Rentals in Florida Keys
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Water Front Living - Gulf Paradise in Key Largo!
Key Largo Condo - 4.8 Star Review
Beautifully upgraded condo on the Gulf of Mexico! Located at Mile Marker 104. Great for families, fishermen, divers and snorkelers, and those who want to just want to get away!
Recently remodeled, fully equipped kitchen with granite counter tops new appliances, and a dining room table for 6. Newly tiled floors in the kitchen and living.......read more
2 Bedroom(s)
Sleeps 6
Condo
Spacious Ocean Front Resort - 3 Bedroom Condo
Key West Condo - 4.6 Star Review
This 2,000-square ft-condo is unique in that it has two large master bedroom suites with changing areas and private baths plus a third bedroom w/bath. A pull out sofa bed allows for total accommodations for 8 people. With the master suites on opposite ends of the condo, it is a great set-up for 2 or 3 couples as well as for friends or families who .......read more
3 Bedroom(s)
Sleeps 8
Condo
Waterfront Penthouse sleeps 16 w/Pool & Boat Dock
Key West Condo - 4.0 Star Review
Summary:
Gorgeous completely renovated 2400sqft waterfront Penthouse condo in downtown Key West. Boat slips available on-site with commercial ice machine, fish cleaning station and BBQ. Located in historic downtown Key West. 4B/4B with loft, sleeping 16. Less than 1mi to Duval Street, Historic Seaport, Hemingway House, etc. On-site amenities: he.......read more
4 Bedroom(s)
Sleeps 16
Condo
Charming oceanfront condo with pool, beach access, tennis, & washer/dryer
Islamorada Condo
Escape to the Keys A6
Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'
Escape the hustle and bustle of everyday life in the tropical Florida Keys, where tranquility and fun await. This condo is steps away from the water, with all you ever need for .......read more
2 Bedroom(s)
Sleeps 8
Condo
Summer Breeze: Spectacular View, the Beach, Pool and all the Amenities. 2BR/2BA
Key West Condo
*BRAND NEW LISTING* 'Summer Breeze' will make you and your family feel fine! This is a gorgeous, clean, upgraded, top floor, 2/2 condo, with a spectacular view! Common pool, grill area, tennis court and a nice friendly atmosphere will make you and your family happy to have chosen this great property. Smathers Beach is across the street, Higgs Be.......read more
2 Bedroom(s)
Sleeps 6
Condo
2 bdrm Condo w/ boat slip Pelican Landing Bermuda
Key West Condo - 4.4 Star Review
Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or a penthouse for up to twelve guests you will enjoy your stay at Pelican Landing. If traveling with a boat, the facility is boat accessible by powerboat only, because a fixed bridge offers only an 18-foot clearance. The marina off.......read more
2 Bedroom(s)
Sleeps 8
Condo
Your Happy Place - gorgeous 2 bed 2 bath oceanfront suite with full kitchen
Tavernier Condo
Experience the ultimate coastal getaway at Ocean Point in Tavernier, Florida. Nestled along the stunning shores of the Atlantic Ocean, our exquisite 2 bedroom, 2 bathroom condo offers unrivaled ocean views from the moment you step through the door.
Step outside and immerse yourself in the salty paradise of the pristine beach or take a leisu.......read more
2 Bedroom(s)
Sleeps 7
Condo
DOWNTOWN KEY WEST 2BED OCEANFRONT!
Key West Condo - 4.0 Star Review
This is a great OCEANFRONT unit with large balcony to watch sunsets. Hyatt Sunset Harbor is perfectly located in downtown Key West next to Mallory Square and the Mel Fisher Museum. Walk along the boardwalk, shop in the local stores, or head to Duval Street only a couple blocks away. The resort has pool, hot tub, and grills for use during your stay........read more
2 Bedroom(s)
Sleeps 6
Condo
Islamorada Oceanfront Paradise
Islamorada Condo - 5.0 Star Review
Escape to the Keys at this renovated condo in the heart of Islamorada. Walking distance from some of the best local restaurants as well as Bud N’ Mary’s Marina- you’ll be living like a true islander in no time! Your days will be filled lounging by the pool or relaxing down by the ocean. End the day hosting your own happy hour at the tiki bar’s min.......read more
2 Bedroom(s)
Sleeps 4
Condo
Cozy & Charming Waterfront Condo
Marathon Condo - 5.0 Star Review
Completely renovated waterfront crystal clear deep water canal condo with easy access to the bay and ocean with boat dock. Two bedrooms, 2 baths, full kitchen, spacious dining & living room, two new TV's, cable TV, WiFi, heated pool, BBQ and Tiki Hut. Reserved parking. Conveniently located walking distance from supermarkets, restaurants, shops, .......read more
2 Bedroom(s)
Sleeps 6
Condo
Modern 2BR Condo Old Town/Balcony & Pool
Key West Condo
Come enjoy this fully updated 2/BR condo in the heart of Old Town. The perfect balance of being close to all the action & far enough away to enjoy a quiet getaway. Get comfortable in this clean & comfy home, which offers two private balconies, updated kitchen & modern bath. Desirable Southard Square is surrounded by tranquil tropical gardens & a he.......read more
2 Bedroom(s)
Sleeps 4
Condo
HONEY~ Adult Only, 2nd Floor 1 King Bedroom Unit w/ Shared Pool!
Key West Condo - 4.9 Star Review
Gorgeous 2nd floor king room and ample balcony space...
DELIGHT IN OLD WORLD ALLURE...
Bask in the charming ambience of the adults-only Scarlet Mango Inn which houses 6 stunning rooms. Built during the Lincoln Era, this architectural gem is a destination to Key West classic Bahamian-style design. Originally a Conch Republic estate, this d.......read more
Studio
Sleeps 2
Condo
Gulf View Retreat @ Bay Harbor
Islamorada Condo - 4.7 Star Review
Escape to the breathtaking Gulf View Retreat in the highly coveted Bay Harbor community! Prepare to be enchanted by this hidden gem, nestled on the pristine shores of Lower Matecumbe Key in Islamorada, eagerly awaiting your arrival for your next unforgettable vacation. Discover the allure of Bay Harbor, a captivating four-building complex offering .......read more
2 Bedroom(s)
Sleeps 4
Condo
**PROMENADE TO PARADISE @ THE ANNEX** Ocean Condo & Pool + LAST KEY SERVICES...
Key West Condo - 5.0 Star Review
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!
If you dream of waking up to expansive water views and island breezes, and walking out your front door right onto the streets of Old Town Key West in the center of it all - PROMENADE TO PARADISE is everything you are looking for. With a .......read more
2 Bedroom(s)
Sleeps 5
Condo
Historic Caroline Street Condo!1 Bedroom 2 Bath, Pool, Amazing Old Town Location
Key West Condo - 5.0 Star Review
The gracious building at 616 Caroline Street, exquisitely renovated into 6 condominiums, claims a long and proud history that befits its esteemed place along one of the most elegant streets in Key West. Unit # 6 is a second floor, 1BR/2BA unit that is entered on the left side of the building. The condo unit includes hardwood floors, granite counter.......read more
Studio
Sleeps 2
Condo
Centrally located gem with shared pool/hot tub, fast WiFi, patio, grill & AC
Key West Condo
Porter Paradise
Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'
Get ready for packed days of coastal fun here at Porter Place, your very own sliver of Key West! Sitting within walking distance of a plethora of shops, restaurants, and attractions, .......read more
2 Bedroom(s)
Sleeps 4
Condo
?AQUAMARINE OCEANVIEW?FLASH⚡️SALE+DOCK+TENNIS+POOL+SPA+GYM+⭐️BEST REVIEWS
Islamorada Condo - 5.0 Star Review
? PLEASE EMAIL US WITH ANY QUESTIONS??? WE ARE HAPPY TO PROVIDE THE ANSWERS ABOUT OUR PROPERTY, OUR RESORT, RESTAURANTS, WATER SPORTS and ACTIVITIES!
?WE ARE ONE OF ONLY A FEW LEGAL 7 NIGHT RENTALS IN ISLAMORADA AND THE FLORIDA KEYS -THERE IS A 28 NIGHT MINIMUM RENTAL LAW & ILLEGAL RENTALS ARE SHUT DOWN DAILY- BUYER BEWARE!
?CONCIE.......read more
2 Bedroom(s)
Sleeps 6
Condo
Oceanfront Luxury ~ 4-bedroom on white sand beach! 311 Mariners Club Key Largo
Key Largo Condo - 5.0 Star Review
NEW ON THE RENTAL MARKET!
If this villa has come up in your search for that ‘special’ vacation accommodation…you can stop right now. Villa 311 Mariners Club is your destination for total rest and relaxation or a jumping-off point for watersports, sightseeing and eco-adventures in Key Largo and throughout the Florida Keys.
.......read more
4 Bedroom(s)
Sleeps 10
Condo
OCEAN BREEZE at The Truman Annex in Key West
Key West Condo - 4.6 Star Review
Gorgeous open water views from this 2-bedroom, 2.5 bath condominium in Harbour Place in the award-winning Truman Annex! | Directly facing the ocean, where the Gulf of Mexico and Atlantic Ocean meet, this nicely furnished condominium enjoys a large waterfront plaza with chaise lounges and front row seating for sunset. | There is a beautiful communit.......read more
2 Bedroom(s)
Sleeps 5
Condo
Truman Annex unit 254
Key West Condo - 4.8 Star Review
Key Lime has a large open kitchen, vaulted ceilings and tile floors throughout. This immaculate unit has two-bedrooms, 2 baths and private patio with tropical views. Amenities include: Central AC, Dishwasher, Washer/Dryer, Color Cable TV, VCR, CD Player, Ceiling Fans, Sleeper Sofa, Community Pool, Sleeper Sofa, Full Kitchen,
This and.......read more
2 Bedroom(s)
Sleeps 5
Condo
STAY SALTY! ??Amazing Ocean Views!
Tavernier Condo - 4.9 Star Review
2 bedroom/2 bath condo has amazing views and is located on the top (4th) floor. Balcony in main living area and private balcony in primary bedroom EnSuite. Ocean Pointe Resort is located approximately 70 miles south of Miami International Airport (MIA) and 98 miles from Fort Lauderdale airport (FLL). Clean and comfortably furnished. Beds have comfo.......read more
2 Bedroom(s)
Sleeps 6
Condo
**THE OSPREY'S NEST @ SUNRISE SUITES** Condo & Pool + LAST KEY SERVICES…
Key West Condo
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!
Want to be in Key West, have access to all the fun, but not be in the middle of the crowd at the end of the day? Then step away from the hustle and bustle and come roost at… THE OSPREY’S NEST. Boasting views from your private balcony on .......read more
2 Bedroom(s)
Sleeps 6
Condo
Bayside Condo with Boat
Key Largo Condo - 4.3 Star Review
One bedroom unit with queen sleeper in living room. Unit has washer, dryer, barbecue, wifi, cable tv.. The condo is located near shops and restaurants and there is a dive shop and bait shop located on the premises. The large screened patio overlooks the dock and the Mako Center Console that is included in the rental. The pool at the Jacobs Aqua.......read more
Studio
Sleeps 4
Condo
Stunning Condo ✺ Unwind in Tropical Oasis
Tavernier Condo - 4.1 Star Review
Welcome to Ocean Pointe Suites!
Come unwind in our tropically inspired 2 bedroom 2 bath condo – an escape to paradise awaits! This vacation condo offers a fully equipped kitchen, washer/dryer and living area. We are set on a 60 acre sanctuary– no city lights – no traffic sound - simply paradise! Close to all attractions in Key Largo and Isl.......read more
2 Bedroom(s)
Sleeps 6
Condo
Oceanfront Key Largo Paradise ~ Private Beach~Pool~Tennis~Free WiFi & more....
Tavernier Condo - 4.9 Star Review
Welcome to our unobstructed oceanfront Peace of Paradise! Your relaxation, fun, memories for a lifetime starts here.
As you enter this lovely coastal cottage feel condo you are greeted with an amazing panoramic view of the Atlantic Ocean. If you are looking to stay in accommodations of high standards, this is the place for you!
Peac.......read more
2 Bedroom(s)
Sleeps 4
Condo
Ocean breeze- Gorgeous 1 bed/ 2 bath condo with stunning Ocean views & huge pool
Marathon Condo
Welcome to Ocean Breeze! This stunning oceanfront condo with breathtaking views of the sparkling blue water is waiting to be your home away from home. It's the perfect place to relax and soak up the beauty of nature.
The kitchen is fully stocked with all the essentials and more, ready for you to whip up delicious meals. The living room is a.......read more
Studio
Sleeps 4
Condo
The Grand Turk by Brightwild | Sunset View & Pool
Key West Condo - 4.3 Star Review
Summary:
- Welcome to the fun-filled Sunrise Suites complex located on the quiet side of Key West.
- Just 1 mile from the beach where aqua blue waters & loungers await.
- Only a 10 minute ride to downtown Duval Street restaurants, attractions & nightlife.
- Top floor condo in a four-story building, located close to the airport and ind.......read more
2 Bedroom(s)
Sleeps 6
Condo
FANTASY WEEK
Key West Condo
Set along the Atlantic Ocean, Hyatt Windward Pointe Resort blends the laid-back Key West style with a modern, upscale resort ambiance. Here is a retreat where you can slow down and forget the rush and stress of your day-to-day life. Bask beside the lushly landscaped pool that gives you the illusion that you’re softly floating on the open sea, grab .......read more
2 Bedroom(s)
Sleeps 6
Condo
Pelican's Retreat, NEW 1B/2B
Marathon Condo
Summary:
Time to relax! Bring your family & friends to this 720 sqft. Oceanview home or just work remotely while enjoying the beautiful sunsets from your dedicated work area. Located in a gated fishing village in Marathon Key, FL.
Fish cleaning station, community clubhouse & grill, open grounds along the waterfront edge, perfect for cornhole.......read more
Studio
Sleeps 4
Condo
Price Reduction!!! Penthouse Suite @ KW, Galleon Resort, Avail 7/11-7/15/2023
Key West Condo - 4.5 Star Review
The Galleon Resort is the best location in Key West, walking location to all the bars and fun, but quiet at night, Old Town location, many restaurants right up the boardwalk and nearby! We own week 26 and 27, so this year, we are staying from the 1st till the 11th, and our Beautiful Penthouse Suite is available from July 11th till July 15th, 2023!.......read more
3 Bedroom(s)
Sleeps 8
Condo
Hyatt Windward Pointe, Key West, Fl. - 2 Bedroom Unit - 1064 sq/ft
Key West Condo
3rd floor (top level accessible by elevator or stairs) Balcony faces the Atlantic Ocean and gardens. 2 bedrooms (large master suite) Full kitchen/dining room, Living room with a pull out sofa to sleep 2 more. Very Clean!!!
.......read more
2 Bedroom(s)
Sleeps 6
Condo
FOREVER YOUNG at The Truman Annex in Key West
Key West Condo - 4.1 Star Review
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water and sunset views from the large and luxurious pool area. This beautifully decorated stately Condo has wonderful views of the Truman's Little White House Museum grounds where United States Presidents and many other world wide heads.......read more
2 Bedroom(s)
Sleeps 5
Condo
FALL 2023 DISCOUNT** Charming Kawama Condo with Pool, Beach & More
Key Largo Condo - 5.0 Star Review
Enjoy Kawama Yacht Club, an oceanside oasis with an abundance of amenities.
Kawama Yacht Club 408 is a charming 2 bedroom, 2 bath condo with a fully equipped kitchen, spacious living room, and a balcony perfect for enjoying the ocean breeze. With a master ensuite and guest bedroom with 2 full beds, this is the perfect family retreat.
2 Bedroom(s)
Sleeps 6
Condo
Islamorada get-away.
Islamorada Condo - 4.0 Star Review
Cozy condo in Islamorada, mile maker 76.5. Walking or biking distance to Robbie's where you can feed the tarpons. Close to great restaurants and shops. 5 minute car ride to Anne's Beach. Canal view. Amenities: Pool with restroom and outside shower on-site, tennis & pickleball courts, Bar B Q Area with tiki, outdoor shuffleboard and horseshoe gaming.......read more
Studio
Sleeps 4
Condo
**OLD TOWN OASIS @ THE ANNEX** Oceanside 2BR/2BA Condo & Pool + LAST KEY SERVICE
Key West Condo - 5.0 Star Review
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!
OLD TOWN OASIS is back! After three years out of the rental program, this luxurious condo has returned, with all the same elegance enjoyed by many guests since 2004, and with many improvements.
You’ll be staying right near the oce.......read more
2 Bedroom(s)
Sleeps 6
Condo
Classic Dog-Friendly Condo with Shared Pool, Central AC, and High-Speed WiFi
Key West Condo - 4.5 Star Review
Sunrise Suites - Butterfly Nest 107
Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'
Wind down at this family-friendly condo in a great Key West location! Central air conditioning will help everyone keep comfortable throughout your stay. But there'.......read more
2 Bedroom(s)
Sleeps 6
Condo
Mariners House @ Landings of Largo
Key Largo Condo - 5.0 Star Review
This one of a king townhouse is just waiting to host your vacation! At the Mariners House you will have access to all the amenities of Landings of Largo such as the pool, shuffle board, tennis courts, basketball court, boat ramp and fishing pier. This home also has bicycles and kayaks for your to use as well!
Relax in one of the two large living.......read more
3 Bedroom(s)
Sleeps 8
Condo
WORLDS END at The Truman Annex in Key West
Key West Condo - 4.6 Star Review
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water and sunset views from the large and luxurious pool area and large terraces. This beautifully decorated two bedroom, two and a half bath stately condo has wonderful views of the Atlantic Ocean and Sunset Key along the length of the.......read more
2 Bedroom(s)
Sleeps 5
Condo
Vibrant, waterfront retreat with WiFi, balcony & dock access
Marathon Condo - 4.0 Star Review
A Little Piece of Paradise
Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'
Set up on the fourth floor with a front-facing view of the adjacent waterway, this comfortable condo is an excellent option for that next romantic escape to the Keys! This .......read more
Studio
Sleeps 3
Condo
Paradise Oasis! Beautifully renovated 2/2 with show stopping Sunset Views
Key Largo Condo - 5.0 Star Review
Recently renovated 2 bedroom 2 bathroom condo overlooking the gorgeous Florida Keys sunsets. If you've been looking for a nice relaxing getaway, look no further! This family friendly community has everything you need! Buttonwood Bay boasts over 42 acres of tropical lush landscaping. Once you drive in, you'll feel like you've been transported to an .......read more
2 Bedroom(s)
Sleeps 6
Condo
Simply Paradise! Key Largo Oceanfront Penthouse Condo-sleeps 6
Tavernier Condo - 4.7 Star Review
Location, location, location is the key to your family vacation ! One of the best locations in the Ocean Pointe Resort with great ocean views, closest building to the pool and since you are in the penthouse, there is no noise to come from above.
Your vacation begins the moment you drive through our gatehouse entrance into our beautifully landsc.......read more
2 Bedroom(s)
Sleeps 6
Condo
Family Condo Vacation paradise, Olympic Pool, Beach, Space to Relax!
Key Largo Condo - 4.7 Star Review
Make your vacations plans to enjoy everything about the Fabulous Florida Keys. Our beautiful condominium, Tarpon Cove, is located at OCEAN POINTE RESORT, a private 65 acre Spacious resort. For a limited time, we are offering a "free cleaning" - no expensive cleaning charge in face absolutley free! Our Tarpon Cove unit is the "D" style floor plan.......read more
2 Bedroom(s)
Sleeps 6
Condo
Oceanfront condo in the heart of Key West
Key West Condo - 5.0 Star Review
Enjoy gorgeous waterfront views in one of the most quiet and serene area of Key West while being 5 min away from the iconic Duval Street. This stylish and modern condo offers you all the amenities you need for a memorable stay. Walk out of your master bedroom right into the pool area or enjoy a relaxing evening on the spacious oceanfront porch. Ta.......read more
2 Bedroom(s)
Sleeps 6
Condo
Key Largo Luxury Condo, Floor Level, Canal-Front, Boat Dock
Key Largo Condo - 5.0 Star Review
Beautifully updated and decorated condo in the incomparable Buttonwood Bay community. It is hard to find this level of convenience and comfort and style. This ground-floor unit offers quick and comfortable access to both your car and to the patio for enjoying coffee and cocktails. Not to mention the stunning view of the harbor where you can enjo.......read more
2 Bedroom(s)
Sleeps 4
Condo
**MODERN MAJESTY @ THE ANNEX** Oceanside 3BR/3.5BA Condo & Pool + LAST KEY SERVI
Key West Condo
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!
MODERN MAJESTY is a stunning, freshly renovated three-bedroom condo that checks every box for the perfect vacation rental. This large unit is laid out over one floor, meaning you don’t have to worry about stairs. The three bedrooms are l.......read more
3 Bedroom(s)
Sleeps 6
Condo
Penthouse Level Ocean Views- Live the Dream
Key West Condo - 4.8 Star Review
PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY
You feel the excitement the moment you arrive. The warm tropical breezes, the blue green water. It's a rhythm. A rhythm set into motion over a century ago by pirates, artists, writers and other champions of leisure. Today that same rhythm beckons you to discover the charm and grac.......read more
2 Bedroom(s)
Sleeps 6
Condo
The Palms...A beautiful space in the perfect place.
Key West Condo - 5.0 Star Review
The perfect space in the perfect place.
A quiet oasis on the 2nd floor nestled amongst palm trees in the shipyard section of the Truman Annex, it is perfectly located steps from Duval street, Mallory Square, Zachary Taylor State Beach, Truman Waterfront Park, Bahama Village and all the best that Key West has to offer........read more
2 Bedroom(s)
Sleeps 4
Condo
Tropical Oasis - 1 Bed/2 Bath!
Islamorada Condo
Wake up and enjoy a great cup of coffee on your private balcony. Breathe in the salty sea air as you plan your day. Relax and be lazy on the private beach, or large heated pool. Adventures can try their hand at the plenty of water activities offered onsite and nearby. Although Oceanfront, not all units have a direct Ocean View.
This s.......read more
Studio
Sleeps 6
Condo
Find a Great Selection of Florida Keys & Key West Condo Rentals
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book directly online to save! Choose from rentals with Wi-Fi, Pool, Oceanview, Beachfront and other amenities we have to offer for Florida Keys