Lower Florida Keys Vacation Rentals, Beach Houses & Cottages.

SUGARLOAF KEY Private vacation home 3.8 Star Review

One of a kind beach house with a private sandy beach, dock and boat dockage . A modern tropical ambiance and a family friendly setting that will make you feel like you are in your own private island. Clear blue Florida Keys waters, great for swimming, snorkeling, kayaking, paddle boarding or just relaxing. With its privileged location and its clos.......read more

SUGARLOAF KEY
2 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 8

Big Pine Key Private vacation home

Enjoy uninterrupted natural vistas from this gorgeous home in one of the Lower Keys\' best boating neighborhoods, Pine Channel Estates. This stilted canalfront home with ample concrete dockage on a clean, deep canal is just a few houses in from the channel and just 30 miles from Key West. There are no neighbors across the canal, just trees and key .......read more

Big Pine Key
2 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 6

Big Pine Key Private vacation home 5.0 Star Review

THIS PRICE IS FOR CAMPER ONLY. You must pay campground fee separately. I will deliver and set it up for you at any campground in all the Keys for the same price. This 20 ft long camper is great for a couple or 3 people. 1 queen bed, 1 jack knife sofa and table turns into a bed as well. AC/ hot water - everything you need is there including coffee m.......read more

Big Pine Key
1 Bedroom(s) - 1 Bath(s)
Private vacation home Rental Sleeps 3

Big Pine Key Private vacation home

Welcome to this beautiful beach house bungalow. It boasts a large gated, fenced property with loads of room for entertaining the entire family. Complete with paver patio, outdoor shower, ice maker, refrigerator and freezer. Two separate large bedroom and bathrooms downstairs make it an ideal setup for a larger family or two. Upstairs you\'ll find a.......read more

Big Pine Key
4 Bedroom(s) - 3 Bath(s)
Private vacation home Rental

Big Pine Key Private vacation home

Tradewinds Treat

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click \'Book Now!\'

Nestled directly on a canal with prime water access, this charming family home has been completely renovated to meet your every vacation need. The stunning interior offers an open .......read more

Big Pine Key
2 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 6

Big Pine Key Private vacation home

Luxury Airstream Travel Trailer fully equipped kitchen and bed linens. Book you stay and wake up to a water view every morning and sunsets by the canal every evening. Take advantage of the resorts large deck top pool, marina and boat docks. The general store is perfect for those last minute camping necessities........read more

Big Pine Key
1 Bedroom(s) - 1 Bath(s)
Private vacation home Rental Sleeps 4

Big Pine Key Private vacation home 5.0 Star Review

Terrific tropical getaway for rent!! 2 Bedroom 3 full bath canal front home with large in ground pool, hot tub and 60 feet of dock age! Located in desirable Doctor\'s Arm neighborhood, this house is located just steps from the famous No Name Pub on Big Pine Key. The boating cannel is just 200 yards to open water onto Bogie Channel and Spanish Ha.......read more

Big Pine Key
2 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 6

Big Pine Key Private vacation home 5.0 Star Review

Our 2 bedroom/2 bath vacation rental sleeps 6 and is located in the exclusive Doctors Arm area of Big Pine Key, in the lower keys, just 25-miles from Key West. This water front property sits on a canal with easy access to the Gulf and Atlantic for some of the best fishing and lobster trapping in the world. The home is newly remodeled and high-te.......read more

Big Pine Key
2 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 6

Big Pine Key Private vacation home

**Gorgeous custom pool and spa on the way for winter 2023!**

 

Like-new 4-bedroom, 3-bathroom boating home just four houses in from Pine Channel on the oceanside of Big Pine Key with a custom concrete pool and spa scheduled for completion in fall 2022. 60-foot concrete dock with large fender piles for your big boat. Convenient steps.......read more

Big Pine Key
4 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 10

Big Pine Key Private vacation home

This is a 2 bedroom, 2 bathroom concrete block house. It is located on a clean swimming canal right off Pine Channel. This Big Pine Key home has an open floor plan with updated kitchen, dinning room and living/TV room. The master bedroom has a King size bed with its own en suite. The second bedroom has a Queen size bed and a twin bed. Each bedro.......read more

Big Pine Key
2 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 6

Big Pine Key Private vacation home

An angler\'s dream! Comfy 2 bedroom / 2 bathroom home on a large and lush canalfront property just minutes from the channel. Lots of relaxing outdoor living space. Fully fenced and very private. Close to the community park. Fully outfitted kitchen. Each bedroom has a king bed, and there\'s a queen sofa bed in the living room. Plenty of dockage. Exc.......read more

Big Pine Key
2 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 6

BIG PINE KEY Private vacation home 5.0 Star Review

3 Bedrooms, 2 Baths, Sleeps 6

The 3 bedroom 2 bath canal front home is located in a quiet neighborhood located on Big Pine Key.

Unwind in the sunny living room, furnished with a plush sofa. Watch favorite shows on the 55” flat-screen TV. Sofa has a pull out queen hide-a-bed. Prepare recipes in the fully stocked kitchen, outfitted w.......read more

BIG PINE KEY
3 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 6

Big Pine Key Private vacation home 4.9 Star Review

This two bedroom two bath home open floor concept is very comfortable. Master bedroom has sliding doors to screened in balcony that faces canal. Has a private bath and large closet. Additional room has two twin beds with very spacious walk in closet. Living room,dinning room and kitchen are open floor plan which makes it very comfortable for fa.......read more

Big Pine Key
2 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 6

Little Torch Key Private vacation home 4.9 Star Review

We have our 3 bedroom 2 bathroom home in Little Torch Key available for anyone looking to take a vacation in the lower Florida Keys. This home comes fully furnished with all kitchen appliances including dishwasher along with washer and dryer. Also the home has 43 inch flat screen tv\'s and a 55 inch in the living room and high speed WiFi. The h.......read more

Little Torch Key
3 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 8

Little Torch Key Private vacation home

This is the perfect Keys paradise home. It is in a friendly neighborhood close to all your needs. After a busy day on the water, relax and gaze at the stars in the comfortable adirondack chairs. Fully equipped home that sleeps 6 (king, queen and twins). Large porch overlooking canal with gas grill faces North for great evening entertaining. Enough .......read more

Little Torch Key
3 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 6

Little Torch Key Private vacation home

Torchbearer - Lower

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click \'Book Now!\'

Enjoy a canal-front getaway in the Florida Keys! This colorful, two-bedroom charmer offers a private slice of paradise with easy access to Key West. Entirely ground floor, this .......read more

Little Torch Key
2 Bedroom(s) - 1 Bath(s)
Private vacation home Rental Sleeps 6

Little Torch Key Private vacation home 5.0 Star Review

Little Torch Treasure has been our home for the past 5 years and throughout that time we have made alterations and additions to compliment the laid back lifestyle of the Florida Keys experience. You will find much more than clean well maintained accommodations in that the extra amenities to facilitate a stress free relaxing vacation have been the u.......read more

Little Torch Key
4 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 8

Little Torch Key Private vacation home

This studio bedroom has a private entrance with rustic island feel. It is sufficient for ONE person, only. Queen- size bed, large dresser and armoire, bathroom with toiletries, Cold A/C, and small area for sitting outside. Microwave, coffee maker, refrigerator.
-We Do Not Allow Cooking of any kind. Only microwave.
-300 square feet, inside. .......read more

Little Torch Key
1 Bedroom(s) - 1 Bath(s)
Private vacation home Rental Sleeps 1

Little Torch Key Cottage 4.3 Star Review

These cottages are not fancy, but clean and comfortable. Plenty of space for your boat trailer and public ramp just around the corner. We have 2 cottages on this property. This is unit #2 which is a 2 bedrooms with 1 bath (see below for layout).

Also please view our other unit which is a 1 bedroom, 1 bath which is VRBO listing #791238 for fe.......read more

Little Torch Key
2 Bedroom(s) - 1 Bath(s)
Cottage Rental Sleeps 4

Little Torch Key Private vacation home 4.9 Star Review

Little Torch Cottages is the perfect Keys vacation get away. Our luxury inspired 2 bedroom townhomes with bay / ocean views, a fully appointed gourmet kitchen ,2 tropical resort pools, direct access to the ocean for fishing and boating enjoyment, outdoor kitchen with a propane grilling station, memorable sunsets, close proximity to Bahia State Park.......read more

Little Torch Key
2 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 6

Little Torch Key Private vacation home 5.0 Star Review

New to rental market. .

The 3 bed/3 bath canal front home provides quick access to the Atlantic and Looe Key with no bridges.

60\' of canal front with 40\' of seawall and a cleaning station.

After a day on the water, enjoy the refreshing outdoor shower or soak in the large master bath tub.

The screened patio offer.......read more

Little Torch Key
3 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 6

Little Torch Key Private vacation home

Welcome to "SUNSET LANDING". Located in one of the best boating areas in the Florida Keys, this beautiful 3 bedroom home overlooks the salt ponds facing west for your own private sunset viewing every night. It is tastefully decorated with all the amenities you need to enjoy your stay.

Outside you will find hammocks to relax in, bikes to chec.......read more

Little Torch Key
3 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 6

Little Torch Key Private vacation home 5.0 Star Review

For more pictures on this property look us up on Instagram at sterlingbayhouse. This house is located on the open water with private dock and private in ground pool has five (5) bedrooms with king size beds with private bathroom and the 6th bedroom with three (3) queen size beds and their own bathroom. Bedroom six (6) with queen size beds has Fo.......read more

Little Torch Key
6 Bedroom(s) - 7 Bath(s)
Private vacation home Rental Sleeps 16

Marathon Private vacation home 4.3 Star Review

The Manatee Bay has the best of all worlds. It has a large custom fiberglass pool situated next to a 20 ft+ deep and beautiful swim able and fish-able lagoon. The Lagoon is filled with all sorts of different wildlife, including an occasional manatee, turtles, and all sorts of fish. It is the perfect place to learn to Paddle Board, Snorkel, or Ka.......read more

Marathon
4 Bedroom(s) - 5 Bath(s)
Private vacation home Rental Sleeps 8

Marathon Private vacation home 4.7 Star Review

Tropical Sea Star at Coral Lagoon
A 3 bedroom, 2.5 bathroom villa with resort pool at Coral Lagoon

Coral Lagoon Resort, located immediately adjacent to Key Colony Beach, perfectly embodies the relaxing, tropical ambiance that you came to the Florida Keys to experience. Rated #1 specialty resort in Marathon, Florida on TripAdvisor; Coral L.......read more

Marathon
3 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 8

Marathon Private vacation home 5.0 Star Review

Mockingbird Pointe is a quiet secluded 1/2 acre tropical waterfront paradise in the heart of the Florida Keys with private heated and/or chilled 16\' x 32\' in ground cement swimming pool with splash deck. This two bedroom , two bath home is remodeled, furnished and completely renovated with new furniture, bedding, artwork and linens. Wrap around.......read more

Marathon
2 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 6

Marathon Condo 4.6 Star Review

This listing is for a TROPICAL ISLAND villa, at Cocoplum Beach and Tennis Club and Marina, which is one of the 2 villas close to the office and view of the tennis court and a garden view! Unit 16 or Unt #18. (only a 3-4-minute walk to the beach and pool area). We do not specify exact villa number until day of arrival.

This listing is a Tropi.......read more

Marathon
2 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 6

Marathon Cottage 4.8 Star Review

This listing is for a PALM COURT villa, at Cocoplum Beach and Tennis Club and Marina, which is one of the 6 villas (Units #5,#6,#7,#8,#9 or #10) behind the BEACH FRONT Villas and surrounding the jacuzzi area with a partial view of the Atlantic Ocean. (only a 1-2-minute walk to the beach and pool area)

Perfect for Family Reunions or Two Coup.......read more

Marathon
2 Bedroom(s) - 2 Bath(s)
Cottage Rental Sleeps 6

Marathon Private vacation home 4.7 Star Review

Our home is a bright, open house with huge windows that look out over the Gulf of Mexico and the pool / swim up bar/ outdoor kitchen, with dockage (over 150\') for your boat(s). 2 Paddleboards, 2 kayaks, a hot tub/spa that seats 5/6 people, a Ms. Pac-Man machine, and a Margaritaville frozen drink machine will keep you entertained in comfort and .......read more

Marathon
3 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 8

Marathon Cottage 4.4 Star Review

This listing is for a KEY LIME GROVE villa (Units #11 or #12 or #13 or #14 or #15 or #17 or #19 or #20), at Coco Plum Beach & Tennis Club & Marina. Not a view of the ocean, but only a 3-4-minute walk to the beach, pool & Atlantic Ocean and jacuzzi. We do not specify exact villa number until day of arrival.

We do not allow and motorized water.......read more

Marathon
2 Bedroom(s) - 2 Bath(s)
Cottage Rental Sleeps 6

Marathon Private vacation home 4.8 Star Review

TRULY ONE OF A KIND, FABULOUS WATERFRONT PROPERTY - 4 BR/3BA. 3 BR/2BA home plus an attached 1 bedroom/1bath cottage. Includes your own wonderfully secluded private salt water tidal lagoon with fish, lobster, and all sorts of plants, and aquatic life !

Infinity swimming pool with poolside Tiki hut. Heating available.

Come relax in.......read more

Marathon
4 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 10

Marathon Villa 4.4 Star Review

This listing is for a BEACH FRONT villa, at Cocoplum Beach and Tennis Club and Marina, which is one of the 4 villas (Units #1, #2, #3 or #4) directly overlooking the pool and Atlantic Ocean Beach. We do not specify exact villa number until day of arrival.

Perfect for Family Reunions or Two Couples Traveling together - Deep water docks on pr.......read more

Marathon
2 Bedroom(s) - 2 Bath(s)
Villa Rental Sleeps 6

Marathon Private vacation home 4.0 Star Review

Yellowtail Retreat

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click \'Book Now!\'

Walk through the palm tree door and you\'ll know you\'re in for a fun time at this retreat! Immediately, the wood-style flooring and central air conditioning will help you cool o.......read more

Marathon
3 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 8

Marathon Villa

Walk into this spacious yet cozy villa on the quiet street of Man O War right off the famous Sombrero Beach Road. One of the best beaches in Florida is just less than a mile away. We put a lot of thought into creating a perfectly decorated villa for your amazing keys vacation. Our kitchen is fully equipped with anything you may possibly need to enh.......read more

Marathon
2 Bedroom(s) - 2 Bath(s)
Villa Rental Sleeps 4

Marathon Villa 4.8 Star Review

Come and enjoy Duck Key in the Florida Keys, known as America\'s Caribbean, a lush shangri-la with tropical vegetation and turquoise waters. Enjoy the day fishing from the dock, Lake Lucille, the Atlantic Ocean or the Gulf of Mexico, all interconnected in the sunny Florida Keys. This bit of the American Caribbean is teeming with fish. Walk out your.......read more

Marathon
3 Bedroom(s) - 3 Bath(s)
Villa Rental Sleeps 8

Marathon Villa 4.4 Star Review

This listing is for a KEY LIME GROVE villa (Units #11 or #12 or #13 or #14 or #15 or #17 or #19 or #20), at Coco Plum Beach & Tennis Club & Marina. Not a view of the ocean, but only a 3-4-minute walk to the beach, pool & Atlantic Ocean and jacuzzi. We do not specify exact villa number until day of arrival.

We do not allow and motorized water.......read more

Marathon
2 Bedroom(s) - 2 Bath(s)
Villa Rental Sleeps 6

Marathon Private vacation home 4.5 Star Review

This property is located at 686 25th St Oceanside,Marathon known as the gem of the keys. Boating guests are particularly impressed with this homes 159 feet of deep water dock age and ease of access to open water. Additional amenities for boating guest include a bait freezer and lighted fish cleaning station. . This neat home boasts master suite .......read more

Marathon
3 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 7

Marathon Private vacation home 4.5 Star Review

La Pirata

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click \'Book Now!\'

Completely remodeled by HGTV, this home boasts beautiful furnishings, perfect interior design, and timeless decor that will have you feeling right at home the moment you step through the .......read more

Marathon
3 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 8

Marathon Condo 4.9 Star Review

Welcome to the American Caribbean!
Spacious 2-bedroom, 2-bath condo with queen sofa bed in the living room, sleeps 6.
Tropical Ocean views directly from your private screened balcony! Enjoy your morning coffee watching the sunrise or have a happy hour cocktail on the balcony.

Steps to a 200-foot private beach and heated pool right on .......read more

Marathon
2 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 4

Marathon Private vacation home 4.9 Star Review

This newly renovated tastefully decorated 3 bedroom 3 bath home (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 use are 2 bikes, 3 kayaks and a paddle board! It has a large poo.......read more

Marathon
3 Bedroom(s) - 3 Bath(s)
Private vacation home Rental

Marathon Private vacation home

Sleeps 10, large heated pool, Hot tub, Sandy Beach area, 90\' Dock,Ocean Kayaks

This 4 bedroom 3 Bath House has ample sleeping options for every type of family/friend gathering and provides parking for several vehicles.

The floor plan layout is very balanced; the family room, kitchen, and game / TV room are on the Main Floor and 3 bed.......read more

Marathon
4 Bedroom(s) - 4 Bath(s)
Private vacation home Rental Sleeps 10

Marathon Private vacation home 4.0 Star Review

The Anchor House

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click \'Book Now!\'

It\'s all about the outdoor living at this lovely, central Keys getaway! Your home away from home on Marathon features a private boat dock, pool, and pool table – and you’re wa.......read more

Marathon
2 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 6

Marathon Private vacation home 4.7 Star Review

VACA-21-141
This Brand New Beachy Cottage, has great boating access with a 10 foot draft and 47 feet of dockage. This location is right off Boot Key Harbor and the 7 Mile Bridge. Facing West with a sunsets every night. Large living areas with an open floor plan.  The dining area is right next to the open kitchen. This brand new kitchen incl.......read more

Marathon
2 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 4

Key Colony Beach Private vacation home 4.8 Star Review

This elegantly furnished waterfront retreat is located on 75 7th St. in beautiful Key Colony Beach. This is a fantastic community and is one of the most unique places in the world. The gem clear waters are the home of an almost endless variety of fish and marine life. It has a private vertical dock with deep water that will accommodate almost any s.......read more

Key Colony Beach
2 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 4

Key Colony Beach Private vacation home 4.8 Star Review

Beautiful duplex home in Key Colony Beach. Key Colony Beach is a small, friendly, walkable island with easy access to local restaurants, Cabana Club and Sunset Park. This 3 bedroom, 2 bath home is fully equipped, modern and comfortable.
*Both sides of this duplex home are available to rent together (P63 & P64). As a 6 bedroom, 4 bathroom,.......read more

Key Colony Beach
3 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 8

key colony Beach Private vacation home 4.8 Star Review

Our waterfront home is located on 100 foot wide water canal with 30 feet of dockage. We are pet friendly. Furnished with 1 queen size bed and 1-queen sofa sleeper in living room to accommodate up to 4- people. We have WiFi. You have access to the Private ocean beach club just a 5- minute walk from our home called the Cabana Club. (thecabanaclubkey.......read more

key colony Beach
1 Bedroom(s) - 1 Bath(s)
Private vacation home Rental Sleeps 4

Key Colony Beach Private vacation home 4.8 Star Review

You CAN have it all!

Enjoy this generous private, two-story, single-family residence on the water with great views and 5 min. access to the ocean by boat. This home boasts an expansive custom heated pool, access to exclusive sandy beaches within walking distance, kayaks, awesome boater and angler accommodations, indoor and outdoor dining ac.......read more

Key Colony Beach
3 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 10

Key Colony Beach Private vacation home 4.7 Star Review

Cielos Del Mar 1 at Key Colony Beach

Welcome to Cielos Del Mar! This unique home features two separate 3 bedroom, 2.5 bathroom units which is ideal for large groups as you may rent both sides to accommodate up to 16 guests. If you\'re only renting one half, don\'t worry! Each side has it\'s own private pool and plenty of privacy fencing and .......read more

Key Colony Beach
3 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 8

Key Colony Beach Apartment 5.0 Star Review

Newly renovated DIRECT oceanfront condo in Key Colony Beach. Unit #10 is a studio condo on the 1st floor with stunning ocean views from every window and only steps away from our private beach and heated pool. Condo features a clean white interior and kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, micr.......read more

Key Colony Beach
Studio

Key Colony Beach Private vacation home 4.9 Star Review

Beautiful 2 Bedroom 2 Bath canal front half duplex completely remodeled. Master bedroom has a king bed and private bath Guest bedroom has 2 Full beds. Flat screen TV in each bedroom and in living room, dishwasher,washer and dryer .
Full WiFi through out the house.
40FT of dockage with step down dock fish cleaning station ,bait freezer, Web.......read more

Key Colony Beach
2 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 6

Key Colony Beach Private vacation home 5.0 Star Review

Cielos Del Mar 2 at Key Colony Beach

Welcome to Cielos Del Mar! This unique home features two separate 3 bedroom, 2.5 bathroom units which is ideal for large groups as you may rent both sides to accommodate up to 16 guests. If you\'re only renting one half, don\'t worry! Each side has it\'s own private pool and plenty of privacy fencing and .......read more

Key Colony Beach
3 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 8

Key Colony Beach Private vacation home

The complete package at the end of prestigious 12th Street in beautiful Key Colony Beach! Updated, spacious kitchen with eat-in island opens up to the expansive living area with soaring ceilings! huge windows let the natural light flood in from the canal-front pool deck! Ample comfortable seating, large flat screen TV and powder room round out the .......read more

Key Colony Beach
5 Bedroom(s) - 4 Bath(s)
Private vacation home Rental Sleeps 10

Key Colony Beach Private vacation home 4.9 Star Review

Relax at this wonderful Key Colony beach home right at the canal entrance to the Atlantic Ocean. The home offers ocean and canal views from your private backyard and master balcony. A new heated saltwater pool and spa awaits you as well as 2 new kayaks. In addition, enjoy pool and beach access to the popular Cabana Club a couple blocks away.
read more

Key Colony Beach
3 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 10

Key Colony Beach Private vacation home 5.0 Star Review

Beautiful upscale Key Colony Beach ground level half duplex decorated with a Coastal theme with rentals from Saturday to Saturday only.

COVID19 CLEANING Note: Due to the pandemic, we are taking special precautions and will use a disinfectant on all surfaces prior to all guests checking-in.

OUTSIDE is a super-sized Tiki Hut which is s.......read more

Key Colony Beach
3 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 6

Key Colony Beach Condo 5.0 Star Review

The apartment was completely renovated at the end of 2017.

- New modern bathrooms with rain showers and additional hand showers
- New modern kitchen with oven, stove, microwave, dishwasher and spacious fridge. The kitchen is equipped with everything you need for a relaxed stay (dishes, cutlery, toaster, coffee machine, pots, wine cooler,.......read more

Key Colony Beach
2 Bedroom(s) - 3 Bath(s)
Condo Rental Sleeps 4

Key Colony Beach Private vacation home 5.0 Star Review

This beautiful Keys home has just been completely renovated with new kitchen, bathrooms, tile, the works. All new furniture and appliances. One of the best streets in Key Colony Beach within walking distance of the Captain Jacks Restaurant and the Glunz Hotel.

Beautiful home includes complimentary access to The Cabana Club steps away you wi.......read more

Key Colony Beach
2 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 4

Key Colony Beach Private vacation home 4.9 Star Review

This beach home provides the perfect 2 bedroom and 2 bathroom place to stay in paradise. (Please read the complete description below) The water front location is ideal for boaters, fishing lovers, and vacationers that want to enjoy the outstanding view from sunrise to sunset.

Cabana Club Access and Private 37.5 ft Dock

PARADISE AWAIT.......read more

Key Colony Beach
2 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 5

Key Colony Beach Private vacation home 4.9 Star Review

This welcoming and modern canal front duplex home provides a relaxing and comfortable atmosphere for your vacation in the Florida Keys! Drop your bags and immediately begin to experience the laid back life that is Key Colony Beach.
*********
NOTICE:
One bedroom of 3 the bedrooms here has windows that do not meet emergency egress require.......read more

Key Colony Beach
3 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 6

key Colony Beach Condo 4.9 Star Review

It truly is One of the Best Private Beaches!

I can help you find the best, cheapest flights and car rentals.
Palm Trees, Tropical Plants, Sunshine will surround you in Paradise. Your White Sandy Beach is Private (not open to the public) with Lounge Chairs at the Beach and Pool. The property has a Tiki Hut at the water\'s edge where you c.......read more

key Colony Beach
2 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 4

Key Colony Beach Private vacation home 4.9 Star Review

The perfect vacation home for your large family or group! 7 bedrooms and 6 full baths!! Large and spacious rooms and multiple common areas with plenty of room for your whole family to spread out relax and have fun! SO MUCH CHEAPER THAN HOTEL ROOMS AND SO MUCH MORE FUN TO STAY TOGETHER!! Wether you plan to catch the big one, spend some time on .......read more

Key Colony Beach
7 Bedroom(s) - 6 Bath(s)
Private vacation home Rental Sleeps 14

Key Colony Beach Condo 4.9 Star Review

Gorgeous oceanfront condo! Top floor unit, directly on the beach, 2 bed and 2.5 baths with vast ocean views from the living room, kitchen and master bedroom. Perfect sunset views from the balcony! Complex offers multiple private sandy beaches, fishing dock, pool, tennis court/pickleball court and basketball hoop, covered parking, BBQ grills and ele.......read more

Key Colony Beach
2 Bedroom(s) - 3 Bath(s)
Condo Rental Sleeps 6

Key Colony Beach Condo 5.0 Star Review

Completely Updated 2018 2 Bedroom, 2 Bath, 2 Balcony Ocean View Condo. Sleeps 4

Tropical Paradise in The Florida Keys! Located in desirable Key Colony Beach with 175 Feet of private white sandy ocean beach and swimming pool. A family-friendly community and association with activities for the whole family! This recently updated 2 bedroom 2 ba.......read more

Key Colony Beach
2 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 4

Key Colony Beach Condo 4.7 Star Review

Ocean front unit in the Sea Isle Condos. Prime Key Colony Beach location - ocean front, first floor property, no stairs.

One week minimum, Saturday check in. $1,800 / week Dec - April, $1,600 / week May - Nov.

Tropical air is clean, the water is clear and the sand is white. This ocean front Sea Isle condo has innumerable amenities.......read more

Key Colony Beach
2 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 4

Key West Hotel resort 5.0 Star Review

RESERVATIONS AVAILABLE IN SEVEN NIGHT INCREMENTS ONLY WITH CHECK-INS on SATURDAYS

Overlooking the shimmering span of Gulf of Mexico in historic Old Town, The Galleon Resort puts you in an ideal spot to enjoy the countless charms of Key West. Mingle with friends new and old at the Tiki Bar, or relax and unwind in the swimming pool. The resor.......read more

Key West
2 Bedroom(s) - 2 Bath(s)
Hotel resort Rental Sleeps 6

Key West Condo 4.9 Star Review

The Jungle Breeze condo at LaBrisa Condominiums.
*Ocean View
*Free WiFi
* Free Covered Parking
* Final cleaning included in price
* KING size bed.
* Accommodates 2 adults
* Recently renovated this condo features all new flooring and a brand new kitchen
* Full size washer and dryer.

This is not a hotel; it is a privat.......read more

Key West
1 Bedroom(s) - 1 Bath(s)
Condo Rental Sleeps 2

Key West Private vacation home

*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.

This stunning property overlooking the Gulf of Mexico boasts panoramic views from nearly every room and the private pool. Designed with hand scraped bamboo floors and a beautiful wraparound deck w.......read more

Key West
3 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 6

Key West Private vacation home 5.0 Star Review

PRESTIGIOUS TROPICAL RETREAT...
Indulge in this spectacular two-story home situated in the premier gated community of historic Truman Annex. Escape to a sun-kissed dream as soon you enter this picturesque community, surrounded by swaying palm trees inviting you to enter your island vacation home which is tucked away on a quiet lane. Totaling 4 b.......read more

Key West
4 Bedroom(s) - 4 Bath(s)
Private vacation home Rental Sleeps 8

Key West Apartment 4.9 Star Review

The Simonton Studio is neat, sweet and complete. This pet friendly accommodation is the perfect location for exploring Key West. So, get out there and live it up in Key West and come home to a king size bed and everthing you need to fix your own cocktails and prepare some shrimp on the shared propane grill in the Courtyard.

Located in a .......read more

Key West
Studio

key west Condo 4.9 Star Review

Location, location, location. Our spacious1800 Atlantic 3 bedroom condo offers a fabulous view of the ocean from all three bedrooms, the kitchen and the living room. Birds of various types, boating activities, lush oasis gardens are just a few reasons why people keep returning to our paradise property. "Click" on \'more information\' also "click".......read more

key west
3 Bedroom(s) - 3 Bath(s)
Condo Rental Sleeps 8

Key West Private vacation home 4.9 Star Review

The William Skelton "Pink House" is located just steps from Duval Street in the heart of Old Town Key West. At this very spacious and historic home, you\'ll enjoy 6 comfortable bedrooms, a private backyard pool, two spacious living rooms, shaded outdoor patios and porches, and so much more.

A perfect choice for family reunions, weddings, an.......read more

Key West
6 Bedroom(s) - 4 Bath(s)
Private vacation home Rental Sleeps 14

Key West Private vacation home 5.0 Star Review

Welcome to Bottom’s Up Bungalow located The Meadows subdivision in Old Town Key West.

This pristine Florida Bungalow is 2 bedrooms, 2 bathroom single family home and offers all the amenities you need to make this your perfect vacation. Including off-street parking, swimming pool, quaint gazebo equipped with wet bar and custom seating. Th.......read more

Key West
2 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 6

Key West Condo 4.8 Star Review

Relax at Villa Fleur in luxurious surroundings. Renovated in 2018 it has a fully equipped kitchen with bar seating and dining area. The living room features comfy furniture and a panel TV. One queen bedroom and one twin bedroom. Enjoy outdoor dining on the brick patio surrounded by a tropical landscape.
Villa Fleur is located in the Shipyard Co.......read more

Key West
2 Bedroom(s) - 1 Bath(s)
Condo Rental Sleeps 4

Key West Private vacation home 4.8 Star Review

You will love our newly renovated 2 bed/ 2 1/2 bath private townhome in a secure community. Perfect location. This property doubles as our second home when we are in town. Renovations include new wood flooring, fresh paint, new kitchen with stainless appliances and granite tops. All furnishings and accessories are new. Private courtyard with sunde.......read more

Key West
2 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 6

Key West Condo 4.9 Star Review

Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you\'ll get without sacrificing a good night\'s sleep. This two bedroom Villa Vista is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway.

The number one reaso.......read more

Key West
2 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 4

Key West Condo 4.6 Star Review

Perfect vacation rental that allows you to enjoy breakfast on your private balcony, unwind and relax in the master bath jacuzzi, have front row seats to the variegated lights of Mother Nature\'s Sunrises, have the convenience of a fully equipped kitchen, two sitting areas for extra comfort and flexibility and for countless hours to enjoy the view.......read more

Key West
2 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 8

Key West Condo 4.9 Star Review

Enjoy the New and Completely Renovated bathrooms to this tropical residence. This is quiet, peaceful living on the Atlantic Ocean. The spectacular view can be seen immediately upon entering the condo. The floor to ceiling glass walls provide a full sea panorama from the living room, dining room, kitchen and master bedroom. The 31 foot oceanfront ba.......read more

Key West
2 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 4

Key West Condo 5.0 Star Review

This wonderful 2 bedroom downstairs unit is owner\'s second home and has just been beautifully and professionally decorated. Fresh paint throughout, all new hardwood flooring, new kitchen with granite counter tops, stainless steel appliances, and brand new designer furnishings make this a home away from home. A large rear courtyard with a wood sun .......read more

Key West
2 Bedroom(s) - 1 Bath(s)
Condo Rental Sleeps 5

Key West Private vacation home 5.0 Star Review

THE PROPERTY: Dreams do come true in Key West! As you enter the front gate of this luxury property, you arrive in a private wonderland on the quieter end of Duval Street. Enjoy morning coffee or people watching on the elevated, partially covered front porch. The home’s backyard oasis includes a covered rear patio, a pool with waterfall feature an.......read more

Key West
5 Bedroom(s) - 5 Bath(s)
Private vacation home Rental Sleeps 10

Key West Apartment 4.8 Star Review

Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used to be called the Central Hotel because it’s located at the most central location on Duval bordering Southard Street and is just steps up on the second floor overlooking both Duval and Southard Streets.

The building once housed the Chrysler/Deso.......read more

Key West
1 Bedroom(s) - 1 Bath(s)
Apartment Rental

Key West Condo 4.7 Star Review

Spectacular ocean views from this condo located on the top floor with 1350 sq ft of fabulous living space and a 45 ft private balcony accessible from the living and both bedrooms will make your vacation a memorable one and keep you coming back year after year. If the dates you need are not available check my other Key West vacation rental (Henry\'.......read more

Key West
2 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 5

Key West Private vacation home 5.0 Star Review

Craig & Cindy Truman Annex Foundry Townhouse is a 2 bedroom 2 1/2 bath townhouse in the best location in all of Key West....Truman Annex. We offer 2 Foundry Townhouses practically adjacent to each other. Truman Annex is a six block gated community right at the entrance to Ft. Zachary Beach, 2 blocks from Duval Street, and right next to the nightl.......read more

Key West
2 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 6

Key West Condo 5.0 Star Review

Partial list of rental amenities at Craig & Cindy\'s Truman Annex Shipyard Condos include:

2 bedrooms 1 bath {queen and 2 twins (or we can convert the 2 twins to a king bed with a king converter) plus a sleeper sofa in the living room.

Fully equipped kitchen with upgraded appliances and cooking accessories.
Washer & dryer with iron.......read more

Key West
2 Bedroom(s) - 1 Bath(s)
Condo Rental Sleeps 4

Key West Condo 5.0 Star Review

Our condo is located is in the heart of Key West\'s Old Town. This neighborhood is filled with historic homes dating from the period when Key West was the wealthiest city in the United States. The condo is in a historic home with three other condo units. The location is ideal to explore Key West by foot or bike. Great restaurants are within a f.......read more

Key West
2 Bedroom(s) - 3 Bath(s)
Condo Rental Sleeps 4