Deals on vacations and trips to Upper Matecumbe Key

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The W - Bayshore Unit 1003

The W - Bayshore Unit 1003

3 out of 5
East Fort Lauderdale
Price was $1,711, price is now $554 per person
$554
per person
Jul 7 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
This apartment features dry cleaning, laundry facilities, and valet parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
3BR Pool House Sleeps 8

3BR Pool House Sleeps 8

3 out of 5
Driftwood
Price was $2,737, price is now $709 per person
$709
per person
Jul 10 - Jul 14
found 9 hours ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
An outdoor pool, free self parking, and barbecue grills are featured at this vacation home. WiFi in public areas is free. A garden is also provided.
Family Pool Home by Hollywood Beach

Family Pool Home by Hollywood Beach

2.5 out of 5
Hollywood Hills
Price was $2,444, price is now $646 per person
$646
per person
Jul 10 - Jul 14
found 9 hours ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
An outdoor pool, free self parking, and laundry facilities are featured at this vacation home. WiFi in public areas is free. Barbecue grills and a virtual front desk are also provided.
Miami Downtown Condos

Miami Downtown Condos

5 out of 5
Downtown Miami
Price was $2,033, price is now $700 per person
$700
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This smoke-free condo includes 2 restaurants, an outdoor pool, and a 24-hour gym. Business travelers can take advantage of the business center. A poolside bar, a 24-hour front desk, and a coffee shop are also provided.
Brickell Bay 3304

Brickell Bay 3304

3 out of 5
Brickell
Price was $1,381, price is now $560 per person
$560
per person
Jun 26 - Jun 29
found 10 hours ago
Roundtrip non-stop flight included
New York (NYC) to Miami (MIA)
This apartment features dry cleaning, laundry facilities, and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Top Upper Matecumbe Key hotels deals

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$232 nightly
The price is $261 total per night
$261 total
May 10 - May 11
Total with taxes and fees
A private beach, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind with a drink at the bar/lounge and enjoy perks like free continental breakfast and free WiFi.
On private beach
Pool
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$312 nightly
The price is $351 total per night
$351 total
May 14 - May 15
Total with taxes and fees
This luxury resort features a private beach, a golf course, and a full-service spa. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. There's fun for all ages with a free kid's club and a playground, and families will appreciate the onsite laundry facilities.
On private beach
Pool
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
$269 nightly
The price is $303 total per night
$303 total
May 17 - May 18
Total with taxes and fees
A private beach, 3 restaurants, and 2 outdoor pools are all featured at this hotel. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Families will appreciate the mini golf and complimentary bicycles.
On private beach
Pool
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$249 nightly
The price is $280 total per night
$280 total
May 11 - May 12
Total with taxes and fees
A private beach, 2 restaurants, and an outdoor pool are all featured at this resort. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Enjoy the gym and visit the 3 bars/lounges and poolside bar for drinks.
On private beach
Pool
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$234 nightly
The price is $264 total per night
$264 total
May 13 - May 14
Total with taxes and fees
The private beach and marina are among the highlights at this resort. Enjoy the outdoor pool and perks like a free area shuttle. There's a poolside bar on site, and a 24-hour front desk and wedding services are also provided.
On private beach
Pool
Hadley Resort and Marina

Hadley Resort and Marina

3.5 out of 5
82749 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$164 nightly
The price is $185 total per night
$185 total
May 5 - May 6
Total with taxes and fees
This traditional hotel's private beach and marina are among the highlights. Enjoy a day at the beach kayaking, or relax with sun loungers. Families will appreciate the playground and barbecue grills.
On private beach
Pool
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much are vacation packages to Upper Matecumbe Key?
With vacation packages on offer from just $554, you won't need to drain your bank balance for your getaway to Upper Matecumbe Key. Travelocity is here to help. Bundle hotels, flights and tours into a package and score some exciting discounts. The more you book, the more you save.
Where can I get the best vacation package deals for Upper Matecumbe Key?
It's hard to top Travelocity when it comes to piecing together your Upper Matecumbe Key package deal. There are at least 400 air carriers and 1,000,000 properties around the world to choose from. Book your trip now and get ready to tick another exciting destination off your travel bucket list.
Why should I purchase my Upper Matecumbe Key vacation bundle with Travelocity?
Because you'll never roam alone if you lock in your trip through us, and we offer round-the-clock support and top-notch service to boot. Add to that our Price Match Guarantee and a massive range of destinations to choose from. It's our job to help you jet off on the vacation of a lifetime.
Can I save money on my Upper Matecumbe Key car rental if I book it with hotels and flights?
Combining your bookings into an Upper Matecumbe Key vacation package will save you some serious money. Book a car and flight; a flight, car and hotel; or a car and hotel. There's no better way to discover the greater Upper Matecumbe Key area than with your own rental car. You can also add activities and experiences to your Travelocity package.

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