Upper Matecumbe Key Vacation Packages

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Top Upper Matecumbe Key vacation package deals

Price found within the past 48 hours. Click for updated prices.
Barcelona Studios Guesthouse
2.0-star property

Barcelona Studios Guesthouse

South Beach
9.4/10 Exceptional! (258 reviews)

Oct 31 - Nov 7

7 night stay

Boston (BOS) to Miami (MIA)

American Airlines • Coach

Miami (MIA) to Boston (BOS)

Allegiant Air • Coach
Price was $869, price is now $393 per person
$393
per person
found 1 day ago
This property was absolutely amazing! Not only do they have communal toiletries (sun screen, umbrella, etc.) but they also have beach chairs for you to use, beach towels, and the staff was simply amazing! I can’t wait to return!

Reviewed on Sep 21, 2026

Cavalier Hotel South Beach
3.5-star property

Cavalier Hotel South Beach

South Beach
8.6/10 Excellent! (1,005 reviews)

Oct 31 - Nov 7

7 night stay

Boston (BOS) to Miami (MIA)

American Airlines • Coach

Miami (MIA) to Boston (BOS)

Allegiant Air • Coach
Price was $1,126, price is now $526 per person
$526
per person
found 1 day ago
Love it

Reviewed on Sep 21, 2026

Pelican Hotel
4.0-star property

Pelican Hotel

South Beach
9.2/10 Wonderful! (506 reviews)

Oct 31 - Nov 7

7 night stay

Boston (BOS) to Miami (MIA)

American Airlines • Coach

Miami (MIA) to Boston (BOS)

Allegiant Air • Coach
Price was $1,818, price is now $851 per person
$851
per person
found 1 day ago
Front Desk Staff was GREAT! We ate outside one night and the FOOD was DEEEE-LISH-US!!!! The only two dislikes were the bed was extremely hard. Was not comfortable...and...being on Ocean Dr, the music played until about 1am(ish). All we heard was the Bass. So if you are an early "bedder", you may not want to stsy as any hotel on Ocean Drive. But overall, the Pelican was nice! (PS: the food was really good!!)

Reviewed on Sep 21, 2026

The Retreat Collection at 1 Hotel & Homes South Beach
5.0-star property

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach
8/10 Very Good! (1 review)

Nov 26 - Nov 29

3 night stay

Boston (BOS) to Miami (MIA)

JetBlue Airways • Roundtrip • Coach
Price was $14,195, price is now $7,160 per person
$7,160
per person
found 1 day ago
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

President Hotel
3.5-star property

President Hotel

South Beach
8.4/10 Very Good! (2,738 reviews)

Oct 31 - Nov 7

7 night stay

Boston (BOS) to Miami (MIA)

American Airlines • Coach

Miami (MIA) to Boston (BOS)

Allegiant Air • Coach
Save 100% on your flight
Price was $1,114, price is now $562 per person
$562
per person
found 1 day ago

Top rated hotels for your Upper Matecumbe Key vacation package

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
0.09 mi from city center
$190 nightly
The price is $214 total per night
$214 total
Sep 23 - Sep 24
Total with taxes and fees
Cheeca Lodge & Spa features a private beach, a golf course, and a full-service spa. Free valet and self parking are available, and there's also limo/town car service. The front desk has multilingual staff on hand 24/7 to help with concierge services, luggage storage, and securing valuables. Other amenities at this beach resort include 3 outdoor pools, a 24-hour gym, and a sauna.
On private beach
Pool
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
1.76 mi from city center
$197 nightly
The price is $221 total per night
$221 total
Sep 29 - Sep 30
Total with taxes and fees
Chesapeake Beach Resort features a private beach, a marina, and 2 outdoor pools. The 24-hour front desk has multilingual staff ready to help with concierge services, and answer any questions about the area. Other amenities at this beach hotel include free WiFi in public areas, coffee/tea in a common area, and free use of 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
1.88 mi from city center
$212 nightly
The price is $238 total per night
$238 total
Sep 29 - Sep 30
Total with taxes and fees
At Amara Cay Resort, guests enjoy a private beach, an outdoor pool, and a gym. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include a meeting room, a terrace, and laundry facilities.
On private beach
Pool
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