Vacation Rentals in Islamorada, FL

1696 available vacation rental offers

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

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.

Brand New Private Studio Cabana Style, Keylargo Tavernier - Islamorada, FL
8.0 3 reviews

Brand New Private Studio Cabana Style, Keylargo Tavernier

studio, Tavernier
This brand new, cabana-style studio in Tavernier is situated 5.1 kilometres from Pigeon Key and 11.1 kilometres from Windley Key, offering a quiet retreat with free private parking and WiFi.
This air-conditioned accommodation accommodates up to three guests, featuring a separate bedroom, a fully equipped kitchen, and direct access to a terrace, with nearby attractions including Theatre of the Sea (12.1 km) and John Pennekamp State Park (17.7 km).
Ocean View Condo With Balcony/marina View - Islamorada, FL
9.2 360 reviews

Ocean View Condo With Balcony/marina View

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 the beautiful sands and turquoise waters of the Florida Keys. It has received excellent ratings for location, cleanliness, and user experience.
The 80 square metre property can accommodate up to six guests and features a fully equipped kitchen, a private balcony, a swimming pool, a Jacuzzi, a sauna, a tennis court, and free parking. Guests can also enjoy the outdoor barbecue grills and relax in the spa tub after a day exploring the Keys.
Tikibar With Tv &Stereo, Privatespa, Heated Pool, Hammock,sups, Kayaks,bikes,fp - Islamorada, FL
10 181 reviews

Tikibar With Tv &Stereo, Privatespa, Heated Pool, Hammock,sups, Kayaks,bikes,fp

apartment, Islamorada, Village of Islands
This family-friendly holiday home is located in Islamorada, just a short drive from the San Pedro Underwater Archaeological Preserve State Park, Robbie’s of Islamorada, and Indian Key Historic State Park, all within a 3 km radius. This property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
This two-bedroom dwelling can comfortably accommodate up to five guests. The property offers a range of amenities, including a swimming pool, a Jacuzzi, a terrace, a garden, a spa, and concierge services, as well as a tennis court and free parking.
4 Bedroom Oceanview Villa  Capacity 8 - Islamorada, FL
10 5 reviews

4 Bedroom Oceanview Villa Capacity 8

house, Islamorada, Village of Islands
This Islamorada waterfront villa offers spectacular ocean views and direct beach access within the Village of Islands, conveniently located near local attractions.
The four-bedroom, four-bathroom property sleeps eight guests and boasts a private marina (size restrictions apply), a swimming pool, jacuzzi, fitness centre, and access to on-site activities including yoga, aqua aerobics, pickleball, and bocce ball, plus the Ocean House Bar and Spa.

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.

Beachside Unit With Free Breakfast - Islamorada, FL
10 1 review

Beachside Unit With Free Breakfast

resort, Islamorada, Village of Islands
This Islamorada beachfront apartment offers direct beach access, a short walk (less than 1 km) from the Theatre of the Sea and near Windley Key Fossil Reef and Lignum Vitae Key Botanical State Parks.
The 37 square metre self-catering flat sleeps four guests, boasting two queen beds, a sofa bed, a kitchenette, a balcony, and access to an on-site heated pool, kayaks, paddleboards, bike rentals, daily continental breakfast and housekeeping.
Oceanfront Condo With Beach Access, Pool, Balcony, & Tennis - Marina Available - Islamorada, FL
9.2 104 reviews

Oceanfront Condo With Beach Access, Pool, Balcony, & Tennis - Marina Available

apartment, Tavernier
This oceanfront condominium in Tavernier offers direct water access and sweeping sea views, situated approximately 11 kilometres from the island's main attractions and near landmarks such as the Hurricane Monument and Caribbean Club Bar.
This 69 square metre apartment accommodates up to six guests, featuring two bedrooms and two bathrooms, a fully equipped kitchen with a dishwasher, air conditioning, a private deck, and shared amenities including a swimming pool and tennis court, with opportunities for jet skiing, kayaking, and scuba diving nearby.
Stay Beachside: Ground Floor Studio With Gorgeous Ocean Views - Islamorada, FL
9.6 46 reviews

Stay Beachside: Ground Floor Studio With Gorgeous Ocean Views

studio, Islamorada, Village of Islands
This smoke-free apartment is situated in Lower Matecumbe Beach, a short 4.3 kilometre walk from Sunset Drive Beach and Anne's Beach, with San Pedro Underwater Archaeological Preserve State Park being 4.3 kilometres away. The property has received excellent user ratings, making it a popular choice for travellers. This apartment features one bedroom and can accommodate up to three guests. Amenities include a fully equipped kitchen, two bathrooms, a washing machine, free Wi-Fi, a private balcony, parking, games, a library of books, and a swimming pool.
Cheeca Lodge & Spa - Islamorada, FL
8.8 219 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.

Frequently asked questions about holiday rentals in Islamorada, FL

Popular destinations

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.

Ocean Front 1/1,amazing Ocean/marina Views,tavernier/key Largo Fl. Florida Keys - Islamorada, FL
10 293 reviews

Ocean Front 1/1,amazing Ocean/marina Views,tavernier/key Largo Fl. Florida Keys

apartment, Tavernier
This waterfront apartment is situated in Tavernier, just a 1.6km walk from Baker's Cay Resort Beach and Harry Harris Park, offering a peaceful and scenic setting. The property enjoys an excellent user rating, making it a popular choice for travellers.
The apartment has one bedroom and one bathroom, comfortably accommodating up to four guests. The property offers a range of amenities, including a private pool, a spa, a tennis court, and a garden, ensuring a relaxing and enjoyable stay.
Ragged Edge Resort & Marina - Islamorada, FL
9.5 374 reviews

Ragged Edge Resort & Marina

resort, Islamorada, Village of Islands
Ragged Edge Resort & Marina is located in Islamorada, just a short drive from Windley Key and Upper Matecumbe Key, offering easy access to the area's natural beauty. The resort has consistently received excellent ratings for location, cleanliness, and overall experience.
The accommodation features a mix of rooms and suites, some with balconies offering sea views. Guests can enjoy amenities such as a swimming pool, terrace, free bikes, a communal grill, and free Wi-Fi.
Pines & Palms Resort - Islamorada, FL
9.2 2315 reviews

Pines & Palms Resort

resort, Islamorada, Village of Islands
Pines & Palms Resort is located in Islamorada, close to Alligator Reef and less than a mile from Miss Islamorada Fishing Charters, with John Pennekamp Coral Reef State Park a short 30-minute drive away. This resort has very good user ratings, an excellent location rating and a very good cleanliness rating.
The resort offers a range of apartments with full kitchens and ocean views. Guests can enjoy a private beach, an oceanfront pool, a Tiki Bar, kayak and bike rentals, private boat docks, a covered cabana with a barbecue grill, and premium sport fishing areas.
Bungalow #3 - 2 Bed/1 Bath & Pool In Islamorada - Islamorada, FL
9.6 85 reviews

Bungalow #3 - 2 Bed/1 Bath & Pool In Islamorada

apartment, Islamorada, Village of Islands
This charming cottage is situated in Islamorada, just a short distance from the Village of Islands' centre, offering easy access to fishing piers and the lively downtown area. It has received excellent ratings for location, cleanliness, and user experience, making it a great choice for a relaxing getaway.
The cottage comfortably sleeps four guests in two bedrooms and one bathroom. Guests can enjoy a range of amenities, including a private backyard, a community pool, a fully equipped kitchen, a washer and dryer, a private porch, and bikes for exploring the area.

Best Islamorada, FL holiday rentals with parking

Amazing Ocean View At Ocean Pointe W/heated Pool - Islamorada, FL
9.6 56 reviews

Amazing Ocean View At Ocean Pointe W/heated Pool

apartment, Tavernier
This oceanfront apartment is located in Tavernier, just a short distance from the Florida Keys Dive Center and Bluefin Rock Harbor Marina, offering easy access to the area's attractions and activities. It has received excellent ratings from previous guests, highlighting its comfortable and convenient features.
The two-bedroom, two-bathroom apartment spans 78 square metres and comfortably accommodates up to six guests. It offers a range of amenities, including a swimming pool, a jacuzzi, a terrace, and a garden, as well as a fully equipped kitchen and air conditioning.
Beach View Unit In Islamorada! Pets Allowed, Parking, Pool & Free Breakfast! - Islamorada, FL
8.6 29 reviews

Beach View Unit In Islamorada! Pets Allowed, Parking, Pool & Free Breakfast!

apartment, Islamorada, Village of Islands
This Islamorada beachfront apartment, part of a pet-friendly resort, offers direct beach access and partial ocean views from its 28-square-metre (301 sq ft) balcony, conveniently located near the Islamorada Brewery & Distillery and Indian Key Historic State Park.
The self-catering flat features two queen beds sleeping four, a fully equipped kitchenette including a fridge, microwave, and dishwasher, plus daily housekeeping and continental breakfast; on-site amenities include a heated pool, kayaks, paddleboards, and bike rentals.
Keys Studio At Caloosa Cove - Islamorada, FL
8.0 1 review

Keys Studio At Caloosa Cove

apartment, Islamorada, Village of Islands
This studio apartment is situated in Islamorada, Village of Islands, offering direct access to oceanfront resort amenities and a 25-acre Founders Park with a saltwater swimming area, accessible via the Caloosa KeyCard.
Accommodating up to three guests, this first-floor unit features a queen bed and a twin sofa sleeper, a compact kitchen for light meal preparation, and offers full access to resort facilities including a heated swimming pool with ocean views, along with nearby recreational activities such as shuffleboard, pickleball, and tennis.
Convenient Location! 3 Units, Pool, Pet-friendly, Free Parking + Breakfast! - Islamorada, FL
No reviews

Convenient Location! 3 Units, Pool, Pet-friendly, Free Parking + Breakfast!

apartment, Islamorada, Village of Islands
This Islamorada beachfront apartment, part of a hotel complex, offers direct access to a private beach and boat ramp (fees apply), with the History of Diving Museum and Keys History & Discovery Centre nearby (distances unspecified).
The 75-square-metre property comprises three uniquely decorated rooms, each with two queen-size beds, sleeping up to 12 guests, and includes a fully equipped kitchen, three bathrooms, a swimming pool, concierge service, parking, and daily continental breakfast.

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.

Cheeca Lodge & Spa - Islamorada, FL
9.0 1983 reviews

Cheeca Lodge & Spa

resort, 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.

Islander Resort - Islamorada, FL
9.1 3922 reviews

Islander Resort

resort, Islamorada, Village of Islands
360 Degree Waterview Houseboat - Islamorada, FL
9.9 388 reviews

360 Degree Waterview Houseboat

boat, Islamorada, Village of Islands
Malayan Palm East 1 Bedroom, 1 Bath Garden View - Islamorada, FL
10 177 reviews

Malayan Palm East 1 Bedroom, 1 Bath Garden View

apartment, Islamorada, Village of Islands
Cheeca Lodge & Spa - Islamorada, FL
8.8 219 reviews

Cheeca Lodge & Spa

resort, 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.

Houseboat 2bd, 1 Bath Private Keys Cottage Mullet - Islamorada, FL
9.7 416 reviews

Houseboat 2bd, 1 Bath Private Keys Cottage Mullet

boat, Islamorada, Village of Islands
Premium Suites W/ Kitchenette! Pool, Breakfast! - Islamorada, FL
No reviews

Premium Suites W/ Kitchenette! Pool, Breakfast!

resort, Islamorada, Village of Islands
Waterfront Home In The Heart Of The Fishing Capital Of The World. - Islamorada, FL
10 88 reviews

Waterfront Home In The Heart Of The Fishing Capital Of The World.

apartment, Islamorada, Village of Islands
Paradise Palms Ocean Pointe 1206 - Islamorada, FL
9.5 18 reviews

Paradise Palms Ocean Pointe 1206

house, Tavernier

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.

Saltair Loft Ocean Pointe 2 Br 2 Ba 1411 - Islamorada, FL
10 2 reviews

Saltair Loft Ocean Pointe 2 Br 2 Ba 1411

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

Spacious End Suite With Atlantic Views

apartment, Tavernier
Sea View And Sunrise Ocean Pointe 2412 2ba/2br - Islamorada, FL
9.6 89 reviews

Sea View And Sunrise Ocean Pointe 2412 2ba/2br

apartment, Tavernier
Snorkel Legendary Reefs - Relax Poolside | Op 2315 - Islamorada, FL
9.8 1818 reviews

Snorkel Legendary Reefs - Relax Poolside | Op 2315

apartment, Tavernier
©2026 cozycozy.com