Islamorada Rentals
From $1395 per night (USD)VRBO
4 Family-friendly Rooms w/ Balcony | Refreshing Outdoor Pool & Free Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $1395 per night (USD)VRBO
From $692 per night (USD)VRBO
2 Relaxing Rooms w/ Balcony, Free Parking, 3 Pools & Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Set on 15 oceanfront acres in Islamorada, Three Waters Resort & Marina features island-inspired rooms. Guests enjoy thre ...
From $692 per night (USD)VRBO
From $1046 per night (USD)VRBO
Beachside Solace: Room for Your Perfect Vacation |
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $1046 per night (USD)VRBO
From $1038 per night (USD)VRBO
3 Rooms w/ Balcony, 3 Outdoor Pools, Free Parking & Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Set on 15 oceanfront acres in Islamorada, Three Waters Resort & Marina features island-inspired rooms. Guests enjoy thre ...
From $1038 per night (USD)VRBO
From $552 per night (USD)VRBO
Beachfront Retreat | Suite w/ Balcony, 3 Outdoor Pools & Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Set on 15 oceanfront acres in Islamorada, Three Waters Resort & Marina features island-inspired rooms. Guests enjoy thre ...
From $552 per night (USD)VRBO
From $373 per night (USD)VRBO
King Room w/Ocean View, 3 Outdoor Pools, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Set on 15 oceanfront acres in Islamorada, Three Waters Resort & Marina features island-inspired rooms. Guests enjoy thre ...
From $373 per night (USD)VRBO
From $407 per night (USD)VRBO
Marina Room with Direct Beach Access | Islamorado Ultimate Retreat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $407 per night (USD)VRBO
From $346 per night (USD)VRBO
Island Getaway: Relaxing Room w/ Balcony, Free Parking & 3 Pools
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Set on 15 oceanfront acres in Islamorada, Three Waters Resort & Marina features island-inspired rooms. Guests enjoy thre ...
From $346 per night (USD)VRBO
From $698 per night (USD)VRBO
Beach Getaway: Room with Access to Pristine Sands | 2 Relaxing Rooms
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $698 per night (USD)VRBO
From $238 per night (USD)VRBO
Islamorada Tropical Paradise with New 40 Foot Pool
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your perfect getaway in beautiful Tavernier! This stunning vacation home offers the ultimate Florida Keys exp ...
From $238 per night (USD)VRBO
From $425 per night (USD)VRBO
Oceanview Studio Sleeps 3, Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Nestled on the second floor with breathtaking ocean views, this studio is the perfect retreat for a cozy getaway in the ...
From $425 per night (USD)VRBO
From $369 per night (USD)Expedia
Second Floor Den Suite Sleeps 6 Marina Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
This one-bedroom den suite in beautiful Islamorada offers the perfect blend of comfort and adventure. It has one queen b ...
From $369 per night (USD)Expedia
From $378 per night (USD)VRBO
Studio Escape at Caloosa Cove, Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Embrace island life in the heart of the Florida Keys! Relax on the private beach or rent a charter for world-famous spor ...
From $378 per night (USD)VRBO
From $1529 per night (USD)VRBO
Minutes to Library Beach Park! 2 Villa w/ Living Area | Free Onsite Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Start with your ultimate bayside getaway, located along the stunning coastline. Our idyllic resort offers a tranquil esc ...
From $1529 per night (USD)VRBO
From $186 per night (USD)VRBO
Classic 2 bedroom, 2 Bath Islamorada Home with Dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
** 60 day minimum in peak season (January- March) Enjoy the timeless charm of Old Salt Retreat. This cozy and classic ...
From $186 per night (USD)VRBO
From $560 per night (USD)VRBO
Green Coconut, Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Mile Marker 80 – Heart of Islamorada Located on scenic Old Highway, this inviting Islamorada retreat offers the perfect ...
From $560 per night (USD)VRBO
From $625 per night (USD)VRBO
Galleon Cove, Islamorada
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
This stunning 5-bedroom, 4-bath canal-front getaway has everything you need for the perfect Florida Keys escape—private ...
From $625 per night (USD)VRBO
From $641 per night (USD)VRBO
Reel Paradise, Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Mile Marker 74 – Bayside, Canal front Canal-Front Retreat with Pool & Prime Dockage | Lower Matecumbe Key, Islamorada ...
From $641 per night (USD)VRBO
From $224 per night (USD)VRBO
Updated 3-bedroom Townhome at Executive Bay Club resort
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This spacious, fully remodeled 3-bedroom, 2-bathroom loft townhome is located in the heart of Islamorada at the exclusiv ...
From $224 per night (USD)VRBO
From $257 per night (USD)Expedia
3-bedroom Townhome with Direct Ocean Views at resort in Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to paradise in this gorgeous 3-bedroom, 3-bathroom townhome is located at Executive Bay Club in Islamorada, FL. I ...
From $257 per night (USD)Expedia
From $404 per night (USD)VRBO
3-bedroom, 3-bath Canal front home with private pool in Islamorada, Florida Keys
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Nestled at the quiet west end of Islamorada, minutes from the Channel 2 and Channel 5 bridges famed for Tarpon fishing, ...
From $404 per night (USD)VRBO
From $890 per night (USD)VRBO
Escape in this 2 Sun-Kissed Studios w/Gulf views! Perfect place for relaxation!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $890 per night (USD)VRBO
From $504 per night (USD)VRBO
Ideal Family Haven w/Kitchen, Grill facilities near Breathtaking Ocean access
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This listing is for a room within a hotel. ✦ Your room is 1500 sq. ft, equipped with complimentary toiletries, kitchen ...
From $504 per night (USD)VRBO
From $601 per night (USD)VRBO
Perfect Island Getaway! 2 Studio w/Kitchen & Resort amenities - Onsite Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $601 per night (USD)VRBO
From $403 per night (USD)VRBO
Breathtaking Island Oasis! Relaxing Studio w/Resort amenities & Gulf views!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 331 sq. ft, equipped with complimentary toiletries, kitchen w ...
From $403 per night (USD)VRBO
From $257 per night (USD)VRBO
Waterfront Florida Keys Cottage!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your perfect slice of Old Florida paradise! Tucked away on a spacious waterfront lot, this classic Keys cotta ...
From $257 per night (USD)VRBO
From $659 per night (USD)VRBO
Peaceful Palms Unit 2 – Waterfront Views, Dockage, Pool & Game Room Fun!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Peaceful Palms 2 is a brand-new 3-bedroom, 3-bathroom townhome in Islamorada—bright, breezy, and designed for easygoing ...
From $659 per night (USD)VRBO
From $211 per night (USD)Expedia
Cozy Family Townhome next to Tennis Courts in FL Keys Gated Community
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to this charming townhome in Islamorada. This pleasant retreat features 2 bedrooms with a cozy king, twin, and q ...
From $211 per night (USD)Expedia
From $798 per night (USD)VRBO
Blue Palm Oasis ~ 4 Bedroom Plantation Key Home w/ Pool & 170` of Dockage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Blue Palm Oasis! Escape to paradise at Blue Palm Oasis, a charming 4-bedroom, 3-bath home located on Plantat ...
From $798 per night (USD)VRBO
From $116 per night (USD)VRBO
Open Concept Studio Apartment in Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This cute Studio apartment has just been updated to a fully open concept beautiful apartment. Fully furnished, modern a ...
From $116 per night (USD)VRBO
From $577 per night (USD)VRBO
Private Beach Access: Islamorada Canal-Front Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Full Access to Private White Marlin Beach | Screened Porch | Outdoor Entertaining Space Immerse yourself in the coastal ...
From $577 per night (USD)VRBO
From $423 per night (USD)VRBO
New Bay Hammock Vacation Rental!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Be one of the first guests to experience this brand new vacation rental, perfectly situated in the sought-after, gated c ...
From $423 per night (USD)VRBO
From $802 per night (USD)VRBO
Stunning Islamorada Escape with Dock, Pool, Hot Tub & Direct Ocean Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to O'fish'ally Paradise! This jaw-dropping 3-bedroom, 3-bath Islamorada gem is where luxury meets laid-back isla ...
From $802 per night (USD)VRBO
From $262 per night (USD)Expedia
Lovely 2 bdrm home in a resort, have a coffee and watch the sunrise on the deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to a unique and serene retreat at a beautiful resort perched on the edge of the Atlantic Ocean. This home feature ...
From $262 per night (USD)Expedia
From $318 per night (USD)VRBO
Ocean Resort, Key Largo
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to Paradise in Key Largo: Your Dream Vacation Awaits! Mile Marek 94.8 Welcome to your slice of paradise in Key ...
From $318 per night (USD)VRBO
From $529 per night (USD)Expedia
Charming house boat with 2 bedrooms and WiFi, AC in wonderful Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This amazing house boat in Islamorada is a unique and pleasant retreat for guests. With 2 cozy bedrooms and a comfortabl ...
From $529 per night (USD)Expedia
From $305 per night (USD)VRBO
Beachfront Villa w/ Pier & Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to a tropical paradise at this villa at Topsider Resort in Islamorada. Nestled among lush gardens, this private o ...
From $305 per night (USD)VRBO
From $369 per night (USD)Expedia
2 Bedroom Updated Canal Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Your Dream Florida Keys Escape! This charming retreat offers modern upgrades, blending comfort and style, wit ...
From $369 per night (USD)Expedia
From $518 per night (USD)VRBO
Coconut Hut Oasis - 3 Bedroom Waterfront home with Pool/Spa, Tiki Hut, and Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Waterfront Escape with Heated Pool, Dockage & Hot Tub – Bayside Beauty in Islamorada Welcome to your perfect Keys getaw ...
From $518 per night (USD)VRBO
From $1267 per night (USD)Expedia
Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Escape to paradise in the Jungle Suite, the largest and most luxurious stay at Casa Morada in Islamorada. Unwind in your ...
From $1267 per night (USD)Expedia
From $1529 per night (USD)VRBO
Deactivated due to Bad Review and Low Productivity compared to other listings.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $1529 per night (USD)VRBO
From $926 per night (USD)Expedia
NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Experience waterfront FL Keys living at its finest at The Seascape, a modern, newly constructed retreat nestled directly ...
From $926 per night (USD)Expedia
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Islamorada Suite With Kayaks •Patio & Garden Views - Wildflower Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Stay in the Wildflower Suite at Casa Morada, where relaxation meets island adventure. Enjoy a king-size bed, garden-view ...
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From $1148 per night (USD)Expedia
Cozy Islamorada Stay- Garden, Patio & Living Room - Barefoot Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Unwind in the Barefoot Suite at Casa Morada, your private garden escape in Islamorada. This bright, airy suite features ...
From $1148 per night (USD)Expedia
From $2250 per night (USD)VRBO
Relaxing Garden Suite With Pool @Islamorada- Sea Turtle Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This phenomenal hotel suite in Islamorada offers a cozy retreat with a gorgeous king bed, AC, and WiFi. The bathroom fea ...
From $2250 per night (USD)VRBO
From $1900 per night (USD)Expedia
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Treat yourself to island luxury in the Moon Suite at Casa Morada. Perched on the high floor with garden views, this eleg ...
From $1900 per night (USD)Expedia
Click For PricingVRBO
Jacuzzi Retreat W/ Garden View @Islamorada - Wild Water Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Unwind in the Wild Water Suite, where garden serenity meets indulgent comfort. This king-bed suite features an indoor ja ...
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From $2250 per night (USD)Expedia
Charming Suite @Islamorada With Pool Access - Twilight Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Perched on the upper floor, the Twilight Suite at Casa Morada offers stunning garden views and a peaceful terrace perfec ...
From $2250 per night (USD)Expedia
From $1267 per night (USD)VRBO
Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Discover the Gumbo Limbo Suite at Casa Morada—where island relaxation meets outdoor adventure. Nestled in a tropical gar ...
From $1267 per night (USD)VRBO
Click For PricingExpedia
Garden View Suite w/ Balcony & Seating Area @Islamorada - Sweet Mango Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Step into island serenity in the Sweet Mango Suite at Casa Morada. Designed with lush jungle-inspired decor, this garden ...
Click For PricingExpedia
Click For PricingVRBO
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Treat yourself to island luxury in the Moon Suite at Casa Morada. Perched on the high floor with garden views, this eleg ...
Click For PricingVRBO
Click For PricingExpedia
Oceanview Sun Suite W/ Private Terrace Bliss @Islamorada - Sun Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Soak in sweeping bay views from the Sun Suite, a romantic retreat at Casa Morada in Islamorada. With large picture windo ...
Click For PricingExpedia
From $2532 per night (USD)VRBO
Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to the Iguana Suite, the largest and most luxurious accommodation at Casa Morada. This ground-level retreat feat ...
From $2532 per night (USD)VRBO
From $3767 per night (USD)Expedia
Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Discover the Coconut Palm Suite—a relaxing island retreat at Casa Morada in the Florida Keys. Unwind in a spacious suite ...
From $3767 per night (USD)Expedia
From $2051 per night (USD)VRBO
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Escape to the Jungles Suite at Casa Morada, where tropical vibes meet modern comfort. Featuring a king-size bed, private ...
From $2051 per night (USD)VRBO
Click For PricingExpedia
Terrace & Sea View Suite @Islamorada W/ Pool - Starfish Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Relax in the Starfish Suite at Casa Morada—your peaceful, ground-level escape with direct sea views. This charming suite ...
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From $2064 per night (USD)VRBO
Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The Shangri La Suite offers a peaceful getaway with spectacular views of Florida Bay. This second-level suite includes a ...
From $2064 per night (USD)VRBO
From $798 per night (USD)Expedia
Waterfront / Ocean Access Canal / Kamp Key / Homes
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
This quaint Keys-style home offers timeless charm in a premier waterfront setting on an ocean-access canal. The open-con ...
From $798 per night (USD)Expedia
From $637 per night (USD)VRBO
Fun Under the Sun! Beachfront, w/ Pool Onsite, Free Parking, Pets Allowed!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 370 sq. ft, equipped with complimentary toiletries, TV. ✦ Da ...
From $637 per night (USD)VRBO
From $755 per night (USD)VRBO
Your Key to Unforgettable Island Moments! 2 Relaxing Units with Balcony!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 16
✦ Each room is 1350 sq. ft, equipped with complimentary toiletries, TV. ✦ Daily cleaning services included in the night ...
From $755 per night (USD)VRBO
From $692 per night (USD)VRBO
Island Living! Pool, Spa, 100’ Dock + Paddleboards – Islamorada Gem
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Tucked away on a quiet street in Lower Matecumbe, this beautifully furnished canalfront home is everything you imagine w ...
From $692 per night (USD)VRBO
From $100 per night (USD)Expedia
Turnkey Modern Studio in the Upper Keys – Stylish, Bright & Fully Equipped!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Gorgeous Turnkey Studio with Modern Finishes and Full Kitchen! Step into this beautifully updated, open-concept studio t ...
From $100 per night (USD)Expedia
From $781 per night (USD)VRBO
Off The Charts-Waterfront Tiki Bar & Private Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to a one-of-a-kind Florida Keys escape! This unique home, originally used as the Islamorada Courthouse, has been ...
From $781 per night (USD)VRBO
From $1191 per night (USD)Expedia
Waterfront / Covered alfresco lounge / Heated Pool / Anchor Key
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This waterfront retreat, crafted for the ultimate outdoor lifestyle, features an expansive covered alfresco lounge with ...
From $1191 per night (USD)Expedia
From $537 per night (USD)VRBO
NewBeautifulCanal Home Snake Creek with Bay&Ocean Access Tiki&Pool 100ft Dockage
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
⭐️5 bedroom 4 bathrooms (One bathroom by pool) ⭐️Canal home in Venetian Shores with access to bay and ocean ⭐️100 foot o ...
From $537 per night (USD)VRBO
From $797 per night (USD)Expedia
*Charming Beach House directly ON the beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Islamorada Oceanfront home located directly on a private beach; enjoy swimming snorkeling, and ideal for kitesurfing! ...
From $797 per night (USD)Expedia
From $826 per night (USD)VRBO
Beautiful Pool Home located in Port Antigua
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
PROPERTY NAME: Casa Mar 115 Ponce de Leon Blvd, Islamorada, Florida LOCATION: Bayside Canal home located in the popular ...
From $826 per night (USD)VRBO
From $317 per night (USD)Expedia
Beautiful Pool home in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
PROPERTY NAME: The Bungalow House 32 Park Rd Islamorada, Florida Location: Bayside Very close to the Publix Shopping ...
From $317 per night (USD)Expedia
From $220 per night (USD)VRBO
Paradise in the Heart of Islamorada.Come relax and have the time of your life!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your stunning 2 bed/2 bath “Keys Vibe” condo in the heart of Islamorada—also known worldwide as the Sport‑Fis ...
From $220 per night (USD)VRBO
From $410 per night (USD)Expedia
NEW! Waterfront, 3 Bedroom, 3 Bath. Keys Living, Peaceful Retreat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This home is the definition of 'Keys' living. Situated on an oversized lot this 3 bedroom, 3 bath home offers 68 feet of ...
From $410 per night (USD)Expedia
From $443 per night (USD)VRBO
Oceanfront Islamorada Home with Epic Views from Every Room!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to 137 Ocean Lane in beautiful Islamorada—your private slice of paradise in the Florida Keys. This charming 3-be ...
From $443 per night (USD)VRBO
From $1034 per night (USD)VRBO
Bay Views, Spa, Pool, Tiki Hut, The Perfect Islamorada Getaway!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This stunning, fully renovated retreat checks every box for the perfect Keys escape—sweeping bay views, a private pool a ...
From $1034 per night (USD)VRBO
From $238 per night (USD)VRBO
Cozy Keys Hideaway on the water
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Your Tropical Getaway Experience the ultimate Florida Keys lifestyle in this beautifully renovated 2-bedroom, ...
From $238 per night (USD)VRBO
From $231 per night (USD)Expedia
Spacious Exec Bay Townhouse w/heated pool marina+
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Come and relax in Paradise at our updated Executive Bay Club (EBC) townhouse. EBC is located in Islamorada, mile marker ...
From $231 per night (USD)Expedia
From $603 per night (USD)VRBO
Beautiful two- story beach house
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Your cozy getaway awaits in Islamorada at this superb house. With 4 bedrooms including a king, queen, bunk, and twin bed ...
From $603 per night (USD)VRBO
From $2406 per night (USD)Expedia
Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Stay comfortably in Islamorada at this 1-bedroom hotel suites. The room features a cozy king bed, AC, WiFi, and a conven ...
From $2406 per night (USD)Expedia
From $326 per night (USD)VRBO
Modern 2BR Getaway | Full Kitchen + Bunks + AC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
🌟 HIGHLIGHTS 🌟 🛏 2 Bedrooms: 1 King Bed, 1 Full-over-Full Bunk Bed 🛋️ Stylish Living Area w/ Smart TV & Sofa � ...
From $326 per night (USD)VRBO
From $282 per night (USD)Expedia
Cozy Keys Stay | King Bed + Luxe Bath
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
🌟 HIGHLIGHTS 🌟 🛌🏻 1 Bedroom: 1x King Bed 🚿 1 Full Bathroom w/ Complimentary Toiletries 🍽️ Fully Equipped Kitche ...
From $282 per night (USD)Expedia
From $2213 per night (USD)VRBO
Palm Escape- Beachside Bliss w/ Private Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
🌴 First Time Ever Available – A True Keys Treasure! After 8 years searching, we found paradise. At the heart of the est ...
From $2213 per night (USD)VRBO
From $574 per night (USD)Expedia
Waterfront Florida Keys Home with Boat Dock and Hot Tub!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Discover the beauty of Islamorada and the surrounding Florida Keys from this spacious canal-side townhome! You will slid ...
From $574 per night (USD)Expedia
From $180 per night (USD)VRBO
Modern remodeled 2 bedroom Apt - Summer Sea 434
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This beautiful, modern, upgraded 2-bedroom, 1.5 bath apartment at Summer Sea has everything you would want for your fabu ...
From $180 per night (USD)VRBO
From $376 per night (USD)Expedia
See the sunrises in Islamorada!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Get ready to relax in this 2-bedroom house in Islamorada. This adorable property features AC and a hair dryer for your c ...
From $376 per night (USD)Expedia
From $742 per night (USD)VRBO
Oceanfront Cottage in Islamorada! Swimming Pool, Pets Allowed, Free Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Set along a private beach in Islamorada, La Siesta Resort & Villas features colorful cottages with premium amenities. Gu ...
From $742 per night (USD)VRBO
From $688 per night (USD)VRBO
Ocean view Studio w/kitchenette, Pool, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront studios with premium amenities. G ...
From $688 per night (USD)VRBO
From $693 per night (USD)VRBO
Oceanfront Studio Queen w/Kitchenette, Pool, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront studios with premium amenities. G ...
From $693 per night (USD)VRBO
From $682 per night (USD)VRBO
Ocean Front Studio w/Kitchenette, Pool, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront studios with premium amenities. G ...
From $682 per night (USD)VRBO
From $277 per night (USD)VRBO
Best sunrises in all of Islamorada!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Isla life starts now! This is more than just another day in paradise. Sun Outdoors Islamorada in the Florida Keys is ...
From $277 per night (USD)VRBO
From $1338 per night (USD)VRBO
Two Bedroom Ocean Front Suite w/Kitchenette, Pool, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront suites with premium amenities. Gu ...
From $1338 per night (USD)VRBO
From $998 per night (USD)VRBO
One Bedroom Suite w/2 Queen Beds, Kitchenette, Pool, Free Parking & Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 12
Set along a private beach in Islamorada, La Siesta Resort & Villas features suites with premium amenities. Guests enjoy ...
From $998 per night (USD)VRBO
From $1274 per night (USD)VRBO
2 Separate Unites w/ 2 Bedrooms, Kitchenette, Pool, Free Parking & Pool
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 16
Set along a private beach in Islamorada, La Siesta Resort & Villas features suites with premium amenities. Guests enjoy ...
From $1274 per night (USD)VRBO
From $705 per night (USD)VRBO
Courtyard View Room w/Patio, Outdoor Pool, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located oceanfront in Islamorada, Amara Cay Resort features stylish rooms and suites with balconies in a boutique island ...
From $705 per night (USD)VRBO
From $689 per night (USD)VRBO
2 Queen Beds Room w/Patio, Outdoor Pool, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located oceanfront in Islamorada, Amara Cay Resort features stylish rooms and suites with balconies in a boutique island ...
From $689 per night (USD)VRBO
From $572 per night (USD)VRBO
1 King Room w/ Balcony, 3 Outdoor Pools & Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Set on 15 oceanfront acres in Islamorada, Three Waters Resort & Marina features island-inspired rooms. Guests enjoy thre ...
From $572 per night (USD)VRBO
From $1653 per night (USD)VRBO
4 Rooms w/ Queen Beds, Balcony, 3 Outdoor Pools, Free Parking & Pet Friendly
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Set on 15 oceanfront acres in Islamorada, Three Waters Resort & Marina features island-inspired rooms. Guests enjoy thre ...
From $1653 per night (USD)VRBO
From $963 per night (USD)VRBO
2 Rooms w/ Queen Beds, Balcony, 3 Outdoor Pools, Free Parking & Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Set on 15 oceanfront acres in Islamorada, Three Waters Resort & Marina features island-inspired rooms. Guests enjoy thre ...
From $963 per night (USD)VRBO
From $483 per night (USD)VRBO
2 Queen Bed Rooms w/ Balcony, 3 Outdoor Pools, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Set on 15 oceanfront acres in Islamorada, Three Waters Resort & Marina features island-inspired rooms. Guests enjoy thre ...
From $483 per night (USD)VRBO
From $1087 per night (USD)VRBO
Two Bedrooms Suite w/Ocean View, Pool, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront suites with premium amenities. Gu ...
From $1087 per night (USD)VRBO
From $1114 per night (USD)VRBO
2 Suites w/Queen Beds, Kitchenette, Outdoor Pool, Free Parking & Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 12
Set along a private beach in Islamorada, La Siesta Resort & Villas features suites with premium amenities. Guests enjoy ...
From $1114 per night (USD)VRBO
From $651 per night (USD)VRBO
Courtyard View King Room w/ Balcony, Outdoor Pool & Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Located oceanfront in Islamorada, Amara Cay Resort features stylish rooms and suites with balconies in a boutique island ...
From $651 per night (USD)VRBO
From $1228 per night (USD)VRBO
2 Rooms w/ Balcony, Courtyard View, Outdoor Pool, Free Parking & Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located oceanfront in Islamorada, Amara Cay Resort features stylish rooms and suites with balconies in a boutique island ...
From $1228 per night (USD)VRBO