Islamorada Rentals
From $1734 per night (USD)VRBO
Islander Resort Oceanside | 4 Units | 5 mi to Windley Reef
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Located on the scenic Overseas Highway in Islamorada, this resort offers direct ocean access and close proximity to popu ...
From $1734 per night (USD)VRBO
From $1750 per night (USD)VRBO
Islandstay Kitchen Pool Gym | 5 mi to Windley Reef | Hiking & Kayak Fun
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Set along the scenic Overseas Highway in Islamorada, this oceanside resort offers direct access to beautiful beaches and ...
From $1750 per night (USD)VRBO
From $1177 per night (USD)VRBO
Coastalstay w/ Gym Onsite | 5 mi to Annes Beach | Sunset Swimming
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on Overseas Highway in Islamorada, this oceanside resort offers easy access to Florida Keys attractions and wate ...
From $1177 per night (USD)VRBO
From $1529 per night (USD)VRBO
Island Kitchen Pool Gym | 5 mi to Windley Reef | Kayak & Nature Trails
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located on the scenic Overseas Highway in Islamorada, this oceanside resort offers direct access to beautiful beaches an ...
From $1529 per night (USD)VRBO
From $907 per night (USD)VRBO
Island Oasis Stay | 1 King Bed | Near Islamorada Beaches
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Set along the scenic Overseas Highway in Islamorada, this oceanside resort offers easy access to Florida Keys attraction ...
From $907 per night (USD)VRBO
From $1177 per night (USD)VRBO
Coastal Kitchen Pool Gym | 5 mi to Annes Beach | Swim & Relax on Shore
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience beachfront tranquility at this oceanside resort in Islamorada, offering easy access to local dining and water ...
From $1177 per night (USD)VRBO
From $883 per night (USD)VRBO
Bayview Pool Gym | 6 mi to Robbies | Fish Feeding & Boating
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Set along the scenic Overseas Highway in Islamorada, this oceanside resort offers easy access to beautiful beaches and l ...
From $883 per night (USD)VRBO
From $1179 per night (USD)VRBO
Lagoon w/ Pool Onsite | 6 mi to Hurricane Mon | Historical Walk Tours
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on Overseas Highway in Islamorada, this resort offers easy access to the beautiful Florida Keys and nearby beach ...
From $1179 per night (USD)VRBO
From $1456 per night (USD)VRBO
Beach Heaven | 6 mi to Robbies | Tarpon Feeding Experience
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Set along the scenic Overseas Highway in Islamorada, this resort offers easy access to local beaches and water activitie ...
From $1456 per night (USD)VRBO
From $1086 per night (USD)VRBO
Sunrise Stay | 6 mi to Hurricane Mon | Scenic Walks & Tours
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Set along the stunning Overseas Highway in Islamorada, this oceanside resort offers easy access to local beaches and mar ...
From $1086 per night (USD)VRBO
From $883 per night (USD)VRBO
Reefview w/ Onsite Gym | 7 mi to San Pedro Pk | Dive & Explore Waters
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Set along the scenic Overseas Highway in Islamorada, this oceanside resort offers easy access to local beaches and water ...
From $883 per night (USD)VRBO
From $2296 per night (USD)VRBO
Beachside Access | 3 mi to Diving Museum | Snorkel & Learn Dive
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located on the scenic Overseas Highway in Islamorada, this oceanside resort offers easy access to local attractions like ...
From $2296 per night (USD)VRBO
From $2853 per night (USD)VRBO
Tropic Kitchen Pool Gym | 3 mi to Keys Brewing | Brewery Tour Nearby
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience oceanfront tranquility at this resort located on Overseas Highway in Islamorada. Enjoy easy access to nearby ...
From $2853 per night (USD)VRBO
From $1086 per night (USD)VRBO
Oceanstay w/ Pool Access | 2 mi to Founders Pk | Bike & Picnic Outdoors
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Situated along the scenic Overseas Highway in Islamorada, this resort offers easy access to local beaches and marine att ...
From $1086 per night (USD)VRBO
From $20891 per night (USD)VRBO
Chateau On The Ocean - The Southernmost Shangrila
- Bedrooms:
- 11
- Bathrooms:
- 7
- Sleeps:
- 14
Intention. Attention to Detail. Expectation of Outcome. From the moment you step through the gilded entryway you immedia ...
From $20891 per night (USD)VRBO
From $523 per night (USD)VRBO
Waterfront Home Indian Waterways Heart of Islamorada Pool and Dock, Dogs Welcome
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your island escape in beautiful Islamorada near mile maker 89— our home in the desired Indian Waterways neigh ...
From $523 per night (USD)VRBO
From $2015 per night (USD)VRBO
PRIVATE BEACH / Heated Pool / volleyball court/ Orchid Beach Key
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Immerse yourself in captivating tranquility and sweeping ocean views from the expansive private beach, every corner of t ...
From $2015 per night (USD)VRBO
From $232 per night (USD)VRBO
Charming 2 bedroom townhome at Executive Bay Club!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Your chance to experience one of Islamorada's most sought-after communities has arrived! Brand new to the rental pool, t ...
From $232 per night (USD)VRBO
From $934 per night (USD)VRBO
Luxurious 4BR retreat at 115 Vilabella Drive, Islamorada, with a private pool.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Located in Islamorada's premier neighborhood of Venetian Shores, this stunning 4-bedroom, 4-bath waterfront home offers ...
From $934 per night (USD)VRBO
From $694 per night (USD)VRBO
Luxury Floating Cottage •Upper Florida Keys • walk to restaurants and marina fun
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Welcome aboard Blue BAYou, a brand-new floating luxury cottage in the heart of the Florida Keys. This beautifully desig ...
From $694 per night (USD)VRBO
From $226 per night (USD)VRBO
Gorgeous Newly Renovated 2-bedroom Townhome in Islamorada w/Pool and Boat Slip
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience Islamorada like a local in this perfect 2-bedroom townhome. The master bedroom features a king bed, while the ...
From $226 per night (USD)VRBO
From $1157 per night (USD)Expedia
Exclusive Villa/Private Beach & Oceanfront terrace
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 10
Welcome to your dream coastal getaway! This stunning beachfront villa offers the perfect blend of luxury, comfort, and b ...
From $1157 per night (USD)Expedia
From $314 per night (USD)VRBO
Marlin Beach 3-bedroom house in Islamorada with private beach, hot tub and dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled in Islamorada Sport Fishing Capital this fabulous house offers a tranquil retreat for guests seeking comfort and ...
From $314 per night (USD)VRBO
From $363 per night (USD)VRBO
Explore Islamorada | Ocean View | Free Breakfast, Parking, Pool | Pet-Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Take a break and experience the laid-back lifestyle in the beautiful Islamorada! This listing is for a room within a ho ...
From $363 per night (USD)VRBO
From $727 per night (USD)VRBO
2 Spacious Units | Perfect For Family Stay | Free Breakfast & Parking | Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Take a break and experience the laid-back lifestyle in the beautiful Islamorada! This listing is for 2 separate rooms w ...
From $727 per night (USD)VRBO
From $270 per night (USD)VRBO
Coastal Islamorada Stay | Free Breakfast, Pool, Free Parking & Pets Welcome!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Take a break and experience the laid-back lifestyle in the beautiful Islamorada! This listing is for a room within a ho ...
From $270 per night (USD)VRBO
From $281 per night (USD)VRBO
Affordable Islamorada Stay | Free Breakfast & Parking | Pool | Pet-Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Take a break and experience the laid-back lifestyle in the beautiful Islamorada! This listing is for a room within a ho ...
From $281 per night (USD)VRBO
From $267 per night (USD)VRBO
Islamorada Retreat | Free Breakfast & Parking | Pool, Pets Are Welcome!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Take a break and experience the laid-back lifestyle in the beautiful Islamorada! This listing is for a room within a ho ...
From $267 per night (USD)VRBO
From $398 per night (USD)VRBO
Island Escape in Islamorada | Breakfast, Pool & Pet-Friendly Stay!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Take a break and experience the laid-back lifestyle in the beautiful Islamorada! This listing is for a room within a ho ...
From $398 per night (USD)VRBO
From $363 per night (USD)VRBO
Tropical Escape In Islamorada | Pets Are Welcome | Free Breakfast & Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Take a break and experience the laid-back lifestyle in the beautiful Islamorada! This listing is for a room within a ho ...
From $363 per night (USD)VRBO
From $340 per night (USD)VRBO
Tropical Islamorada Experience | Free Breakfast, Pool, Parking | Pet-Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Take a break and experience the laid-back lifestyle in the beautiful Islamorada! This listing is for a room within a ho ...
From $340 per night (USD)VRBO
From $340 per night (USD)VRBO
Stay Like Home | Pool Access, Free Breakfast & Free Parking | Pets Are Welcome!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Take a break and experience the laid-back lifestyle in the beautiful Islamorada! This listing is for a room within a ho ...
From $340 per night (USD)VRBO
From $259 per night (USD)VRBO
Stay, Unwind & Recharge | Experience Islamorada | Pool, Free Breakfast & Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Take a break and experience the laid-back lifestyle in the beautiful Islamorada! This listing is for a room within a ho ...
From $259 per night (USD)VRBO
From $259 per night (USD)VRBO
Islamorada Retreat | Villa Stay | Free Breakfast and Parking | Pool Access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Take a break and experience the laid-back lifestyle in the beautiful Islamorada! This listing is for a room within a ho ...
From $259 per night (USD)VRBO
From $267 per night (USD)VRBO
Weekend Recharge | Pool Access, Free Breakfast, Free Parking | Pets Are Welcome!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Take a break and experience the laid-back lifestyle in the beautiful Islamorada! This listing is for a room within a ho ...
From $267 per night (USD)VRBO
From $340 per night (USD)VRBO
Perfect Weekend Trip | Free Breakfast, Parking, Pool | Pet-Friendly Stay!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Take a break and experience the laid-back lifestyle in the beautiful Islamorada! This listing is for a room within a ho ...
From $340 per night (USD)VRBO
From $283 per night (USD)VRBO
Experience Island Life | Free Breakfast & Parking | Pool | Pets Are Welcome
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Take a break and experience the laid-back lifestyle in the beautiful Islamorada! This listing is for a room within a ho ...
From $283 per night (USD)VRBO
From $235 per night (USD)Expedia
Handcrafted Luxury Treehouse - Private Florida Keys Retreat, 28+ Nights
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Live among the treetops in a one-of-a-kind handcrafted retreat - your private Florida Keys home for a month or more. Es ...
From $235 per night (USD)Expedia
From $300 per night (USD)VRBO
Islamorada- Amazing Keys 3 bedroom heated pool home.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience coastal living in this elegant ground level concrete pool home located in Islamorada's sought-after Plantatio ...
From $300 per night (USD)VRBO
From $1591 per night (USD)VRBO
Brand-New 4-Bedroom Island Home in the Heart of Islamorada
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Nestled between the Cheeca Lodge and Caribbean Resort, our 4-bedroom oceanside home offers a unique beachfront experienc ...
From $1591 per night (USD)VRBO
From $414 per night (USD)VRBO
Port Palermo - Canal Home w/Dockage, Pet Friendly!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Port Palermo, your perfect Florida Keys getaway in the heart of Islamorada. This charming ground-level waterf ...
From $414 per night (USD)VRBO
From $213 per night (USD)Expedia
Fabulous Waterfront Pool Two Level Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Video of inside, outside, surrounding areas and waterways available upon request. * Each level is a (3/2) for a small gr ...
From $213 per night (USD)Expedia
From $216 per night (USD)VRBO
Beautiful ground floor 1B1b w/open water view #109
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
New to the rental market, this beautiful ground floor 1B1b apartment with a wonderful open water bay view is now availab ...
From $216 per night (USD)VRBO
From $843 per night (USD)Expedia
Luxe Family Retreat W/ Beach, Golf Cart & Pool!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to GQ Vacations — your private waterfront retreat in Islamorada. This peaceful 4 bedroom, 3 bathroom canal-fron ...
From $843 per night (USD)Expedia
From $292 per night (USD)VRBO
Isla Santorini | Islamorada Waterfront Condo, Ensuites, Pool, Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
🏡 Community Amenities: Pool, hot tub, gym, tennis courts & BBQ grills 🌊 Water Views, screened balcony 🛏️ Layout: Two ...
From $292 per night (USD)VRBO
From $494 per night (USD)Expedia
Uncertain Tides - 4 Bedroom on Canal w/Dock & Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to your ultimate Florida Keys escape in one of Islamorada’s most sought-after neighborhoods. This spacious water ...
From $494 per night (USD)Expedia
From $385 per night (USD)VRBO
Canal front. Ocean access via Tavernier Creek. New pool and hot tub. Sleeps 8
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our little piece of paradise! After spending several winters in Islamorada, we completely fell in love with t ...
From $385 per night (USD)VRBO
From $1359 per night (USD)VRBO
Spacious Direct Oceanfront 5-bedroom house in brilliant Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 17
Southern Diversion — Exclusive Oceanfront Estate in Village of Islamorada (2 acres, 200' oceanfront) Private gated ocean ...
From $1359 per night (USD)VRBO
From $716 per night (USD)VRBO
Luxurious Home Located In Venetian Shores
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
PROPERTY NAME: Bella 109 Valencia Drive Tavernier, FL 33036 LOCATION: Bayside Canal home located in the popular Islamor ...
From $716 per night (USD)VRBO
From $566 per night (USD)Expedia
Tarpon Palms - 4 bedroom waterfront home with dock & heated pool in Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Private Waterfront Oasis in Islamorada Welcome to your dream Florida Keys getaway in Islamorada, the Sportfishing Capit ...
From $566 per night (USD)Expedia
From $351 per night (USD)VRBO
Spacious newly renovated 3 bedroom, 2 bath home on the canal in Islamorada, Fl
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located in Tavernier, enjoy what this 3-bedroom house has to offer. The bedrooms feature a king bed, a queen bed, and a ...
From $351 per night (USD)VRBO
From $399 per night (USD)Expedia
Exclusive White Marlin Beach Retreat - Private Beach Access & Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Your Islamorada waterfront getaway awaits at this charming three-bedroom home, offering comfortable accommodations with ...
From $399 per night (USD)Expedia
From $1140 per night (USD)VRBO
Luxury Waterfront Retreat in Islamorada (28 days)
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: Luxury waterfront retreat in the heart of Islamorada! This beautiful 5-bedroom, 3-bath home sleeps up to 10 gu ...
From $1140 per night (USD)VRBO
From $478 per night (USD)Expedia
Islamorada Gem / 5BR Oceanfront Home w/ Stunning Ocean Views
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Pelican Roost — Your Dream Florida Keys Oceanfront Escape Come fall in love with "Pelican Roost," our stunni ...
From $478 per night (USD)Expedia
From $455 per night (USD)VRBO
Beautiful waterfront home in Islamorada, Fl Keys! Ready for only your clothes!!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
Waterfront home on Harbor Drive, perfectly positioned for boating, fishing, and true island living. This charming and th ...
From $455 per night (USD)VRBO
From $385 per night (USD)VRBO
Discover Lower Matecumbe
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your front-row seat to the Atlantic. This true oceanfront Islamorada retreat offers unobstructed turquoise vi ...
From $385 per night (USD)VRBO
From $563 per night (USD)VRBO
2BR, 2.5BA open-water villa in Islamorada with Atlantic views.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Villa Kokomo—your perfect island escape in Islamorada, Florida! This beautifully appointed oceanfront 2-bedro ...
From $563 per night (USD)VRBO
From $7936 per night (USD)VRBO
Villa familiar en un paraíso
- Bedrooms:
- 9
- Bathrooms:
- 1
- Sleeps:
- 14
Bienvenido a una de las propiedades más exclusivas de los Cayos de Florida. Situada en una extensa finca privada frente ...
From $7936 per night (USD)VRBO
From $858 per night (USD)VRBO
Private Beach, Waterfront, Islamorada, Island house with a pool & a boat dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience the ultimate Florida Keys retreat in this modern water front sanctuary with a Private Beach access in Islamor ...
From $858 per night (USD)VRBO