Naples, Florida Listings

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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...

  • Condo
  • 2100
  •  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...

  • Condo
  • 1100
  •  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
Monthly Rent $7,250 - $9,142

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
Monthly Rent $8,130 - $14,748

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,...

  • House
  • 3088
  •  3
  •  3
Monthly Rent $2,760 - $16,670

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...

  • House
  • 1888
  •  3
  •  2
Monthly Rent $4,350 - $5,400

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...

  • Villa
  • 1350
  •  3
  •  2
Monthly Rent $7,008 - $9,827

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
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 $3,600 - $18,650

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

Similar Properties


Monthly Rent $6,250 - $17,710

Waterfront 2BR Oceanfront | Pool | Beach Access Bradenton Beach, Florida, Listing ID: 32361

Stroll out to the sand, swim in the shared pool, or enjoy spectacular sunsets from the balcony of this beautiful Anna Maria Island vacation condo. With an updated, fully equipped kitchen, two bedrooms, and space for four guests, this home is ready-made for your next getaway to...

  • Condo
  • 1195
  •  2
  •  2
Monthly Rent $2,890 - $8,850

Open 1BR Bayview Inn | Patio | Pool Bradenton Beach, Florida, Listing ID: 32362

Take it easy and enjoy the laid-back, coastal lifestyle here in Bradenton Beach with a stay in this sunny condo perfect for a romantic getaway or small family vacation! Guests will love the open concept and bright interior that is flooded with natural light. Spend your days...

  • Condo
  • 550
  •  1
  •  1
Monthly Rent $4,510 - $5,290

1BR 3rd-Floor | Balcony | Pool | Bradenton Beach, Florida, Listing ID: 32363

This one-bedroom condo at Coquina Reef is your ticket to laid-back island living just steps from the sparkling shores of beautiful Bradenton Beach. Take in pool views and Gulf breezes on the private, screened balcony - the perfect spot for morning coffee and afternoon cocktails....

  • Condo
  • 590
  •  1
  •  1
Monthly Rent $5,260 - $7,500

Large 2BR Waterview | Private Pool | Dock | Patio Cape Coral, Florida, Listing ID: 32369

If you're looking for a vacation destination that offers the perfect mix of relaxation and activity, then look no further than this canal-front home in Cape Coral. This rental features an updated, well-equipped kitchen, a private pool, a furnished lanai, and an outdoor grilling...

  • House
  • 1600
  •  2
  •  2
Monthly Rent $3,570 - $6,910

3BR | Private Pool | Screened Lanai | W/D Cape Coral, Florida, Listing ID: 32370

Vacation dreams come true at this getaway, located on a quiet street. Delight in your private oasis in the fenced and grassy backyard. Unwind into vacation mode on the screened lanai. Enjoy a refreshing dip in the private pool. In the evening, keep mealtime simple with a cookout...

  • House
  • 1329
  •  3
  •  2
Monthly Rent $7,500 - $20,150

Upscale 3BR Lakefront | Pool | Dock | Patio Cape Coral, Florida, Listing ID: 32371

Escape to this luxurious lakefront home with an abundance of amenities including a lavish screened pool area for your family's private use. This is one of a limited number of single-level homes that back to a lake for fishing, kayaking, stand-up paddleboarding, and easy access...

  • House
  • 2264
  •  3
  •  2
Monthly Rent $4,500 - $10,260

3BR waterview home with pool & alfresco dining Cape Coral, Florida, Listing ID: 32372

Built in 2022, this Southwest Florida home provides all the comforts you could want on your next vacation getaway. After a day spent stretched out in the sand at nearby beaches or exploring local nature preserves, take a dip in the private saltwater pool. With a gas grill and an...

  • House
  • 1464
  •  3
  •  2
Monthly Rent $3,100 - $10,850

Tranquil 3BR | Private Pool | Patio | W/D Cape Coral, Florida, Listing ID: 32373

Embrace Florida's tropical surroundings at this contemporary Cape Coral vacation rental. Perfect for a wonderful getaway, this blissful home possesses a modernized interior, and a backyard to host you and your friends. The spacious lanai comes equipped with a private pool, a gas...

  • House
  • 2287
  •  3
  •  2
Monthly Rent $2,950 - $6,510

Vibrant 3BR | Hot Tub | Patio | W/D Cape Coral, Florida, Listing ID: 32374

Everything is bright and pristine in this family-friendly Cape Coral home. Enjoy scenic views right from your lanai, which also includes a hot tub that is perfect for a private retreat. For some local fun, you'll be situated in a great location close to water parks, restaurants,...

  • House
  • 1161
  •  3
  •  2
Monthly Rent $2,780 - $4,450

3BR home with pool, patio, lanai & golf Cape Coral, Florida, Listing ID: 32375

Escape from the hustle and bustle of everyday life to this exceptional getaway! Situated on the 17th tee at Palmetto Pines Golf Course, you'll have access to a semi-private course where you are welcome to play. Take a walk to Fellowship Park, where you can treat your family to a...

  • House
  • 2034
  •  3
  •  2
Monthly Rent $2,500 - $4,470

3BR home with a pool, pool spa, W/D, & AC Cape Coral, Florida, Listing ID: 32376

Known for its 400 miles of canals, Cape Coral provides a sunny, serene escape from day-to-day life! Your retreat, nestled amongst the area's many amusements allows for easy access to multiple parks, restaurants, shops, and of course, the beach! Vibrant and friendly, you will...

  • House
  • 1210
  •  3
  •  2
Monthly Rent $3,720 - $11,090

3BR Waterview Dog Friendly | Private Pool | Dock Cape Coral, Florida, Listing ID: 32377

This spacious one-level home is situated alongside a canal, just minutes from the Caloosahatchee River. Tie up a boat at your private boat dock. Unwind in the quiet seclusion of a huge screened lanai, replete with a private pool with a solar cover and a lounge, grill, and dining...

  • House
  • 1861
  •  3
  •  2
Monthly Rent $2,500 - $3,790

Quiet 3BR Dog Friendly | Pool | Deck | W/D Cape Coral, Florida, Listing ID: 32378

Spend leisurely days in the caged pool and entertain easily on the spacious lanai at this dreamy 3BR/2BA home. Nestled in a quiet and centrally located neighborhood, this welcoming retreat also features high ceilings, a 2-car garage, and a gourmet kitchen. A plethora of shops...

  • House
  • 1283
  •  3
  •  2
Monthly Rent $4,650 - $11,290

3BR Waterview Dog Friendly | Pool | Dock | Deck Cape Coral, Florida, Listing ID: 32379

Full of high ceilings and an abundance of natural light, this home is a perfect spot for a family or group to enjoy a peaceful rest from days of adventure. Located a few blocks from a major bike trail, it's perfect for those who enjoy a nice long uninterrupted walk, jog, or bike...

  • House
  • 1922
  •  3
  •  2
Monthly Rent $2,500 - $3,780

3BR Dog Friendly | Enclosed Yard | Washer/Dryer Cape Coral, Florida, Listing ID: 32380

Get ready to experience the best of Cape Coral in no time when you make this centrally-located gem home base! From endless beach days to city exploration, Cardinal Retreat will be the perfect starting point for any adventure. And, when you don't feel like venturing out, the...

  • House
  • 1401
  •  3
  •  2
Monthly Rent $3,570 - $10,120

3BR | Pool | Dog Friendly | W/D Cape Coral, Florida, Listing ID: 32381

Located conveniently close to the Four Mile Cove Ecological Preserve, several fun-filled, local attractions, and downtown Cape Coral, this serene hideaway is a fantastic option for your next big family getaway to sunny southwest Florida! Step inside this single-level home and...

  • House
  • 1500
  •  3
  •  2
Monthly Rent $3,000 - $13,180

Dog Friendly 3BR | Heated Pool | Patio | Garage Cape Coral, Florida, Listing ID: 32382

Paradise awaits at this gorgeous Cape Coral escape. Equipped for family-friendly comfort, this private retreat boasts a spacious, enclosed yard complete with a heated pool and fully screened lanai furnished for outdoor living with a grill, dining table, TV lounge, and sun deck....

  • House
  • 1634
  •  3
  •  2
Monthly Rent $2,760 - $9,480

3BR Waterview Dog Friendly | Pool | Patio | W/D Cape Coral, Florida, Listing ID: 32383

Welcome to your home away from home! This three-bedroom retreat in Cape Coral boasts two living spaces for your family and friends to spread out. However, one of the most sought-after spots is the screened lanai - find a private heated pool, a handful of poolside beach loungers,...

  • House
  • 1486
  •  3
  •  2
Monthly Rent $2,700 - $10,240

Renovated 3BR Dog Friendly | Pool | Patio | W/D Cape Coral, Florida, Listing ID: 32384

Situated in a quiet neighborhood, you can enjoy sweeping canal views from the private covered patio or while taking a dip in the crystal-clear pool. While out on the town, be sure to explore the Rotary Park Environmental Center, Sun Splash Family Waterpark, and Mann Performing...

  • House
  • 1502
  •  3
  •  2
Monthly Rent $2,500 - $4,170

Sunny 3BR | Dog Friendly | Private Pool | Patio Cape Coral, Florida, Listing ID: 32385

Complete with a private pool and furnished lanai, this Cape Coral escape comes primed for your next Gulf Coast getaway. The breezy, single-level interior showcases vibrant beach-inspired decor and all the home essentials to help you slip into vacation mode in no time. Soak up...

  • House
  • 1272
  •  3
  •  2
Monthly Rent $2,670 - $8,970

Beautiful 3BR Dog Friendly | Private Pool | Patio Cape Coral, Florida, Listing ID: 32386

Put your feet up, relax, and enjoy exquisite views of the water from the comfort of this Cape Coral vacation home! Located on the western edge of Cape Coral, with many of the city's popular attractions only a few minutes away, kids and parents alike will delight in visiting Sun...

  • House
  • 1349
  •  3
  •  2
Monthly Rent $3,430 - $7,040

3BR dog-friendly home with heated pool, patio, W/D Cape Coral, Florida, Listing ID: 32387

Conveniently located just four and a half miles from downtown Cape Coral, this dog-friendly home offers the perfect home base for a relaxing and unforgettable vacation with your family and friends! As you step inside, be prepared to be greeted by a warm and inviting atmosphere....

  • House
  • 2053
  •  3
  •  2
Monthly Rent $3,220 - $11,490

3BR Dog Friendly | Pool | Hot Tub | Deck Cape Coral, Florida, Listing ID: 32390

Enjoy Southwest Florida luxury in this spacious, family-friendly home. This house boasts a private enclosed backyard and the lanai covers the spacious pool and poolside dining area so you can enjoy a fun swim all year round. The built-in outdoor kitchen is the perfect spot to...

  • House
  • 1449
  •  3
  •  2
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
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 $3,880 - $10,260

Sweet 3BR Waterview | Pool | Deck | W/D Fort Myers, Florida, Listing ID: 32491

Discover this bright, beautiful home in a gated community just minutes from some of the Gulf's best beaches. Beach chairs, toys, and umbrellas are provided in the vacation rental. A brewery, supermarket, and great restaurants are within walking distance of your door. Take in the...

  • House
  • 1604
  •  3
  •  2
Monthly Rent $3,100 - $4,480

Bahama Breeze | Waterfront House in Ft. Myers Fort Myers, Florida, Listing ID: 32492

This impeccable, waterfront home seamlessly blends style and comfort. However you choose to unwind, you'll immediately feel at home. Stay connected with friends using the complimentary WiFi or effortlessly find directions for your local explorations. Prepare delectable al fresco...

  • House
  • 1256
  •  2
  •  2
Monthly Rent $3,350 - $7,570

Dreamy 3BR Dog Friendly | Pool | Patio Fort Myers, Florida, Listing ID: 32493

Say goodbye to cramped hotel rooms and kitschy condos and say hello to Dover's Retreat, your very own slice of paradise in the heart of Fort Myers. You will have the best of both worlds with many shops and restaurants within walking distance while still having an abundance of...

  • House
  • 1324
  •  3
  •  2
Monthly Rent $3,080 - $11,230

Cheerful 2BR | Patio | Pool | Steps to Beach Holmes Beach, Florida, Listing ID: 32639

Catch some of Florida's most memorable sunsets when you escape to this two-bedroom Holmes Beach condo, where you'll enjoy a shaded patio, a shared pool and tennis court, and direct access to a beautiful white sand beach. This ground-floor condo is located in Nautilus...

  • Condo
  • 1081
  •  2
  •  2
Monthly Rent $4,650 - $19,520

Welcoming 3BR 2nd-Floor | Balcony | Pool Holmes Beach, Florida, Listing ID: 32640

Your luxurious dream getaway is about to come true with this stylish Anna Maria Island vacation rental! This centrally located condo is only moments from the beach, with shopping, dining, and more only a quick walk away. The best beaches on the Gulf of Mexico are only a short...

  • Villa
  • 1610
  •  3
  •  3
Monthly Rent $1,990 - $11,200

Inviting 2BR Bayview 2nd-Floor | Balcony | Pool Holmes Beach, Florida, Listing ID: 32641

Spaciously laid out and cooled by central air conditioning, you'll find it easy to relax in this family-friendly condo! The waterfront location facing Anna Maria Sound means that you'll be able to relax in a peaceful location near Grassy Point. You'll also be able to look out on...

  • Condo
  • 1035
  •  2
  •  2
Monthly Rent $1,520 - $6,690

1BR | Enclosed Yard | Deck | AC | W/D Holmes Beach, Florida, Listing ID: 32642

Your sweet getaway in Holmes Beach awaits with this cute and cozy one-bedroom duplex! You're only about two blocks from the beach, and the sands on Anna Maria Island are some of Florida's finest. Cup of coffee in hand, start your day at the alfresco dining in your backyard or...

  • Duplex
  • 1554
  •  1
  •  1
Monthly Rent $4,460 - $17,660

Sunny 3BR | Private Pool | Deck | W/D | Grill Holmes Beach, Florida, Listing ID: 32643

Find quiet coastal serenity and all of the comforts of home here at Mermaid Sunrise, a wonderful escape perfect for family and friends to enjoy the beauty of Holmes Beach. Sitting away from the hustle and bustle of the main drag of the island, this home will place you in a...

  • Duplex
  • 2671
  •  3
  •  2
Monthly Rent $6,200 - $22,430

Upscale 3BR Oceanfront La Casa Costiera 2nd-Floor Holmes Beach, Florida, Listing ID: 32644

Sitting in a privileged location just steps to the beach, this high-end condo in Holmes Beach is just the place for your next vacation! Boasting amenities including a private jetted bathtub and a large deck space, plus access to a shared pool, you'll have everything you need for...

  • Condo
  • 2136
  •  3
  •  3
Monthly Rent $7,080 - $17,570

Pristine 3BR Oceanfront | Balcony | Holmes Beach, Florida, Listing ID: 32645

Welcome to Gulf Shores Condominiums! This Holmes Beach condo sits right on the sand and features a number of desirable amenities including a furnished and screened balcony with panoramic beach views, a full kitchen, and plenty of space for a family. While you're likely to spend...

  • Condo
  • 1356
  •  3
  •  2
Monthly Rent $7,800 - $9,428

2BR waterview condo with pools - dog-friendly Holmes Beach, Florida, Listing ID: 32646

Centrally located in Holmes Beach in the Sunbow Bay Condominium, this sunlit and inviting condo features several desirable amenities plus amazing views of the water from the living area and the private, screened balcony. Watch the sunrise followed by an alfresco breakfast in the...

  • Condo
  • 1146
  •  2
  •  2
Monthly Rent $1,800 - $3,300

Dog-friendly studio near the beach Holmes Beach, Florida, Listing ID: 32647

Whether you're hanging ten or just hanging loose, this breezy studio in the heart of Holmes Beach is the ideal choice for your next Gulf Coast getaway! From the beach to a fantastic array of bars, restaurants, and local shopping options, the best of Anna Maria Island is at your...

  • Studio
  • 208
  •  0
  •  1
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
Monthly Rent $6,776 - $12,440

Enchanting 2BR | Pool | Deck | W/D Key West, Florida, Listing ID: 32681

Slip into a modern duplex with distinctly bright Key West vibes! One of the two properties to rent at the Tropical Vibes house, this duplex is full of comfy details and punches of color. Not least of which is the home's star: a brilliant private saltwater pool (yes, it's...

  • Duplex
  • 818
  •  2
  •  3
Monthly Rent $11,229 - $12,715

Comfortable 3BR | Private Pool | Patio | W/D Key West, Florida, Listing ID: 32682

Recline next to a shimmering pool, with a banana tree and avocado tree completing your view! This pleasant home is designed for guest comfort from top to bottom, with everything from central air conditioning to a private gas grill to help with vacation cookouts. The home is all...

  • House
  • 1740
  •  3
  •  2
Monthly Rent $5,171 - $8,295

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