Book Direct & Save - No Booking Fees

Florida Keys Vacation Rentals

(576 rentals)
Islamorada Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

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

About this property

We have owned and rented this property for 20 years and have been coming to Seagulls Condominiums for over 40 years. The condo bathrooms and bedrooms have just been updated and the entire building has just finished a major upgrading and painting. If my pics don't import from vrbo 49422, then you...

View all property information

Featured review

"Outstanding view and amenities. Will return soon!"

Classic art deco style building which was fully remodeled both inside and out. The owners are very responsible and have been doing this a long time.

See all reviews

$295
avg per night
Islamorada House
Sleeps 8, 4 bedrooms, 3 bathrooms
4 reviews

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

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

$650
avg per night
Little Torch Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool

About this property

Aaarrrghhhhhhh MATEY! Florida Keys Vacation Rentals – Looking for a perfect sunny get away in the beautiful Florida Keys? Blackbeard’s Bounty is just the place for you and your guests!This tropical oasis is located on Little Torch Key and is only 28 miles from Key West. Situated on a wide...

View all property information

$342
avg per night
Islamorada Condo
Sleeps 6, 2 bedrooms, 1.5 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

Beautiful area of island on ocean

View all property information

$97
avg per night
Key West House
Sleeps 8, 2 bedrooms, 2 bathrooms

Distance to beach: 0.8 miles to Simonton Beach

Key Amenities

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

About this property

AboutClassic Old Key West HomeThis home offers a rare combination of location, charm, and character. With a beautiful mix of historic details and modern updates throughout, it’s perfect for couples traveling together or anyone hosting visitors during their stay in paradise.Primary guest...

View all property information

$259
avg per night

Why Choose FloridaRentals.com?

No booking or service fees

No Booking or Service Fees

Save up to 25% compared to other websites - no hidden costs.

Connect Directly with Hosts

Connect Directly with Hosts

Book with confidence and get the best rates.

Florida's #1 vacation rental listings site

Florida's #1 Vacation Rental Site

Trusted by millions - your go-to for the perfect Florida getaway.

Islamorada House
Sleeps 3, 1 bedroom, 1.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

PROPERTY NAME: Sunshine Place 84371 Overseas Highway, Islamorada, FLLOCATION: Oceanside HouseMINIMUM STAY: WeeklyMILE MARKER: 84.3DETAILS: "Sunshine Place" is setup perfectly for privacy and convenience. The owners of this wonderful property called Sunshine Place are willing...

View all property information

$267
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 4 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Must See Stunning 3095 Sq. Ft 4/4 SFH on ground level with pool, 45 ft of dockage, outdoor kitchen and access to the ocean by boat.This gorgeous property features an open floor plan with elegant furnishings, state of the art kitchen with Viking appliances and an induction cooktop, quartz countertops,...

View all property information

Featured review

"Sunny Daze in Marathon!"

I didn’t know much about Marathon other than it was in the keys. Upon hearing from a family friend that it was the Keys best kept secret we couldn’t resist. The Sunny Daze house was perfect for my family...

See all reviews

$1,216
avg per night
Key West Cottage
Sleeps 4, 2 bedrooms, 1 bathroom
3 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

The Mile Zero House is a MONTLY VACATION RENTAL. Rent one or more months comes completely furnished. Charming conch home with true Key West character. Fenced for privacy with a open style front porch to enjoy the local flavor along with a passing Conch Train. Full size kitchen that is nicely stocked with...

View all property information

Featured review

"Amazing Location!"

Historic Conch House Located Downtown Key West near Duval St and restaurants beach and many attractions ! Private Yard fully locked and fenced with beautiful plants Sitting on the front Porch you feel...

See all reviews

$150
avg per night
Tavernier Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • WiFi

About this property

Relax amongst the tropical sights and sounds in this charming ocean front condo.Ideal for couples, solo & budget travelers, Key West Road Trippers, Snowbirds, Sea-Foodies, Divers, Snorkelers & AnglersSEAS THE DAY - OR JUST RELAX - YOU'RE ON ISLAND TIME!The space With thoughtful and...

View all property information

$235
avg per night
Summerland Key House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to Buccaneer Boathouse! Pack your floral shirts, swimming gear and sandals and come on down to Little Torch Key in the beautiful Florida Keys. This lovely home is spacious with 2 bedrooms and 2 bathrooms. It offers a large open kitchen, dining and living area for everyone to hang-out and plan...

View all property information

$157
avg per night
New
Big Pine Key House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

This charming 2-bedroom, 2-bath rental home is perfect for your tropical getaway! With a minimum stay of 28 days, it accommodates up to 6 adults and 1 child, making it ideal for families or groups. The master bedroom features a king-size bed, while the guest bedroom offers a queen-size bed. Additional...

View all property information

$200
avg per night
New
Tavernier House
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Key Amenities

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

About this property

Bayfront Serenity | Seasonal Waterfront Retreat | 4 En-Suite Bedrooms | Pool, Dock & Sunsets | Tavernier, Village of Islands (Islamorada)Welcome to Bayfront Serenity, a private waterfront retreat in Tavernier’s exclusive Village of Islands in Islamorada, where sweeping bay views, breathtaking...

View all property information

 

Key Largo House
Sleeps 10, 5 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Private pool
  • WiFi

About this property

This lovely house in Key Largo offers 5 cozy bedrooms with a mix of queen, king, and full beds. Each of the 5 bathrooms is equipped with a refreshing shower. With AC and heating, guests will stay comfortable year-round. The outside living area has a heated pool and built in gas bbq grill. This marvelous...

View all property information

$650
avg per night
Big Coppitt Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 5 miles to Smathers Beach

Key Amenities

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

About this property

3 bedroom 2 bath home, heated / chilled pool, plenty of parking for trailers / boats / on a deep water canal with a view to die for. Our home is fully fenced with a large gate opening to enter with your boat trailers etc. (Two king size beds and a full size bunk on the bottom and a twin on top. We...

View all property information

$283
avg per night
Key West Condo
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 Please be advised that a balcony restoration project will be underway at 1800 Atlantic from May 2025 through Spring 2026. Important Notes: -Units available for booking will...

View all property information

$1,437
avg per night
Key Largo Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
20 reviews

Distance to beach: 0.1 miles to At Kawama Yacht Club

Key Amenities

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

About this property

Enjoy Key Largo - A Year Round Vacation Paradise *** Short Term Rentals Available**** * * NO PETS * * *NO PETS * * *NO PETS * * *. - the Associate does not permit renter's pets!!!* * * SPECIALS LISTED HERE WHEN AVAILABLE * * * RATE REDUCED - March 7 - 11 (4 nights) Inquire...

View all property information

Featured review

"Nice place"

They are individually owned condos with different layouts. Ours was nice but don’t expect it to be a five star hotel, they’re family vacation homes. There are three pools and a playground. It has a...

See all reviews

$161
avg per night
Cudjoe Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 10 miles to Bahia Honda

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Paradise Palms! This amazing 3 bedroom home on Cudjoe Key is perfect for your next Florida Keys vacation! Tropical landscaping surrounds an inground pool that overlooks a beautiful canal...everything you could want and more! There is also large concrete dock for your boat, quick easy ocean...

View all property information

Featured review

"Excellent location & Super clean Home"

My family and I stayed for the month of June 2022 and this was the first time we had visited Cudjoe Key. The house was beautiful and VERY clean. The kitchen was well equipped with everything you needed...

See all reviews

$290
avg per night
Big Pine Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

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

About this property

This lovely waterfront home has it all. This fantastic community is one of the most unique places in the world. In minutes you can explore the beautiful back country or Ocean by kayak or boat. Marine Life sightings and fishing is the best in this area. You can lay back and relax, away from it all and...

View all property information

Featured review

"Cute tropical home!"

Friendly neighborhood!! Neighbors shared some fresh fish they caught. We loved taking a walk morning and evening to take photos of all the little key deer. Walked to the neighborhood private park to watch...

See all reviews

$145
avg per night
Islamorada Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
9 reviews

Distance to beach: 0.9 miles to Founders Park

Key Amenities

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

About this property

Oceanfront gated community. Offers pool overlooking the ocean, pier which you can fish off of, clubhouse, sauna, exercise room, and very clean bathrooms by the pool. 2 Bed, 2 Bath. Master bedroom offers queen bed, sitting room, coffee, 50 inch smart tv, storage, master bath separate toilet. 2nd Bedroom...

View all property information

Featured review

"Super comfortable condo - amazing location - wonderful host!"

We spent a month in Sharon's condo (January 2025). Upon arrival we had everything we needed for the month! She goes above and beyond stocking the kitchen, cleaning supplies, pantry etc. The bedrooms are...

See all reviews

$150
avg per night
Summerland Key House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

The Shores of Sugarloaf Luxury Waterfront Home with Gorgeous Pool, Tiki Bar and SunsetsWelcome to the Shores of Sugarloaf, the perfect Florida Keys Island Getaway. Check-in to this gorgeous coastal home and enjoy a lovely vacation on one of the Florida Keys most desirable keys-Sugarloaf. This house...

View all property information

$495
avg per night
Islamorada Townhome
Sleeps 4, 2 bedrooms, 2.5 bathrooms
1 review

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

Featured review

"Great Location"

This condo was very conveniently located. We could snorkel at John Pennekamp and kayak the mangroves of Islamorado. Plenty of close good seafood restaurants in vicinity. Spend the day at Bahia Honda.

See all reviews

$265
avg per night
Marathon House
Sleeps 6, 2 bedrooms, 1.5 bathrooms
3 reviews

Distance to beach: 3 miles to Sombrero Beach

Key Amenities

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

About this property

The Cozy Conch is ideally located, just walking distance from the historic 7 mile bridge. Take a bike ride along Overseas Highway, enjoy the nearby beaches or spend the day at our pool. Have a cozy night by the fire pit at the dockside lounge and BBQ area or the hammock park. The lower levels offers...

View all property information

Featured review

"Exceptional Property"

We stayed for two months and the location is great - so close to 7 mile bridge! Owners have thought of everything and very well equipped in kitchen and elsewhere. I’ve never had a rental with the extras...

See all reviews

$112
avg per night
Key Colony Beach House
Sleeps 10, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Plentiful. Key Colony Beach 4 bedroom with 37 Ft Dock, Pool Club. Sleeps 10 Spacious, 2200 sq ft duplex home on a wide canal with dock in beautiful Key Colony Beach.Includes free use of nearby, ocean-front beach club with a huge, temp-controlled pool and Hot Tub!!Lower Level - 1 bedroom, 1 bathroom...

View all property information

$353
avg per night
Tavernier Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
12 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

Coastal décor greets you in this two bedroom two bathroom Oceanfront Condo in Building 3. The comforting living room features a flat screen TV, and sliding glass doors that open to the step-out balcony offering sweeping views of the Atlantic. Visit delicious local restaurants or create amazing...

View all property information

Featured review

"Best place in the Keys!"

I’ve stayed here multiple times and it is always very clean and smelling great! The AC is always kept low and feels great walking in after being out in the Florida heat. PLENTY of things to do and plenty...

See all reviews

$255
avg per night
Ramrod Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Clean, Tropical 3/2 on open canal in quiet residential neighborhood on a cul-de-sac. House is on Gulfside with quick access to Miles Channel Bridge towards ocean or bayside. 50’ concrete dock with fish cleaning station.Master Bedroom has a queen size bed, shower and indoor jacuzzi tub. Second...

View all property information

Featured review

"Wonderful Times!"

Alex and I had a wonderful time in your beautiful home. Loved eating dinners (breakfast and lunch too!) sitting outside. Peaceful and lovely. The storage room downstairs was perfect for storing all our...

See all reviews

$240
avg per night
Key West House
Sleeps 4, 4 bedrooms, 3 bathrooms

Distance to beach: 2 miles to Smathers

Key Amenities

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

About this property

Available for 28 night mimimum stays, due to Key West regulations so the rate for the month is for 28 nights, as we need to be able to get people in to do things/maintenance in between guests. In high season If you are renting for one month only the stay would start on the 1st and end after 28 nights,...

View all property information

$200
avg per night
Key Colony Beach Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

$2,,400 - $3,200/wk., depending on season. 7 night minimum stay. Saturday-to-Saturday only during high season.Key Colony Beach is called the “Gem of the Keys,” and for good reason! Our very well-appointed and recently updated 2BR, 2BA condo is DIRECT beach front, on one of the most beautiful...

View all property information

Featured review

"SNOW BIRD's Stress Relief"

Just what the Wife Ordered:) We own a Little Bar in West Mich. Called Cocktailz Sports Bar & Grill Plus Myself Ernie is a Realtor. We always try to get away in March every year to a Special Place that...

See all reviews

$419
avg per night
Islamorada Townhome
Sleeps 6, 2 bedrooms, 3 bathrooms
1 review

Key Amenities

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

About this property

Enjoy breathtaking sunsets on the private beach while staying in this beautifully remodeled corner unit. The unit was completely gutted in 2021 and features 2 bedrooms plus a built out loft and 3 full bathrooms.The unit has a huge master with a king bed plus a bathroom/walk-in closet and...

View all property information

Featured review

"A perfect place to relax and unwind"

Spending the month of December at this beautiful condo with my family was an unforgettable experience. The condo itself was warm, cozy, and inviting, with all the amenities we could possibly need for a...

See all reviews

$171
avg per night
Key Largo Villa
Sleeps 8, 3 bedrooms, 3.5 bathrooms
4 reviews

Key Amenities

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

About this property

An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. The property is located in Rock Harbor's most upscale neighborhood. The area has the distinction of being Key Largos newest oceanfront gated destination, with some of the most...

View all property information

Featured review

"Amazing accommodations"

Everything about this property was amazing. Nice gated community, well maintained and friendly. Our condo was large with enough space for our children to spread out. Pools and hot tubs were the appropriate...

See all reviews

$387
avg per night
Key West Condo
Sleeps 4, 2 bedrooms, 2.5 bathrooms

Key Amenities

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

About this property

Enjoy the ocean views from this beautifully appointed condo in the exclusive Key West Beach Club.This two-bedroom, two and half-bath waterfront condo that has been newly renovated with casual furnishing and all the comforts of home: central air conditioning, cable TV, washer/dryer, Wi-Fi, and a fully-equipped...

View all property information

$400
avg per night
Marathon House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 1 miles to Sombrero Beach

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Beautifully updated 3 bedroom, 2 bathroom stilted home on exclusive Flamingo Island in the high-demand Sombrero Beach area. This home will not disappoint. Fantastically lush and meticulously landscaped yard by local famous design artist featuring a large, brand new heated/chilled pool with plenty of built...

View all property information

$403
avg per night
Summerland Key Cottage
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

A comfortable well priced home away from home. This charming 2-bedroom, 2-bathroom cottage offers a spacious, living/dining area with a fully stocked kitchen only steps away from the shaded patio with a water view and firepit. NEW to the Property - Heated Swim Spa!Experience the coastal charm and...

View all property information

$214
avg per night
Key West Apartment
Sleeps 2, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • WiFi

About this property

Galveston Porches Stylish one bedroom apartment in the heart of Old Town. Totally renovated and beautifully decorated. Everything you will need for your perfect Key West extended stay. 1 assigned parking space with the apartment. Full kitchen and washer dryer, Central AC and wifi access. The owners have...

View all property information

$126
avg per night
Key Colony Beach House
Sleeps 14, 6 bedrooms, 5 bathrooms

Distance to beach: 0.3 miles to Sunset Park

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This beautiful, modern and stylish home is perfect for families and group vacations and boast 2 full kitchens.It features high quality and modern furniture and beds, a fully equipped kitchens, high-speed wireless internet and a private, heated pool.The Upper side has 3 bedrooms and 2 bathrooms,...

View all property information

$992
avg per night
Key Largo House
Sleeps 10, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

PROPERTY NAME: Twice the Charm 214 S. Ocean Shores Dr, Key LargoLOCATION: Oceanside Canal Front HomeMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 98.5DETAILS: "Twice the Charm" is a gorgeous newly remodeled single family...

View all property information

$333
avg per night
Tavernier Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

Relax & recharge at our quiescent condo with stunning views of the blue-green colors of the Atlantic all nestled on 60 secluded acres. Seas the day – or just relax – you’re on island time!The Space This unit is located in building 3 which is a desirable building. Featuring...

View all property information

$248
avg per night
Key West House
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

This nicely appointed home is located in Key Haven subdivision of fine homes. It offers an expansive living room with upgraded kitchen and appliances. The kitchen is nicely stocked with plenty of room for multiple cooks. The house can accommodate up to six people with 3 bedrooms and 2 full bathrooms....

View all property information

Featured review

"Serene and comfortable"

We absolutely love this home! The interior features plenty of space and storage. The kitchen is well equipped with everything you need and more. The bedrooms very comfortable. The shower in the master has...

See all reviews

$184
avg per night
New
Big Pine Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • WiFi

About this property

Breathtaking sunrises from your balcony at this 3 bedroom, 2 bath home. There's a L shaped floating dock that can host a 24' boat, or you can launch the provided kayaks onsite. The master bedroom has a king bed, a working desk station, balcony access, and a private bath. There is a King bed,...

View all property information

$350
avg per night
New
Summerland Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • WiFi

About this property

Latitude Adjustment equals attitude adjustment! Location Location Location! This vacation rental home is located in the super desirable Summerland Cove neighborhood, with easy quick open water access!Whether you are coming for the weather, the boating, the diving or just to relax, this home has it...

View all property information

$239
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 2 miles to Founders Park

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

*Discover Elevated Island Living at Sea Breeze 41 Luxury 3BR/2BA Condo with Private Boat Slip in Exclusive Coral Harbour Club, IslamoradaWelcome to Sea Breeze 41 — your personal slice of tropical paradise in the heart of the Florida Keys. Nestled within the highly coveted Coral Harbour Club,...

View all property information

 

Islamorada House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 2 miles to Founder's Park

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Long-term rental available in the beautiful Venetian Shores community of Islamorada, Florida. This 3-bedroom, 2-bath home sits on a secluded plugged canal by the water. Enjoy a large master bedroom, a spacious open layout, and a generous outdoor deck ideal for entertaining. Additional features include...

View all property information

$235
avg per night
Key West Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through the Spring of 2026. This construction WILL impact your stay if you are staying during the week days. Please contact All Florida Keys Property Management for more detailed information....

View all property information

Featured review

"SIMPLY DIVINE"

BEST PLACE WE EVER STAYED AT. THERE WERE FOUR OF US. BEAUTIFUL LOCATION. SO COMFORTABLE. KIRK WAS SO HELPFUL TO HELP US GET SETTLED IN. ALL THE TREATS OF HOME. VIEW INCREDIBLE. WANTED OUR TIME THERE TO...

See all reviews

$1,452
avg per night
Big Pine Key House
Sleeps 8, 4 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 3 miles to Bahia Honda Park

Key Amenities

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

About this property

Modern 4 bedroom 2 bath stilt home centrally located in Big Pine. Heated salt water swimming pool. Corner canal front lot with 120 ft of dockage. 5 min. to the Gulf and 10 min. to the Atlantic. Close to the Winn Dixie grocery store. Free public boat ramp 5 min away. Room on property to park 6+ cars...

View all property information

Featured review

"Croton house"

Well, we think the house is very nice and clean. Great location, lovely neighbors nice quiet place we have only positive things to say and nothing negative so have a great day

See all reviews

$200
avg per night
Summerland Key House
Sleeps 10, 4 bedrooms, 5 bathrooms

Key Amenities

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

About this property

This Summerland Key home is perfect for the avid fisherman. Deep Water Canal with easy access to both the Gulf and Atlantic. Sea Wall has room for (1) 24' boat. This home can sleep 7 adults and 2 small children. There are 4 bedrooms and 4-1/2 bath. Fully stocked modern kitchen, great out door space...

View all property information

$428
avg per night
Key Largo Villa
Sleeps 10, 4 bedrooms, 3.5 bathrooms
3 reviews

Key Amenities

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

About this property

Villa, 4 Bed + Convertible bed(s), 3.5 Baths (Sleeps 6 - 10), Free Secure WiFi! An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. The property is located in Rock Harbor's most upscale neighborhood. The area has the distinction...

View all property information

Featured review

"60th Birthday celebration"

This was a great location to celebrate my husband's 60th birthday with our adult children and significant others. The condo was conveniently located in Key Largo and the grounds were well maintained and...

See all reviews

$409
avg per night
Cudjoe Key Cottage
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 15 miles to Bahia Honda State Park

Key Amenities

  • Air conditioning
  • Oceanfront
  • Rentals by owner
  • WiFi

About this property

Minimum Rental is 28 Days to a single family or party (no subleases allowed).PLEASE DO NOT REQUEST for less than 28 night rental. A fine of $16,000.00 is imposed by Monroe county for less than 28 nights. Less than 28 nights is simply non-negotiableNO PETS ALLOWED. IF YOU WANT TO BRING PETS,...

View all property information

Featured review

"Beautiful Sunsets"

The home was clean and full of amenities. Great place to spend a month escaping harsh Wisconsin winters. Owners were attentive and easy to deal with. A great boat launch should you need one. Neighborhood...

See all reviews

$199
avg per night
Key Largo Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 3 miles to John Pennekamp State Park

Key Amenities

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

About this property

Enjoy the panoramic view this tropically decorated, fifth-story unit has to offer of the Atlantic Ocean and the adjacent Wildlife Sanctuary. The unit affords its guests the spectacular sunsets the Florida Keys are famous for, right from your balcony and living room.Kawama Yacht Club is situated at...

View all property information

Featured review

"Boys week"

Great atmosphere, two minutes to the Atlantic. Jose great host, very clean. Thank you Jose for sharing your home.

See all reviews

$213
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 2 bathrooms
7 reviews

Key Amenities

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

About this property

Great house! Great location!HOUSE ON CANAL… 34 foot concrete dock with fish cleaning stand, water and electricity. 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. We are also...

View all property information

Featured review

"Excellent vacation rental"

This house is beautiful. Right on a canal where we kept our boat for the week. Manatees came by to visit daily. Caught keeper mangrove snapper right there. Neighbors were amazingly friendly. Everything...

See all reviews

$297
avg per night
Marathon House
Sleeps 6, 2 bedrooms, 2 bathrooms
20 reviews

Distance to beach: 2 miles to Sombrero Beach

Key Amenities

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

About this property

A beautiful waterfront half duplex home in a tropical setting with views of the Gulf of Mexico and incredible sunsets. Recently renovated octagonal shaped home with wide open water views from every window. Newly furnished comfortable interior with all the amenities you'd expect. Brick pavers surround...

View all property information

Featured review

"Tropical oasis"

We have rented Brian A for the last 3 Januarys to escape the cold north. The location is wonderful because we like the 4 mile walk around the airport. We enjoy the heated pool and the occasional manatee...

See all reviews

$374
avg per night
Tavernier House
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

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

About this property

The Atlantic Ocean greets you in this charming 1 bedroom condo on the top floor of building two, located in Ocean Pointe Suites Key Largo. Ideal for Friends, Couples, Solo & Budget Travelers, Key West Road Trippers, Snowbirds, Sea-foodies, Divers, Snorkelers & Anglers. Within a 10 minutes drive...

View all property information

$250
avg per night
Full map
Map

FAQ

Location & Specific Keys

What is the difference in atmosphere between the Upper, Middle, and Lower Keys?

The Upper Key has a relaxed vibe with a lot of nature preserves and parks to see. The Middle Keys have a laid-back vibe along with popular places to snorkel, dive, and swim. The Lower Keys, along with Key West, have an energetic vibe.

Which Key is best for nightlife and attractions versus quiet relaxation?

The Lower Keys have a vibrant nightlife, while the Middle Keys offer a relaxing atmosphere.

How do I choose the right Key to stay on for my vacation goals?

One of the simplest ways to choose a Key is to decide which attractions you want to see. Then, choose the Key that gives you the easiest access to those attractions.

Are there any lesser-known Keys that offer good rental options?

Sugarloaf Key, Little Torch Key, and Tavernier Key are lesser-known Keys with houses and other types of vacation rentals.

Activities & Lifestyle

Which Key is the best home base for fishing, diving, or snorkeling trips?

The Middle Key is your best bet for fishing, diving, and snorkeling fun, particularly off the coast of Marathon.

What are the "must-do" activities when staying in the Florida Keys?

Some “must-do” activities include snorkeling and swimming around the reefs, visiting the Hemingway Home and Museum, touring Marathon Marine Park, and visiting Dolphins Plus Bayside.

Are the rentals close to good restaurants, marinas, and public beaches?

Yes. Many Florida Keys vacation rentals are close to restaurants, marinas, and public beaches. Some properties are close to shopping areas, state parks, boat rentals, and breweries as well.

What is the best way to get around the Keys – is a car necessary?

Though there is public transportation like the Freebee Shuttle, renting a car is a great way to take in the sights around the Keys.

Booking & Logistics

What are the pros and cons of renting directly from an owner versus a property manager?

One pro of renting directly from an owner is flexibility. You may be able to negotiate on rent or fees with a property owner, whereas a property manager isn’t likely to negotiate. However, a property owner may not be as quick as a property manager to address rental issues, including maintenance.

What are the best websites for finding "For Rent By Owner" (FRBO) properties in the Keys?

Florida Rentals is one of the best websites to find FRBO properties.

How can I protect myself from scams when booking directly with an owner?

One way to protect yourself is to conduct an address search to ensure the property exists. Also, don’t pay the rent with a gift card, cash, check, or wire transfer. Be suspicious of a large property with lots of amenities and very low rent.

Do rentals by owner offer more flexibility on price or stay dates?

Yes. Rentals by owner offer more flexibility regarding price and stay dates. While a property management company has to answer to the owners, the owner of a rental can make changes at will.

Property Type & Communities

What types of houses are common for rent in the Keys (e.g., stilt homes, bungalows, canal-front homes)?

Canal-front homes, bungalows, and cottages are common rentals in the Florida Keys.

What is the benefit of renting a house on a canal versus one that is oceanfront?

A house with a canal gives you a place to boat and fish in still water right in front of the property. Renting an oceanfront home offers a great view of the ocean, but not a convenient place for fishing and boating.

Do most house rentals come with private boat dockage?

Yes, many house rentals in the Florida Keys include private docks.

Are there large houses available that can accommodate multiple families or big groups?

Yes, there are large houses in the Florida Keys suitable for big groups. Use the search filter to find a rental that can accommodate all of your guests.

Amenities & Features

What are the essential amenities for a Keys rental (e.g., boat slip, fish cleaning station, outdoor seating)?

Essential amenities for Florida Keys rentals include a patio or deck, boat slip, Wi-Fi, heated pool, and kitchen.

Is a private pool a common feature for house rentals in the Keys?

Yes, a private pool is a common sight in a description of house rentals in the Keys.

What should I look for in terms of parking, especially if I'm bringing a boat trailer?

Look at the property’s description to see if there is parking available. Some owners have parking areas for boat trailers. If you don’t see any information about trailer parking, message the property owner to get specifics.

Are kitchens in these homes typically well-equipped for cooking a fresh catch?

Yes. Along with a fish cleaning station, many rentals have a well-stocked kitchen with appliances for cooking seafood.