Holiday Rentals in Islamorada, FL

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Islamorada, FL holiday rentals
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1696 Holiday rentals and Airbnb in Islamorada, FL

Best family friendly Islamorada, FL holiday rentals

Among the 1696 accommodations in Islamorada, FL, here are the 4 best family friendly rentals

Ocean Pointe Ocean View W/heated Pool Beach Marina - Islamorada, FL
8.6 13 reviews

Ocean Pointe Ocean View W/heated Pool Beach Marina

apartment, Tavernier
This beachfront apartment in Tavernier, Florida, offers direct access to the Atlantic Ocean and is minutes from local restaurants and John Pennekamp Coral Reef State Park.
The 79-square-metre (850 sq ft) self-catering property sleeps six guests, boasting two bedrooms, two bathrooms, a fully equipped kitchen, in-unit laundry, and access to resort amenities including a heated pool, jacuzzi, and tennis/pickleball courts.
Brand New Oceanside Paradise Waterfront With Pool And Hot Tub - Islamorada, FL
10 1 review

Brand New Oceanside Paradise Waterfront With Pool And Hot Tub

house, Key Largo
This Key Largo oceanfront property is situated 1 kilometre from Pigeon Key, 13.5 kilometres from John Pennekamp Coral Reef State Park, and 16 kilometres from Windley Key, offering easy access to major attractions.
This 250 square metre house boasts three bedrooms, three bathrooms, sleeps up to 17 guests, and includes a private pool, Jacuzzi, and a fully equipped kitchen; water sports are available on-site.
Oceanview / Oceanfront Apartment With Resort Amenities, Key Largo, Tavernier - Islamorada, FL
10 196 reviews

Oceanview / Oceanfront Apartment With Resort Amenities, Key Largo, Tavernier

apartment, Tavernier
This Tavernier apartment is conveniently located just a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to both relaxation and exploration. The apartment has received excellent ratings for user experience, location, and cleanliness, ensuring a comfortable and enjoyable stay.
The 81 square metre apartment comfortably accommodates up to 4 guests in its two bedrooms and two bathrooms. Enjoy a range of amenities including a private pool, a fully equipped kitchen, a DVD player, and a balcony, perfect for relaxing and enjoying the Florida sunshine.
Ocean View Two Penthouses | Pool | Vista Key - Islamorada, FL
10 4 reviews

Ocean View Two Penthouses | Pool | Vista Key

apartment, Islamorada, Village of Islands
This expansive Islamorada duplex penthouse boasts stunning panoramic ocean views and is conveniently located near the beach and Islamorada's waterfront restaurants.
The property, sleeping up to 24 guests across six bedrooms and six bathrooms, offers a chef's kitchen, private beach access, heated pool, jacuzzi, tennis court, rooftop terrace, and a fitness centre, along with additional services such as chef services and early/late check-in/out.

Best Islamorada, FL holiday rentals with a pool

Among the 1696 accommodations in Islamorada, FL, here are the 4 best rentals with a pool

Isla Guava: Free Boat Dockage Sept-oct Only! - Islamorada, FL
9.8 13 reviews

Isla Guava: Free Boat Dockage Sept-oct Only!

house, Islamorada, Village of Islands
Isla Key Guava (Villa #4), situated in Islamorada's Art District, offers easy access to Islamorada Library Beach Park (less than 1 km away), the Morada Way Arts & Cultural District (under 0.5 km), and attractions such as Robbie's Marina (approximately 1.5 km) and Theatre of the Sea (around 0.8 km).
This three-bedroom, three-bathroom luxury villa sleeps six guests and boasts a private pool, bayside boat dock access (dockage extra), a fully equipped kitchen, and pickleball equipment, all within a community of nine upscale holiday homes.
Villa ∙ 3 Bedrooms ∙ 6 Guests - Islamorada, FL
10 2 reviews

Villa ∙ 3 Bedrooms ∙ 6 Guests

house, Islamorada, Village of Islands
Palm Cottage South, located in the Port Antigua community of Islamorada at Mile Marker 75, offers direct canal frontage with dockage for a 24-foot boat and exclusive access to a private white sand beach within 500 meters. This elevated villa provides 4 bedrooms accommodating up to 8 guests, featuring a heated swimming pool, air conditioning, a kitchen with a fridge, microwave oven, and dishwasher, alongside internet access, garden, and parking.
King Balcony Room By Marina With Boat Ramp Access | Pets Are Welcome - Islamorada, FL
No reviews

King Balcony Room By Marina With Boat Ramp Access | Pets Are Welcome

apartment, Islamorada, Village of Islands
This Islamorada apartment is located in the village centre, directly on the beach, and offers convenient access to Hurricane Monument and Indian Key Historic State Park.
This pet-friendly studio apartment for two features air conditioning, Wi-Fi, a private beach, a heated outdoor pool with ocean views, and bike, kayak, and paddleboard rentals, with cleaning services and a kitchen included.
Ocean Pointe 2309 - Islamorada, FL
8.9 10 reviews

Ocean Pointe 2309

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.

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Best Islamorada, FL holiday rentals with a balcony

2 Br End Suite W/ Vast Views+pool, Beach & Bar - Islamorada, FL
9.8 137 reviews

2 Br End Suite W/ Vast Views+pool, Beach & Bar

apartment, Tavernier
This waterfront apartment in Tavernier is conveniently situated just a short walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to beautiful beaches and natural attractions. The apartment has received excellent ratings for its location, cleanliness, and overall user experience, ensuring a comfortable and enjoyable stay.
The two-bedroom, two-bathroom apartment spans 87 square metres and comfortably accommodates up to six guests. The property is fully equipped with modern amenities, including a swimming pool, Jacuzzi, tennis court, and a fully equipped kitchen, making it ideal for families or groups seeking a relaxing and active holiday.
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.
Snorkeling & Kayaking Resort! Seaside Villa, Patio, Breakfast, Pool, Parking! - Islamorada, FL
9.0 9 reviews

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

apartment, Islamorada, Village of Islands
This 'Snorkeling & Kayaking Beach Resort! Seaside Villa W\/patio! Marina, Pool, Parking' is located in Islamorada, just a short walk from Florida Keys Brewing Co. and Bud n' Mary's Dive Center, offering a convenient location to explore the area. The resort is situated right on the beach, giving guests direct access to the beautiful Florida Keys waters.
The one-bedroom villa offers a comfortable 28 square metres of space and can accommodate up to four guests. The resort provides a range of amenities, including a heated pool with ocean views, a private beach, access to kayaks and paddleboards, and a continental breakfast each morning.
House ∙ 3 Bedrooms ∙ 6 Guests - Islamorada, FL
No reviews

House ∙ 3 Bedrooms ∙ 6 Guests

house, Islamorada, Village of Islands
This canalfront property is located in Lower Matecumbe, Islamorada, offering a private Keys escape with 100 feet of private dockage providing quick ocean access, ideal for boating and fishing enthusiasts.
This 3-bedroom, 4-bathroom holiday home accommodates up to 6 guests and features a private heated pool and spa, two paddleboards for canal exploration, and a fully stocked kitchen, all within proximity to Islamorada's restaurants and marinas.

Best Islamorada, FL holiday rentals with parking

Ragged Edge Resort & Marina - Islamorada, FL
9.5 382 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.
2/1 House On Canal . - Islamorada, FL
10 2 reviews

2/1 House On Canal .

apartment, Islamorada, Village of Islands
This canal-front property in Islamorada, Florida Keys, offers 60 feet of private dockage and is a short walk from local beaches.
The two-bedroom, one-bathroom house sleeps five guests and boasts multiple outdoor spaces, a fully equipped kitchen with stainless steel appliances, smart TVs, high-speed WiFi, and proximity to restaurants.
Oceanfront Wow | Studio With Endless Blue Views - Islamorada, FL
No reviews

Oceanfront Wow | Studio With Endless Blue Views

apartment, Islamorada, Village of Islands
This second-floor studio apartment is located directly on the Atlantic Ocean in Islamorada, Village of Islands, offering unobstructed ocean views and a constant salt breeze.
This studio offers a queen bed and sofa bed, accommodating up to three guests, with a kitchenette featuring full-size appliances, air conditioning, and access to resort amenities including a heated pool and Founders Park, all accessible via the Caloosa KeyCard.
2-room Group Package: 4 Queen Beds, Breakfast & Pool Included - Islamorada, FL
No reviews

2-room Group Package: 4 Queen Beds, Breakfast & Pool Included

apartment, Islamorada, Village of Islands
This two-bedroom, two-bathroom apartment in Islamorada, Village of Islands, is located in the town centre directly on the beach, offering convenient access to Windley Key Fossil Reef Geological State Park and Indian Key Historic State Park.
This pet-friendly accommodation for up to eight guests features air conditioning, Wi-Fi, a heated swimming pool with ocean views, daily continental breakfast, bike and kayak rentals, and outdoor BBQ facilities, with complimentary self-parking available.
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