Florida Keys Vacation Rental in Key West, Dog Friendly

Key West FL Vacation Home For Rent

1 bedrooms/1 baths 

Sleeps: 4

Price: $630 avg per night

Credit: VRBO

4.9/5 ⭐⭐⭐⭐⭐

>> Book Here <<

Key West Pet Friendly Florida Vacation Property For Rent. Tucked away on a vibrant lane just a stone's throw to all the desirable destinations, this island retreat offers the ultimate serenity. A bright and cheery greeting from this saltwater abode welcomes you as you step into your slice of Paradise. Sink down into the cozy sectional in the Great Room area with a flat screen TV for movie nights. The kitchen comes fully equipped and offers a bar area for...view more details 

 View: >> Key West Pet Friendly Vacation Rentals  <<
Explore: >> Things to do in the Keys  <<

Key West, Florida 

Stretching 126 miles south toward Cuba, the stunning Florida Keys are a perfect escape. Highlights along the way include Key Largo, Islamorada, Marathon, Big Pine Key and the irrepressible Key West. Get up close with an amazing array of fish while snorkeling, diving or fishing in the warm turquoise waters. Creeks, coral and costumed spectacles are other lures along the way. Highway 1 is a spectacular ribbon tying together the islands and atolls of this paradise between the Gulf of Mexico and the Atlantic.

Source: Key West, FL Pet Friendly Vacation Property For Rent By Owner

Florida Keys Pet Friendly Vacation Cottage for Rent by Owner in Key West

 Key West, FL Vacation Rental with Dip Pool 

3 BR/ 2 BA

Rate: from $328 nightly

Source: VRBO

5/5 ⭐⭐⭐⭐⭐

>> Book Here <<

Florida Keys Vacation Home For Rent with Pool in Key West, Dog Friendly. This Key West charmer is just a short stroll away from the award winning restaurants and delightful shopping in historic Bahama Village. This quaint retreat greets you with a relaxing front porch that beckons you to sit and stay a while...view more details

View: >> Vacation Rentals in the Florida Keys <<

View: >> Explore the Keys  <<

Key West, Florida 

Forever in summer, Key West is all about kicking back. Everyone and everything here seems to go at its own easy pace. But it’s not all hammock time—the diving here is phenomenal, as is the food. Travelers keep coming back for the must-eats: Cuban sandwiches, Cuban coffee, and key-lime pie, along with outstanding seafood. No surprise, the weather, the food, and the scenery have lured lots of crowds, but you can escape them with a well-timed visit in early spring—or just get out on the water where you can stake out your own private spot in the Gulf of Mexico.

Source: Key West FL Vacation Home for Rent with Dip Pool

Key West FL Pet Friendly Vacation Cottage For Rent

 Florida Keys Vacation Property For Rent By Owner

1 bedroom / 1 bath 

Price: $354 avg per night

Source: VRBO

4.8/5 ⭐⭐⭐⭐⭐

>> Book Here <<

Key West  Florida Vacation Home For Rent, Dog Friendly. This home is perfect for one couple planning on having guests or children join them.  Sit back, relax, and enjoy! Peaceful colors throughout with nautical décor add a nice tropical feel to this retreat. Feel like you're relaxed and in the tropics whether indoors or out.  This home  feels spacious due to the beautiful wood vaulted ceilings in the living room and kitchen, and nice high ceilings in the bedroom. Hardwood floors throughout and plenty of windows for natural sunlight...view more details 

View: >> Florida Keys Vacation Rentals <<

Explore: >> Things to do in the Keys  <<

Key West, Florida 

Stretching 126 miles south toward Cuba, the stunning Florida Keys are a perfect escape. Highlights along the way include Key Largo, Islamorada, Marathon, Big Pine Key and the irrepressible Key West. Get up close with an amazing array of fish while snorkeling, diving or fishing in the warm turquoise waters. Creeks, coral and costumed spectacles are other lures along the way. Highway 1 is a spectacular ribbon tying together the islands and atolls of this paradise between the Gulf of Mexico and the Atlantic.

Source: Florida Keys Vacation Home For Rent in Key West, Dog Friendly

Florida Keys Vacation Cottage For Rent By Owner, Dog Friendly

 Key West FL Vacation Property for Rent near Duval Street

1 bedroom / 1 bath

Rate: $351 avg per night

Source: VRBO

4.8/5 ⭐⭐⭐⭐⭐
 >> BOOK HERE <<

Key West Florida Pet Friendly Vacation Rental. lush landscaping outdoors will give you that tropical island feeling you are looking for. Warm wood tones and exposed beams can be found in the main living area. The family room with sofa, chair, and TV is open to the kitchen and dining areas. A wooden island with seating is the perfect place to enjoy a snack or beverage. A bright kitchen provides all that you will need to prepare meals. However, while on vacation, you may prefer to walk to one of Old Town’s amazing restaurants. ...view more details

View: >> Pet Friendly Vacation Rentals in the Florida Keys  <<

View: >> Explore the Keys  <<

Key West, Florida 

Forever in summer, Key West is all about kicking back. Everyone and everything here seems to go at its own easy pace. But it’s not all hammock time—the diving here is phenomenal, as is the food. Travelers keep coming back for the must-eats: Cuban sandwiches, Cuban coffee, and key-lime pie, along with outstanding seafood. No surprise, the weather, the food, and the scenery have lured lots of crowds, but you can escape them with a well-timed visit in early spring—or just get out on the water where you can stake out your own private spot in the Gulf of Mexico.

Source: Key West FL Pet Friendly Vacation Rental

Key West FL Dog Friendly Beach Cottage For Rent By Owner

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Florida Keys Vacation Rental with Pool, Key West 

2 br/2 ba 

Sleeps: up to 6

Rate: from $246 nightly

5/5 ⭐⭐⭐⭐⭐ (1 Reviews)

Source: VRBO

>> Book Here <<

Florida Keys Pet Friendly Vacation Home For Rent in Key West. This quaint little cottage is located in the center of Old Town on the island's highest point. In addition to the superb location, this home also offers top-notch amenities. With a private front porch, a private heated pool, a covered lanai, and plenty of indoor/outdoor space LA CASITA EN CIMA has everything you'll need for your time in paradise. LA CASITA EN CIMA has a spacious living area that includes a large sofa that pulls out into a Queen sleeper for additional guests, and a large flat screen TV. Adjacent to the living room is the sitting room, equipped with another comfy couch and a desk. The French doors and windows throughout this home allow in plenty of natural light and tropical breezes. The kitchen includes a range, an vintage-style, oversized fridge, a beautiful porcelain sink, and plenty of counter and cabinet space. There is an adorable outdoor four-person dining table located on the side deck when you want to enjoy a meal in the fresh air...view more details

 View: >> Key West Pet Friendly Vacation Rentals  <<

View: >> Key West Calendar of Events  <<

Key West, Florida 

Stretching 126 miles south toward Cuba, the stunning Florida Keys are a perfect escape. Highlights along the way include Key Largo, Islamorada, Marathon, Big Pine Key and the irrepressible Key West. Get up close with an amazing array of fish while snorkeling, diving or fishing in the warm turquoise waters. Creeks, coral and costumed spectacles are other lures along the way. Highway 1 is a spectacular ribbon tying together the islands and atolls of this paradise between the Gulf of Mexico and the Atlantic.

What's nearby

Key West Cemetery - 4 min walk

Duval Street - 5 min walk

San Carlos Institute - Casa Cuba - 6 min walk

Southernmost Point - 15 min walk

Mallory Square - 16 min walk

Getting around

Key West Intl. Airport (EYW) - 12 min drive

Restaurants

Willie T's - 5 min walk

Bourbon Street Pub - 5 min walk

801 Bourbon Bar - 4 min walk

Mangoes Restaurant & Island Cuisine - 3 min walk

DJ's Clam Shack - 3 min walk

Florida Keys Dog Friendly Vacation Rental, Key West

 Key West FL Vacation Home For Rent By Owner 

1BR/1BA

Price: $302 avg per night

4.9/5 ⭐⭐⭐⭐⭐ 

Source: VRBO
 >> BOOK HERE <<

Key West Florida Vacation Property For Rent. Conch Cottage is fully furnished & features a renovated, fully equipped kitchen w/ SS appliances & stackable W/D. The living and dining areas are open concept. There is a flat screen, cable TV & couch. The open space allows full view of the French doors leading to your private rear deck. The bedroom has a queen bed and a door to the private back deck. The rear deck has all the amenities you could need. The space has a lounging area, an outdoor seating area w/ an umbrella, hot tub, & a grill.   ...view more details

View: >> Pet Friendly Vacation Rentals in the Florida Keys  <<

View: >> Explore the Keys  <<

Key West, Florida 

Forever in summer, Key West is all about kicking back. Everyone and everything here seems to go at its own easy pace. But it’s not all hammock time—the diving here is phenomenal, as is the food. Travelers keep coming back for the must-eats: Cuban sandwiches, Cuban coffee, and key-lime pie, along with outstanding seafood. No surprise, the weather, the food, and the scenery have lured lots of crowds, but you can escape them with a well-timed visit in early spring—or just get out on the water where you can stake out your own private spot in the Gulf of Mexico.

Source: Key West FL Pet Friendly Vacation Cottage For Rent By Owner

Key West FL Pet Friendly Vacation Rental with Pool

Florida Keys Vacation Property For Rent By Owner, Key West

2br/2ba 

Sleeps: up to 6

Price: from $481 nightly

4.6/5 ⭐⭐⭐⭐⭐ (52 Reviews)

Source: VRBO

 >> Book Here <<

Key West Florida Dog Friendly Vacation Property For Rent. Slip into vacation mode as you explore Duval Street and dive into the beach scene when you book your trip to this dog-friendly Key West cottage. Featuring street parking, a relaxing shared pool, and a location that puts you right in the heart of the action, up to six guests and a canine companion (for a small nightly fee) can come and enjoy! Wake up with a stroll along the beach to a small cafe for a fresh seaside breakfast. Spend the day working on your tan by the crashing waves, or get out on the water with a stand-up paddle-board session or a deep sea fishing adventure. Unwind poolside at the shared pool, then use the community grill to put a sear on some fresh seafood. Connect to the free WiFi to stream some music as you lounge ...view more details

 View: >> Florida Keys Pet Friendly Vacation Rentals  <<

Explore: >> Things to do in the Keys  <<

Key West, Florida 

Stretching 126 miles south toward Cuba, the stunning Florida Keys are a perfect escape. Highlights along the way include Key Largo, Islamorada, Marathon, Big Pine Key and the irrepressible Key West. Get up close with an amazing array of fish while snorkeling, diving or fishing in the warm turquoise waters. Creeks, coral and costumed spectacles are other lures along the way. Highway 1 is a spectacular ribbon tying together the islands and atolls of this paradise between the Gulf of Mexico and the Atlantic.

What's nearby

• Duval Street - 4 min walk
• South Beach - 5 min walk
• Key West Butterfly and Nature Conservatory - 5 min walk
• Southernmost Point - 6 min walk
• Ernest Hemingway Home and Museum - 13 min walk

Restaurants

• Louie's Backyard - 3 min walk
• Banana Cafe - 6 min walk
• Santiago's Bodega - 18 min walk
• Blue Heaven - 16 min walk
• The Lobster Shack Key West - 3 min walk

  Popular Amenities: 💦Pool       🐶 Pet Friendly

Florida Keys Vacation Home For Rent, Key West

Key West, FL Vacation Rental By Owner with Lazy River Pool

3 bedrooms/ 3 baths      

Sleeps : up to 6

5/5 ⭐⭐⭐⭐⭐ (33 Reviews)

 >> BOOKHERE <<

Source: VRBO

Key West Florida Vacation Property For Rent. A colorful 3 bedroom, 2 full bath, private, and historic home is a wonderful spot to vacation, live like a local, honeymoon, or work from home. Tucked quietly on a lazy lane 2 blocks from world famous Duval Street! You will be just around the corner to The Hemingway House , famous Blue Heaven Restaurant and the Key West Lighthouse. Our quiet lane starts on Petronia Street, which has become the culinary center of Key West. VIV wine bar, Le Creperie, and Rams Head are at the end of the road. Our location is simply perfect! Two FREE bicycles come with the property and a parking spot option- not that you need it- Key West is a walker's paradise from your perfect location....view more details

View: >> Florida Keys Vacation Rentals <<

View: >> Things to do in the Keys  <<

What's nearby

• Ernest Hemingway Home and Museum - 2 min walk
• Key West Lighthouse and Keeper's Quarters Museum - 2 min walk
• Duval Street - 3 min walk
• Southernmost Point - 9 min walk
• Mallory Square - 17 min walk

Getting around

• Key West Intl. Airport (EYW) - 13 min drive

Restaurants

• Santiago's Bodega - 3 min walk
• Blue Heaven - 3 min walk
• La Creperie - 2 min walk
• Better Than Sex - 6 min walk
• DJ's Clam Shack - 5 min walk

Key West, Florida 

Forever in summer, Key West is all about kicking back. Everyone and everything here seems to go at its own easy pace. But it’s not all hammock time—the diving here is phenomenal, as is the food. Travelers keep coming back for the must-eats: Cuban sandwiches, Cuban coffee, and key-lime pie, along with outstanding seafood. No surprise, the weather, the food, and the scenery have lured lots of crowds, but you can escape them with a well-timed visit in early spring—or just get out on the water where you can stake out your own private spot in the Gulf of Mexico.

Key West FL Vacation Home For Rent

 

Florida Keys Beachfront Vacation Rental By Owner, Key West

1br/1.5ba    

Sleeps: up to    

Price: from $597

4.9/5 ⭐⭐⭐⭐⭐ (56 Reviews)

 >> Book Here <<

Source: VRBO

Key West  Florida Vacation Home For Rent. Hidden Beach Unit 3 - In Old Town, just 3 blocks from Duval Street; this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort. Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure. It is a short walk to many of Key West’s best attractions. ...view more details

View: Vacation Rentals in the Florida Keys  🏖

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Key West, Florida 

Stretching 126 miles south toward Cuba, the stunning Florida Keys are a perfect escape. Highlights along the way include Key Largo, Islamorada, Marathon, Big Pine Key and the irrepressible Key West. Get up close with an amazing array of fish while snorkeling, diving or fishing in the warm turquoise waters. Creeks, coral and costumed spectacles are other lures along the way. Highway 1 is a spectacular ribbon tying together the islands and atolls of this paradise between the Gulf of Mexico and the Atlantic.

  Popular Amenities:  🌊Beachfront   

Florida Keys Beachfront Vacation Rental By Owner, Key West

Key West FL Vacation Condominium Home For Rent with Pool

2br/2ba    

Sleeps: up to 6   

Price: from $639 nightly

4.9/5 ⭐⭐⭐⭐⭐ (19 Reviews)

 >> Book Here <<

Source: VRBO

Key West  Florida Vacation Property For Rent. Key West FL Beach Vacation Property Rental. Enjoy this spectacular condominium home with an oceanfront view of Key West harbor for your next getaway in the Key West! Located in Truman Annex, this home boasts beautiful water views from the balcony and all around the condo, you'll be sure to feel inspired during your stay! This rental has a full kitchen for easy meal preparation and plenty of seating for dining. Guests will also enjoy access to a shared, on-site pool! Free WiFi + Elevator in the building + Full kitchen with dishwasher. There is free parking for 1 vehicles...view more details

View: Vacation Rentals in the Florida Keys  🏖

View: Things to do in the Keys  🌴

Key West, Florida 

Stretching 126 miles south toward Cuba, the stunning Florida Keys are a perfect escape. Highlights along the way include Key Largo, Islamorada, Marathon, Big Pine Key and the irrepressible Key West. Get up close with an amazing array of fish while snorkeling, diving or fishing in the warm turquoise waters. Creeks, coral and costumed spectacles are other lures along the way. Highway 1 is a spectacular ribbon tying together the islands and atolls of this paradise between the Gulf of Mexico and the Atlantic.

  Popular Amenities: 💦Pool    🌊Beachfront 

What's nearby

• Harry S. Truman Little White House - 2 min walk
• Audubon House and Tropical Gardens - 4 min walk
• Duval Street - 5 min walk
• Mallory Square - 6 min walk
• Southernmost Point - 3 min drive

Getting around

• Key West Intl. Airport (EYW) - 13 min drive
  

Restaurants

• Santiago's Bodega - 13 min walk
• Blue Heaven - 14 min walk
• Glazed Donuts - 6 min walk
• Smokin' Tuna Saloon - 5 min walk
• La Creperie - 13 min walk

Key West FL Vacation Home For Rent with Pool

Florida Keys Vacation Rental By Owner

2br/2ba    

Sleeps: up to 6   

Price: from $729 nightly

4.9/5 ⭐⭐⭐⭐⭐ (105 Reviews)

>> Book Here <<

Source: VRBO

Key West Florida Vacation Property For Rent.  Formerly La Bonne Vie, SMOOTH SAILING has been meticulously furnished with a modern coastal feel, and the only beauty that competes with the interior is the spectacular views from your private oceanfront balcony. You'll be able to enjoy quiet afternoons with those balmy Key West breezes wafting through the floor-to-ceiling glass doors from the living room, and sunrise shadows from your bedroom balconies in the morning. This home is located in an upscale private community within walking or biking distance to all of your favorite Key West spots, including beaches, restaurants, shopping, and the beautiful waters surrounding the island. You'll be hard pressed to find a more stunning mix of upscale furnishings and water views than SMOOTH SAILING....view more details

Popular Features:  🏊 Pool    🔥 Hot Tub        🌊 Beach-Front  

View: Vacation Rentals in the Florida Keys  🏖

View: Things to do in the Keys  🌴

Key West, Florida 

Stretching 126 miles south toward Cuba, the stunning Florida Keys are a perfect escape. Highlights along the way include Key Largo, Islamorada, Marathon, Big Pine Key and the irrepressible Key West. Get up close with an amazing array of fish while snorkeling, diving or fishing in the warm turquoise waters. Creeks, coral and costumed spectacles are other lures along the way. Highway 1 is a spectacular ribbon tying together the islands and atolls of this paradise between the Gulf of Mexico and the Atlantic.

What's nearby

• Higgs Beach - 14 min walk
• Smathers Beach - 1 min drive
• Duval Street - 5 min drive
• South Beach - 5 min drive
• Key West Butterfly and Nature Conservatory - 5 min drive

Getting around

• Key West Intl. Airport (EYW) - 3 min drive

Restaurants

• Louie's Backyard - 4 min drive
• Salute - 17 min walk
• Key Plaza Creperie - 5 min drive
• Fernandy's Café - 4 min drive
• El Siboney Restaurant - 4 min drive

Florida Keys Beachfront Vacation Rental, Key West

Key West FL Vacation Condominium For Rent By Owner, Oceanfront 

1BR/1BA    

Sleeps up to: 5    

Price: from $550

Features:  🏊 Pool    🔥 Hot Tub    🌊 Beach-Front  

Source: VRBO

BOOK HERE

  

Key West Florida Vacation Condo For Rent. This one of a kind  large 1br/1ba condominium home on the 6th floor of the Galleon Resort & Marina. It features a fantastic, fully equipped kitchen with new cabinetry and granite countertops, dining room, living room and a very spacious master bedroom & bath.  This suite will sleep 5, with a king bed and a twin pullout in the master bedroom and a queen pullout in the living room.  Also, one of a kind, is the huge deck with an outside table & chairs, lounge chairs, private hot tub and a spiral staircase to a private rooftop...view more details

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Reviews 4.8/5 ⭐⭐⭐⭐⭐ (103 Reviews)

Mike - August, 2023

4/5 - We came down from Key Largo for a night. Great spot and definitely a great room, private roof top deck to watch sunset. We will be back and stay here again

Debbie F. - July, 2023

5/5 - Beautiful unit, very clean and plenty of room. Galleon facility was extremely nice, very attentive staff, and plenty of places to walk for food. The only complaint is the bed was a bit too hard for our liking. I would definitely stay again. Also, the other property owners and guests were very friendly.

Key West, Florida 

Forever in summer, Key West is all about kicking back. Everyone and everything here seems to go at its own easy pace. But it’s not all hammock time—the diving here is phenomenal, as is the food. Travelers keep coming back for the must-eats: Cuban sandwiches, Cuban coffee, and key-lime pie, along with outstanding seafood. No surprise, the weather, the food, and the scenery have lured lots of crowds, but you can escape them with a well-timed visit in early spring—or just get out on the water where you can stake out your own private spot in the Gulf of Mexico.

Florida Keys Vacation Rental By Owner, Key West

Key West FL Vacation Home For Rent with Pool 

3 bedrooms/2.5 baths

Sleeps: up to 8

Rate: from $895 nightly

Source: VRBO

4.7/5 ⭐⭐⭐⭐⭐ (26 Reviews) 

Florida Keys Vacation Property Rental. Enjoy a beautiful private home located in the Historic Truman Gated Community Old Town Key West. Only steps away from Duval Street and all the activities and restaurants of Key West. Swim in the private heated pool with spa jets, large outdoor patio and back deck with grill. Relax on the upstairs wrap around porch. W/D, pots, pans, kitchen utensils, towels ; bedding central air, ceiling fans, WiFi..view more details

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Key West, Florida 

Key West is Florida’s irreverent southernmost subtropical paradise, a unique blend of history, climate, natural beauty, cultural diversity, architecture and unabashed romantic appeal. Palm-lined streets with gingerbread mansions and tin-roofed conch houses were home to Ernest Hemingway, Tennessee Williams, Elizabeth Bishop, and a few of the famous people who discovered solace and inspiration in the island city, whose heritage in large part was inspired by Bahamian wreckers, commercial fishermen, spongers and Cuban cigar makers. In Key West, you can visit a host of historic attractions by biking, walking, convenient public transportation, pedi-cabs, tour trains, trolleys or taxis.

Source: Key West FL Vacation Rental with Pool

Florida Vacation Rental in Key West, Pet Friendly

Key West, FL Dog Friendly Vacation Home For Rent By Owner   

Source: VRBO

2BR/1BA

Sleeps: up to 4 

Price: $474 avg per night

Features:  🆒 A/C    💻 WiFi       🐶 Pet Friendly    

 🍳 Kitchen    👕 W/D   

  

Key West FL Beach Vacation Property Rental. Take advantage of this premier opportunity to indulge in all your desired Key West bucket list items at this crisp condo centered in the heartbeat of Duval St. Located in the upbeat and lively district of Key West, this home is just steps to high end art galleries, museums, The Southernmost Point of the U.S. and all best nightlife action yet tucked away above the action for a peaceful evening's rest. *PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE* Book Here

Details & Amenities

This island retreat resides on a second-floor level off Duval St. for incredible convenience to everything. Tile floors and a vaulted, open Great Room with a flat screen TV create a welcoming space for your happy hour before hitting the town. Enjoy an updated and fully equipped kitchen featuring granite counters, stainless steel appliances and bar seating for 3. 

Sleeping Arrangements 

Totaling 2 bedrooms, this condo is equipped with 2 guest bedrooms to accommodate 4 people. Both rooms come with queen beds, closet space, ceiling fans and a shared bathroom featuring a shower/tub combination. One bedroom opens up to the outdoor balcony to catch your island breeze! 

Outdoor Living

Start your morning perched above an attractive, tropical courtyard area with your cup of coffee at the table for 2 while you plan the day’s activities. Parking in the downtown area is a rarity but this gem features a parking space but oversized SUVs and trucks will not fit. Make the most out of your vacation by being located in the heart of it all! 

Pets

Pets are considered except for puppies or barking dogs.

View: Key West FL Vacation Rentals 🏖

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REVIEWS 4.9/5 ⭐⭐⭐⭐⭐ (71 Reviews)

Diana L. - September, 2023

5/5 - Walk to Duval St and Oceanfront dining, sunsets. Great location, beautiful condo, walk to everything, communication with property mgr excellent

Richard T. - September, 2023

5/5 - Great stay! Very nice place; incredibly clean and conveniently located off Duval. Would definitely stay here again!

Heidi B. - August, 2023

5/5 - Lovely location. Had a great time.

Key West, Florida

Forever in summer, Key West is all about kicking back. Everyone and everything here seems to go at its own easy pace. But it’s not all hammock time—the diving here is phenomenal, as is the food. Travelers keep coming back for the must-eats: Cuban sandwiches, Cuban coffee, and key-lime pie, along with outstanding seafood. No surprise, the weather, the food, and the scenery have lured lots of crowds, but you can escape them with a well-timed visit in early spring—or just get out on the water where you can stake out your own private spot in the Gulf of Mexico.