Vacation rentals in Islamorada, FL

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Islamorada, FL vacation rentals
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Best Vacation rentals and Airbnb offers in Islamorada, FL

Best Islamorada, FL vacation rentals with a balcony

Key Lime Cottage In The Heart Of Islamorada - Islamorada, FL
10 5 reviews

Key Lime Cottage In The Heart Of Islamorada

house, Islamorada, Village of Islands
Key Lime Cottage, a two-bedroom Islamorada vacation home, is conveniently located 1.6 miles from Sea Oats Beach, 5.3 miles from Upper Matecumbe Key, and 8.4 miles from Windley Key.
This 530-square-foot rental boasts a private terrace, swimming pool, and fully equipped kitchen, accommodating up to nine guests and offering free on-site parking.
Ocean View Corner Penthouse Ocean Pointe 5416 - Islamorada, FL
9.9 191 reviews

Ocean View Corner Penthouse Ocean Pointe 5416

apartment, Tavernier
This penthouse apartment is located in Ocean Pointe Suites, midway between Key Largo and Islamorada in the Florida Keys, offering easy access to both towns and their attractions. The unit has received excellent ratings for location, cleanliness, and user experience.
This two-bedroom, two-bathroom vacation rental comfortably accommodates up to six guests. The apartment features a range of amenities, including a swimming pool, jacuzzi, tennis and pickleball courts, a private beach, a marina, a pool bar, and direct access to a nature preserve.
214 M² House ∙ 4 Bedrooms ∙ 10 Guests - Islamorada, FL
No reviews

214 M² House ∙ 4 Bedrooms ∙ 10 Guests

house, Islamorada, Village of Islands
This oceanfront house in Islamorada, Village of Islands, offers direct, unobstructed Atlantic views and a private oceanfront living experience on the Atlantic shoreline, with convenient access to Whale Harbor Channel.
This 2300 square foot home features 4 bedrooms, 3 bathrooms, and accommodates up to 10 guests, boasting a private coral rock boat basin, ocean access, outdoor shower, and opportunities for wildlife observation.
Amazing Ocean View At Ocean Pointe W/heated Pool - Islamorada, FL
9.6 57 reviews

Amazing Ocean View At Ocean Pointe W/heated Pool

apartment, Tavernier
This Tavernier apartment is located directly on the beach, within easy reach of the Florida Keys Dive Center and Bluefin Rock Harbor Marina. It boasts excellent user ratings, making it a popular choice for travelers.
This two-bedroom, two-bathroom condo offers 840 square feet of space, comfortably accommodating up to six guests. You'll enjoy amenities like a swimming pool, jacuzzi, terrace, garden, and parking, as well as access to a heated pool, picnic area, tennis/pickleball courts, and a marina within the Ocean Pointe community.

Our Favorite Family-Friendly Vacation Rentals in Islamorada, FL

Find the perfect family vacation rental or Airbnb in Islamorada, FL with plenty of room to spread out near local beaches.

Deja Blue Suite  [Ocean Pointe 1409] - Islamorada, FL
9.8 177 reviews

Deja Blue Suite [Ocean Pointe 1409]

apartment, Tavernier
This waterfront apartment is located in Tavernier, Florida, just a short walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the beautiful Florida Keys waters. The apartment consistently receives excellent ratings for its cleanliness, location, and overall experience.
This 2-bedroom, 2-bathroom apartment comfortably accommodates up to 6 guests in its 980 square feet of space. The apartment offers a range of amenities for a relaxing stay, including a swimming pool, a spa, a tennis court, and a garden, as well as a fully equipped kitchen and free WiFi.
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 two-bedroom, two-bathroom vacation rental in Islamorada's exclusive Anglers Reef neighborhood, is located approximately 100 feet from an oceanfront community pool.
This Key West-style home sleeps six, boasts a full kitchen with dishwasher, offers complimentary paddleboards, kayaks, and bicycles, and is near Islamorada's attractions and restaurants.
Isla Honeydew: 3 En-suite Bedrooms, Pool, Dock - Islamorada, FL
10 9 reviews

Isla Honeydew: 3 En-suite Bedrooms, Pool, Dock

house, Islamorada, Village of Islands
Isla Honeydew, a three-bedroom waterfront villa in Islamorada's Matecumbe district, is a short walk from the Islamorada Brewery & Distillery and Keys History & Discovery Center, and within 15 minutes of the History of Diving Museum.
This 1680-square-foot vacation home boasts four bathrooms, accommodates six guests, and features a private balcony, pool, dock, garden, and fully equipped kitchen with free WiFi.
Heart Of Islamorada ~ Private Boat Dockage - Islamorada, FL
9.9 36 reviews

Heart Of Islamorada ~ Private Boat Dockage

house, Islamorada, Village of Islands
This Islamorada boat rental is located in Coral Cove, a secluded community in Islamorada, within walking, biking, or paddling distance of the town center and less than a mile from restaurants, bars, and shops.
This 4-bedroom, 3-bathroom house comfortably accommodates up to 8 guests and offers a private boat dock, a heated plunge pool, and a golf cart rental option for easy exploration of the surrounding area.

Frequently Asked Questions about vacation rentals in Islamorada, FL

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Best Islamorada, FL vacation rentals with parking

360 Degree Waterview Houseboat - Islamorada, FL
9.9 391 reviews

360 Degree Waterview Houseboat

boat, Islamorada, Village of Islands
This unique houseboat is moored a half-mile off the coast of Islamorada, providing a secluded and immersive experience. It has earned excellent ratings for user experience, location, and cleanliness.
The houseboat features one bedroom and one bathroom, accommodating up to two guests. It includes a full kitchen, outdoor grill, and a rooftop deck, plus a 12-foot skiff, kayak, paddleboard, and snorkeling gear for exploring the waters of Islamorada.
Light, Bright & Nautical Condo At Ocean Pointe - Islamorada, FL
9.9 179 reviews

Light, Bright & Nautical Condo At Ocean Pointe

apartment, Tavernier
This waterfront condo in Tavernier is located just a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the beautiful Florida Keys. This rental has earned excellent ratings for its cleanliness, location, and overall user experience.
The 950-square-foot apartment comfortably sleeps four guests in its two bedrooms and two bathrooms. Enjoy swimming, relaxing in the Jacuzzi, grilling outdoors, and taking advantage of the tennis court, all while taking in the stunning waterfront views from your private balcony.
Oceanfront Studio In Islamorada, Behind Main House - Islamorada, FL
10 1 review

Oceanfront Studio In Islamorada, Behind Main House

apartment, Islamorada, Village of Islands
This Islamorada studio offers direct beach access and is within walking distance to popular restaurants, shops, and activities, providing a prime location for exploring the Village of Islands. Enjoy shared oceanfront amenities including a vanishing edge pool and spa, fishing from a 450ft pier, and accommodations for up to four guests with a queen bed and sofa bed.
Oceanside Getaway: Beautiful Home With Boat Slip, Pool & Beach - Gated Community - Islamorada, FL
9.8 178 reviews

Oceanside Getaway: Beautiful Home With Boat Slip, Pool & Beach - Gated Community

apartment, Islamorada, Village of Islands
This waterfront vacation home is located in Islamorada, just a short drive from Windley Key Fossil Reef Geological State Park, Rain Barrel Village, and Founders Park, offering easy access to the area's attractions. The property has received excellent user ratings, indicating a comfortable and enjoyable stay.
The house features two bedrooms and can comfortably accommodate up to six guests. Enjoy the Florida sunshine with a refreshing dip in the private pool, relax in the peaceful garden, and prepare meals in the fully equipped kitchen.

Search Vacation Rentals with Swimming Pool in Islamorada, FL

Choose a vacation rental with a pool in Islamorada, FL to perfectly complement your day of adventures.

2402 Ocean Pointe - 2 Bedroom Condo Upgraded With Clean Lines And Coastal Colors - Islamorada, FL
9.2 30 reviews

2402 Ocean Pointe - 2 Bedroom Condo Upgraded With Clean Lines And Coastal Colors

apartment, Tavernier
This Tavernier condo, near Harry Harris Park, Mariners Hospital, and Pigeon Key, offers easy access to recreation, healthcare, and historical sites.
The 850-square-foot unit features two bedrooms, two bathrooms, a sofa bed accommodating up to six guests, and amenities including a pool, jacuzzi, and free Wi-Fi.
Bay Harbour Islamorada Oceanfront Views 3/2.5 Updated Condo Dock - Islamorada, FL
10 24 reviews

Bay Harbour Islamorada Oceanfront Views 3/2.5 Updated Condo Dock

apartment, Islamorada, Village of Islands
This 3-bedroom, 2-bathroom Islamorada condo is located in the gated Bay Harbour community at MM 77.5 bayside, within a mile of Anne's Beach and near San Pedro Underwater Archaeological Preserve State Park.
This waterfront condominium offers a private screened terrace with sunrise views, a gourmet kitchen, expansive ocean-view glass doors, and a 31-foot dock with a boat lift, accommodating up to 6 guests with amenities including air conditioning, a swimming pool, and Wi-Fi.
Relaxed Boho Vibes & Views [ Ocean Pointe 2315] - Islamorada, FL
9.8 1725 reviews

Relaxed Boho Vibes & Views [ Ocean Pointe 2315]

apartment, Tavernier
This Tavernier beach condo is a short walk from Baker's Cay Resort Beach and Harry Harris Park and is located in a peaceful, quiet area. The resort has received excellent ratings for its location, cleanliness, and overall experience.
The Keys Life At Ocean Pointe condo has two bedrooms and a sofa bed for comfortable accommodation. Amenities include a swimming pool, jacuzzi, tennis court, and a fully equipped kitchen, offering a relaxing and enjoyable stay with plenty of activities.
Serene Cozy Cottage In Islamorada With Heated Pool - Islamorada, FL
9.6 161 reviews

Serene Cozy Cottage In Islamorada With Heated Pool

apartment, Islamorada, Village of Islands
This charming cottage is located at mile marker 76.7 in Islamorada, just a short drive from Caloosa Cove Marina and Robbie's Marina, offering a peaceful retreat away from the hustle and bustle of the main tourist areas. The cottage has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The cottage has two bedrooms and comfortably accommodates four guests. Enjoy a refreshing dip in the heated swimming pool, shared exclusively with a select few cottages at Shady Palms, and take advantage of the starter pack with essential supplies, convenient parking, and family-friendly features.

Search Coastal Vacation Rentals near Islamorada, FL

These seaside vacation rentals in Islamorada, FL provide an excellent base for exploring the coast. Browse top local properties and plan your beach-town trip.

Anglers Reef 103 - 2 Br - Beach Access Kayaks - Islamorada, FL
9.7 7 reviews

Anglers Reef 103 - 2 Br - Beach Access Kayaks

house, Islamorada, Village of Islands
Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking - Islamorada, FL
No reviews

Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking

apartment, Islamorada, Village of Islands
Deluxe Oceanfront 1/1 Sleeps 4. Cafe & Pool Bar. - Islamorada, FL
9.7 131 reviews

Deluxe Oceanfront 1/1 Sleeps 4. Cafe & Pool Bar.

apartment, Tavernier
Aqua Lodge Houseboat 2bd/1bth! - Islamorada, FL
9.7 117 reviews

Aqua Lodge Houseboat 2bd/1bth!

barge, Islamorada, Village of Islands

Browse Luxury Vacation Rentals in Islamorada, FL

Premium waterfront rentals in Islamorada, FL combine upscale design with refined service for a truly superior getaway.

Islamorada Hideaway - Islamorada, FL
No reviews

Islamorada Hideaway

house, Islamorada, Village of Islands

Choose the Right Vacation Rentals with a Steam Room in Islamorada, FL

Relax with an on-site sauna at these vacation rentals in Islamorada, FL, perfect for a steam session after a day by the water.

Cheeca Lodge & Spa - Islamorada, FL
9.0 2006 reviews

Cheeca Lodge & Spa

resort, Islamorada, Village of Islands
Islamorada Oceanfront Luxury Living - Islamorada, FL
No reviews

Islamorada Oceanfront Luxury Living

apartment, Islamorada, Village of Islands
Two Spectacular Ocean Views From The Living Room And Master Bedroom Of The Condo - Islamorada, FL
9.6 233 reviews

Two Spectacular Ocean Views From The Living Room And Master Bedroom Of The Condo

apartment, Tavernier
Oceanfront 4br Retreat W/ Private 31' Boat Slip, Pool & Beach, Gourmet Kitchen - Islamorada, FL
9.8 47 reviews

Oceanfront 4br Retreat W/ Private 31' Boat Slip, Pool & Beach, Gourmet Kitchen

apartment, Islamorada, Village of Islands
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