Islamorada, Florida Listings

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Monthly Rent $6,744 - $15,109

Relaxing 3BR Oceanfront | Dock | Deck | W/D Islamorada, Florida, Listing ID: 32659

*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. Enjoy incredible beach and ocean views from this family-friendly, waterfront retreat. This home features a beautiful, sandy backyard...

  • House
  • 1150
  •  3
  •  3
Monthly Rent $2,974 - $6,703

Beautiful 2BR 1st-Floor | Patio | Pool Islamorada, Florida, Listing ID: 32660

Whether you spend your next Florida vacation playing in the cool surf or hanging out with good friends on the private patio, you will love staying in this gorgeous retreat. Inside, an open and spacious living area features comfortable furniture, attractive wall art, and a large...

  • Condo
  • 1342
  •  2
  •  2
Monthly Rent $3,262 - $5,822

Charming 2BR | Balcony | Pool | Islamorada, Florida, Listing ID: 32661

Escape the hustle and bustle of everyday life in the tropical Florida Keys, where tranquility and fun await. This condo is steps away from the water, with all you ever need for entertainment in a 10-mile radius. Tour the area and check out Rain Barrell Village, Theater of the...

  • Condo
  • 1344
  •  2
  •  3
Monthly Rent $2,842 - $4,887

2BR Waterview | Dock | Deck | Garage Parking Islamorada, Florida, Listing ID: 32662

If you're seeking the ideal Florida Keys retreat, look no further! Several beaches are ready and waiting for you to sink your feet into the sand and enjoy the water. If you'd prefer to have fun on the water instead of in it, check out a nearby charter for a relaxing ride or a...

  • House
  • 960
  •  2
  •  2
Monthly Rent $5,400 - $8,900

Oceanfront, Dog-Friendly Home w/Private Dock, Free WiFi, Gas Grill, A/C Islamorada, Florida, Listing ID: 28675

Perched across the lane from a white sand beach and abutting the canal, this double-waterside home is a tropical paradise. Your renovated retreat features coastal-chic interiors and large picture windows that face the ocean. With lovely views and direct canal access, your home...

  • Home
  • 1517
  •  3
  •  3
Details No Image Available

$Multi-Month Discount!

Monthly Rent $8,500 - $9,300

Beautiful home in the heart of the Florida Keys. Located in sought-after neighborhood near prime dining and attractions. Islamorada, Florida, Listing ID: 29352

Beautiful home in the heart of the Florida Keys for your winter escape. There are many prime restaurants and attractions just a short drive away. The home is situated in one of the most sought-after, family oriented neighborhood in the Keys. Relax and talk the night away on the...

  • Home
  • 2320
  •  3
  •  2

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  • 0
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Beautiful condo steps from Vanderbilt beach with its own private entrance! Fully furnished with everything Naples, Florida, Listing ID: 29479

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Details No Image Available

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  •  5
  •  3
Details No Image Available

$Multi-Month Discount!

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First floor , two bed and two baths. It has wood floors, walk-in closet, assigned parking space and pool. Directly across the street from the beach. Aventura Mall, The Gulfstream Park , Hollywood Beach , Walmart, supermarkets and restaurants are near by.

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Astounding estate furnished to an impeccable standard. It’s the ideal retreat for an exquisite & upscale stay, located in the heart of Fort Lauderdale. On the water, with the sun in the horizon. We believe it’s the ultimate location to experience Fort Lauderdale the way it...

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Maison Du Luc fort lauderdale, Florida, Listing ID: 30573

Discover a mid-century modern haven at the edge of Birch State Park. This home is as chic as it is fun: explore the waters on the kayaks, host stylish family affairs in the sophisticated dining area or screened-in porch. When you’re ready to explore, the beach—home to Fort...

  • HOUSE
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  •  5
  •  4
Details No Image Available

$Multi-Month Discount!

Monthly Rent $13,000

Located near Key West, this one-of-a-kind home features 3BRs and a shared pool. Key West, Florida, Listing ID: 30640

Please note that this home is available for 28+ night stays only. Coral Palm is a lovely 3 bedroom, 3 bathroom, 2 story townhome located in the private gated community of Coral Hammock on Stock Island. The property is less than 5 miles from downtown Key West allowing you to...

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  • 1,420
  •  3
  •  3
Details No Image Available

$Multi-Month Discount!

Monthly Rent $2,650

CALUSA CAMPGROUND AND MARINA KEY LARGO FLORIDA KEY LARGO, Florida, Listing ID: 30679

1750 SQUARE FOOT LOT. INCLUDES COVERED TERRACE. FITS UP TO 50 FOOT TRAILER AND ADDITIONAL PARKING SPACE FOR SMALL VESSEL AND VEHICLE. 24 HOUR MARINA AND BOAT RAMP. 24 HOUR SECURITY ON DUTY. CLOSE TO MAJOR ATTRACTIONS IN UPPER FLORIDA KEYS.

  • RV Lot
  • 1750
  •  0
  •  

Gorgeous water views and stunning sunsets! Immaculate townhome with your boat slip out your front door. Beautiful unit! Marathon, Florida, Listing ID: 30704

Fisherman’s delight with your boat slip out front door suitable for up to 32ft boats,kayak racks and grills on property. Close to restaurants and amenities. Beautifully landscaped property with a gorgeous pool and also a fitness center on property. This villa is in the best...

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  • 0
  •  3
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Details No Image Available

$Multi-Month Discount!

Monthly Rent $4,000

Unused brand new apartment, everything is new. It is located on the lower floor of new house, canal front. KEY LARGO, Florida, Listing ID: 30742

The apartment is brand new including unused furniture. First time offered to rent apartment. Place to have jet ski or canoe in front of the house or a small boat under 18 feet. the community is well maintained and safe.

  • Apartment
  • 950
  •  1
  •  1
Details No Image Available

$Multi-Month Discount!

Monthly Rent $3,000 - $6,500

Brand-new listing! Gorgeously-refreshed 2 BR, 2BA+den/office in Highland Woods Golf and Country Club in Bonita Springs Bonita Springs, Florida, Listing ID: 30778

Brand new to the rental market, book your extended Florida vacation at Casa Familia. This bright, gorgeously refreshed 2nd-floor condo has a stunning lake view over the 16th fairway of Highland Woods Golf and Country Club--a bundled golf community. Every detail of this 2 BR, 2...

  • Condo
  • 1441
  •  2
  •  2
Details No Image Available

$Multi-Month Discount!

Monthly Rent $2,200

Quiet, cozy garden-style apartment just three blocks from Ft. Lauderdale beach! Ft. Lauderdale, Florida, Listing ID: 30785

FULLY-FURNISHED SHORT-TERM RENTAL, AVAILABLE FOR A MINIMUM OF FOUR MONTHS UP TO A MAXIMUM OF SIX MONTHS, BEGINNING DECEMBER 2023 THROUGH MAY 2024. MUST BE 55 YEARS OF AGE OR OLDER. Just a five-minute walk from the world-famous Ft. Lauderdale beach and a wide variety of...

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  •  1
Monthly Rent $4,500

Brand New Lakefront Townhouse. Fish from your own backyard! Spacious with 3 bedrooms, 2.5 bathrooms + Loft DEERFIELD BEACH, Florida, Listing ID: 30814

Gorgeous designer finishes, including custom window treatments, luxury Europian wallpaper, and sleek light fixtures complement contemporary look. Our guests enjoy a modern open floor plan, comfortable designer furnishings. Unbeatable location - 1.4 miles to I-95, just 4 miles to...

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  • 1980
  •  3
  •  2 1/2
Monthly Rent $5,500

Our property is centrally located in Key Largo. Close by, you can find attractions, restaurants, groceries, souvenir etc key Largo, Florida, Listing ID: 30976

We are The Valdes family and we have been living in Miami for the last 20 years. We love traveling and meeting other cultures. We really hope that you and your family enjoy this piece of heaven, our second home. Our property is centrally located in Key Largo. Close by, you can...

  • House
  • 1056
  •  2
  •  1

Tarpon Cove - Tavernier, FL Tavernier, Florida, Listing ID: 31437

*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.

This home is perfect for anyone coming to the Keys to spend time on the water. The two-story home sits on the...

  • House
  • 0
  •  2
  •  2
Monthly Rent $4,620 - $5,775

Sunrise Delight - Hollywood, FL Hollywood, Florida, Listing ID: 31475

Let Sunrise Delight host your next getaway to Hollywood, Florida! Create lovely memories with your group that will last a lifetime! This one-level, dog-friendly duplex boasts a spacious and comfortable kitchen/dining/living area equipped with a flatscreen TV to watch...

  • House
  • 0
  •  1
  •  1
Monthly Rent $3,880 - $7,293

BOAT-FRIENDLY, DOG-FRIENDLY, newly renovated 2BR Home (Sleeps 6) High-Speed WiFi, Canal-front Dock, Private Boat Ramp! Tavernier, Florida, Listing ID: 31490

Book this newly renovated home that sits on a major canal, where guests can tie off a boat, in the Indian Waterways neighborhood. The nautical-themed decoration throughout the house will truly help you leave all of your worries behind and focus on having a great time!...

  • Home
  • 0
  •  2
  •  1
Monthly Rent $2,112 - $5,533

Serene Getaway - Goodland, FL Goodland, Florida, Listing ID: 31628

Located in a charming and historic fishing village, this 2BR/2BA second-floor unit is your ideal canal-side getaway. Highlights include gorgeous hardwood floors, three flat-screen TVs, and a screened porch offering spectacular sunset views over the...

  • House
  • 0
  •  2
  •  2
Monthly Rent $1,672 - $5,522

Ocean Reserve 1607 - Sunny Isles Beach, FL Sunny Isles Beach, Florida, Listing ID: 31668

Perched on the 16-floor overlooking the ocean, this 1BR/1.5BA condo is the perfect coastal getaway to Sunny Isles Beach. Spend sun-soaked days at the complex sparkling pool, or walk just 6 minutes to dip your toes in the Atlantic. An abundance of convenient amenities...

  • Condo
  • 0
  •  1
  •  1
Monthly Rent $6,300 - $7,678

Turtle Beach Retreat: 2BR Oceanfront home (duplex) beachfront balcony, private beach, pier, gas grill, and deck! Long Key, Florida, Listing ID: 31698

This remodeled home is set right on the beach, and is equipped for guests to have a lot of fun on the beach! Towels, a beach umbrella, and four beach chairs are included for guest use on the private sandy beach. Shower off the sand before coming inside the covered...

  • Home
  • 0
  •  2
  •  1
Details No Image Available

$Multi-Month Discount!

Monthly Rent $20,000 - $28,500

Tiki Beach Retreat - Southern Facing - Bike2Vanderbilt Beach & Wiggins State Park - Heated Pool/Spa - 70+ Amenities Naples, Florida, Listing ID: 31777

This home has a one-of-a-kind design that distinguishes it from others. It features three generously sized bedrooms, two contemporary bathrooms, and a gorgeous Tiki Hut with a view of the backyard Oasis. The house spans 1500 square feet and has recently undergone upgrades,...

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  • 1545
  •  3
  •  2
Monthly Rent $8,500

Luxury, modern, snowbird ready retreat! 2 bedrooms, 2 bathrooms with a den! Best savings for winter stays! Ft. Lauderdale, Florida, Listing ID: 31784

WELCOME TO UNIT 1902, YOUR HOME FOR A LUXURY SNOWBIRD EXPERIENCE! Expansive Ocean and waterway views right in the heart of Fort Lauderdale! 24 Hour Security! Best Savings for 60 to 90 day Snowbird Rentals! Experience resort style living in this modern, state of the art,...

  • Condo
  • 01737
  •  2
  •  2
Monthly Rent $3,600 - $4,500

AVAILABLE APRIL 2024-APRIL 2025; TERMS NEGOTIABLE-IMPECCABLE,FULLY FURNISHED,SPACIOUS MODERN CONDO in PRIVATE COMMUNITY Fort Myers, Florida, Listing ID: 31869

First floor 3 bedroom, 3 bathroom condo in Fort Myers, available IMMEDIATELY. Perfect for a family or as a vacation retreat, this home is ideally located to enjoy beaches, cafes and restaurants, and shopping. Fifteen minutes from Sanibel Island, Fort Myers Beach, and downtown....

  • Condo
  • 1800
  •  3
  •  3
Details No Image Available

$Multi-Month Discount!

Monthly Rent $2,900

Excelent location. Close to Gulfsream, the beach, Walmart, supermarkets and restaurants. Very comfortable, two bedroom. Hallandale, Florida, Listing ID: 31906

Gorgeous and fully furnished 2 bedroom 2 bath apartment, it has 2 private close balconies overlooking the waterway. It is fully furnished and has all the necesary applicances in mint conditon, ready to move in. Excelent location close to supermarkets, Walmart, parks and...

  • Apartment
  • 1500
  •  2
  •  2
Monthly Rent $ 18,180

3BR Sleeps 10, Fenced Patio & Pool w/Shower, Tiki Bar/Torches & Bikes, or Walk to Beach! Bluewaters Beach House Fort Myers Beach, Florida, Listing ID: 31907

The Fun Starts here! Bluewaters Beach House is rebuilt and ready for more fun in the sun. This perfectly located Mid Island gem is Old Florida Charm. Expect to be delighted by the charm and surprised by comfort. Bluewaters Beach House is filled with a light and happy coastal...

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  • 1052
  •  3
  •  3
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3BR Canal-front Balcony Home Private Heated Pool & Hot Tub: Beach across street: Sunny Canal Fort Myers Beach, Florida, Listing ID: 31908

Looking for a unique waterfront home with a gorgeous private pool and spa to stay during your next Ft. Myers Beach vacation? Then look no further than 245 Carolina Ave! This home has an open floor plan, updated interior and gorgeous water views with a North End location that...

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  • 1408
  •  3
  •  3
Monthly Rent $3,750 - $3,960

2BR 2BA Home w/Fenced Pool Sleeps 8! Covered Parking, Walk to Beach: Blue Oasis Fort Myers Beach, Florida, Listing ID: 31909

Completely renovated and the vacation home of your dreams awaits you! This over-sized 2 bedroom/2 bathroom home will sleep up to 8 people very comfortably. The open-floor plan lends itself to family get togethers, game nights and so much more. Don’t want to hang with the...

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  • 1260
  •  2
  •  2
Monthly Rent $4,020 - $4,140

BOAT-FRIENDLY! 3BR Home Sleeps 10 w/Screened HEATED Pool, Pvt Beach Access/Gazebo, Boat Dock Across St., Foosball Table Fort Myers Beach, Florida, Listing ID: 31910

This beautifully remodeled pool home, pool is heated, is just a short walk to the beach and has gorgeous views of the bay across the street. The neighborhood shares a boat dock right across the street from the home and has its own private beach access and gazebo. Completely...

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  • 1472
  •  3
  •  2
Monthly Rent $3,750 - $3,870

2BR Home (Duplex) w/Screened Balcony Overlooking Private Fenced Pool & Hot Tub! Walk to Beach: Beach Bungalow 1 Fort Myers Beach, Florida, Listing ID: 31911

Beach Bungalow duplex
Welcome to the Beach Bungalow duplex, a charming tropical retreat nestled in the community of Fort Myers Beach. Situated just steps away from the shimmering shores of the Gulf of Mexico, this home provides easy access to the sandy beaches that...

  • House
  • 900
  •  2
  •  1

Downtown Naples paradise Steps from the beach Fully renovated Naples, Florida, Listing ID: 31931

This is Olde Naples living at its best. Steps from 3rd street, walking distance to famous 5th Ave and two blocks from the beach! Available for seasonal or annual rent furnished or unfurnished. Completely renovated. Brand new floors, kitchen, appliances and bathroom. New...

  • Condo
  • 600
  •  1
  •  1

Comfortable luxury home in peaceful neighborhood close to the beach, restaurants, malls and entertainment Hallandale Beach, Florida, Listing ID: 31940

Create unforgettable memories staying at this modern tropical vacation home. Centrally located close to sandy beaches of Sunny Isles, Hallandale, Hollywood, great restaurants, bars, water sports, recreational areas and malls. 30 min away from Wynwood, Design District and...

  • House
  • 1800
  •  3
  •  3
Details No Image Available

$Multi-Month Discount!

Monthly Rent $10,500 - $15,000

2,200 SF 4BR/2BA home with heated pool & lanai, dual living rooms, kids' room with bunk beds, and huge backyard Marco Island, Florida, Listing ID: 31949

Welcome to your perfect Marco Island retreat! This exceptional 2,200 SF 4-bedroom, 2-bathroom single-family home sits on a spacious triple lot, a rarity on Marco Island, ensuring ample privacy and room to unwind. Step inside and discover the luxury of two separate living...

  • House
  • 2200
  •  4
  •  2

2bedroom/2bathroom Beach House Key West, Florida, Listing ID: 31954

his two-bedroom, two-bath classic contemporary is the perfect headquarters for your dream vacation. The entire inside is painted cloud white. This choice creates not only a crisp, clean elegance but also serves as the perfect backdrop for an amazing art collection. It's fitting...

  • House
  • 881
  •  2
  •  1/2
Monthly Rent $5,702 - $7,695

Beautiful 2BR Waterview | Dock | Balcony | W/D Big Pine Key, Florida, Listing ID: 32349

Right by the glistening waters of Florida lies this beautiful home! You'll be within driving distance of some amazing attractions such as the National Key Deer Refuge Nature Center, where you can experience the natural beauty of the world around you and contribute to something...

  • House
  • 1304
  •  2
  •  2
Monthly Rent $5,630 - $7,856

3BR Oceanfront Dog Friendly | Dock | Balcony Big Pine Key, Florida, Listing ID: 32350

Situated along the canal with approximately 150 feet of seawall, this newly constructed home puts water activities right outside your doorstep. Untie your boat from the provided dock space and take a laidback boat ride into ocean or Gulf waters via the Bogie Channel. Enjoy...

  • House
  • 1190
  •  3
  •  2
Monthly Rent $2,770 - $9,620

2BR 2nd-Floor | Balcony | Pool | Washer/Dryer Bonita Springs, Florida, Listing ID: 32353

Welcome to this convenient condo in Bonita Springs! Recently renovated as of summer 2022, this is the perfect spot for families or couples. There is a private furnished balcony where you can enjoy your morning coffee or enjoy a romantic dinner in the evening. The condo is...

  • Condo
  • 1268
  •  2
  •  2
Monthly Rent $5,365 - $11,484

3BR water view on golf course with pools & deck Bonita Springs, Florida, Listing ID: 32354

Tucked into a tropical garden setting at the edge of the Bonita Bay Golf Course, this three-bedroom condo provides beautiful space inside and out where you can relax with friends and family. This condo is on the ground floor of Waterford at Bonita Bay, a gated community offering...

  • Condo
  • 2293
  •  3
  •  3
Monthly Rent $6,090 - $10,682

2BR Lakefront 1st-Floor | Patio | Pool Bonita Springs, Florida, Listing ID: 32355

Make your next vacation one you'll remember forever at this lakeside condo! For those who would like to enjoy the outdoors, try Riverwalk Park for a scenic walk along the water or a nearby charter for a relaxing ride. Head west to Bonita Beach and sink your feet into the sand...

  • Condo
  • 1256
  •  2
  •  2
Monthly Rent $3,880 - $8,180

Walk Everywhere 2BR Dog Friendly | Patio Bonita Springs, Florida, Listing ID: 32356

In the heart of historic downtown Bonita Springs, you'll find the family- and dog-friendly Birdsong Cottage. Step out your front door and walk to Riverside Park, restaurants, coffeeshops, and bars, then hop in the car for a quick drive nine miles west to the beach. Kayak rentals...

  • House
  • 980
  •  2
  •  1
Monthly Rent $8,846 - $12,656

Amazing 3BR Oceanfront | Private Pool | Dock Cudjoe Key, Florida, Listing ID: 32401

Located between Sugarloaf Key and Big Pine Key, this upscale, three-bedroom, waterfront house is beautifully furnished, and with its amazing sunset views, a private pool, and a 40-foot dock, it's perfect for your family's next sun-filled getaway! First thing: step into the...

  • House
  • 1495
  •  3
  •  2
Monthly Rent $3,690 - $6,071

2BR Waterview Dog Friendly | Patio | W/D Cudjoe Key, Florida, Listing ID: 32402

With a waterfront location overlooking the canals of Cudjoe Key, this comfy and convenient home is going to be the ideal place to enjoy some time with family and friends. The living room is spacious and attractive, featuring burnished floors, a mounted flatscreen TV, and a large...

  • House
  • 1200
  •  2
  •  3
Monthly Rent $9,800 - $12,582

2BR Oceanfront Dog Friendly | Pool | Dock Cudjoe Key, Florida, Listing ID: 32403

Set on a quiet corner lot with a private, heated pool, 50-foot seawall, outdoor bar, and a yard peppered with key lime, dragon fruit, mango, and coconut trees, this unique waterfront retreat is sure to be the highlight of your next vacation in the Keys! When you want to get out...

  • House
  • 1120
  •  2
  •  2
Monthly Rent $2,640 - $4,290

1BR 1st-Floor | Patio | Dog Friendly Deerfield Beach, Florida, Listing ID: 32429

Just minutes from the beach and surrounded by great food and drink options, this Deerfield Beach condo offers laid-back South Florida at its finest. This ground-floor getaway comes fully equipped for comfort, with home essentials including central air-conditioning and free WiFi....

  • Condo
  • 650
  •  1
  •  1