Florida Keys Vacation Rentals

(250 rentals)
Blue Water Retreat - Location!!!! Gorgeous house with Pool and Ocean Views.

$183

per night

View Details

Key Amenities

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

About this property

Minimum Rental: 28 Days "Blue Water Retreat" is all about the location, location, location! This home has it all - ocean side Lower Matecumbe location, remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from ...

View all property information

Property Type

Islamorada House

Show less

Flamingo Cottage - Adorable 2 bedroom, 2 bath cozy cottage with pool.

Key Amenities

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

About this property

Minimum Rental: 28 DaysFlamingo Cottage is an adorable 3 bedroom stilt home nestled among tropical foliage. There are two bedrooms and one bath on the main living level of this home plus a private studio type apartment with a private bath on the ground level. This home has a cozy cottage like feeling ...

View all property information

Property Type

Islamorada House

Show less

NEW 3/2 POOL HOME

3 BR | 2 BA | Sleeps 6 | Quick View

$300

per night

View Details

Key Amenities

  • Air Conditioning
  • Private Pool

About this property

30 MINUTES TO KEY WEST. BEAUTIFUL LOT WITH COCONUT TREES. BEAUTIFUL BRAND NEW FURNISHINGS. 65" LCD TV IN LIVING ROOM 50" LCD IN MASTER BEDROOM. WORLD FAMOUS LOOE KEY JUST OFF SHORE. TWO QUEEN BEDS AND TWO TWIN BEDS IN THREE BEDROOMS. SONOS MUSIC SYSTEM WITH KLIPSH OUTDOOR SPEAKERS. RELAX IN ...

View all property information

Property Type

Big Pine Key House

Show less

Mitchell's Bayview Villa - Islamorada House on the Bay

$242

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool

About this property

We have recently completed an inside and outside renovation. The Bayview Villa is a private, secluded villa facing Florida Bay and in view of the fabulous Everglades and gorgeous sunsets. Quick access to offshore fishing. Located in a lush tropical hammock in a quiet, one acre residential area (rare). ...

View all property information

Property Type

Islamorada House

"Excellent -- perfect place to stay!"
Reviewed July 30, 2018

This property is amazing -- beautiful and spotless. If you are lucky enough to stay here -- you will appreciate the breathtaking view, gorgeous dock, perfect location and nicely furnished/decorated villa. ...

See all reviews

Show less

Gulfview Getaway - Bayfront Home with Private Beach

$400

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly

About this property

Minimum Rental: 28 Days"Gulfview Getaway" is a FABULOUS BEACH FRONT HOME! This is what you've been dreaming of - your very own single family home with a private sandy beach in the Keys. This home is new to the rental market. It is located in a highly desirable area of Islamorada on ...

View all property information

Property Type

Islamorada House

Show less

Conch Cottage

2 BR | 1 BA | Sleeps 4 | Quick View

$414

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Stay in a beautifully appointed villa or cottage located directly on the Atlantic Ocean. Only a 15 minute drive to Key West's history, restaurants and nightlife, this tropical retreat known as Sea Vista, is as serene as a private island.Enjoy full use of direct TV channels, free current video library ...

View all property information

Property Type

Key West House

Show less

Water Front 3/3 Family and Boat Friendly Home, Great Views

$235

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly

About this property

This beautiful well-kept and spacious two story bay-side waterfront home is a perfect rental home for you and your family. The home has three bedrooms and three baths, 2/2 upstairs and 1/1 down. The expansive great room (22 ft. X 38ft.), which includes the kitchen, dining, sitting and living rooms with ...

View all property information

Property Type

Islamorada House

Show less

Immerse yourself in "The Keys Life"

$167

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Minimum 28 or more days rentalLocated at Mile Marker 90 Ocean Side just minutes to the ocean or bay! Immerse yourself in "The Keys Life" from this Three Bedroom 2.5 Bath waterfront home on a wide canal just off Tavernier Creek enjoy the best boating in the Florida Keys. This desirable location ...

View all property information

Property Type

Tavernier Apartment

Show less

Keys Escape

3 BR | 3 BA | Sleeps 6 | Quick View

$771

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront

About this property

Escape from all your cares at this wonderful vacation rental on Cudjoe Key. Just the spot to unwind and let your hair down. There are 3 bedrooms and 3 baths plus a recreation room for the kids to get away. Open and airy living and kitchen area for friends to gather.Full walk around screened porches ...

View all property information

Property Type

Summerland Key House

Show less

Palms #301 - Darling condo with panoramic views of the Atlantic Ocean.

$77

per night

View Details

Key Amenities

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

About this property

Minimum Rental: 28 Days"The Palms #301" is an 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 ...

View all property information

Property Type

Islamorada Condo

Show less

Bayside Breeze - Beautiful Home with open living, gourmet kitchen and boat lift.

$165

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

Minimum Rental: 28 Days"Bayside Breeze" is a wonderful 2013 built stilt home. Features include an open living area with gourmet kitchen, stainless steel appliances, including a wine refrigerator and granite counters. The oversized center island in the kitchen makes a perfect snack ...

View all property information

Property Type

Plantation Key House

Show less

Best Marathon House

3 BR | 2 BA | Sleeps 8 | Quick View

$214

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Completely remodeled 3 bedrooms, 2 bath house in Marathon - the middle of the Florida Keys, on Mile Marker 51, only one hour to Key West. OUR WEEKS ARE SATURDAY - SATURDAY. Beautiful place in a quiet neighborhood. Direct access to the ocean, with 37 feet of dockage. House set up for fishing and relaxing. ...

View all property information

Property Type

Marathon House

Show less

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

$233

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. Quiet neighborhood with convenient access to grocery stores and other services. Large master bedroom upstairs with big screen TV. Large living room with big screen TV and shuffle board table. Large porch balcony for watching ...

View all property information

Property Type

Big Pine 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

Green Turtle Landing

3 BR | 2 BA | Sleeps 6 | Quick View

$600

per night

View Details

Key Amenities

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

About this property

Sugarloaf Key is one of the most desirable islands in the Lower Keys. Large roomy lots, plenty of biking and walking trails in the area. Kayaking , boating and diving are just some of the water sports you will enjoy during your stay.Green Turtle Landing is just the right spot to spend your Florida ...

View all property information

Property Type

Summerland Key House

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

Show less

Key Lime Sunrise 526 Sombrero Beach Road Marathon, FL

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 1 miles to Sombrero Beach

$243

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Key Lime Sunrise Watch the sunrise & feel the tropical breezes while sipping your coffee from the comfort of the upstairs screened terrace of this lovely and neatly maintained 1,440 sq. ft. two bedroom two & a half bath home situated on Sombrero Beach Road. This charming getaway is within walking/biking ...

View all property information

Property Type

Marathon House

Show less

$1480 wk. AVAILABLE - NO DAMAGE FROM HURRICANE IRMA

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Smathers Beach

$211

per night

View Details

Key Amenities

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

About this property

'TEE BY THE SEA' vacation rental(we include 7 bikes free for our guests!!!)MY VAC. RENTAL SUSTAINED NO DAMAGE FROM HURRICANE IRMA. ITS DOING FINE AND READY TO ACCOMMODATE GUESTS. OUR CONDO COMPLEX IS FINE TOO AND WE ARE READY TO RECEIVE GUESTS. PLEASE MAKE YOUR RESERVATION.We're less then ...

View all property information

Property Type

Key West Condo

Show less

Mobile Home, 2 Bedrooms, 2 Baths, (Sleeps 2-4)

$120

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

This property is located on a very unique spot. Very private. Too perfect to describe.During the day you could sunbathe while fishing for snappers, tarpon and lobsters from your private dock. Later on you may want to jump in for a swim or cruise the area on the kayak At early evening you may enjoy ...

View all property information

Property Type

Tavernier Mobile Home

Show less

MA869

6 BR | 5 BA | Sleeps 14 | Quick View

$514

per night

View Details

Key Amenities

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

About this property

***PLEASE NOTE 7 night minimum***All holidays and lobster weeks are $5200*** Room for everyone with 3 master suites, each with a king size bed and an ensuite bath. One guest room has a queen. There is a small bunk bedroom for the kids. In addition, off one of the master bedrooms there is a twin bedroom ...

View all property information

Property Type

Marathon House

Show less

Manatee Manor - Opportunity to experience The Florida Keys at its best.

$198

per night

View Details

Key Amenities

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

About this property

Minimum Rental: 28 Days"Manatee Manor" is a 3 Bedrooms and 2 ½ Baths home with POOL, Dock, and all new furnishings make this your opportunity to experience The Florida Keys at its best. Conveniently located on a deep and wide canal with easy access to the Bay or a short ride to Tavernier ...

View all property information

Property Type

Tavernier House

Show less

Sunrise on Sunset

3 BR | 3 BA | Sleeps 12 | Quick View

$300

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly

About this property

**AMAZING SPECIAL! 25% OFF RENT MARCH THROUGH AUGUST 2019!** MINIMUM STAY: 28 DAYS “Sunrise on Sunset” is the ULTIMATE BEACH FRONT HOME. There are BREATH TAKING OCEAN VIEWS from almost every room in this house! Play in the sand, walk into the ocean or sit under the covered ground level ...

View all property information

Property Type

Islamorada House

Show less

Beautiful Ocean Sunrise Views!

3 BR | 2.5 BA | Sleeps 6 | Quick View

3

$321

per night

View Details

Key Amenities

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

About this property

Enjoy the sunrise over the Atlantic ocean or relaxing on a private, sunny lanai. Take a cruise around the many canals or out to Florida Bay to capture the sunset. A 30' boat slip is included with the rental. Beautifully furnished living spaces, large dining area, granite counter tops and stainless ...

View all property information

Property Type

Islamorada Condo

"Beautiful Condo"
Reviewed August 15, 2018

We love Bay Harbour Condos! We've stayed in the community 3 times so far and this condo- WILL NOT DISAPPOINT. It's beautifully decorated and very spacious. Owners are sweet and communicate very well! We ...

See all reviews

Show less

Private House Facing the Ocean with New Heated Swim/Pool/Spa LOC LOC LOC

$357

per night

View Details

Key Amenities

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

About this property

Come enjoy the cool clear blue waters of the Florida Keys. The weather is great, lobster season is open from Aug.6th to April 1st. This is a spacious oceanfront home with breathtaking open water views! It is located on beautiful Ramrod Key 85 ft concrete seawall facing the priceless Atlantic ocean teaming ...

View all property information

Property Type

Ramrod Key House

"Fabulous vacation home"
Reviewed August 21, 2018

The home was amazing, plenty of room, lots of fun stuff to do at the home. Beyond amazing cross breezes. Swim spa was really nice. The bikes were great. And the kayaks were a lot of fun. We found lobsters ...

See all reviews

Show less

Palms #214 - Lovely condo with panoramic views of the Atlantic Ocean.

$73

per night

View Details

Key Amenities

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

About this property

Minimum Rental: 28 Days "The Palms #214" is a 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 ...

View all property information

Property Type

Islamorada Condo

Show less

KLYC#20 - 3 BR Townhouse Oceanside with 30' Dock and Boat Lift

$127

per night

View Details

Key Amenities

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

About this property

Minimum Rental: 1 MONTH This is a gorgeous 3 bedroom townhouse in a private upscale ocean front condominium community! Everything you could want is located within the community - heated pool; hot tub; covered seating area; tennis court; children's playground; basketball court; boat ramp; boat slip ...

View all property information

Property Type

Key Largo House

Show less

Plantation Adventure - Sensational remodeled home awaits your arrival.

$217

per night

View Details

Key Amenities

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

About this property

Minimum Rental: 28 Days "Plantation Adventure" is a sensational remodeled single family home on Plantation Key awaits your arrival. The gorgeous POOL, HOT TUB, and TIKI BAR are ready and waiting. Imagine fun filled days and evenings relaxing in the patio and yard area! The patio is spacious ...

View all property information

Property Type

Plantation Key House

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

Islamorada Luxurious Private Sandy Beach Access Tiki Huts Hammocks & more

3 BR | 2 BA | Sleeps 6 | Quick View

3
Owner special: Had a cancellation just now for March 13th to 27th. Available , will give incentives !

Distance to beach: 0.5 miles to White Marlin Beach

$457

per night

View Details

Key Amenities

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

About this property

House, 3 Bedrooms, 2 Baths, Sleeps 6Villa Marlin , 122 Nautilus Drive, Islamorada, Florida Keys mile marker 74.5 bay side, White Marlin Beach located 75 miles south of Miami and 75 miles North of Key West. It has three bedrooms, two bath, private home totally renovated and remodeled, new furniture ...

View all property information

Property Type

Islamorada House

"We'll Be Back!"
Reviewed August 11, 2018

I am SO glad I found this website and this house! After hours spent reviewing properties on other websites and then trying to ask questions through email, it was great to be able to talk directly to the ...

See all reviews

Show less

30 night minimum stay, SUNSET KEY, LUXURY UPSCALE HOME RIGHT ON THE BEACH,

$399

per night

View Details

Key Amenities

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

About this property

30 day stay minimum, 3000 SF, 3BDR, 2.5BATHS, SLEEPS 6 Treat yourself to a dream vacation in our beachfront residence on the private island of Sunset Key, located in the middle of Key West Harbor. Our tastefully designed upscale villa has beautiful ocean views, private pool, and 2 hot tubs for our guests ...

View all property information

Property Type

Key West House

Show less

Instant Ocean Access

3 BR | 2 BA | Sleeps 8 | Quick View

Distance to beach: 4 miles to Sombrero

$279

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Lovely home with lots of glass windows looking towards the ocean. 50 ' of dockage with instant ocean access. 12 Therapy jets in the 14 X 30 pool that ranges from 3' to 5' in depth. The pool overlooks the canal and the ocean. Pool heat is add'l if requested, $200 Three bedrooms, two baths, over 1900 ...

View all property information

Property Type

Marathon House

Show less

Mermaid's Rest

3 BR | 2 BA | Sleeps 6 | Quick View

$543

per night

View Details

Key Amenities

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

About this property

Dreaming of an awesome Florida Keys vacation? This is your perfect pick! This Cudjoe Key home has everything you could wish for and a perfect vacation spot!The home is designed with rich and warm wood tones making it the perfect place to relax after a long wonderful day of fishing and diving in the ...

View all property information

Property Type

Cudjoe Key House

Show less

Deluxe Key West Condo - Minimum 28 days Rental

$150

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Our beautiful deluxe one bedroom condo in Key West Florida on Southard Street is just blocks from the ocean and Duval street. Located in historic old town, the condo is enclosed in a beautiful garden on the ground floor.It is approximately 950 sq ft of air- conditioned luxury. There is a king size ...

View all property information

Property Type

Key West Condo

Show less

Moon Bay A206 - Totally Remodeled Condo with Pool and Dock in Key Largo

$150

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Minimum Rental: 7 DaysSATURDAY to SATURDAY "Moon Bay A206" is calling all fishermen and divers... Whether you plan to fish or dive on your next visit to the Keys, you will find these exceptional accommodations first class and affordable. World famous dive sites are minutes away and phenomenal ...

View all property information

Property Type

Key Largo Condo

Show less

Waterfront / Pool / Two Tiki Huts!

4 BR | 2 BA | Sleeps 8 | Quick View

Distance to beach: 5 miles to Bahia Honda State Park

$167

per night

View Details

Key Amenities

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

About this property

Sorry NO SMOKING or PETS!Minimum 28 days / Please check availabilityGround level 4 bedroom, 2 bath waterfront home on a double lot with a saltwater pool with hot and cold shower, large pool deck and two Tiki Huts. 180 ft of waterfront and 90 feet of dock space with a double fish cleaning table. ...

View all property information

Property Type

Big Pine Key House

Show less

Truman Annex Shipyard Condo-1BR/1BA w/Loft

$185

per night

View Details

Key Amenities

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

About this property

1BR/1BA w/ Loft in Truman Annex close to Ft Zachary Taylor beachThis condo easily accommodates both couples and small families with its unique layout. It features a private bedroom, loft area and sleeper sofa for flexible sleeping accommodations. Located within the gated community of Truman Annex, ...

View all property information

Property Type

Key West Condo

Show less

Direct Oceanfront Views at Sea Gulls

2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 4 miles to Harry Harris Park

$229

per night

View Details

Key Amenities

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

About this property

Sea Gulls 511 is one of the nicest condos in the Islamorada area. It has been completely rebuilt following Hurricane Irma so everything about it is new, upscale, and extremely clean.The living area is open plan with a large island, full kitchen, and most importantly, a fabulous direct ocean view ...

View all property information

Property Type

Tavernier Condo

Show less

Moon Bay A410 - End unit in one of Key Largo's finest bay front condo complexes

$150

per night

View Details

Key Amenities

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

About this property

Minimum Rental: 7 Days"Moon Bay #A410" is a 4th floor end unit in one of Key Largo's finest bay front condominium complexes offers a beautiful view of the Florida Bay and lots of natural light. You'll love the updated kitchen with granite counters, new cabinetry and appliances. New linens ...

View all property information

Property Type

Key Largo Condo

Show less

Key Colony Vacation Rental by Owner

$114

per night

View Details

Key Amenities

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

About this property

Tads Place has everything you need for your Keys Vacation. 30ft of boat dockage,ample parking for your boat trailer and vehicles.Full kitchen all towels and linens provided.Great out door sitting area and grill. Walk in freezer. Washer and Dryer and Cabana Club membership for pool.

View all property information

Property Type

Key Colony Beach Condo

Show less

Luxury Home with Dock, Waterfall Pool, HotTub, Wi-Fi deep water dock up to 60 ft

$400

per night

View Details

Key Amenities

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

About this property

Venetian Shores 4-Bed/4-Bath Luxury Pool Home with 100' Dock & Opt. ElevatorMINIMUM STAY: 29 DAYS Dreaming of a Florida Keys vacation where you can boat, fish, dive, snorkel, or stay home and swim in your own private heated pool? This is it. This home offers a professionally-designed living environment ...

View all property information

Property Type

Islamorada House

Show less

Islamorada Paradise Vacation Home on the Water

$229

per night

View Details

Key Amenities

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

About this property

Great house! Great location!House On Canal… 60 foot concrete dock with fish cleaning stand, water, electricity and dock ladder. Bring your boat, great boat ramps. The house is a short distance to supermarkets, movie theaters, dive shops, and full service marinas with fuel, bait and tackle. ...

View all property information

Property Type

Islamorada House

Show less

Key West Beach Front Rental! Beach Studio Ocean views

Studio | 1 BA | Sleeps 2 | Quick View

Distance to beach: 22 yards to Public use + Private views Waldorf Astoria Resort

$269

per night

View Details

Key Amenities

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

About this property

Ocean View Unit offers, private unit - kitchen/bath, private patio! See calendar before flights! Read base rates before asking rate.Requesting under minimum stay? Just might fly fine! ask new rate. Please {2 person stay} or Add your teen call first. Casa Marina District but ocean side {honestly ...

View all property information

Property Type

Key West Studio

Show less

W. Plaza del Lago - Promises to be a favorite!

2 BR | 2 BA | Sleeps 5 | Quick View

Distance to beach: 0.3 miles to Port Antigua Neighborhood Beach

$133

per night

View Details

Key Amenities

  • Air Conditioning
  • Kid Friendly

About this property

Minimum Rental: 28 Days"West Plaza Del Lago" promises to be a favorite. Beautifully remodeled roomy single family stilt home with vaulted ceilings and located in prestigious Port Antigua on a deep and wide canal. You will love the interior of this home as much as the exterior! As you enter ...

View all property information

Property Type

Islamorada House

Show less

Tree House

3 BR | 2 BA | Sleeps 6 | Quick View

$429

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

Welcome to the Tree House on Ramrod Key. This home is a delightful Florida Keys get-a-way. This home is roomy and spacious to please the whole family. The combination kitchen, dining and living room is just perfect for everyone to gather around and make super cocktails and snacks while planning the adventures ...

View all property information

Property Type

Ramrod Key House

Show less

Waterside Bay

3 BR | 3 BA | Sleeps 6 | Quick View

$714

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront
  • Private Pool

About this property

Come enjoy the breathtaking open water views from the multi-level porches of Waterside Bay!This 3 story custom home has 3 bedroom and 3 baths and has upscale yet comfortable living. Complete with a Gourmet Kitchen of stainless steel appliances and granite counters making entertaining a breeze. The ...

View all property information

Property Type

Summerland Key House

Show less

Conch Bar South - 4 Bedroom Waterfront Home with Swimming Pool

4 BR | 3 BA | Sleeps 10 | Quick View

Distance to beach: 3 miles to Founders Park Beach

$298

per night

View Details

Key Amenities

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

About this property

***FALL SPECIAL*** RECEIVE 20% OFF RENT FOR ALL BOOKINGS IN NOVEMBER AND DECEMBER. Minimum Rental: 28 Days"Conch Bar South" is a magnificent home is located at the mouth of a wide canal in Plantation Key and offers phenomenal open water views. The furnishings are new and provide a comfortable ...

View all property information

Property Type

Tavernier House

Show less

Sunset Oasis

2 BR | 1.5 BA | Sleeps 6 | Quick View

Inquire for rates

View Details

Key Amenities

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

About this property

From the luxury and comfort of the living room or master bedroom you will enjoy a beautiful marina and bay view. Step out onto the first floor floor screened porch and get an even better view. These porch areas are where you will probably spend a lot of time relaxing, reading, doing things on your computer, ...

View all property information

Property Type

Key Largo Townhome

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

$342

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

Barry Beach - Waterfront Cozy House with Dock & Heated Pool!

4 BR | 3 BA | Sleeps 8 | Quick View

1

Distance to beach: 5 miles to Bahia Honda State Park

$429

per night

View Details

Key Amenities

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

About this property

Welcome to paradise! Come experience the amazing Keys and beautiful open water home with 200 foot long dock for your boat. Exclusive heated pool to relax and enjoy the surrounding ocean view - just breath taking! The private lot is .81 acre with one other rental and still very spacious. Stunning panoramic ...

View all property information

Property Type

Little Torch Key House

"Barry Beach"
Reviewed November 1, 2018

Enjoyed every minute....great layout and even better for the watercraft...thank you.

See all reviews

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
  • Kid Friendly
  • Pet Friendly
  • Pool

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

Expand map | Close map
Florida Keys Vacation Rentals