Cudjoe Key Listings

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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 $5,400 - $9,932

Dazzling Bayfront Home w/ 2 Boat Docks, Huge Deck, Kayaks, Pool Table - 1 Dog OK Cudjoe Key, Florida, Listing ID: 28690

You’ll be wowed by the incredible, 180-degree views of Cudjoe Bay at this three-bedroom home in Cudjoe Key. Completely remodeled inside and out, this high-end home boasts an expansive wrap-around deck, multiple outdoor seating areas, and two private docks that are ideal for...

  • Beach Home
  • 2048
  •  3
  •  2 1/2

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Ft. Lauderdale Beach - 9th Floor Ocean View Condo Fort Lauderdale, Florida, Listing ID: 25048

9th floor sunny apartment available for short term rental. 1 bedroom with ocean panoramic view, central A/C, furnished and equipped. Available for 3 month rental term. 2 block walks from beach, close to shopping and entertainment. Excellent location, between ocean and...

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Cute dog-friendly tropical condo close to attractions w/a pristine shared pool Key West, Florida, Listing ID: 26085

This dog-friendly cottage includes street parking, a shared pool, and a location near Duval Street. Nestled in a quiet neighborhood about a mile from Higgs Beach Dog Park and a little under a mile to Mallory Square, you'll be able to get out and about with ease. With fresh...

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$Multi-Month Discount!

Monthly Rent $1,900 - $3,500

2BR With Heated Pool! Only 2 Blocks To Beach! Walking distance everywhere! Lauderdale by the Sea, Florida, Listing ID: 26453

Walk to the Beach and downtown Lauderdale By the Sea from this beautiful 2 bedroom 1 1/2 bath gated home. Supermarket and shopping plaza are also walking distance, no car is necessary! There is 1 bedroom with one king bed and walk in closet and 1 bedroom with two twin beds....

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Luxury Fiddler's Creek 3Br condo in gated golf resort community with tennis and multiple pools, paths, spa, fitness Naples, Florida, Listing ID: 27548

This luxury resort offers security at gate. The community is over 54,000 acres with walking paths, nature areas, water features, and gorgeous landscaping. Golf course on site. Tennis and pickleball. Each small community has a private pool and the clubhouse has a large waterfall...

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Charming Naples seasonal & monthly rental in tastefully decorated Villa minutes from beaches, Downtown & Marco Island Naples, Florida, Listing ID: 28418

This immaculate beautifully remodeled 1350 sf, 3-bedroom, 2-bathroom villa in Naples’ Shadowood Villas lives like a single-family home with one shared wall. Features open concept main level living, vaulted ceilings, attached 2-car garage, south facing screened lanai (both...

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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...

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  • 1517
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  •  3
Monthly Rent $3,051 - $6,260

Lovely Dog-Friendly House near Water w/Deck, Free WiFi, Central AC, & Boat Ramp Key Largo, Florida, Listing ID: 28678

Relax into easy living on Key Largo in a recently upgraded, Key West-style home. Your dog-friendly retreat includes expansive wraparound porches and a private and third-floor main suite with peekaboo ocean views. You’ll have plenty of room to park a boat, and the water is just...

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  • 1512
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Monthly Rent $7,506 - $18,600

Wonderful Condo in Key West w/Free WiFi, Lanai, A/C, Shared Hot Tub & Pool Key West, Florida, Listing ID: 28689

An exceptional stay awaits at this three-bedroom, two-bath condo. Inside, the suite is open and inviting, with a large flatscreen TV and comfy furnishings in the living room, plus a well-equipped kitchen with stainless steel appliances that include a French-door refrigerator....

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  • 1395
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Monthly Rent $3,672 - $7,452

Summerland Canal-Front Escape w/ Plunge Pool, Dock, Tiki Bar, WiFi & Laundry! Summerland Key, Florida, Listing ID: 28763

Boasting a canal-front location, this two-bedroom home is a dream retreat on Summerland Key. Tie up a boat of up to 24 feet at the private dock and a smaller vessel in the adjacent basin. Cruise the canal with ease, travel mere minutes to prime fishing and diving locations, and...

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  • 0
  •  2
  •  1
Monthly Rent $2,600

Breathtaking view of the Ocean!! Gorgeous 1/1 oceanfront condo, on the Hollywood Broadwalk Hollywood, Florida, Listing ID: 28910

Snowbird Heaven! Breathtaking view of the Ocean!! Gorgeous 1/1 oceanfront condo, come and enjoy this beautiful gem available with access to the huge terrace in front of the ocean. Enjoy bike rides on the Hollywood beach boardwalk or just walk to your favorites restaurants in...

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  • 686
  •  1
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Details No Image Available

$Multi-Month Discount!

Large Home in Tavernier Key, 45-foot dock, bay sunset views Tavernier, Florida, Listing ID: 29330

3 story home, open first floor with seating, dining and hammock. 45 foot dock with sunset views of the bay. Close to restaurants, brewery, grocery store. Neighborhood has a private beach and lighthouse.

  • Home
  • 3000
  •  4
  •  4
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...

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  • 2320
  •  3
  •  2
Monthly Rent $4,500 - $5,500

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

Location, location, location! 3 minute walk from elevator to the beach!!! Don't miss this vacation rental with access to Vanderbilt Beach and Delnor-Wiggins State Park. Steps from one of the most beautiful beaches of Naples Located just steps from the beach our vacation...

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  • 1100
  •  2
  •  2
Monthly Rent $8,850 - $10,500

Beach Front Condo with Ocean Views, Community Pool, and Spacious Covered Parking. Marathon, Florida, Listing ID: 29951

Ocean views in the front, pool views in the back. Enjoy the ultimate relaxation with endless activities for all of your guests to enjoy at The Salty Shores. This condo unit is convienenty located right on the beach with incredible views of the Atlantic Ocean. This unit offers...

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  • 1200
  •  2
  •  2
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$Multi-Month Discount!

SPECTACULAR South Florida Oasis. Two Bedroom Two Bathroom Charming Home with pool. 3 miles from beaches. Pets welcome! Pompano Beach, Florida, Listing ID: 30040

Spectacular charming private home only 3 miles from pristine South Florida beaches. Close to shopping malls, beautiful golf courses, parks and grocery stores. This amazing home is just what you are looking for if you want to relax in warm weather and the beautiful South Florida...

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  • 1600
  •  2
  •  2
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Snowbird heaven! All included: water, electricity, basic cable, wifi, parking, bikes, beach chairs, tents, cooler, ice Miami Beach, Florida, Listing ID: 30341

Great location in mid Miami Beach! Walking distance or short drive away from great restaurants and stores. Building with valet, security, self parking, direct beach access, pool attendants, ocean view heated pool and jacuzzi, indoor racquetball court, ocean view gym, tennis...

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  • 1,300
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  •  2
Monthly Rent $15,475 - $17,717

Secluded Corner Florida Ranch House, Heated Pool Pompano Beach, Florida, Listing ID: 30450

Welcome to Beachway Per Ankh (House of Life). We love our great guests and we absolutely love our repeat guests! We offer our returning guests a 10% discount to enjoy Beachway Per Ankh once again for a future trip! We manage our own property because a call center with...

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  • 1500
  •  5
  •  3
Details No Image Available

$Multi-Month Discount!

Monthly Rent $4,000

Spend winter months in the warmth of Hallandale Beach Florida. Next to the intracoastal a walk across from the beach. Hallandale Beach, Florida, Listing ID: 30543

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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Monthly Rent $128,997 - $152,955

Waterfront Mansion for all reunion needs Fort Lauderdale, Florida, Listing ID: 30571

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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  •  7
  •  7
Monthly Rent $51,117 - $60,555

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...

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  • 3500
  •  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
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  •  0
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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...

  • Villa
  • 0
  •  3
  •  2 1/2
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 $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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  • 790
  •  2
  •  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...

  • House
  • 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...

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  • 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,...

  • Home
  • 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
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

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 $2,765 - $5,505

Canal-front, dog-friendly 2BR with dock & pool Duck Key, Florida, Listing ID: 32477

Lobster Lodge is the perfect retreat for your family getaway to the Sunshine State! This canal-front half-duplex features a 35-foot seawall dock. Relax out on the patios overlooking the canal or sit by the shared pool after taking a refreshing dip. Cozy up in the living area for...

  • Duplex
  • 1554
  •  2
  •  2
Monthly Rent $2,765 - $5,748

Dog-friendly 2BR on the canal with pool & dock Duck Key, Florida, Listing ID: 32479

Make yourself at home at this lovely, dog-friendly getaway featuring a 35-foot seawall dock! Prepare delicious meals and beach snacks and enjoy them on the expansive deck overlooking the canal. This family-friendly home also grants you access to a shared, heated swimming pool -...

  • Duplex
  • 1554
  •  2
  •  2
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 $4,660 - $7,750

Gorgeous 2BR Oceanview | Dock | Patio Key Colony Beach, Florida, Listing ID: 32669

If you've been dreaming of living the Florida Keys lifestyle, now's your chance. This canal-front, two-bedroom home in Key Colony puts you right in the center of the Keys, with easy access to fishing, water sports, state parks, and that gorgeous drive over Seven Mile Bridge....

  • House
  • 952
  •  2
  •  2
Monthly Rent $2,093 - $3,653

Spacious 2BR Waterview | Balcony | W/D Key Largo, Florida, Listing ID: 32670

This canal-front home has a nice upper-level balcony overlooking the water, which is excellent for morning coffee or evening cocktails. The spacious living area invites everyone to kick back, relax, and enjoy watching TV or planning their next adventure. Take advantage of the...

  • House
  • 884
  •  2
  •  1
Monthly Rent $5,396 - $9,193

Modern 3BR Oceanview | Dock | Deck | W/D Key Largo, Florida, Listing ID: 32671

Ideally located for anglers, boating enthusiasts, and anyone looking to get out on the water, this canal-front home in Key Largo allows you to take in the beauty of the Florida Keys right from your terrace. You'll have your very own dock to set sail from each morning, a fleet of...

  • House
  • 2227
  •  3
  •  2
Monthly Rent $1,554 - $2,581

Inviting 1BR Dog Friendly | Balcony | Firepit Key Largo, Florida, Listing ID: 32672

*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. Escape the rat race and unwind in the beauty of the tropics when you book your soothing vacation to this Key Largo retreat. Built in...

  • House
  • 880
  •  1
  •  1
Monthly Rent $3,625 - $4,393

Sunny 2BR Dog Friendly | Private Pool | Deck Key Largo, Florida, Listing ID: 32673

Craving a beachy house with a yard? This home is perfect for those who want to get away from the hustle and bustle of the city and sink into a stool at the tiki bar. Relax on the shaded porch or in the private pool Throw some fish or hot dogs on the private gas grill, or just go...

  • House
  • 896
  •  2
  •  2
Monthly Rent $4,256 - $8,286

3BR Dog Friendly | Balcony | W/D Key Largo, Florida, Listing ID: 32674

Full of sunlight and modern coastal furniture, this home is ideal for a family or group looking to get away from it all. Recline on your personal screened-in balcony, or spread out within the comfortable living room. The open kitchen features everything guests need to cook up...

  • House
  • 1467
  •  3
  •  2
Monthly Rent $10,185 - $18,983

Lush 3BR | Pool | Balcony | W/D Key West, Florida, Listing ID: 32675

*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. Casual elegance and lush tropical foliage await at this beautiful Key West home only blocks from Higgs Beach! Boasting a private...

  • House
  • 1672
  •  3
  •  3
Monthly Rent $3,528 - $6,206

Upgraded 1BR | Near Beach & Duval St. | Shared W/D Key West, Florida, Listing ID: 32676

*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 simple, modern cottage apartment is an ideal space for a couple or a solo traveler looking to explore the heart of Key West!...

  • Apartment
  • 403
  •  1
  •  1
Monthly Rent $3,985 - $6,627

Walk to Beach/Dining 1BR | Patio | Central Locale Key West, Florida, Listing ID: 32677

*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 cozy-yet-modern cottage apartment in Key West is a wonderful escape for any party of two! A flatscreen TV in the living room...

  • Apartment
  • 460
  •  1
  •  1
Monthly Rent $8,140 - $14,935

Updated 2BR with loft, private pool, patio & grill Key West, Florida, Listing ID: 32678

Enjoy the superb location of this updated Old Town Key West home! This adorable vacation rental features a private pool with a furnished deck and grill -ideal for summertime cookouts. Enjoy a furnished loft area and a cozy front porch. You'll be within walking distance of the...

  • House
  • 720
  •  2
  •  2
Monthly Rent $4,875 - $7,821

1BR | Deck | Outdoor Pool | Ground-Floor Key West, Florida, Listing ID: 32679

Book this wonderful, ground-level, Old Town getaway with all the comforts of home including central air conditioning and complimentary internet access! This vacation rental features a spacious floor plan with doors that open out to the back patio to create an indoor/outdoor...

  • Condo
  • 649
  •  1
  •  1
Monthly Rent $6,781 - $12,620

Bright 2BR Duplex | Pool | Deck | W/D Key West, Florida, Listing ID: 32680

Enjoy a soak in your own private, heated saltwater pool at this lovely duplex! Part of the Tropical Vibes home, this duplex is a charming hideaway with plenty of room to hang out. Open the sizable glass sliding door to create a seamless indoor/outdoor space between the kitchen,...

  • Duplex
  • 818
  •  2
  •  3