Florida Keys Vacation Rentals

(529 rentals)
booking message booking message
Islamorada House
3 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 2 bathrooms
16 reviews

$446

avg/night

$446
avg per night
View Details

Key Amenities

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

About this property

''BEAUTIFUL BAYFRONT PROPERTY!!!!''** 2022 Remolded bathrooms, 2021 NEW POOL** Fully furnished, 1 story offering 3bd/2ba. The house can sleep up to 8. There is a 1/1 guest suite attached which does have its own separate and private access with full kitchen and bath. Entire house ...

View all property information

Property Type

Islamorada House

Featured review

"The BEST of the BEST in every way!"

By far and away, this was the best rental property we have ever stayed! We have been visiting Islamorada for nearly 20 years and have stayed almost everywhere you can imagine, and we have now struck gold ...

See all reviews

Show less

Key West Townhome
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1.5 bathrooms
2 reviews

Distance to beach: 2 miles to Smathers Beach

$161

avg/night

$161
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Come stay in a premier development in Key West. If you're looking for a monthly stay of 29 days or more then this is the place. You would be close to everything Key West has to offer stay at our peaceful serenity of your temporary home in Paradise. Our house offers many amenities to make your stay ...

View all property information

Property Type

Key West Townhome

Featured review

"Three months in Paradise"

The townhouse and grounds are exactly as pictured and described! Staying on Stock Island was a great experience. Close enough to beaches and downtown Key West and the island itself offers a number of terrific ...

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

$165

avg/night

$165
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 Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

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

$334

avg/night

$334
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

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

View all property information

Property Type

Islamorada Condo

Featured review

"A great two weeks in beautiful Islamorada."

This two bedroom apartment in the beautiful Bay Harbour condominium was special. The views of the ocean and the apartment complexes marina were exceptional. The apartment was well stocked with all the cooking ...

See all reviews

Show less

Summerland Key House
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 House
3 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 4 bathrooms

Distance to beach: 0.5 miles to ANNE'S BEACH

$425

avg/night

$425
avg per night
View Details

Key Amenities

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

About this property

Located in the desirable Islamorada which is know as the “Sportfishing Capital of the World” and where you will find the most beautiful crystal clear waters. The house is just minutes from Channel 5 and Channel 2 which give you quick access to the best ocean and backcountry fishing. You are ...

View all property information

Property Type

Islamorada House

Show less

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

Distance to beach: 800 yards to Ft. Zachary Taylor State Park

$418

avg/night

$418
avg per night
View Details

Key Amenities

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

About this property

Envision yourself relaxing in a beautiful wood framed conch cottage with overhead fans lazily turning below the sloping tin roof in the heart of Old Town in Key West. This is the best value in Key West as it is no cookie cutter small rental condo but a private town home (one of only seven available for ...

View all property information

Property Type

Key West Cottage

Featured review

"Island Magic"

Great location! Great people! Very nice place that gave us memories of a lifetime! I’ll be returning soon!

See all reviews

Show less

Marathon House
6 BR | 5 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 5 bathrooms
4 reviews

$1243

avg/night

$1,243
avg per night
View Details

Key Amenities

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

About this property

Great for Family Reuions, and Large Groups vacationing in the Florida Keys! Fabulous 6500 sq ft. vacation paradise. Includes everything you need for a perfect Family Reunion or large destination vacation.Private Vacation Rental Waterfront Home with 6 Bedroom 5 Baths Private Pool and Spa ~Tiki Hut, ...

View all property information

Property Type

Marathon House

Featured review

"Family Vacation In The Heart of Paradise"

From beginning to end it was a pleasure working with Liz to secure the week of family fun! The estate was everything that we needed it to be with plenty of room for our children and grand children. The ...

See all reviews

Show less

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

$350

avg/night

$350
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

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

$621

avg/night

$621
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

The Blue Turtle 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 with a heater and a chiller, and all the amenities you would ...

View all property information

Property Type

Key Colony Beach Villa

Show less

Islamorada Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
5 reviews

$361

avg/night

$361
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This Condo is located on Lower Matecumbe Key, close to restaurants, shopping and Tiki bars. With pool, tennis courts and a protected marina, Bay Harbour is a preferred residence for repeat visitors to the Keys. Elevators for easy access and a second floor location make it easy to enjoy your stunning view ...

View all property information

Property Type

Islamorada Condo

Featured review

"Feels like home"

We have rented a condo at Bay Harbour for many years now. We love the location and the complex amenities. I fish a lot so my husband is happy with the workout room, pool, safe bike paths, hot tub and ...

See all reviews

Show less

Islamorada Condo
3 BR | 3 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 3 bathrooms
3 reviews
owner special
Owner special: Book 7 nights in May and get 1 of those nights for free!

$660

avg/night

$660
avg per night
Owner special:
Book 7 nights in May and get 1 of those nights for free!

View Details

Key Amenities

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

About this property

Escape to Paradise at Peaceful Palms in Islamorada!Welcome to your luxurious condo with ocean views, in the heart of the Florida Keys! Located in the exclusive, gated community of Peaceful Palms, this spacious and beautifully appointed property is perfect for families, couples, or groups seeking a ...

View all property information

Property Type

Islamorada Condo

Featured review

"Vacation"

Beautiful place, upon arrival beautiful flowers were left :) spotless clean everything that you need… From coffee to beach towels…Very relaxing and quiet . beautiful pool, huge garage…. It’s ...

See all reviews

Show less

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

Distance to beach: 0.5 miles to White Marlin Beach

$643

avg/night

$643
avg per night
View Details

Key Amenities

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

About this property

House, 3 Bedrooms, 2 Baths, Sleeps 6 Pure High End Luxury with all the Bells and Whistles Boat Friendly Vacation Rental with DockVilla 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. ...

View all property information

Property Type

Islamorada House

Featured review

"Couldn't be better"

What a beautiful fantastic home!! Perfect location....quiet, peaceful, a 2 minute car ride to a lovely quiet small beach (or a ten minute walk which we preferred). Orlando is just a pure gentleman....kind, ...

See all reviews

Show less

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

Distance to beach: 17 miles to Bahia Honda

$376

avg/night

$376
avg per night
View Details

Key Amenities

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

About this property

Looking for a vacation rental to get away from it all in the Fabulous Florida Keys? Look no further than our beautifully renovated home with open water and sunset views! This home has three bedrooms and two full bathrooms, open floor plan with designer kitchen and views from every room! You can enjoy ...

View all property information

Property Type

Cudjoe Key House

Show less

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

$566

avg/night

$566
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to your private slice of paradise in the heart of the Indian Waterways! This newly constructed Coastal Contemporary Caribbean-style home, with 165 feet of waterfront, invites you to experience the ultimate blend of luxury and tranquility.Unwind in Style: From the moment you step into the ...

View all property information

Property Type

Islamorada House

Show less

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

$317

avg/night

$317
avg per night
View Details

Key Amenities

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

About this property

Looking to ​ Relax Renew Recharge? We got you. Your own Key West Sanctuary awaits! Escape to a classic Conch family home perfectly tucked away for privacy yet, only 5 Blocks from famous Duval Street. The best of both worlds! Morning yoga class on the deck, late night dip in the pool, and sunset ...

View all property information

Property Type

Key West House

Featured review

"Great location!"

We loved this house at the end of a quiet lane. Huge pool! The location was perfect, walking was easy to so many places. Fully fenced and a small backyard made it perfect for our dog. And the shower ...

See all reviews

Show less

Key Largo House
5 BR | 4.5 BA | Sleeps 14 | Quick View
Sleeps 14, 5 bedrooms, 4.5 bathrooms

$1933

avg/night

$1,933
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

Cudjoe Key House
5 BR | 3 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 3 bathrooms
2 reviews

$709

avg/night

$709
avg per night
View Details

Key Amenities

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

About this property

This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1. Located just 20 miles away from Key West. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Downstairs grill, upstairs grill, Jacuzzi. Full WiFi. TVs in every ...

View all property information

Property Type

Cudjoe Key House

Featured review

"Squillets & Manor Wedding"

We had a great time, we will definitely be back! Fun in the sun! Close to restaurants and grocery store.

See all reviews

Show less

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

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

Key Colony Beach House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms

$470

avg/night

$470
avg per night
View Details

Key Amenities

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

About this property

Watch dolphins play in Shelter Cove while swimming in our oversized poolRelax in the private pool with the Spectacular Shelter Bay in the background...Our home is located directly on Shelter Bay in Key Colony Beach with some of the most spectacular views of open water a guest can ask for. We have ...

View all property information

Property Type

Key Colony Beach House

Show less

Islamorada Townhome
6 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 4 bathrooms
3 reviews

Distance to beach: 0.5 miles to Port Antigua Private Beach

$416

avg/night

$416
avg per night
View Details

Key Amenities

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

About this property

This recently renovated property enjoys 6 bedrooms, 4 bathrooms and separate kitchens, living rooms and laundry facilities. It shares an ocean facing veranda with 2 dual gas grills and multiple seating and lounging areas. It has ample offstreet parking for vehicles and trailers. The Admiral on the Cove ...

View all property information

Property Type

Islamorada Townhome

Featured review

"A Spectacular Spot"

We enjoyed our stay at this beautifully furnished and well stocked house. George and Bonnie responded quickly to any questions that we had. The separate living areas allowed us to enjoy family and friends ...

See all reviews

Show less

Islamorada House
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms
8 reviews

$789

avg/night

$789
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 ADMIN OR CC 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

"Fabulous place to stay!"

This unit on Islamorada provides wonderful oceanfront views. Our group included five retired women who all worked together in the past. We try to make a reunion vacation happen once a year. This is the ...

See all reviews

Show less

Plantation Key House
4 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 4 bathrooms
1 review

$857

avg/night

$857
avg per night
View Details

Key Amenities

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

About this property

Sanctuary in Paradise Unique property featuring: ~1BR 1BA main house ~2BR 2BA downstairs apt. ~1BR CottageWhether your ideal vacation is relaxing in a hammock in view of the ocean with a good book or hosting parties late into the night, Sanctuary in Paradise can accommodate you. We have a quiet ...

View all property information

Property Type

Plantation Key House

Featured review

"It was a wonderful Florida keys vacation"

Andy was a wonderful host and his property was gorgeous. My family, including kids and grandkids took full advantage of the water access and all of the fun amenities. There was plenty of room for our two ...

See all reviews

Show less

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

$816

avg/night

$816
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Book your stay between June 1st through August 31st before April 1, 2025, and enjoy 15% off the nightly rate! Don’t wait—secure your slice of paradise now and save!Blue Turtle Villa at The Tides of Vaca Cut (Unit #4), is a brand new 5 bedroom 4 bath home with a private pool, boat slip, ...

View all property information

Property Type

Marathon House

Featured review

"Beautiful vacation rental"

The home is absolutely beautiful and in a great location, beautiful views and has all the amenities needed for a great family vacation!

See all reviews

Show less

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

$839

avg/night

$839
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Pineapple Tides, located at "The Tides at Vaca Cut" (Unit #8), is a new 5 bedroom 4 bath home with a private pool and boat slip!Perfectly situated on the water with stunning views, sunrise and sunset colors, and direct quick access to both the Atlantic Ocean and the Gulf of Mexico via Vaca ...

View all property information

Property Type

Marathon House

Show less

Key West House
4 BR | 4 BA | Sleeps 11 | Quick View
Sleeps 11, 4 bedrooms, 4 bathrooms

$550

avg/night

$550
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Tranquil Midtown Estate feels worlds away, while just minutes to delectable dining and nightlife in exciting Key West! Nestled on nearly a quarter-acre of gated, lush tropical gardens, this spacious 3/3 main house plus 1/1 guest house comes move-in ready; boasting elevated coastal design where modern ...

View all property information

Property Type

Key West House

Show less

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

$835

avg/night

$835
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Sailfish Villa, unit #6, is a brand new gorgeous, professionally decorated 5 bedroom 4 bath Villa with open water views on Vaca Cut! Enjoy sunrise and sunset colors and direct ocean and Gulf access! It has a private pool and boat slip for a boat up to 35' including motors. There is no additional ...

View all property information

Property Type

Marathon House

Featured review

"Grateful"

I have been coming to marathon with family for many years and have had many rentals.. Meredith I have to say is the best.. she worked with me with every question and plans that I had . Definitely would ...

See all reviews

Show less

Islamorada Condo
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms

$460

avg/night

$460
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

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

View all property information

Property Type

Islamorada Condo

Show less

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

$622

avg/night

$622
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 Townhome

Show less

Marathon Villa
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
8 reviews

$541

avg/night

$541
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Reel Life 2 has everything! 4 bedroom 3 bathrooms, canal front, private dock (boat up to 35'), large private pool, Tiki Hut with flat screen TV, large grill, 2 bikes, 2 paddle boards, 1 kayak and a natural landscape view across the canal! Plus, Sombrero Beach is just down the street (1.3 miles). ...

View all property information

Property Type

Marathon Villa

Show less

Marathon Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 0.1 miles to On site

$463

avg/night

$463
avg per night
View Details

Key Amenities

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

About this property

BEST SUNSETS in the Keys, Key Colony Point unit #15, Ocean Beach Front, 2 bedroom, 2 bath ensuite, newly remodeled Condo with new furniture.COMPLEX: KEY COLONY POINT UNIT #15 Perfect get away for a week or a month.BEACH is 30 feet from our balcony. 150 feet to pool with hot tub. Great fishing ...

View all property information

Property Type

Marathon Condo

Featured review

"Best ever"

Absolutely the best view and pool in Key Colony. Spacious and well appointed condo. Would repeat #15 Very quiet and relaxing without crowds and annoying children!

See all reviews

Show less

Islamorada House
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
6 reviews

Distance to beach: 2 miles to Founders Park

$435

avg/night

$435
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Welcome to your dream getaway in Islamorada! This 3-bedroom, 2.5-bath paradise boasts a gourmet kitchen with a Viking gas stove, a spacious dining area, and Internet-ready TVs for game days or movie nights.On the first floor, you will find two bedrooms, a full bathroom and a large entertainment area ...

View all property information

Property Type

Islamorada House

Featured review

"Awesome House & Canal"

We had a wonderful time here. The location is perfect. Close to restaurants, shops, and attractions. We spent a lot of time floating and frolicking in the canal. The house was spotless. The kitchen was ...

See all reviews

Show less

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

$200

avg/night

$200
avg per night
View Details

Key Amenities

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

About this property

Beautiful oceanfront apartment with easy access to pool, spa, and beach. Dock with boat slips and tiki hut overlooking the Atlantic Ocean. Community exercise room Master Bedroom overlooking the ocean Two bedrooms, two full baths. Gourmet equipped kitchen Laundry room Balcony with spiral stairs ...

View all property information

Property Type

Islamorada Condo

Show less

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

$453

avg/night

$453
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

"Perfect Family Vacation"

Best Thanksgiving Trip! The house was beautiful and all accommodations were perfect! The owners were very helpful. Thank you!

See all reviews

Show less

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

$359

avg/night

$359
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

Tavernier House
5 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4 bathrooms

$467

avg/night

$467
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Greetings from Captain's Quarters! Located on Plantation Key (Mile Marker 90), this beautifully updated five bedroom and four bathroom canal-front home offers a resort-like experience.The main living area, located on the second floor, includes three bedrooms, two full bathrooms, comfortable open ...

View all property information

Property Type

Tavernier House

Show less

Key West Townhome
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
4 reviews

$233

avg/night

$233
avg per night
View Details

Key Amenities

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

About this property

Welcome to Key West Getaway in Old Town!In the heart of Old Town, Southard Square Condominiums is an award-winning condo development with stunning gardens, a clubhouse with changing rooms/baths, seating area, kitchenette and one of the largest private community swimming pools in Key West. Staying ...

View all property information

Property Type

Key West Townhome

Featured review

"Old Town Getaway"

Excellent property; highly recommended. Holly is an amazing host: very responsive and accommodating. She provided detailed check in/out instructions, descriptions of the property amenities, and a tour guide ...

See all reviews

Show less

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

$565

avg/night

$565
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Tingler Retreat is a newly renovated tastefully decorated 3 bedroom, 3 bath home with a pull-out couch, has a peek-a-boo view of the ocean and is seconds to open water in your boat! It has an open floor plan and is ground level with plenty of natural light and a fully fenced yard! Available for guest ...

View all property information

Property Type

Marathon House

Show less

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

$175

avg/night

$175
avg per night
View Details

Key Amenities

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

About this property

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

View all property information

Property Type

Islamorada Apartment

Featured review

"Paradise"

Lovely setting. Our host was very accommodating. Beach beautiful and private. Will definitely plan to return

See all reviews

Show less

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

$521

avg/night

$521
avg per night
View Details

Key Amenities

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

About this property

Welcome to our private stand-alone oceanfront home 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 ...

View all property information

Property Type

Marathon House

Featured review

"Great house with fabulous views!"

In summary, fabulous views! From the roof you get both the Atlantic and gulf. Unobstructed 180 degree gulf view. The house is great too. Everything you need to sleep comfortably, relax, cook. Space for ...

See all reviews

Show less

Cudjoe Key House
4 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 2 bathrooms
5 reviews

$407

avg/night

$407
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

BOAT RENTAL: We offer to rent our personal boats to our guests, only. We own: Flats Boat - 17 ft Ranger with E Tech 75 Bay Boat - 24 ft Bay Scout with 225 HP Yamaha Open Fisherman - 29-ft Ocean Runner with twin 300 HP Verrado's These boats are set up with everything you need to fish the Keys, ...

View all property information

Property Type

Cudjoe Key House

Featured review

"Vacation 2024/2025"

Southern Sunset is an excellent place to stay! The hosts are very accommodating and were great to chat with and helped make our stay even better. The property is clean and well kept and has a fabulous outdoor ...

See all reviews

Show less

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

Distance to beach: 8 miles to Bahia Honda State Park in the keys

$128

avg/night

$128
avg per night
View Details

Key Amenities

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

About this property

Ocean access waterfront canal with 40’ dock and all the fixins. Looe key reef straight out canal. 2/2 house with nice size porch

View all property information

Property Type

Ramrod Key House

Featured review

"A MONTH IN THE KEYS! WHATS NOT TO LIKE!"

I was really worried house was going to be too small, as it is a 2 bedroom. We ended up having plenty of room. Beds were very comfortable and A/C would freeze us . Dock was plenty big for our 35’ center ...

See all reviews

Show less

Marathon House
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms
2 reviews

$366

avg/night

$366
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

This 3 bedroom, 2.5 bath single-family modern home is great for entertaining! Enjoy the outdoor area with a pool and a separate hot tub or catch a game of pool on the main floor. This home is located on the 63rd Street canal and being ocean-side, it's just a quick trip out to sea where you'll ...

View all property information

Property Type

Marathon House

Featured review

"Loved Keys Retreat"

Spent Thanksgiving week at The Keys Retreat. Perfect location, house was very clean and kitchen stocked with everything you need. Really enjoyed the outside area in the pool and jacuzzi.

See all reviews

Show less

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

$482

avg/night

$482
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 | 3 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 3 bathrooms

$790

avg/night

$790
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to your spacious, five-bedroom waterfront pool home in Marathon, just steps from Sombrero Beach! Enjoy multiple entertaining areas inside and out, with a screened-in patio and sparkling pool (pool heat available for an extra fee). The open-concept interior features cathedral ceilings, a modern ...

View all property information

Property Type

Marathon House

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

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

$271

avg/night

$271
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

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

$550

avg/night

$550
avg per night
View Details

Key Amenities

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

About this property

VACA-22-238 BRAND NEW BUILD! 3- bedrooms with king beds and full size bathrooms, and 1/2 bath for guests. Large common area living room and open kitchen. Located on canal three houses from the ocean, with great open water views. Pool with sitting area under the house. Our home offers a 60' ...

View all property information

Property Type

Marathon House

Featured review

"Awesome Rental"

We have been going down to the Keys for years in August. Happened to find Sandy Flats two years ago and loved it. House is beautifully redone and owners are super friendly and very responsive. Loved that ...

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

$534

avg/night

$534
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • 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 | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 3 bathrooms

$982

avg/night

$982
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Relish ocean serenity in this residence set directly on a secluded beach, where an open-concept design seamlessly merges the living area and gourmet kitchen with a grand terrace, all framed by uninterrupted ocean views. Bask in the heated pool, unwind on the covered patio, or step onto your private dock ...

View all property information

Property Type

Islamorada House

Show less

Map
Expand map Close map
Florida Keys Vacation Rentals