Florida Keys Vacation Rentals

(298 rentals)
Better than a tent

1 BR | 1 BA | Sleeps 4 | Quick View

$86

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Nightly rental in the middle of the lower keys, located in Breeze Pines RV resorts, with a heated pool and walking distance to many restaurants and shopping.The longer you stay the less you pay per day, there is a $100 one time fee.The address is 29859 Overseas Hwy Big Pine Key FL, and is on US1 ...

View all property information

Property Type

Big Pine Key Mobile Home

Show less

Summer Breeze (Family Escape)

4 BR | 3 BA | Sleeps 10 | Quick View

$457

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

The Summer Breeze is a beautiful family getaway on the waters edge. This oasis features a brand new in-ground salt water pool just feet away from the breath taking view of the turquoise waters of the Atlantic. Inside this newly renovated beach themed escape features an open kitchen and family room concept, ...

View all property information

Property Type

Marathon House

Show less

Upscale Home in Truman Annex!

1 BR | 1 BA | Sleeps 3 | Quick View

Distance to beach: 0.3 miles to Ft. Zachary Taylor

$178

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool
  • Rentals by Owner

About this property

Beautifully Remodeled -1BR/1BA End Unit Shipyard Condo in Truman Annex Location, Beauty and Comfort! Southard Breezes has what you are looking for! This gorgeous home has been meticulously renovated with our guests' complete comfort in mind. Located in the gated community of Truman Annex: a popular and ...

View all property information

Property Type

Key West Condo

Show less

Pete's Cottages

4 BR | 2 BA | Sleeps 8 | Quick View

$477

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

These twin homes have the charming original style of the Key West "shot gun" cottages and have been restored with a beautiful natural cypress exterior. Each cottage opens to it's own semi-private deck and lounge area with access to a large free-form pool with waterfall.Inside, the comfortable ...

View all property information

Property Type

Key West House

Show less

Breezy Palms

4 BR | 3 BA | Sleeps 10 | Quick View

$414

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This spectacular home has everything you will need to enjoy paradise! Situated in a very quiet and desirable neighborhood close to the beach and shopping. This home is a private oasis with mature landscaping on both sides, the golf course on the street side and only mangrove fringe across the canal. private ...

View all property information

Property Type

Marathon House

Show less

Beautiful Key Largo Water Front Two Bedroom Condo

2 BR | 1.5 BA | Sleeps 4 | Quick View

1

Distance to beach: 200 yards to Marriott

$142

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool
  • Rentals by Owner

About this property

Moon Bay on the ocean in the fabulous Florida Keys - Thank you for your interest in my Key Largo vacation home. If you love the ocean, I can guarantee you will not be disappointed spending a vacation anywhere in the Florida Keys.The condo you'll be enjoying is located in a complex called Moon Bay, ...

View all property information

Property Type

Key Largo Condo

"Key Largo Condo"
Reviewed February 7, 2019

Great location, very clean and friendly. Great pool and marina. Located along route 1 Florida Keys.

See all reviews

Show less

SPECTACULAR Indigo Reef Waterfront Home #41 - Marathon, Florida

3 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 5 miles to Sombrero

$225

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

Indigo Reef #41 is the BEST KEPT SECRET in the Florida Keys!! This home is spectacular in every sense of the word and not one detail has been overlooked. It is every renter's dream.Luxury and tranquility await you in this beautiful 3BR, 2.5 BA home at Indigo Reef Marina, named one of Marathon, Florida ...

View all property information

Property Type

Marathon Villa

Show less

Reduce Price Jan 18-25: Waterfront, Gulf Access, Dock, Pool, Spa

$189

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

With quick, easy access to the Gulf and Atlantic Ocean, this home is perfect for fishing, snorkeling and boating. This three-bedroom, two-bath home, which sleeps eight, has a 60-foot dock with ample room for your boat. It is only one house away from the mouth of a deep-water canal that leads directly ...

View all property information

Property Type

Marathon House

"Great location"
Reviewed October 14, 2019

Our visit was a two week stay in a really great location. Now first the bad, ok now that that's out of the way let's get on to the great! First off the location to the open water and dock are perfect, ...

See all reviews

Show less

Florida Vacation Home, Great View Over Cudjoe Bay. Private heated POOL

$364

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Vacation home sits close to the water and has a view over Cudjoe Bay to the Atlantic. Has a private heated pool, 4 bedrooms and 2 bathrooms. Large deck with water access for a boat. Vacation home sits far off of the main road for a great quiet vacation. We have 3 Florida Keys vacation homes on this property. ...

View all property information

Property Type

Cudjoe Key House

"A Perfect Vacation"
Reviewed January 22, 2019

Our stay was perfect! The scenery was beautiful, and the house was very well cleaned and decorated. The manager Steve was very friendly and helpful as well! I would highly recommend this rental to anyone ...

See all reviews

Show less

Kens Cozy Conch Key Cottage-2Br/2Bth Getaway + Optional motor boat rental

2 BR | 2 BA | Sleeps 5 | Quick View

1

Distance to beach: 4 miles to Long Key or Curry Hammock

$286

per night

View Details

Key Amenities

  • Air Conditioning

About this property

We are a small romantic cottage in a quaint OLd Florida Keys style Lobster fishing village, on a tropical island named Conch Key. We are located about 10 miles from Marathon and close to various state parks and beaches.Sorry but we are a NO SMOKING , NO PET, NO PARTY HOUSE OR LARGE GATHERING RENTAL.If ...

View all property information

Property Type

Marathon Cottage

"Relaxation vacation"
Reviewed January 27, 2019

Our first visit to the keys was stress free with this cottage rental. From first inquiry to end of vacation, Ken made this so easy. The cottage had everything we needed. After a day of exploring it was ...

See all reviews

Show less

Casa de Cuba

3 BR | 2 BA | Sleeps 6 | Quick View

$501

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, the location can't be beat. The home's history is rich; neighboring the historic Gato Cigar factory which is now restored ...

View all property information

Property Type

Key West House

Show less

Truman Annex unit202-3

2 BR | 1 BA | Sleeps 4 | Quick View

Inquire for rates

View Details

Key Amenities

  • Air Conditioning
  • Pool

About this property

Truman Annex unit202-3This upstairs unit has beautiful views and offers a private front and back porch. There is a queen bed in the master bedroom and 2 twins in the second bedroom.

View all property information

Property Type

Key West Condo

Show less

Lost In Paradise

2 BR | 2 BA | Sleeps 4 | Quick View

$140

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

What better get- a-way vacation than to get "Lost in Paradise".The location is a little off the beaten path to ensure wonderful privacy. Fully fenced, pet friendly and a wonderful pool area to lounge in the Florida Keys sunshine. This superb home has just been nicely updated in 2017. There ...

View all property information

Property Type

Big Pine Key House

Show less

Vista Fresco

2 BR | 2 BA | Sleeps 4 | Quick View

1

$251

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst friendly neighbors. The 1800 Atlantic complex sits on 400 feet of oceanfront property. An expansive pool and spa sits ocean side, surrounded by a lushly landscaped garden of native Key West plants ...

View all property information

Property Type

Key West Condo

"Waterview Condo"
Reviewed February 18, 2019

The condo was as advertised. It had a spacious kitchen and was nicely decorated. We had a beautiful view of the ocean and sunrises. You will need a car or bicycle to get to town. The bed we slept in ...

See all reviews

Show less

Beach Club #204

2 BR | 2 BA | Sleeps 4 | Quick View

$275

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Unique oceanfront living only 65 feet from the Atlantic!The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit.This is one of the most elegant and colorful 2 bedroom units in the Key ...

View all property information

Property Type

Key West Condo

Show less

Chillax

4 BR | 3 BA | Sleeps 10 | Quick View

$321

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

"Chillax" Vacation Rental ~ rent one side or both! It is a gorgeous brand new beautifully decorated 4 bedroom 3 bath canal front Villa (pull out couch)! With a private dock that can accommodate a boat up to 40', private pool, plenty of parking for cars and boat trailer and a two minute drive ...

View all property information

Property Type

Marathon Villa

Show less

3 BR | 2.5 BA | Sleeps 6 | Quick View

$400

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

View all property information

Property Type

Islamorada Condo

Show less

Brand New 6 Bedroom 5 Bath 65 Foot Deep Water Dock, Heated Pool Outdoor Kitchen

6 BR | 5 BA | Sleeps 14 | Quick View

1

Distance to beach: 0.1 miles to Sombrero Beach

$643

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

Brand New Construction, 6 Bedroom , 5 Bathroom canal views, On the HIGHLY sought after Sombrero Beach !!! 100 Foot Deep Water Dock (my 23 foot boat sits in a lift so you get 65 foot to use) 10 minute ride through the famed Sisters Creek to the open ocean, 15 minute to the seven mile bridge, six NM to ...

View all property information

Property Type

Marathon House

"Paradise!!!"
Reviewed October 9, 2019

This house wonderful! Even better than the pictures. The layout allows for a large group. The outdoor kitchen is a gathering place. Many hours were spent relaxing at the hot tub and pool. Our 30 ft boat ...

See all reviews

Show less

Waterfront Get Hooked

4 BR | 3 BA | Sleeps 10 | Quick View

3

$364

per night

View Details

Key Amenities

  • Air Conditioning

About this property

Waterfront Home in the heart of the Florida Keyes. Come relax and enjoy the beautiful waters of Sombrero and Bahia Honda Beaches. Both nearby. There is plenty of room and comfort in our 4 bedroom, 3 bath home. Two King Master Suites with attached baths. Satellite Flat Screen TV's in each bedroom. Fully ...

View all property information

Property Type

Marathon House

"Great value - perfect for 4 people"
Reviewed April 29, 2019

4 Guys looking for a great location near Colony Beach for fishing. The unit was exactly as described and then some. I would recommend this for anyone looking to visit the Keys. Close to all shopping ...

See all reviews

Show less

Pool Home Fisherman's Dream Ocean Side

$150

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

4 Bedroom 2 bath home with private dock and private pool with direct open access to the ocean and convenient access to the bayside through Tavernier Creek. This is both family friendly and a fisherman's dream. Our home sleeps 8 (max) with every comfort you would want while on vacation in the keys...Large ...

View all property information

Property Type

Islamorada House

Show less

'A little Piece of Paradise" Islamorada, Fl. On the water! 3/2, 90 Ft of dock

$350

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Rentals by Owner

About this property

''BEAUTIFUL BAYFRONT PROPERTY!!!!'' Fully furnished, 1 story offering 3bd/2ba. The house can sleep up to 10. There is a 1/1 guest suite attached which does have its own seperate and private access with full kitchen and bath. Entire house has been remodeled, fully furnished, with a 90 ft Dock. Bring ...

View all property information

Property Type

Islamorada House

"Paradise!"
Reviewed October 30, 2019

Stay here only if you are ready to relax and enjoy everything the Keys has to offer, by boat or car. We loved every minute of our stay here. Well appointed and comfortable inside and out! Beautiful location ...

See all reviews

Show less

Luxury Florida Keys Estate

3 BR | 3 BA | Sleeps 8 | Quick View

$714

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

Ocean Front, Lush Gardens, Private Beach, Deep-Water Dockage, Brand new Pool with Spa.This luxurious and newly renovated home is situated on the very desirable Lower Matecumbe Beach in Islamorada. This gated home offers supreme peace and privacy overlooking the Atlantic Ocean. Over 4,000 sq feet of ...

View all property information

Property Type

Islamorada House

Show less

Bayside: 1st Floor Apartment in Native Hammock on Florida Bay

1 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 4 miles to Founders Park

$214

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

Bayside is a first floor apartment overlooking the water. Bayside is located on a small resort property nestled in a native hammock on Florida Bay. An easy 90 minute drive from Miami International Airport, this property is located in the heart of Islamorada, directly on Florida Bay. Bayside is fully air ...

View all property information

Property Type

Islamorada Condo

Show less

Waterfront Bungalow. Cute waterfront home with a Bohemian Island feel!

2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 3 miles to Sombrero Beach

$131

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly

About this property

This house is a 2 bedroom, 1 bathroom newly renovated waterfront half duplex. There's a screened in porch, so you can relax in comfort on the water. There is 24' of dock space. There's a BBQ grill, 2 kayaks, Cable TV, WIFI, washer/dryer, and all the amenities of home. The house was undamaged in the hurricane ...

View all property information

Property Type

Marathon House

Show less

Bali Hideaway

Studio | 1 BA | Sleeps 2 | Quick View

$203

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Perfect for two, this Bali-style studio cottage has it all: comfort, privacy and location.The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics ...

View all property information

Property Type

Key West Studio

Show less

Southard Street - Queen Conch

4 BR | 4 BA | Sleeps 8 | Quick View

$750

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool, or combines for a wonderful four bedroom retreat.Downstairs there is a large, open floor plan with living ...

View all property information

Property Type

Key West House

Show less

Louisa's Hideaway

3 BR | 3 BA | Sleeps 6 | Quick View

$551

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Tucked away near the quite end of Duval Street, you'll find this stylish, newly renovated, three bedroom, three bath home. Thoughtful details are luxuriously appointed to appeal to the traveler looking for privacy, style and elegant design.Walk up the brick drive and enter the gate to the palm tree-lined ...

View all property information

Property Type

Key West House

Show less

Toes in the Water

4 BR | 3 BA | Sleeps 10 | Quick View

$321

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

"Toes in the Water" ~ Rent one side or both! It is a gorgeous brand new beautifully decorated 4 bedroom 3 bath canal front Villa (pull out couch)! With a private dock that can accommodate a boat up to 40', private pool, plenty of parking for cars and boat trailer and a two minute drive to the ...

View all property information

Property Type

Marathon Villa

Show less

Bay Harbor 110C​

2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 1 miles to Anne's Beach State Park

$257

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

This Condo sleeps 4 and comes with a 30' Boat slip, Tennis courts, pool, club house, undercover parking and elevators for easy access. Located on quiet Lower Matecumbe Key, Bay Harbour is just 7 miles from Islamorada's center with nearby beaches and parks. Newly refurnished and refurbished, this condo ...

View all property information

Property Type

Islamorada Condo

Show less

Beach Club #408

4 BR | 3 BA | Sleeps 8 | Quick View

$400

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Welcome to your quiet and relaxing Key West vacation! The Key West Beach Club stretches along the Atlantic Ocean shores. This top floor penthouse has it all: 15 foot vaulted ceilings, a well equipped kitchen, huge oceanfront balcony, four bedrooms and three baths. Enjoy breathtaking views of the ocean ...

View all property information

Property Type

Key West Condo

Show less

Shipyard Palms

2 BR | 1.5 BA | Sleeps 4 | Quick View

$203

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

In the heart of old town Key West, nestled within the secluded and lush community of private homes and condominiums of Truman Annex, this Shipyard Condominium has convenient access to both the gorgeous Fort Zachary State Park Beach and historic old town Key West.This colorful and whimsically decorated ...

View all property information

Property Type

Key West Condo

Show less

Waterfront Hideaway. Cute waterfront home with a Bohemian Island feel!

2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 3 miles to Sombrero Beach

$97

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly

About this property

This house is a 2 bedroom, 1 bathroom newly renovated waterfront half duplex. There's a screened in porch, so you can relax in comfort on the water and is 24' of dock space. There's a BBQ grill, 2 kayaks, Cable TV, WIFI, dishwasher, washer/dryer, and all the amenities of home. The house was undamaged ...

View all property information

Property Type

Marathon House

Show less

Caribbean Cove/beautiful waterfront view

$83

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

Come to relax in one of Big Pine's most peacefully secluded waterfront retreats!Tastefully decorated with favorable Key West colors. Very clean and well maintained. This cozy and comfortable decor will make you feel right at home. Completely furnished.For those of you who enjoy boating, fishing, ...

View all property information

Property Type

Big Pine Key House

Show less

Single Family Home, 3 Bedroom, 2 Bath, Pool and Electric Car, Great Value!

$117

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Private home located in New Town available for 4 week minimum rental. Beautifully landscaped yard with secure private back yard and pool. Use of bicycles and four passenger electric car provide flexible transportation all over the island. The home features a modern kitchen with all appliances and granite ...

View all property information

Property Type

Key West House

"Perfect vacation!"
Reviewed September 10, 2019

What a lovely stay - I heartily recommend and hope that I will be back in the future. The house was great, but I think the pool was my favorite place to be! Really enjoyed the owners’ thoughtful attention ...

See all reviews

Show less

Panoramic Ocean View, Pool, Hot Tub, Tennis & Fishing

2 BR | 2.5 BA | Sleeps 6 | Quick View

Distance to beach: 5 miles to Sombrero Beach

$328

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Pool

About this property

Entering our luxurious condo, you will be impressed with expansive ocean views, literally from every room. Corner-sited and on the 1st floor (above parking), the wrap around private balcony, with all-new wicker lounge furniture, is but a stone toss to the ocean. Travertine tile floors and granite counters ...

View all property information

Property Type

Key Colony Beach Condo

Show less

Bay Front Cottage W/ Free Sailboat, Kayaks, Bikes, Snorkel/Fish Gear

$225

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Rentals by Owner

About this property

Welcome to our unique little hideaway. Secluded, serene, and perfectly located, our self-contained cottages have everything you need for a relaxing waterfront vacation.There are no hidden charges – your stay includes: Unlimited private sailboat use (for experienced sailors) Kayaks Snorkel ...

View all property information

Property Type

Key Largo Cottage

Show less

Colony Sunset Suite

1 BR | 1 BA | Sleeps 2 | Quick View

$180

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool

About this property

Located in The Colony, a secluded compound just steps from Duval Street, Colony Sunset is a colorful and relaxing retreat. Walk up the flagstone path and enter the home through the vivid and cheerful living space, accented with cerulean blue walls and splashes of tropical art. A vaulted ceiling with ...

View all property information

Property Type

Key West Condo

Show less

5 Bedroom 4 Bath Canal Front Home Sleeps 12. (28 day min. rental)

5 BR | 4 BA | Sleeps 12 | Quick View

3

Distance to beach: 4 miles to Bahia Honda

$217

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

Large home located on a double lot with plenty of parking and 200 feet of seawall. There is a step down platform for getting in and out of your boat. This area also has whip lines to keep you boat off of the seawall. Quiet neighborhood with convenient access to grocery stores and other services. Large ...

View all property information

Property Type

Big Pine Key House

"Great Stay in the Keys"
Reviewed May 21, 2019

I had the pleasure to stay at Ken and Maureen’s rental recently and can tell you it was one of the most fantastic experiences I can remember as I have rented often in the Keys.The house itself had ...

See all reviews

Show less

SPA VILLA ON BLUE WATER LAGOON

2 BR | 2.5 BA | Sleeps 6 | Quick View

1

$150

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

COZY VILLA WITH YOUR OWN PRIVATE SPA OVERLOOKING BLUE WATER LAGOON TWO BEDROOM 2 1/2 BATH VILLA QUEEN BEDS WITH PILLOW TOP MATTRESSES, VERY COMFORTABLE QUEEN PLUS SOFA BED. VILLA SLEEPS SIX COMFORTABLY. EACH BEDROOM HAS SEPARATE BATH WITH TUB/SHOWER AND TV. FULLY EQUIPPED KITCHEN TO COOK YOUR ...

View all property information

Property Type

Duck Key Villa

"Relaxing Vacation"
Reviewed November 18, 2018

The place we stayed was absolutely gorgeous! Everything was clean and in working order. Location was great because we were able to go south to Key West if we wanted and also North to a few areas we wanted ...

See all reviews

Show less

Duval Square Courtyard Condo

3 BR | 2 BA | Sleeps 6 | Quick View

1

$400

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

n the heart of Old Town and convenient to just about everything, this condo is set above a quaint brick and tree-lined courtyard that includes shops and restaurants. This three bedroom, two bath unit is in one of the only "stand-alone" buildings in the Duval Square complex. Simply walk down ...

View all property information

Property Type

Key West Condo

"Wedding in Key West "
Reviewed April 11, 2019

Loved the location,place was very nice and relaxing. We really enjoyed ourselves. Would stay here again in a heartbeat.

See all reviews

Show less

Canal Front Villa with a Tiki Hut, Kayaks, Bikes, Pool, Neighborhood Beach!

$321

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

"Dockside Retreat" ~ rent one side or both! Warm and inviting coastal decor, this 4/3 villa is the perfect vacation home! This beautifully decorated Villa is truly a relaxing retreat and a vacation home that offers you everything you need for a fun filled Keys vacation, including an oceanfront ...

View all property information

Property Type

Islamorada House

Show less

JUST RENOVATED, WATERFRONT, WALK TO CABANA CLUB , * FALL SALE *Nov. 2-11* $798WK

2 BR | 2 BA | Sleeps 5 | Quick View

5

Distance to beach: 0.0 miles to Inch Beach - Just a 3 minute walk

$114

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Rentals by Owner

About this property

Welcome to Casa Mar Azul Il, JUST COMPLETELY RENOVATED, 2 Bedroom, 2 Bath vacation home that sleeps up to 5 people and located at 12 7th Street in Key Colony Beach. That's right, we Just Renovated this vacation home into a Tropical Piece of Paradise that you will fall in love with once you see how beautiful ...

View all property information

Property Type

Key Colony Beach House

"You have to stay here !!!"
Reviewed August 1, 2019

This house was wonderful. The location was perfect. The house was clean and very well maintained. The AC worked and very well! It has a washer and dryer which is great for a family. The dock was great and ...

See all reviews

Show less

Ocean Front building with Ocean Front pool in beautiful Islamorada!

$129

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool
  • Rentals by Owner

About this property

Luxurious and large 2 bedroom 2 bath condo with balcony, large heated swimming pool, stainless steel appliances, flat screen televisions in every room in the beautiful Florida Keys.Huge ocean front dock with plenty of room for fishing! Wifi, deluxe cable, and restaurants within walking distance.2 ...

View all property information

Property Type

Islamorada Condo

"Wonderful location and hosts."
Reviewed January 10, 2019

This home was perfect for our family of five. Spacious bedrooms, living area and bathrooms. We also had use of the storage unit for our fishing gear and coolers. The pier is breathtaking. Our thoughtful ...

See all reviews

Show less

Southard Rooster Conch Suite

1 BR | 1 BA | Sleeps 2 | Quick View

$202

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool or combines for a wonderful four bedroom retreat. The two one bedroom suites are located on the second floor, ...

View all property information

Property Type

Key West House

Show less

Beach Club #304

2 BR | 2 BA | Sleeps 4 | Quick View

$275

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water as few do in Key West. The breathtaking view can be seen as soon as you enter this spacious 2 bedroom condo. It has just been purchased and newly refurnished ...

View all property information

Property Type

Key West Condo

Show less

ANOTHER DAY IN PARADISE

3 BR | 2 BA | Sleeps 6 | Quick View

$233

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

It’s more than just another Day in Paradise, it’s an incredibly wonderful and memorable vacation stay in the fabulous Florida Keys!Please come stay with us in this large 3 bed 3 bath heated and chilled pool home on deep water canal in Summerland Key. Entering the home by way of the 2 story ...

View all property information

Property Type

Summerland Key House

Show less

Ann Street Tranquility

1 BR | 1 BA | Sleeps 2 | Quick View

$236

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

This charming one bedroom cottage is the perfect hideaway.The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy Joe's, ...

View all property information

Property Type

Key West House

Show less

MARGARITA VILLA

3 BR | 2 BA | Sleeps 6 | Quick View

$140

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

Welcome to Margarita Villa! Located in Jolly Roger Estates on Little Torch Key, where you’ll find some of the best deep water boating in the Lower Keys!Decorated in fine island-style this private home is definitely a 5-star proprety. Tile floors, open and airy kitchen, living and dining area ...

View all property information

Property Type

Summerland Key Villa

Show less

Islamorada Beachfront Apartment - Great Sunsets! Private Beach!

$120

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Oceanfront
  • Rentals by Owner

About this property

The Jetson's House apartment (Located on the prestigious White Marlin Beach - which is considered one of the nicest natural sand beaches in the Florida Keys) features great swimming, snorkeling, and spectacular sunsets right off the beach! Have fun exploring an artificial reef! What makes the beach ...

View all property information

Property Type

Islamorada Apartment

"Wonderful!"
Reviewed June 2, 2019

I have stayed here twice and can’t recommend this property enough! I struggled to write this because there are so many wonderful things about this little piece of paradise! The beach in unbelievably ...

See all reviews

Show less

Dreaming on Duval

5 BR | 4 BA | Sleeps 10 | Quick View

$1150

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Luxury on Duval Street in historic Key West? Luxury is not a word most people associate with Duval Street... until you look at Dreaming On Duval! There are very few private homes on this famous street, let alone a single-family, free-standing vacation rental that is just steps away from everything Key ...

View all property information

Property Type

Key West House

Show less

Expand map | Close map
Florida Keys Vacation Rentals