Islamorada Vacation Homes

Islamorada Vacation Homes
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A beach with white lounge chairs, a covered pavilion, and palm trees.

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Our top choices for Islamorada holiday homes

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

A dining area with a round table, four chairs, a white vase, and a ceiling fan.

A covered outdoor area with a bench and a door.

1. Little Peace of Haven

Little Peace of Haven

Key Largo

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"Lovely clean, quiet, perfect location for exploring the upper keys! An fantastic value!"

Mitchel R.

The price is HK$1,200

HK$1,200

HK$3,275 total

includes taxes & fees

2 Nov - 3 Nov

Little Peace of Haven

A modern living room with a flat-screen TV, a black leather sofa, and a white ottoman.

A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a yellow tablecloth.

A two-story house with a balcony on the upper floor.

A neatly made bed in a hotel room with a ceiling fan, a bedside table with a lamp, and a wardrobe with frosted glass doors.

2. Charming Home in Key Largo

Charming Home in Key Largo

Key Largo

10.0 out of 10, Exceptional, (41 reviews)

10/10

Exceptional

(41 reviews)

"Awesome house, convenient to everything we needed. Super clean and everything was pretty modern. I would definitely stay again and would definitely recommend this property"

JOHN P.

The price is HK$854

HK$854

HK$2,878 total

includes taxes & fees

27 Oct - 28 Oct

Charming Home in Key Largo

A table with a glass of beverage, a mug, and a plate with food, overlooking a pool with boats and palm trees under a sunset sky.

A bedroom with a wooden headboard, a bed with white bedding, a small round table, and a view of a swimming pool through a door.

A waterfront hotel with a row of rooms, a grassy lawn, and a calm river.

A waterfront property with a dock, clear blue water, and lush greenery.

3. 4. Cozy Key Largo Waterfront Studio | Dive

4. Cozy Key Largo Waterfront Studio | Dive

Key Largo

9.8 out of 10, Exceptional, (13 reviews)

9.8/10

Exceptional

(13 reviews)

"We loved our stay at the waterfront cabanas! The location is 10/10 with an awesome waterfront bar/restaurant and coffee truck within walking distance. We truly felt like keys locals staying here - highly recommend! "

Brittany M.

The price is HK$1,525

HK$1,525

HK$3,015 total

includes taxes & fees

9 Nov - 10 Nov

4. Cozy Key Largo Waterfront Studio | Dive

A modern kitchen with white cabinetry, a granite countertop, and a ceiling fan.

A modern kitchen with white cabinets, a central island, and bar stools.

A wooden deck with a table and chairs, surrounded by white picket fences and tropical plants.

A modern kitchen with white cabinets, granite countertops, and stainless steel appliances.

4. Keys Cottage with Beach and Dockage! Bayfront Property!

Keys Cottage with Beach and Dockage! Bayfront Property!

Key Largo

9.4 out of 10, Exceptional, (36 reviews)

9.4/10

Exceptional

(36 reviews)

"We had such a wonderful time here! The house was perfect and the grounds were beautiful! We will definitely come again! "

Julia W.

Keys Cottage with Beach and Dockage! Bayfront Property!

A beachside wooden deck with Adirondack chairs, a thatched-roof gazebo, and a grill.

An aerial view of a coastal marina with boats docked, a sandy beach, and a rocky shoreline.

A resort with a central swimming pool, surrounded by palm trees and a view of a water body.

5. Key Largo Villa, Kawama P6, 3/3

Key Largo Villa, Kawama P6, 3/3

Key Largo

9.8 out of 10, Exceptional, (151 reviews)

9.8/10

Exceptional

(151 reviews)

"Beautiful, clean home. Loved the property and the inlet with all the fish was amazing. Would stay again."

Sandra C.

The price is HK$1,961

HK$1,961

HK$4,457 total

includes taxes & fees

27 Oct - 28 Oct

Key Largo Villa, Kawama P6, 3/3

A modern living room with a large TV, grey sofas, a coffee table with decorative items, and a kitchen in the background.

A modern kitchen with white cabinetry, stainless steel appliances, a central island with bar stools, and a large window providing natural light.

A beach setting with white chairs arranged around a fire pit, a thatched-roof structure, and a view of the ocean.

A wooden boardwalk leading to a body of water, surrounded by trees and a fence.

6. Key Largo Kawama Villa L1, 3/3

Key Largo Kawama Villa L1, 3/3

Key Largo

9.4 out of 10, Exceptional, (231 reviews)

9.4/10

Exceptional

(231 reviews)

"Love the place , only problem with out a gulf car the beach and fishing area is too far away"

Dayanis

The price is HK$2,059

HK$2,059

HK$4,441 total

includes taxes & fees

27 Oct - 28 Oct

Key Largo Kawama Villa L1, 3/3

A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

A modern living room with a glass dining table, a sofa, and a TV mounted on the wall.

A deck with white Adirondack chairs, a glass-top table, and a view of a lake.

A modern bedroom with a large bed, bedside tables, and a view of greenery through the windows.

7. Oceanside Retreat w/Rooftop, Pool & Kayaks

Oceanside Retreat w/Rooftop, Pool & Kayaks

Key Largo

The price is HK$2,823

HK$2,823

HK$6,334 total

includes taxes & fees

28 Oct - 29 Oct

Oceanside Retreat w/Rooftop, Pool & Kayaks

A modern kitchen with a large island, stainless steel appliances, and a view of the water.

A balcony with a view of the sea, a modern building, and a wooden chair.

A modern living room with a large TV, comfortable seating, a coffee table, and a view of the ocean.

An aerial view of a coastal resort with modern buildings, a central pool area, and clear turquoise waters.

8. New Oceanside Paradise with Pool and Waterfront Views!

New Oceanside Paradise with Pool and Waterfront Views!

Key Largo

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Everything was great "

Ravone L.

The price is HK$4,241

HK$4,241

HK$8,141 total

includes taxes & fees

1 Nov - 2 Nov

New Oceanside Paradise with Pool and Waterfront Views!

A modern indoor space with a pool, white wicker furniture, and a white crib.

A bedroom with a bed, bedside table, and a ceiling fan.

A swimming pool with lounge chairs, a thatched-roof structure, and palm trees.

A dining area with a glass-top table, wicker chairs, a white ceiling, and a painting on the wall.

9. El Encanto: private saltwater pool & tiki lounge

El Encanto: private saltwater pool & tiki lounge

Key Largo

The price is HK$2,823

HK$2,823

HK$5,751 total

includes taxes & fees

27 Oct - 28 Oct

El Encanto: private saltwater pool & tiki lounge

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

A beach setting with white chairs arranged around a fire pit, overlooking the ocean.

10. Key Largo Villa, Kawama K5, 3/3

Key Largo Villa, Kawama K5, 3/3

Key Largo

10.0 out of 10, Exceptional, (68 reviews)

10/10

Exceptional

(68 reviews)

"Lovely location and nice kitchen."

Susan S.

Key Largo Villa, Kawama K5, 3/3

11. Kawama G12 Upscale OceansideVilla with Marina 2/2

Kawama G12 Upscale OceansideVilla with Marina 2/2

Key Largo

10.0 out of 10, Exceptional, (10 reviews)

10/10

Exceptional

(10 reviews)

"We had a wonderful stay, well stocked! Our host was not easy to get a hold of, but we would definitely stay again! "

Brooke B.

Kawama G12 Upscale OceansideVilla with Marina 2/2

BBQ charcoal grills and tikies by the ocean

12. Oceanside Kawama Villa R5

Oceanside Kawama Villa R5

Key Largo

9.2 out of 10, Wonderful, (184 reviews)

9.2/10

Wonderful

(184 reviews)

"Great place to stay"

Eric B.

The price is HK$2,388

HK$2,388

HK$4,872 total

includes taxes & fees

27 Oct - 28 Oct

Oceanside Kawama Villa R5

A beach with white Adirondack chairs, a clear pool, and a building with blue and white exterior walls.

A clear water body with a wooden deck and railing, surrounded by trees and a building in the background.

An aerial view of a coastal property with a marina, tennis courts, and a large building with a circular top.

An aerial view of a resort with multiple buildings, a central pool area, and a beach.

13. NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

Key Largo

10.0 out of 10, Exceptional, (62 reviews)

10/10

Exceptional

(62 reviews)

"Great house and even better location!"

Sofia C.

The price is HK$2,117

HK$2,117

HK$4,713 total

includes taxes & fees

2 Nov - 3 Nov

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

A large swimming pool surrounded by palm trees and a beach, with a building in the background.

A spacious sunroom with a ceiling fan, large windows, a dining area, and a view of a pool and palm trees.

A sunlit room with large windows, a pool view, a light blue sofa, and a dining table with chairs.

A beach with blue lounge chairs, a thatched umbrella, and palm trees.

14. Sunrise Retreat: Ocean & Pool Views, Gym, PB Courts, Game Room, Marina and more

Sunrise Retreat: Ocean & Pool Views, Gym, PB Courts, Game Room, Marina and more

Rock Harbor

10.0 out of 10, Exceptional, (21 reviews)

10/10

Exceptional

(21 reviews)

"Beautiful property Great location Gorgeous pool and great facilities available Perfect stay"

Jennifer

Sunrise Retreat: Ocean & Pool Views, Gym, PB Courts, Game Room, Marina and more

A modern kitchen with a large island, wooden ceiling, and a view of the pool.

A spacious living area with a wooden ceiling, a television, a sofa, and a kitchen in the background.

A swimming pool with lounge chairs and palm trees, surrounded by a resort building.

A modern kitchen with white cabinets, stainless steel appliances, and a wooden dining area with a bench.

15. Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10

Key Largo

9.8 out of 10, Exceptional, (75 reviews)

9.8/10

Exceptional

(75 reviews)

"Great unit and wonderful host. We will be back!"

Lauren S.

The price is HK$1,950

HK$1,950

HK$5,885 total

includes taxes & fees

28 Oct - 29 Oct

Sunrise Escape - Ocean Front Villa - Sleeps 10

A sunlit room with large windows, a wicker chair, a small table, and a view of a tree and water.

A spacious living room with a large sofa, wicker furniture, and a dining area with a table and chairs.

An aerial view of a resort with a swimming pool, palm trees, and a building with a blue facade.

A resort with a swimming pool, thatched-roof structures, and lush greenery.

16. New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools

New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools

Key Largo

9.2 out of 10, Wonderful, (24 reviews)

9.2/10

Wonderful

(24 reviews)

"The lagoon was beautiful and fun."

Teresa H.

The price is HK$2,345

HK$2,345

HK$4,312 total

includes taxes & fees

2 Nov - 3 Nov

New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools

A covered walkway with a brick floor, a red umbrella, a white chair, and a fountain.

A spacious dining area with a wooden table and chairs, a chandelier, and a view through a large window.

A spacious living room with a fireplace, a dining area with wooden chairs, and a chandelier.

A bedroom with a bed, nightstands, a dresser, a mirror, a ceiling fan, and a view of the outdoors.

17. The Coral House - Bayside Retreat for 6-8 guests

The Coral House - Bayside Retreat for 6-8 guests

Key Largo

7.0 out of 10, Good, (9 reviews)

7.0/10

Good

(9 reviews)

"Great location with private beach loved it "

Bobby A.

The price is HK$7,843

HK$7,843

HK$8,956 total

includes taxes & fees

27 Oct - 28 Oct

The Coral House - Bayside Retreat for 6-8 guests

A balcony with a view of the ocean, furnished with a table and chairs, and palm trees.

A pool area with lounge chairs, a barbecue, and a view of the beach and ocean.

A modern beachfront property with a swimming pool, palm trees, and ocean views.

A beachfront property with a white building, a pool, and palm trees.

18. Private Beach / Private overwater dock / Heated Pool / Mahi Key

Private Beach / Private overwater dock / Heated Pool / Mahi Key

Matecumbe

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Our stay here was very nice. Everything was clean and comfortable. The pool was enjoyable the one time we used it. Sitting on the deck gazing out to sea was exactly what I needed. Spotting a crocodile swim by was exciting!"

Anonymous traveller

Private Beach / Private overwater dock / Heated Pool / Mahi Key

A large swimming pool surrounded by palm trees and a building with multiple balconies.

A beach with rows of blue lounge chairs, a thatched-roof umbrella, and palm trees.

A modern interior with two large, woven pendant lights, a wooden console table with decorative items, and a dining area with a light-colored rug and white spherical ornaments.

A dining area with a wooden table, four rattan chairs, and two hanging wicker lamps.

19. NEW! 4-Story Villa in Marina Resort with Private Rooftop, 2 pools and Hot tubs

NEW! 4-Story Villa in Marina Resort with Private Rooftop, 2 pools and Hot tubs

Rock Harbor

10.0 out of 10, Exceptional, (8 reviews)

10/10

Exceptional

(8 reviews)

"Enjoyed our stay very much. Plenty of space for the 6 of us. Beds were very comfy. Kitchen was well stocked. We really liked the variety of amenities of the Mariners Club."

Lisa B.

The price is HK$4,735

HK$4,735

HK$8,581 total

includes taxes & fees

1 Nov - 2 Nov

NEW! 4-Story Villa in Marina Resort with Private Rooftop, 2 pools and Hot tubs

A beach setting with white chairs, a fire pit, and a thatched-roof structure.

A marina with boats, a sandy beach, and a rocky shoreline.

20. Kawama L4 - Upscale Oceanside Villa with Marina

Kawama L4 - Upscale Oceanside Villa with Marina

Key Largo

9.6 out of 10, Exceptional, (155 reviews)

9.6/10

Exceptional

(155 reviews)

"Very well appointed!! Nicely decorated and very clean."

Teresa K.

Kawama L4 - Upscale Oceanside Villa with Marina

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.

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Top Islamorada Hotel Reviews

La Jolla Resort

10/10 Excellent

"Place clean, comfortable and very nice. Could use some dressers for somewhere to put clothes. But I definitely would stay here again."

Daniel 4-night trip

Posted 1 hour ago

La Jolla Resort

Coconut Cove Resort and Marina

10/10 Excellent

"This is a family run resort. The grounds are beautiful and the pool is amazing. We will be back!"

Deanna 3-night trip

Posted 19 hours ago

Coconut Cove Resort and Marina

Amara Cay Resort

10/10 Excellent

"Great property however the rooms could use an update."

Michelle 2-night trip

Posted 19 hours ago

Amara Cay Resort

Islander Resort

10/10 Excellent

"💜"

Carolyn 7-night trip

Posted 20 hours ago

Islander Resort

Matecumbe Resort

8/10 Good

"Property can used some much need tlc. Rooms are a little too dark. Sandflies on the beach makes it hard to enjoy the beautiful sceanary. But overall its very personable and a home away from home."

Chandradat 2-night trip

Posted 22 hours ago

Matecumbe Resort

Fisher Inn Resort & Marina

10/10 Excellent

"Every thing excellent"

HECTOR 2-night trip

Posted 2 days ago

Fisher Inn Resort & Marina

Pines & Palms Resort

10/10 Excellent

"We stayed at one of the bungalows which were very new, cozy and comfortable. It had 3 bedrooms which was perfect for us!"

Karin 1-night trip

Posted 3 days ago

Pines & Palms Resort

Treasure Harbor

10/10 Excellent

"Had a very enjoyable stay at Hemingway House. The place was spotless! All staff were very friendly and helpful. Would highly recommend staying here!"

Diane 3-night trip

Posted 3 days ago

Treasure Harbor

Breezy Palms Resort

10/10 Excellent

"Right on the ocean. Beautiful views. Very relaxing. Not busy this time of year and it was great."

Judy 3-night trip

Posted 4 days ago

Breezy Palms Resort

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