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The Florida Keys are one of the top getaways in the U.S. and one of the best destinations to visit in March because the weather is warm and sunny, and it’s a great starting point to explore more of the Caribbean. So I’ve rounded up the best Florida Keys luxury vacation rentals.
Top Getaways in the Southeast
These vacation homes are the perfect island paradises for exploring The Keys. Plus, you’ll have more space and amenities than a hotel can give you – pools, yards, office spaces, game rooms, and outdoor living.
Here are the best Florida Keys Luxury Vacation Rentals for your trip!
Tranquility Cottage
Tranquility Cottage
Key West
2 guests1 bedroom1 bed1 bath
This small cottage packs a big punch with its bamboo accents, coastal colors and decor, Cuban tile floors, and the private courtyard and deck. You’ll have access to the complex’s pool and garden, and this home is just a short walk to the beach, Historic Seaport, and Duval Street.
Luxury Houseboat
Key West
6 guests2 bedrooms3 beds2.5 baths
On this spacious houseboat, you’ll have 950 square feet of outdoor living space, including a massive third level sun deck. This property is part of a yacht club, so you’ll have access to all of the club’s amenities – a pool, private beach, gym, restaurant, and oceanside tiki bar.
Paradise
Lower Matecumbe Key
8 guests3 bedrooms beds baths
This is beachfront living! You’ll love the incredible ocean views, the sandy backyard that leads directly to the ocean, the private boat dock, the four beach cruisers, the hammock, the beach chairs and umbrellas, and the screened-in and furnished back patio.
Real World MTV House
Key West
16 guests10 bedrooms12 beds5.5 baths
If you want to live one of your reality TV fantasies, you can stay in this house, which was featured in The Real World season 17 in 2006. This over-the-top house has a gym, pool table, racket ball court, boat dock, kayaks, paddleboards, bikes, and an amazing pool and patio. So get your crew together to party here!
Big Blu
Key West
12 guests5 bedrooms5 beds4 baths
Here, you’ll be ideally situated just a few blocks from the sea, restaurants, and shops. The floor-to-ceiling windows make the house bright, open, and airy, and the kitchen is a chef’s dream. The saltwater pool is heated with jacuzzi jets, and the patio will make you feel like you’re at a luxury resort.
Heavenly Zen
Key West
8 guests bedrooms beds · 3 baths
You’ll never want to leave this island paradise. The inside has vaulted ceilings, open-concept living, coastal decor, and massive doors and windows that make the inside and outside flow together. This home’s courtyard is incredible with a pool, waterfall, covered, lush tropical landscaping, hot tub, and outdoor shower.
Oceanfront Retreat
Oceanfront Retreat
Cudjoe Key
4 guests2 bedrooms beds2 baths
Enjoy breathtaking ocean views from this beautiful stilt home. You’ll have a full-length concrete seawall, a dock for two boats, heavy-duty dock posts, boat cleats, a swim ladder, a fish cleaning table, and a water hose. You’ll also have an elevator and access to complimentary beach cruiser bikes.
Calle Ensueno
Marathon
10 guests4 bedrooms4 beds3 baths
This tropical oasis is located on Crystal Lagoon and comes with a dock and boat slip. You won’t want to leave the fabulous pool, patio, and wrap around porch, and the kitchen is a chef’s dream come true.
Recommended Tours in The Florida Keys
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What are your favorite Florida Keys luxury vacation rentals? Share with us in the comments!
Plan The Rest Of Your Trip
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Florida Keys Luxury Vacation Rentals
Frequently Asked Questions
Where should I vacation in the Southeast US?
If you want large cities, I recommend Nashville, Miami, New Orleans, or Charleston. For national parks, head to The Great Smoky Mountains, Shenandoah, or New River Gorge. If you want beaches, then I suggest the Florida Keys, Destin, or The Outer Banks. For food and culture, taste your way across the Monticello Wine Trail, drive the Kentucky Bourbon Trail, and visit St. Simons Island.
What is the best Southern state to visit?
Every state in the Southeast USA has incredible cities, national and state parks, and scenic drives. Florida is the most-visited state in the Southeast USA for beaches and amusement parks. Tennessee and North Carolina are the most-visited states for hiking and outdoor adventures.
No matter what kind of trip you want to have, you can find the perfect destination in the Southeast USA!
Where should I travel in the South?
Epic places to visit in the Southeast USA:
1. The Great Smoky Mountains
2. Miami
3. New Orleans
4. Savannah
5. Charleston
6. The Kentucky Bourbon Trail
7. Dry Tortugas National Park
8. The Monticello Wine Trail
9. The Outer Banks
10. The Florida Keys
Where should I go for a 3 day vacation?
The best weekend getaways in the Southeast USA are:
1. Georgia’s Golden Isles
2. The Great Smoky Mountains
3. Charleston, South Carolina
4. Miami, Florida
5. The Florida Keys
6. New Orleans, Louisiana
7. Destin, Florida
8. Chattanooga, Tennessee
9. Savannah, Georgia
10. Highlands, North Carolina
Is a 3 day vacation worth it?
Yes, getting away for a short trip is worth it! Short getaway vacations are good for your mental health and allow you to travel on a budget. It can be rewarding and exciting to explore destinations close to home for a couple of days. You could even have a staycation in your hometown if you want a break from work without having to pack a suitcase.
Destinations in the Southeast USA that can be explored in a couple of days are:
1. Savannah, Georgia
2. Georgia’s Golden Isles
3. The Great Smoky Mountains
4. Nashville, Tennessee
5. Asheville, North Carolina
6. New Orleans, Louisiana
What are some good girl trips?
The best girlfriend getaways in the Southeast USA are:
1. Charleston, South Carolina
2. Nashville, Tennessee
3. Miami, Florida
4. New Orleans, Louisiana
5. Savannah, Georgia
Where can I go on a road trip in the South?
The best road trips and scenic drives in the Southeast USA are:
1. Kentucky Bourbon Trail
2. Blue Ridge Parkway through Virginia and North Carolina
3. Highway 276 through Pisgah National Forest in North Carolina
4. Ozark National Forest on the Pig Trail Scenic Byway
5. Seaside Loop in Florida
6. The Overseas Highway through the Florida Keys
What are cheap vacation ideas?
Ways to travel the Southeast USA on a budget are:
1. Tour your own city on a staycation
2. Camp
3. Go to off-the-beaten-path destinations
4. Visit less popular beaches
5. Stay with friends or family
6. Book hotels with travel reward points
7. Travel during the off-season
8. Take a weekday trip
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This article about the best Florida Keys luxury vacation rentals is not a sponsored post, and the thoughts and opinions expressed in this post are entirely my own. Some of the links in this post about the best Florida Keys luxury vacation rentals are affiliate links, and, at no cost to you, I may earn a small commission.
