Florida Keys Vacation Rentals

(486 rentals)
booking message booking message
Key West House | On the beach
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1 bathroom
3 reviews

$456

avg/night

$456
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

The Sea View Cottage is a 2 bedroom, 1 bath home built within feet of the Atlantic Ocean with 180 degree ocean views.The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge.Fishing and diving just steps outside your door. Then at night, Key West is ...

View all property information

Property Type

Key West House

Featured review

"The Perfect Relaxing week!!"

My family booked Seaview Estates for our 25th Anniversary trip! We rented both houses so we had the property to ourselves. Upon arrival, Carol met us at the gate and began our tour of the property. The ...

See all reviews

Show less

Key Colony Beach House
4 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 4 bathrooms
2 reviews

Distance to beach: 0.5 miles to Key Colony Cabana Club Beach

$558

avg/night

$558
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Beautiful 2-story half duplex home on wide canal with boat slip. Sleeps 10 comfortably. 4 bedrooms, bathrooms and lower-level family room with mini kitchen make this a great place for multiple families to have private space or gather together.Plenty of parking for boat trailer and multiple vehicles, ...

View all property information

Property Type

Key Colony Beach House

Featured review

"Plenty of room and a great location!"

Rare find of 4 full baths and 4 real bedrooms (not a daybed stuck in a sunroom like some rentals market as a bedroom). House comes with everything you need - beach towels, coffee maker, toaster, blender, ...

See all reviews

Show less

Marathon House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

$403

avg/night

$403
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Welcome to “Take it Keysie” your tropical/waterfront retreat in Marathon, Florida!Located in the heart of the Florida Keys, Take it Keysie, offers the perfect blend of luxury, comfort, and adventure for your vacation getaway. Our waterfront property with quick ocean access offers 3 bedrooms ...

View all property information

Property Type

Marathon House

Show less

Marathon House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms
1 review

$575

avg/night

$575
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to our waterfront family home located in a quiet, yet friendly gated community in Marathon, Florida! If you’re looking for a relaxing and low-energy getaway for your family, you’ve found the perfect place.Consider a 14-day stay and receive an 8% discount OR 28-day stay and receive ...

View all property information

Property Type

Marathon House

Featured review

"Great Rental in Marathon, Fl."

Great house in a great location. It is very accommodating for 8 people. We enjoyed the view, the hot tub, the kindness of the owners, etc. Highly recommended!

See all reviews

Show less

Marathon House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
6 reviews

$365

avg/night

$365
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Our waterfront, single-family home, affectionately named “Turtle Cove”, offers 3 bedrooms, 2 baths, and an 80 ft seawall with quick ocean access! This tastefully furnished Keys home is located on a quiet side street in a residential neighborhood on the Atlantic side of the Island, just 5 houses ...

View all property information

Property Type

Marathon House

Featured review

"Customer Service Outstanding"

House was clean, pool area great, any small issues we encountered dealt with promptly. Close to everything needed.

See all reviews

Show less

Islamorada House | On the beach
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms

Distance to beach: 50 yards to Private sunning beaches at Anglers

$647

avg/night

$647
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

SAVE VRBO's $500-600 Booking fee!!Welcome to Anglers Reef, a very special community of vacation homes. And to Anglers Reef 140's OceanFRONT location with its unique UNOBSTRUCTED OCEAN VIEWS FROM EVERY ROOM and spacious wraparound decks!Boat slip is optionally available for $375/wk, Christmas ...

View all property information

Property Type

Islamorada House

Show less

Key Colony Beach Villa
4 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 4 bathrooms
10 reviews

$663

avg/night

$663
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

The Blue Manatee (formerly Sunshade Villa), located in Key Colony Beach, in the Marathon area, is a gorgeous, brand new, designer decorated canal front duplex with a modern coastal feel! Each side is rented separately and has 4 bedrooms, 4 bathrooms, a private pool and all the amenities you can imagine ...

View all property information

Property Type

Key Colony Beach Villa

Show less

Key West Townhome
1 BR | 1.5 BA | Sleeps 6 | Quick View
Sleeps 6, 1 bedroom, 1.5 bathrooms
8 reviews

$263

avg/night

$263
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

**Available for rent by the month. Although you rent it for a month, you may of course come late and/or leave early. The monthly price is generally half of what you would pay for a daily-rate comparable unit, and it gives you a lot more options and freedom.Located on a side street off Duval and ...

View all property information

Property Type

Key West Townhome

Featured review

"Beautiful Stay!"

This unit is in a tucked away little oasis one street over from all the action on Duval street. If is a very peaceful and unique spot. The unit itself is exceptionally clean and well appointed. It has ...

See all reviews

Show less

Key West House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
6 reviews

$317

avg/night

$317
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Adorable historical conch house 2 bdrm, 2 full bath on quiet street with all the modern day amenities & decor in convenient location, relax by your private heated/chilled pool surrounded by decking and palm trees. Enjoy your morning sitting on the front porch watching the breeze travel through the ...

View all property information

Property Type

Key West House

Featured review

"Key West paradise"

Beautiful home on a quiet street and close to everything. No need for a car. You can walk or ride bikes to anywhere on the island. Outdoor area is just right for a group of six. Totally enjoyed the ...

See all reviews

Show less

Islamorada Cottage | On the beach
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

$1286

avg/night

$1,286
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Private pool

About this property

Mile Marker 83 – OceanfrontTwo adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada! This stunning property is truly a tropical paradise with a private, sandy beach and skiff dock. Relax at the beach or cool down in the beachside pool.The front home ...

View all property information

Property Type

Islamorada Cottage

Featured review

"Osprey Bay January"

Just finished a week at Osprey Bay nice house a little too much up and down with all the steps but spacious Need a larger trash can in the kitchen put it next to the wall near toaster Also new pillows ...

See all reviews

Show less

Key Largo House | On the beach
5 BR | 3.5 BA | Sleeps 14 | Quick View
Sleeps 14, 5 bedrooms, 3.5 bathrooms

$1799

avg/night

$1,799
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

First time offered - only property of its kind the keys -as featured in Global Mansion - Wall Street Journal. A true resort style peninsula surrounded by over 25 acres of park nature, providing the upmost privacy anywhere in the world.Feel the joy of living on a truly beach home. Snorkel, ...

View all property information

Property Type

Key Largo House

Show less

Summerland Key House
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Distance to beach: 6 miles to Baja Honda

$167

avg/night

$167
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Rentals by owner
  • WiFi

About this property

Conchcanary is located on Little Torch Key, in the heart of the Florida Keys. Come relax in our hammocks with a tropical beverage or bring your boat for some fantastic fishing.Enjoy your morning coffee with a canal views from the screened balcony. Newly updated kitchen with top of the line appliances, ...

View all property information

Property Type

Summerland Key House

Featured review

"Honeymoon in the Keys"

My wife and I spent the first 7 days of our married life living it up in the Keys. We loved it. Kayaking in the bay. Trips to the beach (very different from other beaches). Snorkeling in the ocean! Live ...

See all reviews

Show less

Marathon House
4 BR | 4.5 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 4.5 bathrooms
3 reviews

Distance to beach: 1 miles to Sunset Park

$593

avg/night

$593
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Family-friendly Waterfront Oasis w Heated Lazy River Pool and 70' Dock Summary: Bring the family to the Florida Keys vacation of your dreams! Located in family-centered Marathon while still located in the middle Keys with the best access to the whole of the Keys for exploration. Enjoy ...

View all property information

Property Type

Marathon House

Featured review

"Private Paradise"

We could not have stayed at a better place in Marathon. The owners Roger & Amy are great hosts. We hardly saw them but it was nice knowing if we needed something they were close by. The view from the ...

See all reviews

Show less

Islamorada House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$217

avg/night

$217
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner

About this property

The moment you step inside this calming retreat in exclusive Venetian Shores you feel on vacation with permanently assigned boat slip in private marina just around the corner. All new kitchen, baths, porcelain tile flooring, fully furniture and LOTS more. Three bedrooms, two bath home on a peaceful plugged ...

View all property information

Property Type

Islamorada House

Show less

Marathon House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms

$488

avg/night

$488
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Ocean OasisEscape to this newly built, stunning 4-bedroom, 3-bathroom vacation home nestled in the heart of Marathon, FL. Perfectly situated in Coco Plum and boasting a private pool and dock, this retreat offers everything you need for an unforgettable getaway in the Florida Keys.••• ...

View all property information

Property Type

Marathon House

Show less

Marathon House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
7 reviews

$540

avg/night

$540
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This beautiful 4 bedroom, 3 bath home is less than 2 minutes from Sombrero Beach just down the street (oceanfront) and less than 15 minutes to open water! Private pool with outdoor tv on the patio, private dock (1/2 the dock), 2 bikes, 2 kayaks, bait freezer, gas grill! The private dock can accommodate ...

View all property information

Property Type

Marathon House

Featured review

"Family reunion"

Excellent stay, everything in the house worked smoothly, nice big pool, kayaks at our disposal, Sombrero beach, groceries in just few minutes of drive. One ctisism: no garbage recycling option.

See all reviews

Show less

Marathon House
5 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4 bathrooms
3 reviews

$1714

avg/night

$1,714
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Located on the Highly sought after Sombrero Beach area of Marathon, which is the beginning of the lower keys just 50 min from Key West is our Florida Keys Tropical Paradise . Less than a third of a mile to the Sombrero Beach and the Sombrero Beach Park, With a deep water concrete dock with ocean access ...

View all property information

Property Type

Marathon House

Featured review

"Great house and location"

Highly recommend this home. My family of 5 just spent the week there and had a fabulous time. It had everything we needed. It was close to some amazing restaurants. Publix was around the corner. The beach ...

See all reviews

Show less

Islamorada Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 100 feet to Front door

$227

avg/night

$227
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

MINIMUM STAY: 30 daysSpacious and beautiful 2 bedroom/2 bath ocean front condo unit with unobstructed ocean views. BOAT SLIP is available upon request for up to a 46 foot boat, low tide draw is 30 inches. There is an additional fee for boat slip.Walk out your front door and go boating.You’ll ...

View all property information

Property Type

Islamorada Condo

Featured review

"Ocean Harbor M3 is Fabulous!"

Priceless view of the ocean. Nice marina. Workout room is great with a view. The condo is clean and spacious. Every thing you need is here. Very easy to maintain. During my 3 month stay from May to August ...

See all reviews

Show less

Key West Condo
Studio | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 0 bedrooms, 1 bathroom
1 review

Distance to beach: 0.5 miles to South Beach

$292

avg/night

$292
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

This Studio is a lovely charmer nestled in a 6 unit compound in a residential neighborhood in the center of Old Town Key West. * Pet Friendly for flat fee of $90 * King size bed * WiFi included * check-out cleaning is an additional fee of $70 * 2 wall AC units * flat screen TV * Shared gas grill ...

View all property information

Property Type

Key West Condo

Featured review

"Perfect Place to Stay"

This was our 3rd time staying in Pam's wonderful little cottage. My husband and I really love this place. Pam is awesome to work with, she always answers all my questions quickly. It was great being close ...

See all reviews

Show less

Key Colony Beach House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
8 reviews

Distance to beach: 0.2 miles to Cabana Beach Club

$232

avg/night

$232
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

This is a large stilted duplex located in a tropical paradise. The water view property is located on the island City of Key Colony Beach in the Middle Keys (near Marathon). This is a canal-front unit with a 37.5 step down concrete dock with quick easy access to ocean. Dock comes with ladder access and ...

View all property information

Property Type

Key Colony Beach House

Featured review

"Paradise"

The place is beautiful, spotless on arrival, and I made sure it was spotless when I left. The entire time I was at your property an old late 80's song by David Lee Roth kept running through my mind -"This ...

See all reviews

Show less

Tavernier Apartment | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$217

avg/night

$217
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Oceanfront condo with large screened in deck . We have wi fi and great views. We have a pool . They are working on the grounds . 55” tv in living room and flat screen TVs in bedroom. It has a king bed and guest room is queen. There is a sofa sleeper in living room . We are away from the road ...

View all property information

Property Type

Tavernier Apartment

Show less

Key Largo Condo
2 BR | 1.5 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 1.5 bathrooms
last minute deal
LAST MINUTE DEAL 11/12 - 11/26: December Discount - $1500 off the rental price.

Distance to beach: 175 yards to K Building

$208

avg/night

$208
avg per night
Offer for: Nov 12 - Nov 26:
December Discount - $1500 off the rental price.

View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

This beautiful end unit is nestled in the most charming area of the best condominium complex in Key Largo. As you walk up to the front of the unit, you will be pleased by the inviting seating area and the paved walkway. It is close to the community beach and near the inlet. Your end unit allows you the ...

View all property information

Property Type

Key Largo Condo

Show less

DEAL
Key West House
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms

$608

avg/night

$608
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Dos Casas can be the answer to your fabulous Old Town Key West vacation. We've been renting to discerning travelers for over 15 years. Our guests come back over and over, finding the comfortable spaces, stocked with amenities and ideal location the perfect spot to enjoy all that Key West has to offer.Dos ...

View all property information

Property Type

Key West House

Show less

Key West House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms
5 reviews

$817

avg/night

$817
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

2/2 Main House, 1/1 Bunglow, Large Pool And Hot Tub On Beautiful Old Town LaneMulti-month Discounts availableHidden at the end of one of the most beautiful lanes in Old Town, Casa Escondida awaits you with its tropical seclusion and quiet serenity. Nestled amongst mature tropical landscaping, ...

View all property information

Property Type

Key West House

Featured review

"A little slice of heaven on earth"

The location is perfect - about 3 blocks from Duval, and 3 blocks from Truman, and a short bike ride to Ft. Zachary beach. We did not have a car, and did two Uber runs for groceries at Publix, then used ...

See all reviews

Show less

Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

$135

avg/night

$135
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to our beautiful, private and secure gated community with all of the amenities to make your vacation as relaxing or exciting as you wish. Located on Plantation Key in Islamorada at mile marker 88.5 on the bay side and boasting a great 60 slip marina, it provides quick access to the ocean via Snake ...

View all property information

Property Type

Islamorada Condo

Featured review

"Wonderful"

I highly recommend this vacation spot. Not only is the condo very nice the whole property is set up for your every need. The owner and property manager are very nice and accommodating. I was amazed by the ...

See all reviews

Show less

Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$470

avg/night

$470
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to Mother Ocean!This stunning ocean view condo boasts three bedrooms and two full bathrooms, making it perfect for a family or group of friends. It features modern amenities and coastal decor throughout, providing a comfortable and inviting atmosphere for your stay. The spacious living room ...

View all property information

Property Type

Islamorada Condo

Show less

Marathon House
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1.5 bathrooms
1 review

Distance to beach: 3 miles to Sombrero Beach

$306

avg/night

$306
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to DragonFly Lite our home in Marathon, FL in the heart of the beautiful Florida Keys, the house has 2 bedrooms a Queen in the master and 2 twins in the guest room, one bathroom + our outdoor shower, all the towels you will need for the pool or beach (please leave the sand outside). It’s ...

View all property information

Property Type

Marathon House

Featured review

"A Magical Place to Isolate"

Though Dragonfly Lite would be a marvelous place to vacation anytime, it proved especially so in a global pandemic. We had everything we needed right there on property. The pool is pristine, the home was ...

See all reviews

Show less

Little Torch Key House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
4 reviews

Distance to beach: 9 miles to Bahia Honda

$160

avg/night

$160
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Enjoy the Florida Keys in this beautiful canal front two bedroom two bath house in a beautiful area on Little Torch Key. The house features a master bedroom with a king size bed, flat screen TV, and the second bedroom also has a king size bed. A well designed and fully equipped kitchen with everything ...

View all property information

Property Type

Little Torch Key House

Featured review

"Beautiful Escape"

We enjoyed our stay in this extremely comfortable home. Beds were very comfortable and location was close to lots of restaurants and local attractions. Having a place for our boat was the best. We could ...

See all reviews

Show less

Key Largo House
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1 bathroom
1 review

Distance to beach: 6 miles to John Pennekamp State Park

$160

avg/night

$160
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront

About this property

1 BR/1 Bath Rare Find! Lovely oceanfront home with large private boat basin. This ground-level house has two enclosed sleeping areas - a master bedroom with a king bed, and a private alcove providing sleeping space for up to 4, with 2 bunks and a full-sized bed (separated from the living room by an ...

View all property information

Property Type

Key Largo House

Featured review

"Mahalo ocean view"

We loved every minute of our vacation. The sunsets were magnificent. Fun meter is high with a unique blend of restaurants and tiki bars. So convenient having a boat slip. We will be back!

See all reviews

Show less

Islamorada House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 3 miles to Anne's Beach State Park

$311

avg/night

$311
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

This 3-bedroom bayfront property is located on Lower Matecumbe in Islamorada. The view is spectacular with sunsets on the water most of the year. There is plenty of room for boat trailers, RVs and other toys inside the fence. There is covered parking for your vehicles and a seawall out front to tie your ...

View all property information

Property Type

Islamorada House

Featured review

"Lower Matecumbe"

All I can say is that this place never fails to impress! The views from every inch of the property are the best in all of the keys! Great communication with Rich and his office. Would recommend every ...

See all reviews

Show less

Islamorada House
2 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 2 bedrooms, 2 bathrooms
7 reviews

$371

avg/night

$371
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

1440 sf - Sleeps 4 adults (also includes xtra bed in guest room plus EZ-Bed electric queen Bed and large sectional couch with chaise lounge and cuddler for larger families). Fully renovated and updated in 2021. 70ft foot dock and cleaning table. Great ambience, quiet home like feel. Private community ...

View all property information

Property Type

Islamorada House

Featured review

"BEST TROPICAL VACATION EVER!!!!!!!!"

Here is the review I am trying to post via for our March 2024 stay.Wonderful! Fantastic! Amazing!Wonderful Hosts!!! Jay and Sharon are so welcoming and supportive! We felt at home before we ...

See all reviews

Show less

Islamorada Townhome
2 BR | 2.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2.5 bathrooms

$276

avg/night

$276
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Breathtaking Waterfront 2/2.5 Townhouse In Desirable Futura Yacht Club. Lots of outdoor living space,great for entertaining and enjoying the magnificent unobstructed Bayviews and beautiful sunset! Futuravis a gated community with a large pool tennis courts, boat ramp,beach and boat/trailer storage,parking ...

View all property information

Property Type

Islamorada Townhome

Show less

Islamorada House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
4 reviews

$690

avg/night

$690
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This beautiful, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. Situated in a beautiful upscale neighborhood of all waterfront homes, the house is equipped with all the comforts of home. It is extra clean and modernly furnished.Upstairs ...

View all property information

Property Type

Islamorada House

Featured review

"Perfection in paradise!"

This was a perfect house! Easy and quick access to ocean and gulf, docked 35’ boat right at the house, large pool with hot tub, plenty of parking for vehicles and trailers, very clean, well stocked, tiki ...

See all reviews

Show less

Marathon House
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

$250

avg/night

$250
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Our wonderful, Oceanside and waterfront home is just two minutes from the Atlantic Ocean and Vaca Cut. No bridges to the Atlantic and super easy to access the Gulf via Vaca Cut.This home is completely remodeled and features brand new furniture throughout. The 55 foot dock is brand new and awaits your ...

View all property information

Property Type

Marathon House

Featured review

"Great Vacation Rental"

We came in by boat and had a wonderful stay in this home. Rooms are large and plenty of space to move around. Sunrises are beautiful. Outside freezer for fish and bait was a great asset. Nice area to take ...

See all reviews

Show less

Marathon House
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms
18 reviews

$444

avg/night

$444
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

We would love for you to come visit our renovated ground level Florida Keys home! We decided to call our home "TIGHT LINES", because my wife loves to fish. Our conch home consists of 3 bedrooms with king size beds with ensuite bathrooms. A half bath for guests. We have a 60 foot dock with ...

View all property information

Property Type

Marathon House

Featured review

"Wonderful experience!"

Everything was just as we had hoped for. Lynn and Freida always make you feel right at home-- only better! Thank you again for your hospitality and the sharing of your beautiful home!

See all reviews

Show less

Little Torch Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 2 miles to Picnic Island (by Boat)

$160

avg/night

$160
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Beautifully kept private and secure canal front (220' of waterfront) home. Located at the end of a dead end street in a residential neighborhood alLows for privacy and extra relaxation. Fully updated kitchen, fully equipped with coffee maker, espresso maker, blender, bullet blender, etc. Ideally ...

View all property information

Property Type

Little Torch Key House

Featured review

"Perfect place"

The property is updated, super comfortable, spacious, and beautifully decorated. We will be visiting again!

See all reviews

Show less

Summerland Key House | On the beach
7 BR | 5.5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 5.5 bathrooms
5 reviews

$750

avg/night

$750
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Minimum 28-day rental. NO, this is NOT available to rent for fewer than 28 nights. Please don't ask.Breathtaking property located on desirable Summerland Key right on the ocean. There are three structures on the property....two large cottages (each two-bedroom) and a main house overlooking the ...

View all property information

Property Type

Summerland Key House

Featured review

"Perfect Tropical Oasis"

This is an incredible find! If you’re interested in this property, do not hesitate! In almost 30 years of traveling at least 15 times to Florida, this is by far the nicest place we’ve stayed. Whether ...

See all reviews

Show less

Islamorada Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$250

avg/night

$250
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

MM 87.7 . 2 Bedroom & 2 Bath. Rented 28 days minimum Experience the epitome of oceanfront luxury in this exquisite paradise! Delight in fishing the pristine waters of the Keys with the convenience of your own 30ft slip in a secure marina. Unwind in the comfort of your spacious condo that boasts ...

View all property information

Property Type

Islamorada Condo

Show less

Big Pine Key House
3 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Enjoy breathtaking views of ISLAND TIME PARADISE (our nickname) in Big Pine Key. Its our spacious 3 bedroom 2 bathroom ISLAND TIME PARADISE HOUSE that will accommodate a total of 8 people. You will see it as the perfect blend of tranquil beach living and modern convenience. This home is the ideal place ...

View all property information

Property Type

Big Pine Key House

Featured review

"Wonderful home"

Loved staying at this home! Very comfortable! Owners were great to work with and extremely easy to work with! Got our security deposit back within a good time frame! I have no complaints except for the ...

See all reviews

Show less

Islamorada Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

$271

avg/night

$271
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Tropically furnished condominium with amazing views of the Gulf of Mexico, located at the Futura Yacht Club in the Village of Islamorada. Futura Yacht Club is a gated community located on the Gulf of Mexico and consisting of 70 units. Enjoy your morning coffee, watching the boats go out. Relax, ...

View all property information

Property Type

Islamorada Condo

Featured review

"Fantatic"

Fantastic host. fantastic location, fatastic accomodations! Looking forward to returning in 2022. Thank you Susan

See all reviews

Show less

Islamorada House | On the beach
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms

$948

avg/night

$948
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool

About this property

Introducing the "Bonefish House" at Tarpon Point!This opulent, luxury, home is equipped to accommodate eight adults with 4 bedrooms & 4 full bathrooms. The open living space offers easy entertaining and direct panoramic views of the community pool and Atlantic Ocean. The well-appointed ...

View all property information

Property Type

Islamorada House

Show less

Islamorada Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$209

avg/night

$209
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

This condo is located in one of Islamorada's most prestigious condo complexes.PROPERTY NAME: Beacon Reef #407 83201 Old Highway, Islamorada, FloridaLOCATION: Ocean side CondoMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months Allowed MILE MARKER: 83.2DETAILS: ...

View all property information

Property Type

Islamorada Condo

Show less

Islamorada House | On the beach
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms
7 reviews

$859

avg/night

$859
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

‘The Beach House’ at Tarpon Point in Islamorada- DIRECT RENTAL WITH NO ADDITIONAL FEES‘The Beach House’ is a luxurious oceanfront home in a private gated enclave of only 12 houses. This end home offers privacy and beautiful ocean views including of Indian Key Historic State ...

View all property information

Property Type

Islamorada House

Featured review

"Very peaceful and beautiful accommodations"

Impressive location. View from master bedroom is fantastic. House was clean, comfortable, well furnished and great layout. Area is easy to navigate and lots of great restaurants close bye. Green Turtle ...

See all reviews

Show less

Key Largo House
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1 bathroom
1 review

$278

avg/night

$278
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Gorgeous views over Largo Sound in Key Largo Florida. You will be very comfortable in the 2 bedroom 1 bath home with brand new bathroom and updated kitchen. The kitchen has all you need to prepare meals and prepare your favorite frozen drinks, all appliances are brand new. Nautical decor gets in the beachy ...

View all property information

Property Type

Key Largo House

Featured review

"Visit to Paradise"

We loved the house! It had everything we needed! It is close to all activities & right across the road from the sound! The outdoor deck was a great place for kicking back for happy hour! We'll be back!!

See all reviews

Show less

Tavernier House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

$286

avg/night

$286
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool

About this property

Swim. Sleep. Repeat., at Manatee Manor. This 3-bedroom, 2.5-bath home on Plantation Key has something for everyone. Enjoy a drink by the tiki bar, rack ‘em up at the billiard table, or soak up some vitamin D next to the pool. With an entrance just off the carport, the downstairs offers a comfortable ...

View all property information

Property Type

Tavernier House

Show less

Islamorada House
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
2 reviews

Distance to beach: 0.3 miles to Anne's Beach

$144

avg/night

$144
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner

About this property

Enjoy this modern lagoon front ground-level one-bedroom apartment in a single-family home with exclusive use of backyard, pool, dock, and carport. Located on the Gulf side of Lower Matecumbe (Islamorada MM 73.5), minutes from the Channel 2 and Channel 5 Bridges, offering immediate access to the Oceanside. ...

View all property information

Property Type

Islamorada House

Featured review

"Overall excellent .... very comfortable for two with great outdoor ammenities."

this property was great for us as an older couple....park under cover steps from the front door..beautiful pool and canal front and a quiet location. the home is clean and easy to care for and the owner ...

See all reviews

Show less

Islamorada House
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4 bathrooms

$547

avg/night

$547
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Paradise Palms!Located on a cul-de-sac in the charming city of Islamorada, this beautifully- appointed five-bedroom, four and a half-bath home serves as an excellent setting for your tropical getaway. Ideally located in Islamorada on Lower Matecumbe Key, you will have convenient access ...

View all property information

Property Type

Islamorada House

Show less

Lower Matecumbe Key House
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1.5 bathrooms
6 reviews

Distance to beach: 0.5 miles to Anne Beach

$225

avg/night

$225
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Island Conch Cottage A quaint ground level conch style cottage located at the end of a private street in a very quiet setting. Cottage and grounds have privacy fence and gate. The grounds are displayed as a sand beach setting. This property has 60’ of canal frontage located on an extra wide canal ...

View all property information

Property Type

Lower Matecumbe Key House

Featured review

"ANOTHER GREAT EXPERIENCE !!!"

This is my fourth year visiting Islamorada. Something that I look forward to each year. And every year I book this Cottage , I won't stay anywhere else!! It's always clean. If there is anything you need ...

See all reviews

Show less

Islamorada Apartment
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
5 reviews

$150

avg/night

$150
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • WiFi

About this property

The apartment is in a house on the canal and across from the beach with beach access. It is situated on the ground floor of a two storey Keys house where you would be the only residents. All the amenities would be yours and you would have space, tranquility and privacy in the tropically planted landscape. ...

View all property information

Property Type

Islamorada Apartment

Featured review

"Perfect rental for one couple"

This is the perfect apartment for one couple. Wonderful location on the oceanside with ocean views across the street. Has a great dock for your boat with great ocean access. Fish cleaning table is under ...

See all reviews

Show less

Islamorada House | On the beach
6 BR | 5 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 5 bathrooms

$5536

avg/night

$5,536
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Welcome to Caribee Beach House!Discover the enchanting charm of Caribee Beach House, where the timeless allure of old-school Islamorada beautifully melds with stylish comforts. Tucked away in the heart of downtown Islamorada, this hidden gem offers an extraordinary retreat with 200 feet of private ...

View all property information

Property Type

Islamorada House

Show less

Map
Expand map Close map
Florida Keys Vacation Rentals