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

Boat Slip Included August-november 2026! - Islamorada, FL
9.9 111 reviews

Boat Slip Included August-november 2026!

apartment, Islamorada, Village of Islands
This waterfront vacation home is located just a short distance from Windley Key Fossil Reef Geological State Park and within a few miles of Founders Park and Islamorada County Park. Guests consistently rate this property excellent for its location, cleanliness, and overall experience.
This 2-bedroom house can comfortably accommodate up to 6 guests. Enjoy the convenience of a fully equipped kitchen, a refreshing swimming pool, a relaxing balcony, and the option to grill outdoors.
Deja Blue Suite  [Ocean Pointe 1409] - Islamorada, FL
9.8 172 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.
Pets Are Allowed Here! 2 Comfortable Units, Free Breakfast, Parking, Pool - Islamorada, FL
No reviews

Pets Are Allowed Here! 2 Comfortable Units, Free Breakfast, Parking, Pool

apartment, Islamorada, Village of Islands
This 2-bedroom, 2-bathroom beachfront condo in downtown Islamorada offers a prime location, just a 3-minute walk to Windley Key Fossil Reef Geological State Park and a 9-minute walk to Hog Heaven.
This Islamorada rental sleeps 8 guests and features a private balcony, shared swimming pool, air conditioning, free Wi-Fi, and on-site parking, with concierge service available.
Best Location In The Keys Waterfront 3/3 Home, Boat Dock, Great Layout! - Islamorada, FL
10 2 reviews

Best Location In The Keys Waterfront 3/3 Home, Boat Dock, Great Layout!

apartment, Islamorada, Village of Islands
This waterfront home is located in Indian Waterways, a neighborhood in Tavernier, just a short ride from Founders Park, the beach, and John Pennekamp Coral Reef State Park. The house is perfect for a family getaway or a group of friends looking for a relaxing vacation.
The home features two bedrooms and two bathrooms, accommodating up to four guests. Enjoy the modern amenities, including a kitchen with a fridge, microwave, dishwasher, and a private garage. You can also take advantage of the bikes provided to explore the surrounding area.

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.

Isla Lychee: Free Boat Dockage Sep-oct Only! - Islamorada, FL
10 7 reviews

Isla Lychee: Free Boat Dockage Sep-oct Only!

house, Islamorada, Village of Islands
Isla Key Lychee Villa #6, located in Islamorada's Art District, offers easy walking access to local shops, restaurants, and parks, and is a short drive from attractions like Robbie's Marina and the Theater of the Sea.
This three-bedroom, three-bathroom upscale villa sleeps six guests and features a private deck, top balcony with partial water views, a community pool, and proximity to Islamorada Library Beach Park.
Waterfront Condo | Heart Of Islamorada | Boat Slip - Islamorada, FL
10 1 review

Waterfront Condo | Heart Of Islamorada | Boat Slip

apartment, Islamorada, Village of Islands
This waterfront condo in Islamorada's Bay Harbour community offers prime access to premier dining, sandbars, snorkeling, and sunset viewing, all within minutes of the village.
This family-friendly apartment accommodates up to 6 guests with 3 bedrooms and 2 bathrooms, featuring air conditioning, a full kitchen, a swimming pool, hot tub, gym, and tennis court, making it ideal for sport fishing enthusiasts and those seeking relaxation.
Light, Bright & Nautical Condo At Ocean Pointe - Islamorada, FL
9.9 175 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.
Florida Keys Getaway - Slps 4 -  Ocean View - Islamorada, FL
9.9 79 reviews

Florida Keys Getaway - Slps 4 - Ocean View

apartment, Tavernier
This oceanfront condo rental in Tavernier, Florida, is located 0.7 miles from Harry Harris Park and within 3 miles of Mariners Hospital and the Florida Keys Dive Center.
This 930-square-foot, two-bedroom unit sleeps four guests and boasts a fully equipped kitchen, two bathrooms, in-unit laundry, a private balcony, and access to a swimming pool, jacuzzi, tennis court, and barbecue grills.

Frequently Asked Questions about vacation rentals in Islamorada, FL

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Best Islamorada, FL vacation rentals with parking

Pristine Islamorada Pool Home With Ocean View And - Islamorada, FL
10 25 reviews

Pristine Islamorada Pool Home With Ocean View And

apartment, Islamorada, Village of Islands
This two-bedroom townhouse is located in Islamorada, overlooking the resort-style swimming pool at Angler's Reef Resort Villas & Marina, just three miles south of Alligator Reef and the only living coral barrier reef in the Continental United States. The apartment has excellent user, location, and cleanliness ratings.
The townhouse offers ocean views and can accommodate up to six guests. Amenities include a full kitchen, two spacious decks, a swimming pool, a garden, parking, internet access, and access to kayaks and a nearby beach.
Aqua Lodge Houseboat "Sea Turtle" - Islamorada, FL
9.3 44 reviews

Aqua Lodge Houseboat "Sea Turtle"

barge, Tavernier
This houseboat in Tavernier offers a unique on-the-water experience with stunning views and a serene atmosphere. It's conveniently located within walking distance of Baker's Cay Resort Beach and Mariners Hospital, and has received excellent user, location, and cleanliness ratings.
The boat has a spacious layout with one bedroom and one bathroom, accommodating up to two guests. It features modern amenities such as a fridge, microwave oven, air conditioning, and internet access. Guests can also enjoy the outdoor pool, terrace/balcony, garden, and parking. Nearby activities include scuba diving and snorkeling excursions offered by the Florida Keys Dive Center.
Sea La Vie At Executive Bay Club - Islamorada, FL
No reviews

Sea La Vie At Executive Bay Club

apartment, Islamorada, Village of Islands
This waterfront apartment at Executive Bay Club in Islamorada, Village of Islands, offers direct marina views on Executive Bay and is located 0.2 miles from Founders Park.
This Islamorada condo accommodates up to 6 guests with 2 bathrooms and features a private balcony, a resort-style swimming pool, beach access, and boat dock access, with an in-unit kitchen equipped with a fridge, microwave, and dishwasher, plus air conditioning and internet.
Rare Gem! 4 Units, Free Parking, Pool + Breakfast! - Islamorada, FL
9.5 4 reviews

Rare Gem! 4 Units, Free Parking, Pool + Breakfast!

resort, Islamorada, Village of Islands
This Islamorada resort, offering four separate 301-square-foot units, boasts private beach access and is within walking distance of the Theater of the Sea, near Windley Key Fossil Reef and Lignumvitae Key Botanical State Parks.
Each unit features two queen beds, a kitchenette, dining area, and balcony with partial ocean views, accommodating up to 16 guests with on-site amenities including a heated pool, kayaks, paddleboards, bike rentals, and a daily continental breakfast.

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.

Houseboat 2bd, Private Keys Cottage Loggerhead - Islamorada, FL
9.4 611 reviews

Houseboat 2bd, Private Keys Cottage Loggerhead

boat, Islamorada, Village of Islands
This boat is located in Islamorada, a popular destination in the Florida Keys, just a short distance from the village center. It has excellent user, location, and cleanliness ratings.
This rental offers two bedrooms and one bathroom. It includes amenities like air conditioning, a kitchen, and a garden, and guests can enjoy private boat rentals, fishing, and discounted boat rentals.
Snorkeling & Kayaking Resort! Seaside Villa, Patio, Breakfast, Pool, Parking! - Islamorada, FL
8.8 8 reviews

Snorkeling & Kayaking Resort! Seaside Villa, Patio, Breakfast, Pool, Parking!

apartment, Islamorada, Village of Islands
This Islamorada resort is located on a private beach, with access to a private marina, a heated pool, and a variety of complimentary amenities like kayaks and stand-up paddle boards. The resort is centrally located in the Village of Islands, making it a great base for exploring the area.
The resort offers a range of room types, including the Balcony Room Main, which offers partial ocean views and a private balcony. All rooms are air-conditioned and have access to free Wi-Fi. The resort also offers a variety of on-site amenities, including a front desk, luggage storage, and a picnic area. The Snorkeling & Kayaking Beach Resort! Seaside Villa W\/patio! Marina, Pool, Parking is a great option for travelers looking for a comfortable and convenient stay in Islamorada.
Strong Waves At Harry Harris Beach! Marina, Pool! - Islamorada, FL
No reviews

Strong Waves At Harry Harris Beach! Marina, Pool!

resort, Islamorada, Village of Islands
This Islamorada, Florida apartment rental boasts private beach access and is within walking distance of the Theater of the Sea, near Windley Key Fossil Reef and Lignumvitae Key Botanical State Parks.
The one-bedroom, one-bathroom unit sleeps four guests comfortably in two queen beds, offering a balcony with partial ocean views, a full kitchen with dishwasher, daily housekeeping, and access to resort amenities including a heated pool, kayaks, and paddleboards.
Aqua Lodge Houseboat "Yellow Tail " - Islamorada, FL
9.6 80 reviews

Aqua Lodge Houseboat "Yellow Tail "

boat, Tavernier
This houseboat is located in Tavernier, just a short walk from Baker's Cay Resort Beach and Mariners Hospital, offering a tranquil escape from the hustle and bustle of everyday life. Guests have consistently rated the accommodation excellent for its cleanliness, location, and overall experience.
The houseboat comfortably sleeps up to 5 guests and features a kitchen with a fridge and microwave, air conditioning, a swimming pool, a garden, and parking. Guests can enjoy a variety of amenities including internet access, a smoke-free environment, and the opportunity to engage in water activities like swimming, fishing, and kayaking.

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.

Vacation Day Is Always A Great Idea! 4 Units, Free Breakfast & Parking! - Islamorada, FL
No reviews

Vacation Day Is Always A Great Idea! 4 Units, Free Breakfast & Parking!

apartment, Islamorada, Village of Islands
Condo ∙ 2 Bedrooms ∙ 6 Guests - Islamorada, FL
No reviews

Condo ∙ 2 Bedrooms ∙ 6 Guests

apartment, Islamorada, Village of Islands
Perfect Escape To The Ocean - Islamorada, FL
9.6 64 reviews

Perfect Escape To The Ocean

barge, Islamorada, Village of Islands
Sportfishing In Florida Keys! Large Unit W/ Private Beach Access! Free Breakfast - Islamorada, FL
No reviews

Sportfishing In Florida Keys! Large Unit W/ Private Beach Access! Free Breakfast

apartment, 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.

Beach View Unit In Islamorada! Pets Allowed, Parking, Pool & Free Breakfast! - Islamorada, FL
8.6 28 reviews

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

apartment, 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
8.8 219 reviews

Cheeca Lodge & Spa

resort, Islamorada, Village of Islands
Condo In Islamorada
Blue Paradise - Islamorada, FL
No reviews

Condo In Islamorada Blue Paradise

apartment, Islamorada, Village of Islands
Cheeca Lodge & Spa - Islamorada, FL
9.0 1953 reviews

Cheeca Lodge & Spa

resort, Islamorada, Village of Islands
Book Your Dream Vacation At  Beacon Reef - Special Summer Deal - Islamorada, FL
9.4 9 reviews

Book Your Dream Vacation At Beacon Reef - Special Summer Deal

apartment, Islamorada, Village of Islands
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