Cudjoe Key Listings

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...

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• 1495
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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...

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• 1200
•  2
•  3

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...

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• 1120
•  2
•  2

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

Colorful 1BR | Pool | Patio | Garage Parking Key West, Florida, Listing ID: 32683

Keep things simple and take in the lovely Key West sun at this colorful cottage just a half-mile from Hemingway House! You'll love relaxing at this home with a white picket fence, all set up in a private compound of four homes. There's plenty of room for guests to relax, and...

• Cottage
• 573
•  1
•  1

Fabulous 3BR | Pool | Deck | Tennis | W/D Key West, Florida, Listing ID: 32684

Whether it's the textured shiplap walls, the sparkling private saltwater pool, or the lovingly curated decor, you're sure to find something you love about this wonderful home. In the spirit of Key West, you'll find nods to Ernest Hemingway, the nautical culture, and much more....

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• 1642
•  3
•  3

Bright 3BR | Deck | Fenced Yard | Porch | W/D Key West, Florida, Listing ID: 32685

Experience the best of Key West living! This classic cottage comes fully updated with modern amenities while boasting a prime, central location with easy access to Key West's iconic attractions and historic sites. Suitable for up to eight guests, this spacious three-bedroom home...

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• 1188
•  3
•  2

Centrally located 2BR Waterview | Balcony | Pool Key West, Florida, Listing ID: 32686

Get ready for packed days of coastal fun here at Porter Place, your very own sliver of Key West! Sitting within walking distance of a plethora of shops, restaurants, and attractions, you will have no delay filling each day with coastal excitement from sunup to sundown. On-site...

• Condo
• 1023
•  2
•  3

3BR Dog Friendly | Pool | Balcony | W/D Key West, Florida, Listing ID: 32690

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 Key West home is waiting for you and your group to make yourselves at home and enjoy lazy days by your private pool. You'll be within easy reach...

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• 1672
•  3
•  3

Prime 2BR | Balcony | Dog Friendly Key West, Florida, Listing ID: 32691

*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. Get away from it all and head to Key West for a sun-filled vacation with this two-bedroom, two-bath condo for six and enjoy easy...

• Condo
• 1800
•  2
•  2

Welcoming 1BR Dog Friendly | W/D Key West, Florida, Listing ID: 32692

*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. If Key West is on your itinerary, make this welcoming, conveniently located one-bedroom home yours and enjoy comfort and the benefit...

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• 700
•  1
•  1

Sunny 2BR Dog Friendly | Chef's Kitchen| Hot Tub Key West, Florida, Listing ID: 32693

Sunshine comes easy in Key West, and you can enjoy it all here. Built in 1945, this beautiful home has been restored to perfection with amenities galore for modern guests to enjoy. Central air conditioning pairs perfectly with the home's high ceilings, creating a sunny...

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• 1053
•  2
•  3

Charming 1BR Dog Friendly | Deck | W/D Key West, Florida, Listing ID: 32695

*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. Take advantage of all that Key West has to offer from the incredible location of this adorable Key West home. This home features a...

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• 524
•  1
•  1

Large 3BR Dog Friendly | Pool | Balcony | W/D Key West, Florida, Listing ID: 32696

This beautiful Key West home has just the right mix of beach vibes and modern amenities to make you feel right at home during your Florida vacation. Multiple Smart TVs, an Alexa home speaker, and Netflix account let you play music and relax on lazy days. A spacious kitchen opens...

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• 1584
•  3
•  3

Charming 2BR Dog Friendly | Deck | W/D Key West, Florida, Listing ID: 32697

This gorgeous home is a perfect escape for a private and quiet getaway. The home is surrounded by palm trees which creates a shaded and private patio. The home has a large 750 square foot master suite that is super luxurious - you may not want to leave the bedroom! A fully...

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• 1873
•  2
•  2

3BR Oceanview Dog Friendly | Dock | Patio Key West, Florida, Listing ID: 32698

Beautifully situated among the palms and right on a canal that leads out to open water, this three-bedroom home on Big Coppitt Key is the perfect Florida Keys escape for boating enthusiasts, anglers, and families and friends in search of waterfront relaxation. This single-story...

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• 1408
•  3
•  2

Upscale 3BR Lakeview Dog Friendly | Pool | Deck Key West, Florida, Listing ID: 32700

Nestled in a peaceful gated community, this two-level townhome is located right on a golf course in the gated grounds of the Key West Golf Club, only a few miles from those pristine Key West beaches. Your group will have multiple private outdoor areas to choose from, depending...

• Townhouse
• 1060
•  3
•  3

Colorful 2BR Oceanview 2nd-Floor | Balcony Key West, Florida, Listing ID: 32701

All the best of Key West is right at your doorstep at this colorful, second-floor condo just across the street from the gorgeous aquamarine water the Keys are known for. Smathers Beach is just down the road, and all the restaurants, bars, and cafs of Duval St. and the historic...

• Condo
• 1186
•  2
•  2

3BR Waterview Dog Friendly | Pool | Deck | W/D Key West, Florida, Listing ID: 32702

Featuring its own backyard oasis, this two-story retreat invites you to experience the best of island living right at home. Surrounded by lush landscaping, the fenced backyard features a private heated pool with a waterfall as well as an outdoor seating area where you can dine...

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• 1750
•  3
•  3

2BR Oceanfront Dog Friendly | Dock | Balcony Key West, Florida, Listing ID: 32703

A serene, canal-front oasis is yours at this Big Coppitt Key retreat. Complete with a private dock and boat ramp offering direct access to the Gulf of Mexico, this dreamy two-story condo comes primed for island living. A breezy, canal-view deck makes a perfect perch for sipping...

• Duplex
• 1095
•  2
•  2

Upscale 3BR Golf Course View Dog Friendly | Pool Key West, Florida, Listing ID: 32704

This vacation home is perfect for your next adventure with family and furry companions. Enjoy a quiet afternoon in the hammock on the balcony that overlooks the golf course and the private pool, where you can venture down for a splash. The enclosed backyard is filled with...

• House
• 1600
•  3
•  3

Walk to Beach 2BR Dog Friendly | Pool | Patio Key West, Florida, Listing ID: 32705

*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.* Small families and close groups of friends will love this dog-friendly home for four in Key West! A shared swimming pool and nearby...

• House
• 694
•  2
•  1

3BR Oceanfront | Dock | Balcony | W/D Little Torch Key, Florida, Listing ID: 32736

Kick back on the canal - this home is ready to host you! Relax in a friendly space with essentials like central air conditioning and a ceiling fan in every bedroom. There's plenty of room to park your boat trailer, perfect for guests that want to launch from the public boat ramp...

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• 1196
•  3
•  2

Amazing View 3BR Oceanfront | Dock | Balcony Little Torch Key, Florida, Listing ID: 32737

Quiet privacy, sweeping water views, and enviable proximity to water activity make this canal-front home a dream retreat. Start vacation days with your morning beverage of choice on the furnished wraparound deck overlooking the Torchwood Hammock Preserve. Swing in the hammock...

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• 984
•  3
•  2

Modern 3BR Oceanview | Pool | Dock | Patio Marco Island, Florida, Listing ID: 32739

This bright and airy retreat offers guests canal views and easy access via bike to the sugar-white sand beaches of Marco Island! This vacation rental is ideal for families or travel groups and offers amazing indoor/outdoor features including a private pool under a lanai, a...

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• 1940
•  3
•  2

3BR Oceanview Dog Friendly | Pool | Dock | Patio Marco Island, Florida, Listing ID: 32741

This lovely canal-side home is sure to make your stay on Marco Island one to remember. Spacious, this single-family home is packed with enjoyable amenities. Enjoy water views from the lanai, or while going for a swim in the west-facing heated pool. Cook on the grill while taking...

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• 1900
•  3
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2BR Gulffront 1st-Floor | Deck | Naples, Florida, Listing ID: 32815

Explore everything Naples has to offer at this premium riverfront condo! Nestled along the Gordon River, you have instant access to the water and are only a short drive away from Naples Beach. Go for a scenic stroll in the sand or take a dip in the Gulf for a relaxing day in the...

• Condo
• 1000
•  2
•  2

Spacious 2BR | Patio | Pool | Washer/Dryer Naples, Florida, Listing ID: 32816

*Please note that this home only allows minimum stays of 30 nights or longer. This is enforced by the HOA and we cannot make any exceptions. Head to Naples for your next Florida getaway and revel in high-end amenities, including a shared resort-style pool, a hot tub, and much...

• Condo
• 1084
•  2
•  2

3BR Lakefront Dog Friendly | Pool | Patio | W/D Naples, Florida, Listing ID: 32817

Cheerful, bright, and full of amenities, this lovely home is ready to welcome families and groups. Enjoy views of a local lake just outside your window, You may spend most of your stay out next to the private pool - the lanai makes it easy to get comfortable no matter what the...

• House
• 1998
•  3
•  2

3BR Dog Friendly | Private Pool | Deck | W/D Naples, Florida, Listing ID: 32818

Nestled within the Moorings, this home is ready to welcome guests with refined furnishings and helpful amenities. From the moment you walk through the front door, you'll feel at ease within the upscale nautical design. The star of the home is undoubtedly the bright private pool,...

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• 3088
•  3
•  3

1BR | Deck | Heated Pool | 1 Block to Beach Pompano Beach, Florida, Listing ID: 32948

* Only registered guests 25 + are allowed on the premises. All guests shall abide by Vacasa's good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10 pm to 8 am and no parties or loud noise is permitted. One vehicle parking per apartment (with...

• Condo
• 660
•  1
•  1

2BR Waterview | Pool | Dock | Balcony | W/D Summerland Key, Florida, Listing ID: 33022

With three separate living areas and a private heated pool, this charming home is full of comfortable spaces for guests to enjoy. Stay in the main house, the downstairs lounge, or in the guest house complete with a full bathroom - each area has its own private entrance. But no...

• House
• 1292
•  2
•  4

Open 2BR Waterview | Balcony | W/D Tavernier, Florida, Listing ID: 33023

*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. Find a charming, sun-splashed home away from home at this canal-front escape in Tavernier! Bring your water toys and use the Harry...

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• 864
•  2
•  1

Charming 3BR Oceanfront | Dock | Patio | W/D Tavernier, Florida, Listing ID: 33024

A fantastic getaway awaits along the Florida keys, perfect for escaping the hustle and bustle of everyday life. With the ocean steps away, rent a boat, paddleboard, kayak, surfboard, or fishing gear to make the most of your oceanside vacation. Tour the sights like Rain Barrell...

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• 1151
•  3
•  2

Ocean-view w/Balcony 1-block to Beach/Shopping/Dining w/Waterfront Pool & Grills | Monthly Rent: $3,040 - $4,800 Fort Lauderdale, Florida, Listing ID: 33151

You'll be able to make the most of everything that Fort Lauderdale offers at this light-filled condo in Harbor Haven, where you'll wake up each morning to views of rustling palms and the shimmering Atlantic Ocean one block away. Leave your car in the private parking space and...

• Condo
• 795
•  1
•  1

Stunning 1BR Oceanview | Balcony Fort Lauderdale, Florida, Listing ID: 33152

Take that much-needed romantic getaway and make this stylish condo your home away from home! With gorgeous views of the Atlantic and downtown from the private balcony, each morning can be spent in the cool breeze with a cup of coffee. You can also spot the intercoastal pool from...

• Condo
• 795
•  1
•  1

Spacious Home with Private Pool Close to Shopping & Beaches Naples, Florida, Listing ID: 33155

A fantastic vacation awaits at this three-bedroom home in Naples, FL. Offering a private pool and access to community amenities, up to six guests will be comfortable here. Located in the gated community of Briarwood, you'll be near shops and restaurants on Fifth Avenue, and an...

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• 1888
•  3
•  2

1BR Oceanview | Balcony | Pool | Miami, Florida, Listing ID: 33278

Located on the 44th floor, this one bedroom provides an ample dining and living space. With an open concept plan, a single-wall kitchen housing sleek cabinets, Wolf appliances, and a SubZero refrigerator, you will definitely feel back at home. This home has balcony access in...

• Apartment
• 1000
•  1
•  1

1BR condo stay with pool, hot tub, & fitness room Miami Beach, Florida, Listing ID: 33279

Placed right in the beautiful Decoplage building, you'll be glad you booked this vacation condo! Slip into your favorite bathing suit and head out to the soft sands of South Beach (just a few steps away from your stay) and read a good book under the shade of an umbrella as your...

• Condo
• 800
•  0
•  1

DOG FRIENDLY Walk to Beach 3BR | Pool | Balcony Key West, Florida, Listing ID: 33333

Newly-Built, Dog-Friendly Home with Shared Pool - Walk to Beach & Dining

*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.*

Head to Key West and revel in...

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• 1400
•  3
•  3

DOG FRIENDLY Classic 2BR | Pool | Deck | W/D Key West, Florida, Listing ID: 33338

Old Town Key West classic with private saltwater pool & enclosed patio- by shops

This home is just perfect for your Keys getaway! The open floor plan and well-appointed kitchen will make your stay more than comfortable. French doors off the living room and...

• House
• null
•  2
•  2

Amazing 2BR 2nd-Floor | Deck | Pool | Marco Island, Florida, Listing ID: 33361

Amazing home w/free WiFi for remote work, screened-in patio near beaches/marina

You're going to love savoring your first cup of morning coffee on the screened-in patio of this beautiful home! When you're not out playing on the beach or exploring Rose Marina,...

• Condo
• 787
•  2
•  2

3BR Oceanfront | Dock | Balcony | W/D Key Largo, Florida, Listing ID: 33363

Oceanfront, Snowbird-Friendly Home with High-Speed WiFi, Ocean Views, and Dock

Prepare for true canalfront living at this home! Casual in nature and comfortable in every room, this home is ready with the central air conditioning and enough seating for everyone....

• House
• 2296
•  3
•  4

Stunning 3BR 1st-Floor | Patio | Pool Naples, Florida, Listing ID: 33364

Stunning Naples Condo Near the Beach & Shopping W/ Shared Pool & Gas Grills

Brand new and perfectly perched in the heart of downtown, this modern getaway will be ideal for the whole family to get a taste of the Naples lifestyle. As soon as you step foot...

• Condo
• 3100
•  3
•  4

Quiet 3BR Lakeview | Patio | Garage Parking | W/D Naples, Florida, Listing ID: 33381

This modern 3BR/2BA bungalow features 1,305 square feet of updated living space and a prime location 2 miles from Naples Beach. Whip up delicious meals with stainless steel appliances, or fire up the gas grill on the spacious screened lanai. Gorgeous granite surfaces add an...

• House
• 1305
•  3
•  2

3BR | Patio | W/D | AC | Snowbird Friendly Key Largo, Florida, Listing ID: 33385

Snowbird-Friendly Home with Central AC, High-Speed WiFi, and Washer/Dryer

Just a short walk from a lovely community park, this friendly home has plenty of room for guests to come in and relax. Unwind in central air conditioning inside, or enjoy a beverage out...

• House
• 960
•  3
•  2

2BR with pool and hot tub - 30-day minimum Naples, Florida, Listing ID: 33386

Upscale marina-view condo with pool, hot tub, & close to beach - 30-day minimum

Enjoy the best of the beach and the bay from this waterfront condo. Explore the waterfront shopping at Tin City, a short walk from home. Check out an event at the bandshell or play...

• Condo
• 1100
•  2
•  2

Canal-front 2BR with amazing views & boat acess Little Torch Key, Florida, Listing ID: 33393

Canal-front Keys escape with amazing view, boat access, firepit, grill, AC, & W/D

Enjoy a canal-front getaway in the Florida Keys! This colorful charmer offers a private slice of paradise with easy access to Key West. Immerse yourself in the wonders of nature...

• Duplex
• 1080
•  2
•  1

DOG FRIENDLY Fenced, BOAT FRIENDLY Boat-Lift & Dock, Canal-front with Balcony Sunset Views, Firepit, Grill, Outdoor Kitchen and Key Largo, Florida, Listing ID: 33394

DOG FRIENDLY Fenced, BOAT FRIENDLY Boat-Lift & Dock, Canal-front with Balcony Sunset Views, Firepit, Grill, Outdoor Kitchen and Basketball court

Welcome to the canal! This home, just one mile from John Pennekamp Coral Reef State Park, is built for good times,...

• House
• 2432
•  2
•  2

2BR dog friendly getaway with a pool Pompano Beach, Florida, Listing ID: 33398

Dog-friendly getaway with a pool, furnished patio, washer/dryer, & tropical yard

Picture yourself at this classic Pompano Beach condo located less than a quarter-mile from the surf and sand. On-site, enjoy immediate access to a sparkling, shared pool, or stay...

• Condo
• 1040
•  2
•  2

DOG FRIENDLY (up to 4 Dogs), BOAT FRIENDLY Waterfront Sunrise Views from Living Room, Balcony, and Back Yard w/Grill, Private Pi Duck Key, Florida, Listing ID: 33403

DOG FRIENDLY (up to 4 Dogs), BOAT FRIENDLY Waterfront Sunrise Views from Living Room, Balcony, and Back Yard w/Grill, Private Pier and Dock: beach escape with bay views, Free Parking

Say hello to pure coastal bliss right on the harbor at this fabulous Duck Key...

• House
• 1260
•  2
•  2

3rd Floor w/Balcony, in Gated Community w/Pool, Fitness Center, on Stock Island (between Key West and Boca Chica Key Islands) Key West, Florida, Listing ID: 33427

Hemingway Hideaway Family home 3rd Floor w/Balcony, in Gated Community w/Pool, Fitness Center, on Stock Island (between Key West and Boca Chica Key Islands)

Tropical charm and southern comfort combine for a memorable getaway at this three-bedroom,...

• House
• 1420
•  3
•  3