Monroe Area Rentals
From $828 per night (USD)VRBO
Balcony on Duval - Duval Dream Loft
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! This un ...
From $828 per night (USD)VRBO
From $879 per night (USD)Expedia
Balcony on Duval - The Collins on Duval
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! The Col ...
From $879 per night (USD)Expedia
From $252 per night (USD)VRBO
This Oceanfront Resort HAS IT ALL!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Fantastic 2 bedroom, 2 bath condo resort. Enjoy the breathtaking view of the Atlantic Ocean from the patio just steps fr ...
From $252 per night (USD)VRBO
From $226 per night (USD)Expedia
Enjoy Caribbean weather in the USA. Discounted rates through 2025!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Our home is a bungalow with cathedral ceilings. It is spacious and sparkling clean. Our home is #655 at Venture Out on ...
From $226 per night (USD)Expedia
From $916 per night (USD)VRBO
Historic Old Town Key West Cigarmaker's Cottage - Conch House, Sleeps 5
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Conch House is a 100+ year old “Cigarmaker’s house. The house is recently renovated, charming, spacious, secluded a ...
From $916 per night (USD)VRBO
From $349 per night (USD)Expedia
Mermaid Magic in Key Colony Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful ground level spacious 3 bedroom 3 bathroom duplex. Updated kitchen with gorgeous wood cabinets and stainless a ...
From $349 per night (USD)Expedia
From $344 per night (USD)VRBO
Splash Pool- Key Colony Villa - KCB#4
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our stunning waterfront unit in Key Colony Beach with its tropical outdoor living & instant ocean access from ...
From $344 per night (USD)VRBO
From $598 per night (USD)Expedia
New 4/3 Private Single Family - 2 min to ocean, kayaks, paddleboards, bicycles
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Blue Treasure at Sombrero Beach is a 2020 built single-family home on a large lot within walking distance to the beautif ...
From $598 per night (USD)Expedia
From $272 per night (USD)VRBO
Beachy getaway with pool, water views, furnished patio, & dock access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
R & R Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $272 per night (USD)VRBO
From $717 per night (USD)Expedia
Sunrise Escape - Ocean Front Villa - Sleeps 10
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Enjoy the sunrise while sitting on one of two terraces while sipping your morning coffee in the exclusive part of Kawama ...
From $717 per night (USD)Expedia
From $247 per night (USD)VRBO
Fairway Villa w/ Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Fairway Villa — a stunning, spacious 3-bedroom, 3-bathroom townhouse nestled on the beautiful Key West Golf C ...
From $247 per night (USD)VRBO
From $268 per night (USD)Expedia
We have a deck water front perfect spot for fishing or relaxing the view
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
The property has a breath taking view of a bay Where you can fish 🐠 and enjoy the Catch of day it has out side Kichen a ...
From $268 per night (USD)Expedia
From $350 per night (USD)VRBO
New pool & Huge master suite! Open water views , 2 stories of wrap around decks
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Captivating views from sunrise to sunset overlooking expansive salt ponds and open water from this newly renovated 2-sto ...
From $350 per night (USD)VRBO
From $188 per night (USD)Expedia
New Tiny House RV, Kayak, Beach, Marina, Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Camper RV at Key Largo Kampground and Marina Resort W/ 24 hour security. 1 Queen Bed, 1 Pull out Sofa, Single bed in Lof ...
From $188 per night (USD)Expedia
![Light, Bright & Nautical Condo - 5 min to Local Attractions [Ocean Pointe 1211]](https://media.vrbo.com/lodging/56000000/55450000/55441700/55441651/833c416d.jpg?impolicy=ccrop&w=350&h=233&q=medium)
From $287 per night (USD)VRBO
Light, Bright & Nautical Condo - 5 min to Local Attractions [Ocean Pointe 1211]
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy our beautifully designed oceanfront condo in Key Largo, nestled beside a tropical mangrove forest. The condo offer ...
From $287 per night (USD)VRBO
From $413 per night (USD)VRBO
Amazing Beach! Near John Pennekamp National Marine Sanctuary, 2 Outdoor Pools!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Oceanfront family-friendly property with direct beach access and pool This listing is for a room within a hotel. ✦ You ...
From $413 per night (USD)VRBO
From $577 per night (USD)VRBO
Ohana Cay 4 bed & 4 bath Unit 906 @Mariners Club - Sleeps 10!!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to our island oasis, Ohana Cay! We would love to welcome you to our recently updated four bedroom/four bathroom ...
From $577 per night (USD)VRBO
From $293 per night (USD)VRBO
Vacation home in Paradise
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
AWESOME View of the Bay- from Chickee Hut Dock to Full Roof Top Patio. 2 Story. Large Master Bedroom with Steam Shower. ...
From $293 per night (USD)VRBO
From $524 per night (USD)VRBO
**CARIBBEAN CHARM @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The sound of ...
From $524 per night (USD)VRBO
From $663 per night (USD)Expedia
P00 - 4 Bedroom Pool Home overlooking Sombrero Bea
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This beautiful 4 bedroom, 4 bath family home is located in the very desirable area of Sombrero Beach and is directly acr ...
From $663 per night (USD)Expedia
From $312 per night (USD)VRBO
Latitude Adjustment in Key Colony Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Latitude Adjustment is a ground-level, updated half duplex featuring 2 bedrooms and 2 bathrooms. The master bedroom offe ...
From $312 per night (USD)VRBO
From $394 per night (USD)Expedia
P49 - Charming 2 bedroom, single family home just a short walk to the beach.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This charming all ground level, 2 bedroom, 2 bath home is walking distance to Sombrero Beach. This truly makes you feel ...
From $394 per night (USD)Expedia
From $435 per night (USD)VRBO
P03 - Charming 4 bedroom home with pool and dock.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This beautiful home is located in the quiet and very desirable Coco Plum neighborhood, a few minutes' walk to the beach. ...
From $435 per night (USD)VRBO
From $234 per night (USD)Expedia
P41 - Beach Front condo with 2 bedrooms, 2 bath, pool and tennis courts!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Condo overlooking the natural beach of Coco Plum. This 2 bedroom, 2 bath congo unit offers 1,280 sq feet of living space ...
From $234 per night (USD)Expedia
From $371 per night (USD)VRBO
P78 - Charming beach home just down the road from
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This 3 bedroom, 2 bath single family home is ideally located in the heart of Sombrero Beach and is an easy 7 minute walk ...
From $371 per night (USD)VRBO
From $456 per night (USD)Expedia
P27 - Private Beach Access! Pool home with everyth
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This beautiful 3 bedroom, 2 bath home located in the very desirable Key Colony Beach, boasts a large open floor plan, pr ...
From $456 per night (USD)Expedia
From $250 per night (USD)VRBO
P29 - Charming 3 bedroom 2 bath duplex with deep water dockage and Cabana...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Key Colony at its most charming! This 3 bedroom, 2 bathroom, half duplex is located in the heart of Marathon in Key Colo ...
From $250 per night (USD)VRBO
From $384 per night (USD)Expedia
P67 - New Construction 3 bedroom 4 bath with priva
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
This lovely two story duplex offers 3 bedroom, 4 bathrooms and abundant living space on both levels. The lower level off ...
From $384 per night (USD)Expedia
From $330 per night (USD)VRBO
P22 - Updated 3 bedroom 2 bath duplex with private
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This lovely 3 bedroom, 2 bath home located on Sixth Street (The Causeway) and boasts a private fenced yard and private h ...
From $330 per night (USD)VRBO
From $284 per night (USD)Expedia
P17 - Charming 3 Bedroom 2 Bath Duplex With Private Pool And Deep Water...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Paradise found in the tropical city of Key Colony Beach! This all ground level home has ease of access inside and out, b ...
From $284 per night (USD)Expedia
From $317 per night (USD)VRBO
P42 - Gulf Front condo with 3 bedrooms 2.5 baths, pool and dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located in the beautiful gated community of Indigo Reef! This 3 bedroom, 2 1/2 bath townhouse boasts plent ...
From $317 per night (USD)VRBO
From $356 per night (USD)Expedia
P62 - 3 Bedroom 2 bath, private pool and beach mem
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful duplex in Key Colony Beach with private fenced yard and private heat optional pool. Three bedroom, two bath ho ...
From $356 per night (USD)Expedia
From $442 per night (USD)VRBO
P34 - Beautiful 4 bedroom 2 bath, single family home with private pool and...
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful and spacious 4 bedroom, 2 bathroom, private pool home in the desirable Key Colony Beach neighborhood located n ...
From $442 per night (USD)VRBO
From $297 per night (USD)Expedia
P51 - 2 bedroom 2 bath, single family pool home wi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This 2 bedroom, 2 bath home has been beautifully updated inside and out. Located oceanside, canal front in Marathon, the ...
From $297 per night (USD)Expedia
From $792 per night (USD)VRBO
P05 - 5 bedroom Ocean Front home with Private pool and deep water dockage.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This custom designed Mediterranean style home is nothing less than exquisite! Located in very desirable Key Colony Beach ...
From $792 per night (USD)VRBO
From $561 per night (USD)Expedia
P28 - Luxury 4 bedroom, single family home with po
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This all ground level 4 bedroom, 3 bath, single family home is located in desirable Key Colony Beach. This home offers a ...
From $561 per night (USD)Expedia
From $261 per night (USD)VRBO
P21 - Charming 3 bedroom 3.5 bath duplex in Key Colony. Offers deep water...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful 3 bedroom, 3.5 bath duplex is located in Key Colony Beach. This home comes with access to The Cabana Club ...
From $261 per night (USD)VRBO
From $588 per night (USD)Expedia
P02 - 5 bed, 3.5 bath home with large private pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This 5 bedroom, 3-1/2 bath home is located in the Sombrero Beach neighborhood! Beautiful hardwood floors, tall ceilings, ...
From $588 per night (USD)Expedia
From $409 per night (USD)VRBO
P10 - Charming 2 bedroom, 2 bath duplex with private pool and deep water...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This lovely 2 bedroom, 2 bath home is located on the gulf side with immediate Gulf water access and near the Vaca Cut fo ...
From $409 per night (USD)VRBO
From $287 per night (USD)Expedia
P72 - Charming 4 bedroom, 2 bath duplex with deep water dockage and Cabana...
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful 4 Bedroom, 2 bathroom duplex in Key Colony Beach. Key Colony Beach is a small, friendly, walkable island with ...
From $287 per night (USD)Expedia
From $542 per night (USD)VRBO
P43 - Updated 3 bedroom 3 bath home with Pool in t
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This tropical pool home offers everything you need for a perfect Florida Keys vacation! This home has been completely up ...
From $542 per night (USD)VRBO
From $591 per night (USD)Expedia
Big Kahuna in Marathon
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to the Big Kahuna an expansive and inviting 5-bedroom, 4-bathroom single-family haven that encapsulates the ess ...
From $591 per night (USD)Expedia
From $482 per night (USD)VRBO
P33 - Charming 4 bedroom house with pool and a sho
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This charming 4 bedroom, 3 bathroom home has it all! Located in the very desirable neighborhood of Sombrero Beach ...
From $482 per night (USD)VRBO
From $570 per night (USD)Expedia
P58 - Gulf Front Luxury 4 bedroom 4 bath with private pool and deep water...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This beautiful Polynesian style home offers 4 bedrooms, 4 baths, beautifully landscaped grounds and a large, private, he ...
From $570 per night (USD)Expedia
From $758 per night (USD)VRBO
Swept Away in Marathon
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
"Swept Away," an exquisite and newly crafted luxury single-family residence boasting three bedrooms and two bathrooms. T ...
From $758 per night (USD)VRBO
From $510 per night (USD)Expedia
Fisherman's dream!!, Privacy, Heated Pool,Hot Tub, 50' Dockage, Tiki, pets ok,
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
copy and paste following URL link for a virtual tour of the property........with 360 walk around of the property... ...
From $510 per night (USD)Expedia
From $3628 per night (USD)VRBO
**ALL TOGETHER NOW @ OLD TOWN** Three Homes & Pools + LAST KEY SERVICES…
- Bedrooms:
- 14
- Bathrooms:
- 13
- Sleeps:
- 32
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Coordinating ...
From $3628 per night (USD)VRBO
From $684 per night (USD)Expedia
Discount to Jan 31! 4/4! Private Pool, Paddleboards & Lots of Great Amenities!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
WE ARE OFFERING A 5% DISCOUNT THROUGH JANUARY 31ST! IT IS AUTOMATICALLY FIGURED INTO THE QUOTE! The Blue Turtle Villa, ...
From $684 per night (USD)Expedia
From $575 per night (USD)VRBO
Waterfront luxury Villa (14) with spectacular sunset views and boat slip
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This spacious 3BD, 2.5BA Villa is the perfect blend of comfort and coastal charm. Each bedroom features its own televisi ...
From $575 per night (USD)VRBO
From $310 per night (USD)Expedia
Ocean Harbour Condominium is an Oceanfront Fisherman's Paradise in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This spacious two bedroom, two bath condominium overlooking the ocean is located on a quiet 12 acre private gated commun ...
From $310 per night (USD)Expedia
From $1929 per night (USD)VRBO
**MAYA’S SECRET TREASURE @ DUVAL** Private Pool & Balcony over Duval + LAST KEY
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Walking along ...
From $1929 per night (USD)VRBO
From $2485 per night (USD)Expedia
Balcony on Duval - Duval's Duet on Duval
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 16
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! Duval's ...
From $2485 per night (USD)Expedia
From $398 per night (USD)VRBO
Anglers Reef Islamorada - 2:2.5, Marina, Pool, Beach.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
- VR#258 - Saturday check-in. 2 bedroom and 2.5 bath at 117 Anglers Way. Awesome family get-a-away in beautiful Islamor ...
From $398 per night (USD)VRBO
From $400 per night (USD)Expedia
Dog-Friendly Home on the Water w/ Dock, Boat Access, Private Pool, & Free WiFi
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Marathon Magic Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $400 per night (USD)Expedia
From $859 per night (USD)VRBO
Waterfront Private Home-7 BR, 6 Full BA, Pool, 80' Dock, Parking, Screened Porch
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 16
Welcome to 'Sombrero Sunset House' located in the heart of Sombrero Beach in Marathon, Florida! This prime waterfront ...
From $859 per night (USD)VRBO
From $422 per night (USD)Expedia
Mini lobster available! Open Water View from porch , dock, bikes, kayaks
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
This beautifully furnished, very clean, well-stocked modern house is located in Venture Out, a private residential commu ...
From $422 per night (USD)Expedia
From $446 per night (USD)VRBO
122 Mariners Club Key Largo | 2 Bed, 2.5 Bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Imagine yourself in this luxury, immaculately maintained two-bedroom, two and one-half bath, 2nd-floor villa with a brea ...
From $446 per night (USD)VRBO
From $331 per night (USD)Expedia
Dazzling Ocean Pointe -OP-Main
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Ocean Pointe Suites in Key Largo is an all-suite resort located directly on the Atlantic Ocean. Our 60 acres in the Flor ...
From $331 per night (USD)Expedia
Click For PricingVRBO
Time share week in a tropical paradise! Jan 31 - Feb 7
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
My loss is your gain. We can't go this year but that means you can! We are unable to visit this year so I'd like to off ...
Click For PricingVRBO
From $301 per night (USD)Expedia
Old Town home a short walk to Duval/Couples Oasis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Add this listing to your wishlist by clicking the ♥ in the upper right hand corner. This 1 bedroom/1.5 bathroom ...
From $301 per night (USD)Expedia
From $253 per night (USD)VRBO
Relaxing island home/Great location/Stylish
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Only 4 short blocks to Duval, this 1 bedroom/1.5 bathroom home is walking distance to your favorite Key West sp ...
From $253 per night (USD)VRBO
From $560 per night (USD)Expedia
SPACIOUS 4/3.5 VILLA! INDOOR PICKLEBALL! MOST UPSCALE OCEANFRONT RESORT IN KL!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Ree ...
From $560 per night (USD)Expedia
From $731 per night (USD)VRBO
5 STAR yet low rates. 3 BR + 1 BR cottage, private pool, close to Duval.
- Bedrooms:
- 0
- Bathrooms:
- 4
- Sleeps:
- 8
Our calendar is updated in real time and our rates are accurately displayed. You can book instantly without waiting for ...
From $731 per night (USD)VRBO
From $723 per night (USD)Expedia
Oceanfront 4 bedroom House, Pool and Deep Water Pier!!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Wow! Mesmerizing views, outstanding location, directly on the Atlantic Ocean, so close to the Ocean that you can practic ...
From $723 per night (USD)Expedia
From $341 per night (USD)VRBO
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
SULTRY GARDEN SANCTUARY... Steal away from reality and find your way to the quintessential, tropical & adults only Trave ...
From $341 per night (USD)VRBO
From $336 per night (USD)Expedia
COCONUT PALM SUITE ~ Adult Only, 1 BR, 1 Ba w/ Kitchen & Shared Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
BOTANICAL MAGIC AWAITS YOU... Only three blocks from all of the fine dining and entertainment of Duval Street, yet tucke ...
From $336 per night (USD)Expedia
From $486 per night (USD)VRBO
Charming Islamorada Villa in Gated Anglers Reef – Pool & Kayaks
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*Boat Slip Available: August 25 - September 5, September 13-19, September 27 - October 10, November 8-22 Keezy Does ...
From $486 per night (USD)VRBO
From $592 per night (USD)Expedia
Beautiful 4 Bedroom/3 Bath Home w/Private Pool,40 ft. Dock near Sombrero Beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
New 4 Bedroom/3 Bath Family Home with private pool and 40ft dock near Sombrero Beach, shopping & dining! This spacious ...
From $592 per night (USD)Expedia
From $330 per night (USD)VRBO
ROYAL PALM SUITE ~ Adult Only, 1 BR, 1 Ba w/ Kitchen and Shared Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
ESCAPE TO A BOTANICAL HIDEAWAY... Immerse yourself at the charming adults only Travelers Palm Inn with unique suites and ...
From $330 per night (USD)VRBO
From $580 per night (USD)Expedia
ISLAND OASIS in the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Island Oasis @ the Truman Annex is beautifully renovated town home in the historic Foundry. | The living area is the ent ...
From $580 per night (USD)Expedia
From $190 per night (USD)VRBO
NEW MONTHLY RENTAL, Old Town Duplex, private backyard, pets welcome, 2BR/2BA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Sea Monkey and The Mermaid. Our home is a duplex located in Old Town and full of Key West charm. Walk to a ...
From $190 per night (USD)VRBO
From $615 per night (USD)Expedia
~The Escape ~ Your own tropical escape on private island!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $615 per night (USD)Expedia
From $845 per night (USD)VRBO
P44 - 4 bed, 3 bath estate home with Southern Char
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This estate style home is breathtaking! Built in beautiful southern tradition, this home does not disappoint with 4 bedr ...
From $845 per night (USD)VRBO
From $606 per night (USD)Expedia
Stunning & Welcoming Pool Home on Canal
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to your dream getaway in the Florida Keys! This spacious 4-bedroom, 3-bathroom waterfront home is designed for r ...
From $606 per night (USD)Expedia
From $388 per night (USD)VRBO
Stay near Jimmy Johnson’s Big Chill – just a 18-min stroll away
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Escape to the stunning shores of Key Largo and experience the ultimate island getaway at our 2-bedroom condo. Nestled ju ...
From $388 per night (USD)VRBO
From $835 per night (USD)Expedia
PARADISE FOUND!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Paradise Found at Mariners Club in Key Largo, FL a beautiful spacious 3-story town-home in an exclusive resort located ...
From $835 per night (USD)Expedia
From $692 per night (USD)VRBO
Enjoy Old Town Key West in this Beautifully furnished house
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We recently bought this house because we LOVE Key West! It is a 2 story Key West style house. The bedrooms are upstair ...
From $692 per night (USD)VRBO
From $484 per night (USD)Expedia
Rx: Paradise in Marathon
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Indulge in the mesmerizing beauty of colorful sunsets during your vacation in this recently renovated property! Unwind o ...
From $484 per night (USD)Expedia
From $504 per night (USD)VRBO
Yellow Room at the Grand Maloney
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $504 per night (USD)VRBO
From $540 per night (USD)Expedia
Blue Room at the Grand Maloney
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $540 per night (USD)Expedia
From $504 per night (USD)VRBO
Green Room at the Grand Maloney
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $504 per night (USD)VRBO
From $570 per night (USD)Expedia
SPECTACULAR Indigo Reef Waterfront Home #41 - Marathon, Florida
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Indigo Reef #41 is the BEST KEPT SECRET in the Florida Keys!! This home is spectacular in every sense of the word and no ...
From $570 per night (USD)Expedia
From $477 per night (USD)VRBO
Angler's Retreat in Marathon
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy the Florida Keys in this beautifully updated 3-bedroom, 2-bath home just minutes from Sombrero Beach! The fully eq ...
From $477 per night (USD)VRBO
From $751 per night (USD)Expedia
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks,SUPs, Extra Frig/Bait Frz
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come stay with us at VENTURE OUT, a fantastic safe, activity filled community in Cudjoe Key, Fl- only 20 miles north of ...
From $751 per night (USD)Expedia
From $271 per night (USD)VRBO
Poolside King Room Steps from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Poolside King Room is a hotel-style room adjacent to the pool. It can sleep up to four persons, two in the king-size ...
From $271 per night (USD)VRBO
From $224 per night (USD)Expedia
Poolside Queen Room Steps from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Poolside Queen Room is a hotel-style bedroom and bath unit that offers the amenities of our Key West villas for thos ...
From $224 per night (USD)Expedia
From $370 per night (USD)VRBO
One Bedroom Deck Villa Steps from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy a wonderful Key West accommodation. Our One Bedroom Deck Villa features a living room, a separate bedroom with ki ...
From $370 per night (USD)VRBO
From $702 per night (USD)Expedia
Casa Calypso- Beautiful Tropical 3 KING Beds, 3 baths - 2 miles to beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This house is a 3 bedroom stand alone unit with 2 king bedrooms upstairs with balconies and own bathrooms and the bedroo ...
From $702 per night (USD)Expedia
From $284 per night (USD)VRBO
Ocean Jewel in Marathon
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
"Ocean Jewel" is a beautifully decorated one bedroom & one bath condo in a resort syle setting with some resort amenitie ...
From $284 per night (USD)VRBO
From $170 per night (USD)Expedia
The Hideaway: Lose Yourself At This Recently Decorated Canal Front Home on Big Torch Key, Dockage!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $170 per night (USD)Expedia
From $482 per night (USD)VRBO
Sombrero Island Breeze 4BD Pool Paradise (M#9)
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Indulge in five-star waterfront luxury at this stunning 4BR, 3BA retreat in one of the Keys' most unique island communit ...
From $482 per night (USD)VRBO
From $233 per night (USD)Expedia
Duval Street Suites on Duval Free Parking and heated Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Cuban Club Suite is a one bedroom (queen) 1 bath suite with a queen murphy bed and kitchen. Overlooking Duval ...
From $233 per night (USD)Expedia
From $255 per night (USD)VRBO
Duval Street Suites full kitchen, free parking, & heated pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Key West Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. In historic O ...
From $255 per night (USD)VRBO
From $252 per night (USD)Expedia
Duval Street Suites full kitchen, free parking, heated pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Paradise Suite is a one bedroom (king bed) 1 bath suite with a murphy bed (queen) and kitchen. In historic Old ...
From $252 per night (USD)Expedia
From $243 per night (USD)VRBO
Duval Street Suites full kitchen and heated pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Little Palm Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (king) and kitchen. Overlooking ...
From $243 per night (USD)VRBO
From $234 per night (USD)Expedia
Duval Street Suites with full kitchen heated pool, free parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Mile Zero Suite is a one bedroom (queen) 1 bath suite with a sleeper sofa (king) and kitchen. Overlooking Duva ...
From $234 per night (USD)Expedia
From $2736 per night (USD)VRBO
6 BR 6 BA Guesthouse Suites on Duval free parking, private pool
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 24
Summary: This can accommodate 24 people, each apartment has 2 beds. You'll have privacy with 6 individual suites each eq ...
From $2736 per night (USD)VRBO
From $527 per night (USD)Expedia
P60 - 4 bedroom 4 bathroom home with pool and dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This fabulous 4 bedroom, 4.5 bathroom home was designed and built for comfort and style! Guests love the different theme ...
From $527 per night (USD)Expedia
From $1045 per night (USD)VRBO
Great deal ! Private pool and dock. Five minute bike ride to Sombrero Beach.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This 3 bedroom and 3.5 bath house has everything you need in order to experience a relaxing and enjoyable vacation at S ...
From $1045 per night (USD)VRBO
From $918 per night (USD)Expedia
ATLANTIS...Ocean Front Cottage Retreat!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need ...
From $918 per night (USD)Expedia