Islamorada Resorts

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Resorts in Islamorada

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$339 nightly
The price is $381 total per night
$381 total
Dec 17 - Dec 18
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
With a stay at Cheeca Lodge & Spa in Islamorada (Matecumbe), you'll be a 4-minute walk from Matecumbe United Methodist Church and 5 minutes by foot from Florida Keys Brewing Co..
On private beach
Pool
Lime Tree Bay Resort

Lime Tree Bay Resort

3.5 out of 5
68500 Overseas Hwy Long Key FL
$179 nightly
The price is $201 total per night
$201 total
Dec 15 - Dec 16
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
When you a stay at Lime Tree Bay Resort in Long Key, you'll be on the waterfront, just steps from Anne's Beach and Sunset Drive Beach.
On private beach
Pool
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
$283 nightly
The price is $319 total per night
$319 total
Dec 7 - Dec 8
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
With a stay at Amara Cay Resort in Islamorada (Matecumbe), you'll be a 4-minute walk from Bud n' Mary's Dive Center and a 2-minute drive from Florida Keys Brewing Co..
On private beach
Pool
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

4 out of 5
97000 Overseas Hwy Key Largo FL
$302 nightly
The price is $340 total per night
$340 total
Dec 15 - Dec 16
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
With a stay at Baker's Cay Resort Key Largo, Curio Collection by Hilton in Key Largo, you'll be on the waterfront, within a 15-minute drive of John Pennekamp Coral Reef State Park and Florida Keys National Marine Sanctuary Visitor's Center.
On private beach
Pool
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

4.5 out of 5
97450 Overseas Highway Key Largo FL
$312 nightly
The price is $351 total per night
$351 total
Dec 15 - Dec 16
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
With a stay at Playa Largo Resort & Spa, Autograph Collection in Key Largo (Rock Harbor), you'll be a 4-minute drive from Jimmy Johnson's Big Chill and 10 minutes from John Pennekamp Coral Reef State Park.
Pool
Hot Tub
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

3.5 out of 5
84001 Overseas Hwy Islamorada FL
$254 nightly
The price is $285 total per night
$285 total
Dec 17 - Dec 18
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
Located in Islamorada, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort is by the ocean, within a 5-minute drive of Windley Key Fossil Reef Geological State Park and History of Diving Museum.
On private beach
Pool
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
$227 nightly
The price is $255 total per night
$255 total
Dec 15 - Dec 16
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
With a stay at La Siesta Resort & Villas in Islamorada (Matecumbe), you'll be within a 15-minute walk of Indian Key Historic State Park and Bud n' Mary's Dive Center.
On private beach
Pool
Matecumbe Resort

Matecumbe Resort

2 out of 5
76261 Overseas Hwy Islamorada FL
$179 nightly
The price is $201 total per night
$201 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Located in Islamorada (Matecumbe), Matecumbe Resort is within a 5-minute drive of Robbie’s of Islamorada and Indian Key Historic State Park.
On private beach
Pool
2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay

2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay

Islamorada FL
Located in Islamorada (Matecumbe), this resort is within a 5-minute drive of Sunset Drive Beach and Robbie’s of Islamorada.
Air conditioning
Laundry
2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL

2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL

Islamorada FL
Located in Islamorada (Matecumbe), this resort is within a 5-minute drive of Robbie’s of Islamorada and Indian Key Historic State Park.
Pool
Hot Tub
Keys Villa

Keys Villa

Islamorada FL
With a stay at this resort in Islamorada (Matecumbe), you'll be steps from Sunset Drive Beach and a 2-minute drive from San Pedro Underwater Archaeological Preserve State Park.
Pool
Free WiFi
Beautiful oceanfront resort located at mile marker 73.8

Beautiful oceanfront resort located at mile marker 73.8

Islamorada FL
With a stay at this resort in Islamorada (Matecumbe), you'll be steps from Sunset Drive Beach and 5 minutes by foot from Anne's Beach.
Pool
Air conditioning
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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.

Islamorada Resorts essential information

Accommodation
15 Resorts
Lowest Price
$201
Highest Price
$381
Popular accommodation
Cheeca Lodge & Spa, Lime Tree Bay Resort, Amara Cay Resort, Baker's Cay Resort Key Largo, Curio Collection by Hilton, Playa Largo Resort & Spa, Autograph Collection, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, La Siesta Resort & Villas, Matecumbe Resort, 2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay, 2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL, Keys Villa, Beautiful oceanfront resort located at mile marker 73.8

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