Highland Village Vacation Packages for 2025

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Highland Village Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Hadley Resort and Marina

Hadley Resort and Marina

3.5 out of 5
Matecumbe
Save 100% on your flight
per person
Aug 9 - Aug 14
found 8 hours ago
Roundtrip flight included
Chicago (CHI) to Miami (MIA)
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Islamorada Brewery & Distillery and History of Diving Museum are located nearby.

Villas At Hawks Cay Resort

Villas At Hawks Cay Resort

4 out of 5
Save 100% on your flight
per person
Aug 9 - Aug 14
found 8 hours ago
Roundtrip flight included
Chicago (CHI) to Miami (MIA)
Stay at this 4-star luxury resort in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Popular attractions Little Conch Key and Walkers Island are located nearby.

Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

5 out of 5
Save 100% on your flight
per person
Aug 9 - Aug 14
found 8 hours ago
Roundtrip flight included
Chicago (CHI) to Miami (MIA)
Stay at this 5-star luxury hotel in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Sombrero Beach and Vaca Key are located nearby.

Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Save 100% on your flight
per person
Aug 9 - Aug 14
found 8 hours ago
Roundtrip flight included
Chicago (CHI) to Miami (MIA)
Book a stay at this beach hotel in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Little Conch Key and Walkers Island are located nearby.

La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
Matecumbe
Save 100% on your flight
per person
Aug 9 - Aug 14
found 8 hours ago
Roundtrip flight included
Chicago (CHI) to Miami (MIA)
Stay at this 4-star beach resort in Islamorada. Enjoy a private beach, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the spacious rooms in our reviews. Popular attractions Bud n' Mary's Dive Center and Hurricane Monument are located nearby.

Tranquility Bay Beachfront Hotel and Resort

Tranquility Bay Beachfront Hotel and Resort

4 out of 5
Save 100% on your flight
per person
Aug 9 - Aug 14
found 8 hours ago
Roundtrip flight included
Chicago (CHI) to Miami (MIA)
Stay at this 4-star beach hotel in Marathon. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Sombrero Beach and Shady Palm Art Gallery are located nearby.

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Top Hotel Deals

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
4441 Collins Avenue, Miami Beach, FL
9.86 km from Highland Village
Stay at this 4.5-star luxury hotel in Miami Beach. Enjoy free WiFi, a full-service spa, and 9 restaurants. Our guests praise the pool and the helpful staff in ...
citizenM Miami Worldcenter

citizenM Miami Worldcenter

4 out of 5
700 NE 2ND AVENUE, Miami, FL
13.86 km from Highland Village
Stay at this 4-star business-friendly hotel in Miami. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the breakfast and the pool ...
InterContinental Miami by IHG

InterContinental Miami by IHG

5 out of 5
100 Chopin Plz, Miami, FL
14.69 km from Highland Village
Stay at this 5-star luxury hotel in Miami. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the breakfast and the helpful staff in our ...
Loews Miami Beach Hotel – South Beach

Loews Miami Beach Hotel – South Beach

4.5 out of 5
1601 Collins Ave, Miami Beach, FL
12.76 km from Highland Village
Stay at this 4.5-star luxury hotel in Miami Beach. Enjoy a full-service spa, 3 restaurants, and a beach locale. Our guests praise the breakfast and the pool ...
Mondrian South Beach

Mondrian South Beach

4.5 out of 5
1100 West Ave, Miami Beach, FL
13.39 km from Highland Village
Stay at this 4.5-star luxury hotel in Miami Beach. Enjoy free WiFi, a full-service spa, and a marina. Our guests praise the pool and the helpful staff in our ...
Hilton Miami Airport Blue Lagoon

Hilton Miami Airport Blue Lagoon

4 out of 5
5101 Blue Lagoon Dr, Miami, FL
18.17 km from Highland Village
Stay at this 4-star business-friendly hotel in Miami. Enjoy 2 bars/lounges, breakfast (surcharge), and a free airport shuttle. Our guests praise the pool and ...
Eden Roc Miami Beach

Eden Roc Miami Beach

4.5 out of 5
4525 Collins Ave, Miami Beach, FL
9.7 km from Highland Village
Book a stay at this luxury resort in Miami Beach. Enjoy 3 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the breakfast and the pool ...
Diplomat Beach Resort Hollywood, Curio Collection by Hilton

Diplomat Beach Resort Hollywood, Curio Collection by Hilton

4.5 out of 5
3555 S Ocean Dr, Hollywood, FL
10.6 km from Highland Village
Stay at this 4.5-star luxury resort in Hollywood. Enjoy a full-service spa, 6 restaurants, and a beach locale. Our guests praise the pool and the helpful staff ...
Sheraton Miami Airport Hotel & Executive Meeting Center

Sheraton Miami Airport Hotel & Executive Meeting Center

3.5 out of 5
3900 NW 21st St, Miami, FL
15.79 km from Highland Village
Book a stay at this golf hotel in Miami. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful ...
B Ocean Resort Fort Lauderdale Beach

B Ocean Resort Fort Lauderdale Beach

4 out of 5
1140 Seabreeze Blvd, Fort Lauderdale, FL
23.53 km from Highland Village
Stay at this 4-star beach resort in Fort Lauderdale. Enjoy 2 outdoor pools, 3 restaurants, and a private beach. Our guests praise the pool and the helpful staff ...
Holiday Inn Miami West - Airport Area by IHG

Holiday Inn Miami West - Airport Area by IHG

3 out of 5
7707 N.W. 103rd Street, Hialeah, FL
17.35 km from Highland Village
Stay at this 3-star business-friendly hotel in Hialeah. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
citizenM Miami South Beach

citizenM Miami South Beach

4 out of 5
1200 Lincoln Road, South Beach, Miami Beach, FL
12.45 km from Highland Village
Stay at this 4-star hotel in Miami Beach. Enjoy free WiFi, breakfast (surcharge), and a 24-hour front desk. Popular attractions Collins Avenue Shopping Area ...
Trump International Beach Resort

Trump International Beach Resort

4.5 out of 5
18001 Collins Ave, Sunny Isles Beach, FL
5.75 km from Highland Village
Stay at this 4.5-star luxury hotel in Sunny Isles Beach. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful ...
Hyatt Place Miami Airport-East

Hyatt Place Miami Airport-East

3 out of 5
3549 NW Le Jeune Road, Miami, FL
15.15 km from Highland Village
Stay at this 3-star business-friendly hotel in Miami. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Kimpton EPIC Hotel by IHG

Kimpton EPIC Hotel by IHG

5 out of 5
270 Biscayne Blvd Way, Miami, FL
14.95 km from Highland Village
Stay at this 5-star luxury hotel in Miami. Enjoy 2 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Wed, May 28 - Tue, Jun 3
ATL
Hartsfield-Jackson Atlanta Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$80 Roundtrip, found 2 days ago
$80
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, May 28 from Hartsfield-Jackson Atlanta Intl. to Fort Lauderdale - Hollywood Intl., returning Tue, Jun 3, priced at $80 found 2 days ago
Frontier Airlines
Sat, Aug 23 - Tue, Aug 26
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$108 Roundtrip, found 5 days ago
$108
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Aug 23 from Hartsfield-Jackson Atlanta Intl. to Miami Intl., returning Tue, Aug 26, priced at $108 found 5 days ago
Frontier Airlines
Sun, Jun 15 - Thu, Jun 19
PHL
Philadelphia Intl.
MIA
Miami Intl.
$108 Roundtrip, found 4 days ago
$108
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, Jun 15 from Philadelphia Intl. to Miami Intl., returning Thu, Jun 19, priced at $108 found 4 days ago
JetBlue Airways
Sun, Aug 17 - Sat, Aug 23
PHL
Philadelphia Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, Aug 17 from Philadelphia Intl. to Fort Lauderdale - Hollywood Intl., returning Sat, Aug 23, priced at $117 found 1 day ago