Holiday homes by the sea in Islamorada
Choose the right place for you
FACILITIES
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Pool
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Pets Allowed
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Non Smoking Only
REVIEWS
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9+ Exceptional
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8+ Fabulous
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7+ Very Good
DISTANCE FROM CENTRE
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Less than 1 km
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Less than 3 km
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Less than 5 km
Holiday rental deals in Islamorada
We have selected the best holiday accommodation by the sea in Islamorada. Bluepillow allows you to save money, by finding the best rates on the main vacation rental websites in Islamorada
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from158€
![Luxury One Bedroom Condo #3]( "This condo is located in Islamorada. USS Alligator Shipwreck is a local landmark, and the area's natural beauty can be seen at Indian Key Historic State Park and San Pedro Underwater Archaeological Preserve State Park. <br> One Bedroom, One Bathroom Condo, Separate Living Space and Fully Equipped Kitchen. Outdoor Fire pit under palm trees with Adirondack Chairs. Ideal location in Islamorada FL.<br>(Four units in building- this one is on the top floor to the left from the entrance)<br>The complex is located a MM 80 on the ocean side and does not have a swimming pool. Public beach is 7 miles South at Anne's beach and 7 miles North at Founder's Park.")
Luxury One Bedroom Condo #3
- 2 Guests 1Bedroom
10 Exceptional (4)This condo is located in Islamorada. USS Alligator Shipwreck is a local landmark, and the area's natural beauty can be seen at Indian Key Historic State Park and San Pedro Underwater Archaeological Preserve ...Check Availability -
from158€
![Hidden Gem Islamorada Top Floor 2Bed/2Bath]( "Located in Islamorada, this apartment is by the sea. Travelers eager for a bit of culture can stop by History of Diving Museum, while those wishing to experience the area's natural beauty can explore Indian Key Historic State Park and San Pedro Underwater Archaeological Preserve State Park. <br> This newly renovated unit is truly is a Hidden Gem in the heart of Islamorada! This duplex is nestled in the trees just a few steps from one of the most amazing sunsets in the Upper Keys. Walking distance to all the wonderful shops, restaurants and breweries that Islamorada has to offer. Bikes and Kayaks can be rented steps away from the front door of this unit. Want to find a place that you'll want to return year after year? Look no further!<br><br>This unique property was originally built as motel in the 1950's. We have taken it upon ourselves to give it a facelift! Expects new bathrooms, flooring, beds, windows, and new split AC units in every room! Cool down when you get inside from that Florida heat! Brrrrr <br>● Maximum 4 guests <br>● Laundry/courtyard/grill is SHARED with guests downstairs <br>● Unit has a courtyard view <br><br><br>Cancellation Policy <br>● 100% refund if you cancel at least 60 days before check-in. <br>● 50% refund (minus service fee) if you cancel at least 30 days before check-in. <br>● No refund if you cancel less than 30 days before check-in. <br><br>We strongly recommend purchasing a separate travel protection policy to cover any refund requests outside the above cancellation rules. <br>Hello and welcome, we try meet and greet all of our guests! Making sure you have a great vacation experience is my passion! We live her locally so will be available for any questions you may have throughout your stay. - Sean<br>Located at Mile Market 82.5 in the heart of Islamorada this unit is central to many shops, restaurants, and bars! Its right across the street from several shops, walking distance to several restaurants, and the famous Islamorada Beer Company! <br><br>We provide a detailed GUESTBOOK with many great recommendations for food, drinks, and activities!!<br>The property is accessed via self check in with a key pad.<br>This unit is 620 sq. ft. located on the second floor. Its two bedroom/two bath with a small kitchen and living room. <br><br>The master bedroom has a King memory foam mattress with an en suite bathroom. <br>The guest bedroom has a King memory foam mattress and an unattached bathroom.<br>There are no dressers or closets in the units. We provide luggage racks, and places to hang clothing. <br><br>This unit is part or a very unique and private wooded property that spans over the bay of the Florida Keys. This unit does has a courtyard view NOT a bay/ocean view. All staying guests have complete access to all the property has to offer. It’s a two minute walk to the boat basin and the most incredible sunset view in Islamorada!<br><br>Guests are allowed to bring one boat up to 25’ foot to keep in the boat basin. There is trailer parking on property for no addition fee.")
Hidden Gem Islamorada Top Floor 2Bed/2Bath
- 4 Guests 2Bedrooms
9.8 Exceptional (27)Located in Islamorada, this apartment is by the sea. Travelers eager for a bit of culture can stop by History of Diving Museum, while those wishing to experience the area's natural beauty can explore Indian ...Check Availability -
from166€
![Hidden Gem Islamorada 1st Floor 2Bed/2Bath]( "Located in Islamorada, this apartment is on the waterfront. While the natural beauty of Indian Key Historic State Park and San Pedro Underwater Archaeological Preserve State Park can be enjoyed by anyone, those looking for an activity can check out Bud n' Mary's Dive Center. <br> <br> This newly renovated unit is truly is a Hidden Gem in the heart of Islamorada! This duplex is nestled in the trees just a few steps from one of the most amazing sunsets in the Upper Keys. Walking distance to all the wonderful shops, restaurants and breweries that Islamorada has to offer. Bikes and Kayaks can be rented steps away from the front door of this unit. Want to find a place that you'll want to return year after year? Look no further!<br><br>This unique property was originally built as motel in the 1950's. We have taken it upon ourselves to give it a facelift! Expects new bathrooms, flooring, beds, windows, and new split AC units in every room! Cool down when you get inside from that Florida heat! Brrrrr <br>● Maximum 4 guests <br>● Laundry/courtyard/grill is SHARED with guests upstairs<br>● Unit has a courtyard view <br><br>Cancellation Policy <br>● 100% refund if you cancel at least 60 days before check-in. <br>● 50% refund (minus service fee) if you cancel at least 30 days before check-in. <br>● No refund if you cancel less than 30 days before check-in. <br><br>We strongly recommend purchasing a separate travel protection policy to cover any refund requests outside the above cancellation rules. <br>Hello and welcome, we try meet and greet all of our guests! Making sure you have a great vacation experience is my passion! We live her locally so will be available for any questions you may have throughout your stay. - Sean<br>Located at Mile Market 82.5 in the heart of Islamorada this unit is central to many shops, restaurants, and bars! Its right across the street from several shops, walking distance to several restaurants, and the famous Islamorada Beer Company! <br><br>We provide a detailed GUESTBOOK with many great recommendations for food, drinks, and activities!!<br>The property is accessed via self check in with a key pad.<br>This unit is 620 sq. ft. located on the first floor. Its two bedroom/two bath with a small kitchen and living room. <br><br>The master bedroom has a Queen mattress with an en suite bathroom. <br>The guest bedroom has a King memory foam mattress and an unattached bathroom.<br>There are no dressers or closets in the units. We provide luggage racks, and places to hang clothing.<br><br>This unit is part or a very unique and private wooded property that spans over the bay of the Florida Keys. This unit does has a courtyard view NOT a bay/ocean view. All staying guests have complete access to all the property has to offer. It’s a two minute walk to the boat basin and the most incredible sunset view in Islamorada!<br><br>Guests are allowed to bring one boat up to 25’ foot to keep in the boat basin. There is trailer parking on property for no addition fee.")
Hidden Gem Islamorada 1st Floor 2Bed/2Bath
- 4 Guests 2Bedrooms
9.7 Exceptional (29)Located in Islamorada, this apartment is on the waterfront. While the natural beauty of Indian Key Historic State Park and San Pedro Underwater Archaeological Preserve State Park can be enjoyed by anyone, ...Check Availability -
from164€
![The Caribbean Resort Malayan Palm North]( "When you stay at this apartment in Islamorada, you'll be in a shopping district, within a 15-minute walk of Matecumbe United Methodist Church and Florida Keys Brewing Co.. This apartment is 12.3 mi (19.7 km) from Long Key State Park and 0.8 mi (1.2 km) from Hurricane Monument. <br> Make yourself comfortable in this apartment, featuring a kitchen with a refrigerator and a stovetop. There's a private balcony. Complimentary wireless Internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include a microwave and a coffee/tea maker.")
The Caribbean Resort Malayan Palm North
- Hotel
When you stay at this apartment in Islamorada, you'll be in a shopping district, within a 15-minute walk of Matecumbe United Methodist Church and Florida Keys Brewing Co.. This apartment is 12.3 mi (19.7 ...Check Availability -
from155€
![Oceanfront Islamorada Condo with T-Dock FREE boat dockage]( "Located in Islamorada, this condo is on the beach. Travelers eager for a bit of culture can stop by History of Diving Museum, while those wishing to experience the area's natural beauty can explore Indian Key Historic State Park and San Pedro Underwater Archaeological Preserve State Park. Discover the area's water adventures with jet skiing, kayaking, and scuba diving nearby, or enjoy the great outdoors with cycling. <br> Come and enjoy our Paradise Found 2nd home. FREE BOAT DOCKAGE In the fishing capital of the world, Islamorada. Beautifully furnished 2 BR 2 BA Condo on second floor.(First is parking only) Spiral Staircase directly down to grounds. Only this floor has the stairs, others have to go through a lobby with a key. The master bedroom and outside patio gives a beautiful view of the OCEAN. Wake up to the sunrise. Inside find a fully equipped kitchen, w/d, games, books comfortable furniture and smart TVs throughout. Go out into the mild weather & wander around among our beautiful tropical gardens, bring your drink down to the waters edge or curl up with a good book. Sandy beach boasts lounge chairs under Tiki huts and wonderful chaise lounges and tables around the pool. Fish or swim from the beautiful newly rebuilt T-dock with electric and water at each slip and another ice machine to stock your boat. A big cleaning station for your fresh catch. Most restaurants will cook it for you. Or just hang out and watch the fishermen come in. The work out center is fully equipped and even has a sauna! Don’t forget to Bring your boat or rent one at the numerous places nearby, FREE DOCKAGE! **MONTHLY RENTALS ONLY!!<br><br>Don't miss the state of the art work out room equipped with a SAUNA, so after a vigorous workout or a day on the water, relax and get rejuvenated in the therapeutic SAUNA.<br><br>Swim in our heated fresh water pool with zero entry or lounge in our huge new therapeutic Jacuzzi. Have a party under the thatched Tiki roofed 'room', can be open air, or clear plastic curtains roll down to keep the wind and weather out. It is fully equipped with ice machine, grills, tables, chairs and benches and a serving bar! A paradise you will want to come back to again and again. Play cards or eat with friends.<br><br>Keywords: Condo, fishing, oceanfront, sandy beach, boating, swimming.")
Oceanfront Islamorada Condo with T-Dock FREE boat dockage
- 4 Guests 2Bedrooms
9.7 Exceptional (18)Located in Islamorada, this condo is on the beach. Travelers eager for a bit of culture can stop by History of Diving Museum, while those wishing to experience the area's natural beauty can explore Indian ...Check Availability -
from122€
![Islamorada Condo with ocean access]( "Located in Islamorada, this condo is on the waterfront. Travelers eager for a bit of culture can stop by History of Diving Museum, while those wishing to experience the area's natural beauty can explore Indian Key Historic State Park and San Pedro Underwater Archaeological Preserve State Park. <br> 2 bedroom 1 bathroom condo with full kitchen on the second floor. Tropical palm tree views outside. The palms property sits ocean side and the pool completely overlooks the ocean along with tiki hut area for lounging and a nice hot tub. Walking distance to great food and fishing marina with charter boats or dockage options available if you bring your own boat. Plenty to see and do in Islamorada just a 5 minute drive north. Lots of restaurants and shopping, art galleries, etc. Reservations are not confirmed until you speak with property manager.")
Islamorada Condo with ocean access
- 4 Guests 2Bedrooms
9.6 Exceptional (10)Located in Islamorada, this condo is on the waterfront. Travelers eager for a bit of culture can stop by History of Diving Museum, while those wishing to experience the area's natural beauty can explore ...Check Availability
Bed and breakfast offers in Islamorada by the sea
Are you looking for an accommodation in Islamorada and do you want to save money? Choose from 3 Bed & Breakfasts in Islamorada
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from1434€
![Anglers Reef Villa 1]( "Located in Islamorada, Anglers Reef Villa 1 is within a 5-minute drive of Windley Key Fossil Reef Geological State Park and Islamorada County Park. This beach villa is 1.8 mi (2.9 km) from Founders Park and 2.1 mi (3.5 km) from History of Diving Museum. <br> Make yourself at home in one of the 2 individually furnished guestrooms, featuring kitchens with full-sized refrigerators/freezers and ovens. Flat-screen televisions with cable programming provide entertainment, while complimentary wireless Internet access keeps you connected. Conveniences include separate sitting areas and microwaves, as well as phones with free local calls.")
Anglers Reef Villa 1
- Hotel
9.4 Exceptional (9)Located in Islamorada, Anglers Reef Villa 1 is within a 5-minute drive of Windley Key Fossil Reef Geological State Park and Islamorada County Park. This beach villa is 1.8 mi (2.9 km) from Founders Park ...Check Availability -
from1429€
![The Islands of Islamorada]( "When you stay at The Islands of Islamorada in Islamorada, you'll be on the beach, within a 5-minute drive of History of Diving Museum and Matecumbe United Methodist Church. This 4-star villa is 1.4 mi (2.3 km) from Florida Keys Brewing Co. and 1.5 mi (2.3 km) from Hurricane Monument. <br> Make yourself at home in one of the 30 individually decorated guestrooms, featuring microwaves and Smart televisions. Your pillowtop bed comes with premium bedding. Rooms have private furnished balconies or patios. Complimentary wireless Internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have designer toiletries and hair dryers.")
The Islands of Islamorada
- Hotel
9.6 Exceptional (57)When you stay at The Islands of Islamorada in Islamorada, you'll be on the beach, within a 5-minute drive of History of Diving Museum and Matecumbe United Methodist Church. This 4-star villa is 1.4 mi ...Check Availability -
from1437€
![The Caribbean Resort Royal Palm North]( "When you stay at this vacation home in Islamorada, you'll be in a shopping district, within a 15-minute walk of Matecumbe United Methodist Church and Florida Keys Brewing Co.. This vacation home is 12.3 mi (19.7 km) from Long Key State Park and 0.8 mi (1.2 km) from Hurricane Monument. <br> Make yourself comfortable in this vacation home, featuring a kitchen with a refrigerator and a stovetop. There's a private balcony. Complimentary wireless Internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include a microwave and a coffee/tea maker.")
The Caribbean Resort Royal Palm North
- Hotel
10 Exceptional (3)When you stay at this vacation home in Islamorada, you'll be in a shopping district, within a 15-minute walk of Matecumbe United Methodist Church and Florida Keys Brewing Co.. This vacation home is 12.3 ...Check Availability
Farmhouse or Hotel? Choose from the best offers
Choose the accommodation tailor-made for you for your next vacation: sleep in a farmhouse or sleep in a hotel?
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![Farmstays in Islamorada]()
Farmstays in Islamorada -
![Hotels in Islamorada]()
Hotels in Islamorada
The best places to stay in Islamorada
Book an apartment in Islamorada and choose the right accommodation for your needs
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from313€
![The Caribbean Resort]( "A stay at The Caribbean Resort places you in the heart of Islamorada, within a 5-minute drive of Hurricane Monument and History of Diving Museum. This family-friendly hotel is 2.3 mi (3.7 km) from Bud n' Mary's Dive Center and 5.2 mi (8.4 km) from Founders Park. <br> Make yourself at home in one of the 14 individually decorated guestrooms, featuring kitchens with full-sized refrigerators/freezers and ovens. Rooms have private balconies or patios. LED televisions with cable programming provide entertainment, while complimentary wired Internet access keeps you connected. Conveniences include separate sitting areas and microwaves, and housekeeping is provided daily.")
The Caribbean Resort
- Hotel
9.8 Exceptional (375)A stay at The Caribbean Resort places you in the heart of Islamorada, within a 5-minute drive of Hurricane Monument and History of Diving Museum. This family-friendly hotel is 2.3 mi (3.7 km) from Bud ...Check Availability -
from134€
![Casa Morada]( "When you stay at Casa Morada in Islamorada, you'll be near the bay, within a 5-minute drive of Matecumbe United Methodist Church and Florida Keys Brewing Co.. This beach hotel is 12.4 mi (20 km) from Long Key State Park and 1 mi (1.5 km) from History of Diving Museum. <br> Make yourself at home in one of the 16 guestrooms featuring minibars and flat-screen televisions. Rooms have private balconies or patios. Cable programming and DVD players are provided for your entertainment, while complimentary wireless Internet access keeps you connected. Bathrooms have designer toiletries and hair dryers.")
Casa Morada
- Hotel
9.3 Exceptional (837)When you stay at Casa Morada in Islamorada, you'll be near the bay, within a 5-minute drive of Matecumbe United Methodist Church and Florida Keys Brewing Co.. This beach hotel is 12.4 mi (20 km) from ...Check Availability -
from137€
![The Islands of Islamorada]( "When you stay at The Islands of Islamorada in Islamorada, you'll be on the beach, within a 5-minute drive of History of Diving Museum and Matecumbe United Methodist Church. This 4-star villa is 1.4 mi (2.3 km) from Florida Keys Brewing Co. and 1.5 mi (2.3 km) from Hurricane Monument. <br> Make yourself at home in one of the 30 individually decorated guestrooms, featuring microwaves and Smart televisions. Your pillowtop bed comes with premium bedding. Rooms have private furnished balconies or patios. Complimentary wireless Internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have designer toiletries and hair dryers.")
The Islands of Islamorada
- Hotel
9.6 Exceptional (57)When you stay at The Islands of Islamorada in Islamorada, you'll be on the beach, within a 5-minute drive of History of Diving Museum and Matecumbe United Methodist Church. This 4-star villa is 1.4 mi ...Check Availability -
from309€
![Islander Bayside Villas and Boatslips]( "With a stay at Islander Bayside Villas and Boatslips, you'll be centrally located in Islamorada, just a 4-minute walk from Hurricane Monument and 9 minutes by foot from Florida Keys Brewing Co.. This beach hotel is 11.3 mi (18.2 km) from Long Key State Park and 0.5 mi (0.9 km) from Matecumbe United Methodist Church. <br> Make yourself at home in one of the 25 guestrooms, featuring kitchens with full-sized refrigerators/freezers and ovens. Your pillowtop bed comes with premium bedding. Rooms have private furnished balconies. 37-inch LCD televisions with satellite programming provide entertainment, while complimentary wireless Internet access keeps you connected.")
Islander Bayside Villas and Boatslips
- Hotel
8.9 Fabulous (780)With a stay at Islander Bayside Villas and Boatslips, you'll be centrally located in Islamorada, just a 4-minute walk from Hurricane Monument and 9 minutes by foot from Florida Keys Brewing Co.. This ...Check Availability -
from123€
![Breezy Palms Resort]( "Located in Islamorada, Breezy Palms Resort is on the beach. While the natural beauty of Indian Key Historic State Park and San Pedro Underwater Archaeological Preserve State Park can be enjoyed by anyone, those looking for an activity can check out Bud n' Mary's Dive Center. <br> <br> At Breezy Palms Resort, hit the beach, relax by an outdoor pool, or spend the day at a marina. Each apartment features a kitchen with a refrigerator and a microwave, plus free WiFi and a TV with cable channels. Other amenities that guests will find include a sitting area and a coffee/tea maker. Weekly housekeeping is available.")
Breezy Palms Resort
- Hotel
8.2 Fabulous (322)Located in Islamorada, Breezy Palms Resort is on the beach. While the natural beauty of Indian Key Historic State Park and San Pedro Underwater Archaeological Preserve State Park can be enjoyed by anyone, ...Check Availability -
from140€
![Sands of Islamorada]( "Located in Islamorada, Sands of Islamorada is in the suburbs and by the sea. Travelers eager for a bit of culture can stop by History of Diving Museum, while those wishing to experience the area's natural beauty can explore Windley Key Fossil Reef Geological State Park and Anne's Beach. <br> An outdoor pool, laundry facilities, and a garden are available at this hotel. WiFi in public areas is free. Additionally, barbecue grills, a picnic area, and a front-desk safe are onsite.")
Sands of Islamorada
- Hotel
8.6 Fabulous (855)Located in Islamorada, Sands of Islamorada is in the suburbs and by the sea. Travelers eager for a bit of culture can stop by History of Diving Museum, while those wishing to experience the area's natural ...Check Availability
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