Places to stay in Islamorada, FL

2091 available accommodation offers

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

2091 Best places to stay in Islamorada, FL

Best Islamorada, FL lodgings with a pool

Among the 2091 accommodations in Islamorada, FL, here are the 4 best ones with a pool

Luxury Waterfront Retreat In Islamorada (28 Days) - Islamorada, FL
No reviews

Luxury Waterfront Retreat In Islamorada (28 Days)

apartment, Islamorada, Village of Islands
This five-bedroom, three-bathroom Islamorada waterfront property offers a prime canal-side location within the Village of Islands, featuring a private 70-metre dock and easy access to local fishing, boating, diving, and dining establishments. This substantial residence accommodates up to ten guests, boasting a private swimming pool, a rooftop terrace with canal views, a private elevator, and extensive indoor/outdoor living spaces, ideal for extended stays of 28 days or more.
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.
Anglers Reef Is Oceanfront, Blue Marlin House2/2.5 - Islamorada, FL
9.7 42 reviews

Anglers Reef Is Oceanfront, Blue Marlin House2/2.5

apartment, Islamorada, Village of Islands
The Blue Marlin house, a Key West-style property in Islamorada's Anglers Reef neighbourhood, is situated approximately 0.03 kilometres from an oceanfront pool and dock (fee applies).
This two-bedroom, two-bathroom villa sleeps six guests and offers a fully equipped kitchen, air conditioning, a private garden, swimming pool access, complimentary paddleboards and kayaks, and proximity to a second, rentable house ideal for larger groups.
Renovated Anglers Reef 2br + Sleeper + Ocean Views - Islamorada, FL
10 14 reviews

Renovated Anglers Reef 2br + Sleeper + Ocean Views

apartment, Islamorada, Village of Islands
This two-bedroom holiday villa is situated in the gated community of Anglers Reef, just a short distance from the heart of Islamorada, offering easy access to the village's restaurants, shops and attractions. Anglers Reef provides a tranquil and secluded setting, with its own private beaches and marina.
The spacious apartment can accommodate up to six guests and features a well-equipped kitchen, two bathrooms and a private balcony with ocean views. Guests can enjoy the community's amenities, including a swimming pool, jacuzzi, and kayaks, or simply relax in the tranquil garden.

Best family friendly Islamorada, FL lodging

Among the 2091 accommodations in Islamorada, FL, here are the 4 best for families

Anglers Reef Islamorada, Bikes,kayak,paddle Boards Dock Available-pool - Islamorada, FL
9.8 113 reviews

Anglers Reef Islamorada, Bikes,kayak,paddle Boards Dock Available-pool

apartment, Islamorada, Village of Islands
This two-bedroom apartment is located in the Anglers Reef community in Islamorada, just a short distance from local shops, bars, and restaurants, and within easy reach of the famous Islamorada "sandbar" and Alligator Reef. The apartment has received excellent ratings from previous guests and offers a peaceful, gated oasis with minimal traffic and stunning ocean views.
The 128 square metre apartment can accommodate up to six guests and features a spacious open layout, granite countertops, updated appliances, and a comfortable king-size bed in the master bedroom. Guests can enjoy a range of amenities, including a private swimming pool, boat docks, private beaches, three flat-screen TVs with Hulu and Netflix, complimentary wireless internet, a Keurig coffee pot, a full-size washer and dryer, and a fully equipped kitchen.
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.
Cheeca Lodge & Spa - Islamorada, FL
9.1 1683 reviews

Cheeca Lodge & Spa

resort, Islamorada, Village of Islands
Cheeca Lodge & Spa, a resort in Islamorada, Village of Islands, offers direct access to a nearby beach, ideal for exploring the coastal beauty of the Florida Keys.
This establishment provides a comprehensive range of amenities including an on-site spa, swimming pool with a poolside bar, fitness centre, and convenient parking, with express check-in/check-out services available.
Oceanfront Islamorada Townhome With Pool & Dock - Islamorada, FL
10 8 reviews

Oceanfront Islamorada Townhome With Pool & Dock

house, Islamorada, Village of Islands
This three-bedroom, three-bathroom house in Islamorada, Village of Islands, offers comfortable accommodation for up to eight guests and includes a swimming pool, garden, and parking.
The property boasts a fully equipped kitchen, air conditioning, and internet access, providing a relaxing base for exploring the Florida Keys, although precise distances to local attractions require further clarification.

Frequently asked questions about accommodations in Islamorada, FL

Popular destinations

Best Islamorada, FL accommodations with a balcony

139 M² House ∙ 3 Bedrooms ∙ 8 Guests - Islamorada, FL
No reviews

139 M² House ∙ 3 Bedrooms ∙ 8 Guests

house, Islamorada, Village of Islands
House listing for 8 guests. You will be based in Islamorada, Village of Islands.
Services and facilities: a kitchen, air conditioning and a fridge. This house also has a terrace!
Island Time - Key Largo! Luxurious 2br/2ba! - Islamorada, FL
9.0 100 reviews

Island Time - Key Largo! Luxurious 2br/2ba!

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.
Drop Anchor Resort & Marina - Islamorada, FL
8.7 1701 reviews

Drop Anchor Resort & Marina

glamping, Islamorada, Village of Islands
This mobile home is located in Islamorada, just a short walk from Theater of the Sea and a short drive from Indian Key Historic Park, offering a convenient base for exploring the area. The mobile home has received very good ratings for cleanliness and user experience, and the location itself is rated excellent.
The mobile home features a kitchen with a fridge and microwave, air conditioning, and a terrace or balcony. Guests have access to a range of amenities, including a swimming pool, a bar, a tennis court, and a garden, as well as kayaks, paddleboards and Wi-Fi.
Marina To Ocean View Key Largo Ocean Pointe 5308 - Islamorada, FL
9.4 71 reviews

Marina To Ocean View Key Largo Ocean Pointe 5308

apartment, Tavernier
This Tavernier waterfront apartment, situated 1.1 kilometres from Harry Harris Park and within 4.8 kilometres of Mariners Hospital and the Florida Keys Dive Centre, offers stunning views.
The 84 square metre property features three bedrooms, two bathrooms, a sofa bed for a total guest capacity of four, and includes a fully equipped kitchen, private balcony, swimming pool, jacuzzi, and parking.

Best Islamorada, FL accommodations with a kitchen

Florida Keys Oasis - Islamorada, FL
No reviews

Florida Keys Oasis

apartment, Islamorada, Village of Islands
This Islamorada apartment rental, situated in the Village of Islands, is conveniently located near Snake Creek, offering easy access to the bay and ocean for fishing and water sports, and is approximately 32km from a popular Tiki bar sandbar and 145km from Miami.
The four-bedroom, two-bathroom dwelling sleeps up to ten guests and features a private dock (35' or 70' option), outdoor gas grill, bait freezer, storage shed, and optional exclusive use of the entire property including a tiki hut and fire pit; on-site assistance is also provided.
3 Bedroom Home W/ Pool, Hot Tub, & Boat Slip. - Islamorada, FL
10 2 reviews

3 Bedroom Home W/ Pool, Hot Tub, & Boat Slip.

apartment, Islamorada, Village of Islands
This Islamorada waterfront property, situated in the Venetian Shores community, offers convenient access to local amenities and attractions in the Village of Islands.
The two-storey house boasts three bedrooms, two bathrooms, sleeping six guests, and features a private pool, hot tub, and boat slip within a community marina, alongside a fully equipped kitchen and laundry facilities.
Islamorada Bungalow 4 - Islamorada, FL
9.7 94 reviews

Islamorada Bungalow 4

bungalow, Islamorada, Village of Islands
This charming bungalow is situated just a short distance from the lively downtown area of Islamorada, offering easy access to the renowned fishing piers and the scenic Overseas Highway. The property has consistently received excellent ratings for location, cleanliness, and overall guest experience.
The cottage comfortably accommodates up to four guests across two bedrooms and one bathroom, spanning 88 square metres. Guests can enjoy a private backyard and porch, a community heated pool, a fully equipped kitchen with modern appliances, a washer and dryer, complimentary bicycles, and a security camera for added peace of mind.
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.
©2026 cozycozy.com