Vacation Rentals By Owner In Islamorada, FL

$2110.32
/ Nightly

Villa

Charming Ocean Front Pool Home with dockage & pool

Islamorada, Florida, United States

5
Bed

4
Bath

10
Sleeps

$2171.25
/ Nightly

Private vacation home

Next available August 15th, 2026 - Stunning Oceanfront Estate - Private Pool

Islamorada, Florida, United States

6
Bed

6
Bath

14
Sleeps

$2241.97
/ Nightly

Private vacation home

Brand New Unique Deep Water Gulf Front Estate. Beach, Pool, Hot tub and docks

Islamorada, Florida, United States

4
Bed

4
Bath

8
Sleeps

$2531.12
/ Nightly

Private vacation home

Experience luxury in this 5-bedroom oceanfront home in Islamorada, perfect for 12 guests.

Islamorada, Florida, United States

5
Bed

5
Bath

12
Sleeps

$2777.65
/ Nightly

Private vacation home

Peninsula Villa | Boat Dock | Heated Pool | Sunset Point

Islamorada, Florida, United States

5
Bed

4
Bath

12
Sleeps

$2859.73
/ Nightly

Condo

Oceanfront 4BR Villa | Resort Access + Bunks

Islamorada, Florida, United States

4
Bed

4
Bath

10
Sleeps

$3453.41
/ Nightly

Villa

10 Bedroom Private Ocean Front Estate

Islamorada, Florida, United States

10
Bed

10
Bath

22
Sleeps

$4417.51
/ Nightly

Private vacation home

PRIVATE BEACH, Pickleball Court and Tiki Bar/ Heated Pool / Designated Paradise Key

Islamorada, Florida, United States

6
Bed

4
Bath

16
Sleeps

$1107.85
/ Nightly

Private vacation home

Experience luxury at Heart of Morada, a 3-bedroom condo in beautiful Islamorada.

Islamorada, Florida, United States

3
Bed

3
Bath

6
Sleeps

$981.86
/ Nightly

Private vacation home

The Bonefish House at Tarpon Point ~ 4 Bed/4 Bath Oceanfront Home

Islamorada, Florida, United States

4
Bed

4
Bath

8
Sleeps