Islamorada (79) Filter Cancel

51-79 of 79 Islamorada Rentals

Sort:
1  2 
Islamorada Florida Vacation Rentals - Home
1 / 17

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

MINIMUM RENTAL 1 MONTH - You will love jewel of a home! Located in Lower Matecumbe, this charming canal front home offers a swimming pool, dockage, direct access to the ocean, covered fish cleaning station, a screened lanai, inviting décor and comfortable accommodations. ...

See more

Close x

Islamorada Florida Vacation Rentals - Home
1 / 16

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 7
Home / 3 Bedrooms / Sleeps 7

from

$127

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$127 - $150
Per week:$887 - $1,050
Pets allowed:Yes
Internet:Yes

Minimum Rental: 1 Month Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open from the dining area into the sunroom overlooking the...

See more

Close x

Islamorada Florida Vacation Rentals - Apartment
1 / 21

Islamorada Apartment
3 Bedrooms / 2 Bathrooms / Sleeps 6
Apartment / 3 Bedrooms / Sleeps 6

from

$117

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$117 - $150
Per week:$817 - $1,050
Pets allowed:No
Internet:Yes

MINIMUM STAY: 29 DAYS Enjoy unobstructed and panoramic views of the Atlantic Ocean from your own private balcony! This 3 bedroom/2 bath condo unit features direct ocean views from the living room, balcony and two of the three bedrooms. Tropical furnishings create a warm and inviting...

See more

Close x

Islamorada Florida Vacation Rentals - Villa
1 / 31

Islamorada Villa
2 Bedrooms / 2 Bathrooms / Sleeps 6
Villa / 2 Bedrooms / Sleeps 6

(2)“ Excellent ”2 Reviews

from

$358

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Villa
Per night:$358
Per week:$2,500
Pets allowed:Yes
Internet:Yes

Minimum Rental: 7 Nights Upper Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month. Each...

See more

Close x

Islamorada Florida Vacation Rentals - Apartment
1 / 16

Islamorada Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6
Apartment / 2 Bedrooms / Sleeps 6

from

$67

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$67 - $117
Per week:$467 - $817
Pets allowed:No
Internet:Yes

Minimum Rental: 1 Month This exceptional condo has been impeccably maintained and is located in one of the finest condo complexes in Islamorada. It features an updated kitchen, remodeled baths and is comfortably furnished. This unit is ready for your arrival. Be sure to look at the...

See more

Close x

Islamorada Florida Vacation Rentals - Apartment
1 / 17

Islamorada Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$134

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$134 - $160
Per week:$934 - $1,120
Pets allowed:No
Internet:Yes

Minimum Rental: 1 Month Extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamorada. It offers 2 spacious...

See more

Close x

Islamorada Florida Vacation Rentals - Home
1 / 16

Islamorada Home
2 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 2 Bedrooms / Sleeps 6

from

$107

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$107
Per week:$747
Pets allowed:Yes
Internet:No

Minimum Rental: 3 Months Beautifully furnished, this almost new single family stilt home sits on an ocean side canal front lot. Bring your boat and your swim suit! This 2 bedroom, 2 bath home has everything you need, including a laundry room with a clothes washer and dryer and...

See more

Close x

Islamorada Florida Vacation Rentals - Home
1 / 23

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

(1)“ Excellent ”1 Review

from

$217

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$217 - $284
Per week:$1,517 - $1,984
Pets allowed:No
Internet:Yes

Minimum Rental: 1 Month Oceanfront - Beach - Protected Dock and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The Florida Keys. From the...

See more

Close x

Islamorada Florida Vacation Rentals - Apartment
1 / 20

Islamorada Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$110

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$110 - $157
Per week:$770 - $1,097
Pets allowed:No
Internet:Yes

Minimum Rental: 1 Month Beacon Reef is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. Picture yourself relaxing on...

See more

Close x

Islamorada Florida Vacation Rentals - Apartment
1 / 15

Islamorada Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$60

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$60 - $117
Per week:$420 - $817
Pets allowed:No
Internet:Yes

Description….. MINIMUM STAY: Minimum Rental: 1 Month 5th Floor unit at one of Islamorada's favorite condo complexes. This unit was recently sold and the new owners are beginning to update some of the décor. You'll love the fantastic panoramic ocean views as you relax or dine on...

See more

Close x

Islamorada Florida Vacation Rentals - Apartment
1 / 18

Islamorada Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$67

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$67 - $124
Per week:$467 - $864
Pets allowed:No
Internet:Yes

Minimum Rental: 1 Month Gorgeous 2 bedroom, 2 bath condo. This is a gated complex located directly on the Atlantic Ocean. This unit has unobstructed views of the ocean from the master suite and the balcony. Wake up every morning, open the curtains and view a panorama of the Atlantic...

See more

Close x

Islamorada Florida Vacation Rentals - Apartment
1 / 14

Islamorada Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$67

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$67 - $114
Per week:$467 - $794
Pets allowed:No
Internet:No

Minimum Rental: 1 Month Comfortably furnished and ready for you. Conveniently located just steps from a full service marina and 2 highly acclaimed restaurants. Watch the sun rise over the ocean as fishing boats leave on their daily charters, or watch the spectacular sunsets over ...

See more

Close x

Islamorada Florida Vacation Rentals - Apartment
1 / 20

Islamorada Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$80

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$80 - $127
Per week:$560 - $887
Pets allowed:No
Internet:Yes

Minimum Rental: 1 Month This exceptional 2 bedroom and 2 bath condo is located in one of the most popular Islamorada condo complexes - The Palms. The balcony is large enough to dine or recline and offers fabulous open water ocean views. Watching the sunrise over the Atlantic Ocean...

See more

Close x

Islamorada Florida Vacation Rentals - Apartment
1 / 24

Islamorada Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$167

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$167 - $200
Per week:$1,167 - $1,400
Pets allowed:No
Internet:Yes

Minimum Rental: 1 Month New on the rental market. This is your opportunity to secure your winter getaway at a luxurious oceanfront condo in one of Islamorada's most prestigious condominium communities. Ocean front dockage is available for boats up to 28' in length (separate rental);...

See more

Close x

Islamorada Florida Vacation Rentals - Apartment
1 / 14

Islamorada Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$74

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$74 - $120
Per week:$514 - $840
Pets allowed:No
Internet:Yes

Minimum Rental: 1 Month Pure pleasure will be yours in this beautifully remodeled and immaculate condo. You'll love the uncluttered and modern décor along with the recent renovations. Enjoy the picturesque views of Alligator Reef and the Atlantic Ocean from this 4th floor balcony....

See more

Close x

Islamorada Florida Vacation Rentals - Apartment
1 / 23

Islamorada Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$107

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$107 - $157
Per week:$747 - $1,097
Pets allowed:No
Internet:Yes

MINIMUM STAY: ONE MONTH. Exceptional 5th floor (top floor) 2 bedroom 2 bath condo at Beacon Reef. Ocean views from the open air balcony. You'll be so glad you have chosen to spend your holiday here. The kitchen was remodeled in 2013 - granite counters, stainless steel appliances,...

See more

Close x

Islamorada Florida Vacation Rentals - Apartment
1 / 18

Islamorada Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$134

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$134 - $167
Per week:$934 - $1,167
Pets allowed:No
Internet:Yes

Minimum Rental: 1 Month This is a very special unit in a premier condominium complex located directly on the Atlantic Ocean and in the heart of Islamorada. This unit provides spectacular ocean views. It is one of the few units that offer spiral stairs to the ground level directly ...

See more

Close x

Islamorada Florida Vacation Rentals - Home
1 / 26

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$140

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$140 - $175
Per week:$980 - $1,225
Pets allowed:Yes
Internet:No

MINIMUM RENTAL: 1 MONTH BEAUTIFUL CANAL FRONT STILT HOME WITH HEATED POOL - For the guest who expects perfection this is it. This is a completely remodeled 3 bedroom/2 bath (2/1 up and 1/1 down) single family home - perfect for one couple or a smaller family. It is conveniently ...

See more

Close x

Islamorada Florida Vacation Rentals - Villa
1 / 27

Islamorada Villa
2 Bedrooms / 2 Bathrooms / Sleeps 6
Villa / 2 Bedrooms / Sleeps 6

(4)“ Excellent ”4 Reviews

from

$358

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Villa
Per night:$358
Per week:$2,500
Pets allowed:Yes
Internet:Yes

Minimum Rental: 7 Nights Lower Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or month. Each unit...

See more

Close x

Islamorada Florida Vacation Rentals - Home
1 / 23

Islamorada Home
2 Bedrooms / 2 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

(1)“ Excellent ”1 Review

from

$100

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$100 - $134
Per week:$700 - $933
Pets allowed:No
Internet:Yes

MINIMUM STAY: 28 DAYS Villa Riolo is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. This home has been meticulously cared for over the years and for the first time the owners are offering you an opportunity...

See more

Close x

Islamorada Florida Vacation Rentals - Apartment
1 / 21

Islamorada Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 5
Apartment / 2 Bedrooms / Sleeps 5

from

$74

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:5
Type:Apartment
Per night:$74 - $127
Per week:$514 - $887
Pets allowed:No
Internet:Yes

Minimum Rental: 1 Month Sensational oceanfront views are yours from both the master bedroom and the balcony of this beautifully appointed condo. Watch the fishing charter boats as they come and go from Bud and Mary's Marina. You'll be able to see cruise ships as they pass by Alligator...

See more

Close x

Islamorada Florida Vacation Rentals - Apartment
1 / 27

Islamorada Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6
Apartment / 2 Bedrooms / Sleeps 6

(4)“ Excellent ”4 Reviews

from

$179

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$179 - $236
Per week:$1,250 - $1,650
Pets allowed:No
Internet:Yes

Minimum Rental: 7 Nights (Saturday to Saturday) BROCKHAUS ON THE GULF is an end unit townhouse on the water's edge with water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the marina. The panoramic...

See more

Close x

Islamorada Florida Vacation Rentals - Villa
1 / 19

Islamorada Villa
1 Bedroom / 1 Bathroom / Sleeps 3
Villa / 1 Bedroom / Sleeps 3

(2)“ Excellent ”2 Reviews

from

$149

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:3
Type:Villa
Per night:$149 - $177
Per week:$1,040 - $1,235
Pets allowed:Yes
Internet:Yes

Minimum Rental: 7 Nights You can have it all – privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people who ...

See more

Close x

Islamorada Florida Vacation Rentals - Apartment
1 / 26

Islamorada Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6
Apartment / 2 Bedrooms / Sleeps 6

from

$92

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$92 - $127
Per week:$642 - $887
Pets allowed:No
Internet:Yes

Minimum Rental: 1 Month A Diamond! Be among the first to rent this gorgeous two bedroom condo. It has been completely renovated from floor to ceiling. The floors have been replaced with tile and the old popcorn ceilings are gone. You'll adore the comfortable living room furnishings...

See more

Close x

Islamorada Florida Vacation Rentals - Villa
1 / 19

Islamorada Villa
2 Bedrooms / 2 Bathrooms / Sleeps 6
Villa / 2 Bedrooms / Sleeps 6

(1)“ Excellent ”1 Review

from

$358

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Villa
Per night:$358
Per week:$2,500
Pets allowed:No
Internet:Yes

Minimum Rental: 7 Nights Cottage - This is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center of the house with kitchen, dining area, sitting area...

See more

Close x

Islamorada Florida Vacation Rentals - Apartment
1 / 15

Islamorada Apartment
1 Bedroom / 2 Bathrooms / Sleeps 4
Apartment / 1 Bedroom / Sleeps 4

(1)“ Excellent ”1 Review

from

$60

/ night

Email Owner
Bedrooms:1
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$60 - $89
Per week:$420 - $619
Pets allowed:No
Internet:Yes

Minimum Rental: 1 Month Everything in this unit is exquisite - furnishings, linens, updated kitchen, appliances, and bathrooms. Great views of Florida Bay and our fabulous Keys sunsets. This complex is conveniently located just steps from a full service marina and 2 highly acclaimed...

See more

Close x

Islamorada Florida Vacation Rentals - Home
1 / 23

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

from

$130

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$130 - $164
Per week:$910 - $1,144
Pets allowed:Yes
Internet:Yes

Minimum Rental: 1 Month Bring your boat your dog and the kids! Relax on the patio or swim in the canal. You will love this ground level single family home located in prestigious Venetian Shores. It has been completely renovated and awaits your arrival. The large open kitchen with...

See more

Close x

Islamorada Florida Vacation Rentals - Home
1 / 24

Islamorada Home
3 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

(1)“ Excellent ”1 Review

from

$175

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$175 - $240
Per week:$1,225 - $1,680
Pets allowed:Yes
Internet:Yes

Minimum Rental: 1 Month Location, location, location! This home has it all - ocean side Lower Matecumbe location, totally remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from almost every room in...

See more

Close x

Islamorada Florida Vacation Rentals - Home
1 / 17

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

(1)“ Excellent ”1 Review

Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:Yes
Internet:Yes

Minimum Rental: 1 Month You will love jewel of a home! Located in Lower Matecumbe, this charming canal front home offers a swimming pool, dockage, direct access to the ocean, covered fish cleaning station, a screened lanai, inviting décor and comfortable accommodations. It...

See more

Close x

1  2 
12
page 2 of 2
Loading...
Click for larger map
Loading...
Show Big Map
  • Price

  • Bedrooms

    Guests

  • Amenities

    • More

About Islamorada

Islamorada, FL Travel Tips

Islamorada vacation rentals are a great choice for families visiting this tropical island. There are fun things to do, see, and explore. Activities are water-based and the family that loves fishing will have plenty of fun in the sun. Boating is a popular activity as well as snorkeling and scuba diving. Islamorada is in the Florida Keys and on the Atlantic Ocean and Florida Bay. Islamorada rentals enable families to enjoy their vacations while keeping the comforts of home. You will need a car to get around the island, so rent one if you are not driving from Miami or other surrounding cities.

Neighborhoods

You can find Islamorada vacation home rentals in each of the island’s three neighborhoods. Lower Matecumbe Beach, Matecumbe, and Plantation Key are popular neighborhoods for Islamorada rentals. Oceanfront Islamorada house rentals are easy to find online and are a perfect way to visit Florida. They provide easy access to water activities without giving up comfort. Traveling families enjoy the ease of staying in a rental home or condo. By-owner properties include necessities such as washers and dryers, kitchens, and full baths. For the family that wants to save on their vacation, rentals in Islamorada, FL, are an excellent choice.

Attractions

There are many attractions in Islamorada and the Florida Keys. One of the most popular attractions is the family-friendly park Theater of the Sea. Kids can swim with dolphins. There are opportunities for interacting with sea lions and turtles as well. Theater of the Sea also provides live snorkeling tours, ensuring fun for the entire family. Coral reef diving is an exciting adventure, and there are always chances for fishing. Rent a boat or join a fishing charter with an experienced tour guide.
San Pedro Underwater Archaeological Preserve State Park is a historical shipwreck site. The water is 18 feet deep and perfect for experienced divers. Another popular family-friendly attraction is the Windley Key Fossil Reef Geological State Park. The park includes hiking and nature trails and features fossilized coral. There are picnic tables and educational tours for kids. The park is home to a variety of birds, and wildlife viewing is a popular activity.
Anne’s Beach is a great place to bring the kids. There are many coves along the white sands, making it easy to find private spots for family fun. Mangroves surround the beach, making it the perfect location to observe ...

Read more