
Florida Keys Rentals
- From $310 per night (USD)
VRBO
Villa 5103 on Duck Key Boat Slip Available - 2BD 2.5BA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Boat slip available for additional $100 a night. Largest boat that can fit is 33 ft. Ask for availability. This villa b ...
From $310 per night (USD)VRBO
- From $236 per night (USD)
Expedia
Dates available Oct, Nov, Dec 2023
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
2/2Come and enjoy this newly renovated home. Be the first to enjoy! Located in one of the best fishing spots in the Flor ...
From $236 per night (USD)Expedia
- From $278 per night (USD)
VRBO
Canal front, dockage, 2 bedroom, 2 bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Open water views from this 2 bedroom, 2 bath stand alone home, 35 foot seawall for docking your boat. Contemporary desig ...
From $278 per night (USD)VRBO
- From $292 per night (USD)
Expedia
Escape to Pickles Reef [Ocean Pointe 1212]
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy affordable fun at our cheeky condo within Building 1 at Ocean Pointe Suites in the Tavernier! Our property is cen ...
From $292 per night (USD)Expedia
- From $548 per night (USD)
VRBO
'Oceanside Oasis' Direct Ocean Views & 3 BR'S
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Imagine waking up every morning to the sun rising over the Atlantic Ocean. That's what you will experience with this bea ...
From $548 per night (USD)VRBO
- From $503 per night (USD)
Expedia
Discount Available! Private Pool, Canal Front, Dock, Bikes, Paddleboards & More!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
WE ARE OFFERING A 5% DISCOUNT THROUGH JANUARY 31ST! IT IS AUTOMATICALLY FIGURED INTO THE QUOTE! Reel Life 2 has everyth ...
From $503 per night (USD)Expedia
- From $1605 per night (USD)
VRBO
3 acres Gated w/Beach,Pool,Bikes,Kayaks,EV charger
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
See why we have ALL 5-star reviews. It's named The Oasis for good reason! Located in the HEART of Islamorada on Upper M ...
From $1605 per night (USD)VRBO
- From $932 per night (USD)
Expedia
Large outdoor space with pool/hot tub, on 200ft wide canal- quick ride to Ocean!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
NEW-“2 homes in 1”- PRIVATE-WATERFRONT HOME -only a 5 minute walk to the beach Located on a large, deep canal and is ...
From $932 per night (USD)Expedia
- From $913 per night (USD)
VRBO
The Lazy Lime in Marathon
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
The Lazy Lime is a stunning gulf front newly updated 5 bedroom 3 bathroom single family home. Ask about adding the garde ...
From $913 per night (USD)VRBO
- From $390 per night (USD)
Expedia
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! TURTLE COVE V ...
From $390 per night (USD)Expedia
- From $401 per night (USD)
VRBO
Super Savings! Paradise found, Cabana club included!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Second Wind is situated on the 9th street canal, a beautiful corner lot with exceptional views and ocean breezes. A two ...
From $401 per night (USD)VRBO
- From $493 per night (USD)
Expedia
Indigo Reef End Unit 3BR Waterfront Townhome w/ Boat Slip, Pool, Gym & Views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your waterfront escape in the heart of the Florida Keys! This rare end unit townhome in the exclusive Indigo ...
From $493 per night (USD)Expedia
- From $406 per night (USD)
VRBO
Big Family Home in Key Largo: Remote Workers’ Dream and Pet Friendly
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 12
**28-day minimum rental only--sorry, local laws enforced!** Pet Friendly with Super Fast Internet My home is 7-bedrooms ...
From $406 per night (USD)VRBO
- From $332 per night (USD)
Expedia
Don't Miss This! Deep Water Canal, Swimspa Pool, Kayaks, Walk to Tiki Bars!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This updated 3 bedroom, 2 bath home with private canal lot is located in the heart of The Florida Keys in Marathon at Mi ...
From $332 per night (USD)Expedia
- From $433 per night (USD)
VRBO
Warm, sunny, perfect vacation in Islamorada's Anglers Reef
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to 128 Anglers Way: "Morada Daydreaming". Our home away from home in the Angler's Reef exclusive gated community ...
From $433 per night (USD)VRBO
- From $401 per night (USD)
Expedia
The Conch House in Marathon
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Conch House Renovated Canal-Front Retreat in MarathonWelcome to The Conch House, a beautifully renovated 3-bedroom, ...
From $401 per night (USD)Expedia
- From $195 per night (USD)
VRBO
Come escape to Island Time Hideaway - Wonderful monthly renovated rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $195 per night (USD)VRBO
- From $454 per night (USD)
Expedia
Majestic Marina View- 2/2.5 townhome looking over Hawks Cay Marina.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Relax with the best views Duck Key has to offer. Enjoy the sunset relaxing on the patio overlooking the marina. If using ...
From $454 per night (USD)Expedia
- From $569 per night (USD)
VRBO
Amazing Key Largo Tropical Paradise 3/3 Townhouse with Water Lagoon view
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful 3 bedroom 3 bath townhome overlooking a tranquil lagoon. Swim or Snorkel the Saltwater Lagoon, relax in the p ...
From $569 per night (USD)VRBO
- From $347 per night (USD)
Expedia
Beautiful Marina location. Gated community. Quite and secure. SUNSETS !!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sunset Marina Condominium Complex is a gated community that has a community pool and spa, and clubhouse. All of the two ...
From $347 per night (USD)Expedia
- From $335 per night (USD)
VRBO
Canal-front home w/dock, resort-style amenities, patio, & high-speed WiFi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Dock Holiday Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $335 per night (USD)VRBO
- From $240 per night (USD)
Expedia
Canal front home w/ a dock, private pool, spacious deck, & easy water access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Sombrero Sands Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $240 per night (USD)Expedia
- From $403 per night (USD)
VRBO
ALL DOCKED OUT~ Key Colony Retreat Sandy beach's and sunsets
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This elegantly furnished 2 bedroom waterfront retreat is located in beautiful Key Colony Beach. This community is one o ...
From $403 per night (USD)VRBO
- From $480 per night (USD)
Expedia
Shipyard 276-Condo in Truman Annex-2 bedroom 2 bath, close to Duval w/ pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $480 per night (USD)Expedia
- From $178 per night (USD)
VRBO
House 2 bedroom 2 bath Large enclosed porch overlooking canal with boat dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2 bedroom 2 bath stilt home with large screened in porch overlooking canal and lush tropical coconut palms. Boat dock Wi ...
From $178 per night (USD)VRBO
- From $279 per night (USD)
Expedia
Spectacular Key Largo Sunsets - 2 bedroom Townhouse sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience paradise in this Bayside "Sunset Side" townhouse in the Florida Keys. Nestled in a private gated community on ...
From $279 per night (USD)Expedia
- From $1589 per night (USD)
VRBO
Oversized home for the whole family w/private pool & dock
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
"Captain's Daughter” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropical ...
From $1589 per night (USD)VRBO
- From $365 per night (USD)
Expedia
Casa Del Pirata / 3 bed / 2 ba Canal Home in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Casa Del Pirata! Located in the heart of Port Antigua, this canal front home boasts tropical vibes and can ...
From $365 per night (USD)Expedia
- From $313 per night (USD)
VRBO
LOCATION, LOCATION, LOCATION, you wont be disappointed with this home.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Looking for a top-rated vacation rental in beautiful Key Colony Beach, Florida? Amberjack House is the spot! Included ...
From $313 per night (USD)VRBO
- From $192 per night (USD)
Expedia
Keys Please in Key Colony Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Keys Please is a 2bed/2bath condo located in desirable Key Colony Beach. The complex is right on the water with its own ...
From $192 per night (USD)Expedia
- From $345 per night (USD)
VRBO
H2O Therapy 2 bed 2 bath on Open Water w/Cabana Cl
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sunrises and Open water, overlooking Bonefish Bay in Key Colony Beach. This property has a private 37 feet of dockage fo ...
From $345 per night (USD)VRBO
- From $226 per night (USD)
Expedia
Islamorada Lovely Panoramic Ocean VIEWS! Oceanfront Corner Condo, Pool, More!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FOR VIEW LOVERS and a favorite of returning visitors. EVERY ROOM has a gorgeous OCEAN view. This totally renovated, Is ...
From $226 per night (USD)Expedia
- From $605 per night (USD)
VRBO
WATERFRONT, VIEWS, HEATED POOL, 130 ft. OF DOCK, PRIVATE RETREAT
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
BOOT KEY RETREAT - OPEN WATER VIEWS - Just updated in 2019 Not your typical canal house, there is plenty of privacy h ...
From $605 per night (USD)VRBO
- From $254 per night (USD)
Expedia
Penthouse Apartment Sunsets in Key Largo, Kawama Yacht Club Tower
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy the panoramic view this tropically decorated, fifth-story penthouse unit has to offer of the Atlantic Ocean and th ...
From $254 per night (USD)Expedia
- From $723 per night (USD)
VRBO
Duck Key Tarpon House 5 Bedroom 3 Baths Duck Key w
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Duck Key Tarpon House ExquisiteHome on Duck Key with 5 bedrooms and 3 baths with Cabrera Marble Countertops and brand n ...
From $723 per night (USD)VRBO
- From $1143 per night (USD)
Expedia
Vaca Cut Sunsets 5 bed 4 bath home with pool Gulf
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Vaca-21-337Location Location Location! Located on the Vaca Cut Channel in Marathon, with immediate boating access to the ...
From $1143 per night (USD)Expedia
- From $1102 per night (USD)
VRBO
4 Bd w/Pool, Bayside - Marlin Bay Resort & Marina
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort fea ...
From $1102 per night (USD)VRBO
- From $531 per night (USD)
Expedia
Vista Marquesa 4/3 Ground Level Home w/ Pool & 50
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
VACA-23-231Friday to Friday Booking only( We will not honor any bookings that do not follow the Friday booking unless pr ...
From $531 per night (USD)Expedia
- From $466 per night (USD)
VRBO
Location, Beauty & Comfort @ Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $466 per night (USD)VRBO
- From $518 per night (USD)
Expedia
Waterfront luxury Villa (21) with sunset views and boat slip
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This spacious 3-bedroom, 2.5-bath Villa blends comfort with coastal charm. Each bedroom includes its own TV, and the liv ...
From $518 per night (USD)Expedia
- From $257 per night (USD)
VRBO
Knee Deep in the Water Somewhere...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The only worry if the tide's reaching your chair! Come on in The waters nice (there's a dock for a 32' boat right out ...
From $257 per night (USD)VRBO
- From $217 per night (USD)
Expedia
P16 - Charming 2 bedroom 2 bath waterfront duplex with Cabana Club.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the heart of the Florida Keys! Located in the very desirable Key Colony Beach, this all ground level 2 bedroo ...
From $217 per night (USD)Expedia
- From $564 per night (USD)
VRBO
Alluring corner unit w/ full kitchen & pool - close to beach/ nightlife
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Seaclusion Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $564 per night (USD)VRBO
- From $437 per night (USD)
Expedia
Waterfront jewel with private guest suite, boat slip, free WiFi, & washer/dryer
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Jewel of Marathon Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $437 per night (USD)Expedia
- From $453 per night (USD)
VRBO
Steps from Duval, Shared Pool – Sky Loft Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Experience the best of Key West from Sky Loft, your perfect weekend getaway! Just one block from the iconic Duv ...
From $453 per night (USD)VRBO
- From $315 per night (USD)
Expedia
★Newly remodeled tropical townhome★ Private plunge pool close to fun activities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the Florida Keys while staying at a cozy recently remodeled tropical delight. High speed internet-1,000mbps and la ...
From $315 per night (USD)Expedia
- Click For Pricing
VRBO
Beautiful Beach Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to our beach house located in the heart of Islamorada. Just a short drive from the best restaurants, bars, state ...
Click For PricingVRBO
- From $323 per night (USD)
Expedia
Key Colony Beach Paradise
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The property is a 2 bedroom, 2 bath over 1,200 square feet very open floor plan home where you can enjoy this wonderful ...
From $323 per night (USD)Expedia
- From $561 per night (USD)
VRBO
Golfside Tropical Retreat With Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Golfside Tropical Retreat! Whether you're an avid golfer, fisherman ( we have got ya covered with a Commercia ...
From $561 per night (USD)VRBO
- From $551 per night (USD)
VRBO
Waterfront Community Townhome with Marina, Beach and a Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
SPRING SPECIAL: SAVE 20% When You Book Between April-June! Take your dream Keys vacation in this spacious 3bd/2bth wate ...
From $551 per night (USD)VRBO
- From $324 per night (USD)
VRBO
Rose All Day in Key Colony Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Rose All Day is a stunning updated 2bed/2bath half duplex in Key Colony Beach. The property features dockage, cabana clu ...
From $324 per night (USD)VRBO
- From $295 per night (USD)
Expedia
Key Largo gem on the water with a little slice of heaven!!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
New waterfront CBS home on a beautiful 200 ft wide basin (not a canal) with immediate access to the bay. Mature lands ...
From $295 per night (USD)Expedia
- From $355 per night (USD)
VRBO
Oceanfront, 2 Bedroom Unit At Ocean Pointe Condominium
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Accommodations: Condominium, 2 Bedroom, 2 Bath (Sleeps 4) This is one of the finest destinations in the Florida Keys. ...
From $355 per night (USD)VRBO
- From $223 per night (USD)
VRBO
Nice home on Atlantic side of Cudjoe Key!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This home would be the perfect vacation spot for a small family or a group of friends. There are plenty of fun restauran ...
From $223 per night (USD)VRBO
- From $562 per night (USD)
VRBO
Seaside Escape: Relax and Recharge with Panoramic Views! 3 Spacious Suites
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 18
Escape to a tropical paradise and experience the ultimate beachfront retreat! Nestled in the heart of Key Largo, this pr ...
From $562 per night (USD)VRBO
- From $192 per night (USD)
Expedia
50’ dock on Vaca Cut, deep wide unlimited dockage.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
One bedroom and one 1/2 baths nicely decorated. Cute and super clean. Tile floors throughout. Kitchen fully equipped. Wi ...
From $192 per night (USD)Expedia
- From $268 per night (USD)
VRBO
3/2 Waterfront / Private Dock / Cabana Club Pool & Beach / Kayaks / Tiki Hut 🏝.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
**IMPORTANT: RENTAL IS SATURDAY TO SATURDAY ONLY, UNLESS APPROVED BY OWNER** The Starfish House is walking distance to ...
From $268 per night (USD)VRBO
- From $368 per night (USD)
VRBO
NEW LISTING 2nd Fl Condo w/private outdoor deck overlooking historic Fleming St.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Airy sun-filled apartment above an art gallery in 100 year old Old Town Conch home. Private cozy quiet & romantic hideaw ...
From $368 per night (USD)VRBO
- From $499 per night (USD)
VRBO
Casa Largo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This great townhome is located in Kawama Yacht Club in the heart of Key Largo. Kawama Yacht club is located minutes away ...
From $499 per night (USD)VRBO
- From $1354 per night (USD)
Expedia
**BELLE OF THE BEACH @ CASA EAST** Beach House + LAST KEY SERVICES…
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Get the gang ...
From $1354 per night (USD)Expedia
- From $2074 per night (USD)
VRBO
Historic Old Town Key West - Main House, 4 beds, 1 Sleeper Sofa, Accommodates 8
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
OVERVIEW The 'Main House' is a two-story, four (4) bedroom, one and a half (1.5) bathroom renovated historic home. The ...
From $2074 per night (USD)VRBO
- From $296 per night (USD)
Expedia
Private Tropical Beach-White Sand, Crystal Clear water! Pool WIFI It's Loaded!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience Paradise at One of the Best Private Beaches! Let me assist you in finding the best and most affordable fligh ...
From $296 per night (USD)Expedia
- From $466 per night (USD)
VRBO
For up to date availability call 510-381-5000
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
A beautifully appointed home with all the amenities you will need to have an enjoyable vacation. The first thing you wil ...
From $466 per night (USD)VRBO
- From $1814 per night (USD)
Expedia
Features.Key West Suites Hotel has an outdoor pool and fitness center
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Key West Suites Hotel Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used ...
From $1814 per night (USD)Expedia
- From $542 per night (USD)
VRBO
Ocean views! <br>Luxury suites
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Your Ocean front vacation house on water awaits you! Experience Key West staying above it's beautiful clear water. The ...
From $542 per night (USD)VRBO
- From $446 per night (USD)
VRBO
Odisa Key Largo Vacation Home with Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to Odisa Key Largo Vacation Home! Nestled in the heart of the stunning Port Largo community, this beautiful tw ...
From $446 per night (USD)VRBO
- From $349 per night (USD)
VRBO
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This oceanside property has 2 beds 2 baths and sleeps 6 with all updated appliances and furniture. There are kayaks and ...
From $349 per night (USD)VRBO
- From $862 per night (USD)
Expedia
AQUA BREEZE at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This two bedroom condo is located in the Truman Annex, Key West's premier residential community in Harbour Place on the ...
From $862 per night (USD)Expedia
- From $386 per night (USD)
VRBO
BE STILL- 4 Bedroom, 3 Bath with POOL & Guest Cottage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Be Still – Your Private Island Oasis in Key West Nestled on an oversized corner lot just a few blocks from W ...
From $386 per night (USD)VRBO
- From $454 per night (USD)
Expedia
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
ALL NEW RENOVATIONS COMPLETED JUST FOR YOU! A perfect oasis with beautiful views all day, every day. Come enjoy your tim ...
From $454 per night (USD)Expedia
- Click For Pricing
VRBO
PARADISE IN YOUR HANDS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful clean and spacious home. Relax on your deck or take your boat out, canal goes out to the gulf or ocean to do s ...
Click For PricingVRBO
- From $567 per night (USD)
Expedia
Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
This modern and beautifully decorated vacation rental is the perfect spot for your next family vacation or couples' geta ...
From $567 per night (USD)Expedia
- From $425 per night (USD)
VRBO
Dock, Pool, FREE RAMP, Kayaks, Jacuzzi, Amazing Ocean Views Pets are Welcomed!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to this beautiful, newly constructed vacation home in Marathon, Florida. With its modern design and a newly inst ...
From $425 per night (USD)VRBO
- From $383 per night (USD)
Expedia
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for compute ...
From $383 per night (USD)Expedia
- From $544 per night (USD)
VRBO
Key largo Kawama Villa N2
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Relax and enjoy our family friendly 3 bedroom/3 bathroom Villa Lago in Key Largo! Salt water swimming lagoon, Pools, the ...
From $544 per night (USD)VRBO
- From $331 per night (USD)
Expedia
Discover Tavernier's Charm [ Ocean Pointe 4315 ]
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Tavernier's tranquil beaches are home to a two-bedroom condominium that is waiting for you. Nestled in a prime location, ...
From $331 per night (USD)Expedia
- From $418 per night (USD)
VRBO
Hidden gem in Key Largo, bunk room, outdoor kitchen, 2 pools, laundry, 2 beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This hidden gem is anything but ordinary! Come enjoy a piece of paradise in Key Largo while you relax in this spacious N ...
From $418 per night (USD)VRBO
- Click For Pricing
Expedia
Marathon 1BR Condo on Resort w/Amenities
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Situated just off the historic Florida Keys Overseas Highway, The Hammocks at Marathon™ lets you and your family experie ...
Click For PricingExpedia
- From $472 per night (USD)
VRBO
Come stay in an amazing house close to everything! Duvall! North Seaport!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
We love this home, and we just know you will too!! A fully renovated conch home with amazing finishes and 3 great bedro ...
From $472 per night (USD)VRBO
- Click For Pricing
Expedia
Marathon 1BR Villa on Resort w/Amenities
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Situated just off the historic Florida Keys Overseas Highway, The Hammocks at Marathon™ lets you and your family experie ...
Click For PricingExpedia
- From $296 per night (USD)
VRBO
New House Paradise Without a Pasport On Atlantic Ocean Deck Sunsets Water Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Brand New Home, Brand New Furniture, Sunset and Ocean Views, Outdoor communal Fire Pits, Outdoor Kitchen, Grill, Possib ...
From $296 per night (USD)VRBO
- Click For Pricing
Expedia
Marathon 1BR Villa on Beautiful Resort w/Amenities
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Situated just off the historic Florida Keys Overseas Highway, The Hammocks at Marathon™ lets you and your family experie ...
Click For PricingExpedia
- From $446 per night (USD)
VRBO
Fish, Swim, Relax, Party - 4bd, 3ba - 75’ Dockage & Private POOL!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
DOWNSTAIRS NOW AVAILABLE! Our 4/3 Beautiful Two Story Home is in Marathon Fl. Located in the middle of the Florida Keys ...
From $446 per night (USD)VRBO
- From $383 per night (USD)
Expedia
Beautiful quiet neighborhood. Sunsets! Huge pool! 10 min to Key West
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful 3 Bedroom 2 full bath home directly on the water with a full wraparound deck and fully fenced!Get away from it ...
From $383 per night (USD)Expedia
- From $244 per night (USD)
VRBO
The Garden Villa in Marathon
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The Garden Villa is a stunning 1bed/1bath unit with its own private pool. This unit has fresh paint, all new furniture a ...
From $244 per night (USD)VRBO
- From $834 per night (USD)
Expedia
Summerland Breeze - Three house retreat, perfect for multiple families
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 14
Breathtaking property located on desirable Summerland Key right on the ocean. There are three structures on the property ...
From $834 per night (USD)Expedia
- From $359 per night (USD)
VRBO
Tropical Breezes in Key Colony Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Tropical Breezes is a spacious 3bed/2bath beautifully decorated half duplex in desirable Key Colony Beach. There is a br ...
From $359 per night (USD)VRBO
- From $985 per night (USD)
Expedia
OCEANFRONT POOL HOUSE WITH 5 BEDROOM 3 BATH, SLEEPS 12 GUESTS.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Breathtaking sunset views from this open water home. Large dock with room for two large boats. Every night a unique su ...
From $985 per night (USD)Expedia
- From $223 per night (USD)
VRBO
Newly Remodeled Corner House on the Water
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
There’s no better place to experience the laid-back calm of the Florida Keys than this bright and newly-remodeled two-be ...
From $223 per night (USD)VRBO
- From $676 per night (USD)
VRBO
CEASAR'S PARADISE - A MODERN LUXURY RETREAT W/ 4+ Bedrooms/ 5.5 Baths
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Modern sophistication is the design aesthetic in this newer built home in Old Town Key West with designer touches throug ...
From $676 per night (USD)VRBO
- From $474 per night (USD)
VRBO
Boli Townhouse - Luxury Rental in gated Truman Annex - Saturday to Saturday only
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
We want you to know that your safety and comfort while in Key West is our utmost priority. Cleaning supplies are availab ...
From $474 per night (USD)VRBO
- From $1107 per night (USD)
Expedia
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Don't miss an ...
From $1107 per night (USD)Expedia
- From $321 per night (USD)
VRBO
Sandbar Sailors Condo in Tavernier near Fishing, Snorkeling and Diving Charters.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Relax & Recharge or plan your next great adventure at our quaint condo with lush mangrove and ocean views nestled on 60 ...
From $321 per night (USD)VRBO
- From $327 per night (USD)
Expedia
Coral Cove - Dream home in Florida Keys
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Coral Cove! This unit is located in the private Buttonwood Bay community, which edges the beautiful bay side ...
From $327 per night (USD)Expedia
- From $313 per night (USD)
VRBO
Beautiful Ocean view with 35' private seawall, 80' Heated Pool, Hottub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Gorgeous stilt home with beautiful ocean views. This Lobstering paradise is just 1 house down from open water on a deep ...
From $313 per night (USD)VRBO
- From $516 per night (USD)
Expedia
TOWNHOUSE FL KEYS ON ATLANTIC, MARINA, PICKLEBALL, TENNIS, POOLS, BIKES, KAYAKS
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
3 bedrooms and 3 full bathrooms townhome. Full bathroom on each floor and 2 separate living rooms to accommodate large f ...
From $516 per night (USD)Expedia
- From $436 per night (USD)
VRBO
Prime location, stunning views from 2 decks—walk or ride to explore the island!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Walk everywhere from this little part of Paradise, you will never need a car. Located in beautiful Old Town, you are vi ...
From $436 per night (USD)VRBO
- From $730 per night (USD)
Expedia
Two Bedroom Two Bath Poolside Villa Steps from Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We have the perfect accommodation for a family vacation or friends getaway in Old Town Key West, Florida. Our Two-Bedroo ...
From $730 per night (USD)Expedia
- From $370 per night (USD)
VRBO
3 Story Waterfront House with a pool and Beautiful Views!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
***NEW POOL***29 DAYS MINIMUM STAY. Bring your boat (20,000 Lbs. boat lift). This is a family-friendly Home. Equipped wi ...
From $370 per night (USD)VRBO
- From $290 per night (USD)
Expedia
Family-friendly oceanfront home with private beach, private gas grill, and deck
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Turtle Beach Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $290 per night (USD)Expedia




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