offers convenient access to the Old Road Gallery and History of Diving Museum, within walking distance depending on location.
The 'Charming 2-bedroom House In Gorgeous Resort' sleeps six, featuring two bedrooms (one king, one double), two bathrooms with bidets, Wi-Fi, air conditioning, and access to resort amenities including two heated pools, a clubhouse, and a games lawn; John Pennekamp Coral Reef State Park and Jacob's Aquatic Centre are a short drive away.
©2026 cozycozy.com