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From $559 per night (USD)
VRBO
Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to paradise! The Silly Sailfish is 1 of 8 stand alone single family homes within the 25 unit community and very ...
From $559 per night (USD)
VRBO
From $246 per night (USD)
Expedia
Heart of Marathon with Gulf and Ocean access
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Uniquely situated in the heart of Marathon, Unit B or 9922 is a 2 bedroom, 2 bath separate private home/villa/bungalow w ...
From $246 per night (USD)
Expedia
From $829 per night (USD)
VRBO
5 Star Modern New Construction Bayfront Home With Private Pool and Dock
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
5 Star Modern New Construction Bayfront Home With Private Dock and Pool Island Dreamz Bay House is a piece of paradise ...
From $829 per night (USD)
VRBO
From $252 per night (USD)
Expedia
It’s all here for you. Lagoon, pool, sun deck, kayaks, sunsets.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Great location on a deep water lagoon in the heart of Marathon. Uniquely situated in the heart of Marathon, Unit A or ...
From $252 per night (USD)
Expedia
From $615 per night (USD)
VRBO
BEAUTIFUL*WATER VIEW*POOL*GYM Room*Private Dock
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Over 100ft of water frontage, with expansive bay view of all the beautiful wildlife that Marathon has to offer! Pets are ...
From $615 per night (USD)
VRBO
From $700 per night (USD)
Expedia
Dolfan Oceanfront Cottage Direct oceanfront with 5
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Vaca-21-243This beautiful and spacious home has Direct Oceanfront Living. Ocean views and deep water dockage with boatin ...
From $700 per night (USD)
Expedia
From $540 per night (USD)
VRBO
PF Pool Beach Kitchen Sleep 6, Hot Tub W&D Marina WiFi Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This listing is for a PALM COURT villa, at Cocoplum Beach and Tennis Club and Marina, which is one of the 6 villas (Unit ...
From $540 per night (USD)
VRBO
From $473 per night (USD)
Expedia
Waterfront home with ocean views, dock, & private outdoor pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Sombrero Beach Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $473 per night (USD)
Expedia
From $423 per night (USD)
VRBO
Enjoy the Florida Keys like a local with this Private Waterfront Home with Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Come enjoy the Florida Keys like a local with a Private Tropical Waterfront Home with over 60 Feet of Deep Water Concret ...
From $423 per night (USD)
VRBO
$30 DAY RENTAL ONLY!\n\nBeautiful 2.5 acre waterfront villa with pool , & tiki bar$
From $1688 per night (USD)
Expedia
30 DAY RENTAL ONLY!\n\nBeautiful 2.5 acre waterfront villa with pool , & tiki bar
Bedrooms:
1
Bathrooms:
0
Sleeps:
0
THIS PROPERTY IS AVAILABLE FOR 30 DAY RENTAL ONLY! Beautiful 2.5-acre waterfront villa with private pool, hot tub and ...
From $1688 per night (USD)
Expedia
From $215 per night (USD)
VRBO
Carpe' Diem Heart of the Fl. Keys Specials
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
****Hi Y’all, Connie here your owner/ hostess at Carpe’Diem Marathon Florida Keys. I are still accepting weekly reserva ...
From $215 per night (USD)
VRBO
From $272 per night (USD)
Expedia
WOW! PRIVATE POOL, OCEAN FRONT, & DOCK Sister house next-door VRBO#1034656
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
From the moment that you arrive you will be swept away by the views this house offers. Perfect for a family, or friends ...
From $272 per night (USD)
Expedia
From $415 per night (USD)
VRBO
Waterfront Oasis w/ Pool, Tiki Lounge, Dock & BBQ
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Discover your dream vacation in this freshly remodeled 3-bedroom, 2-bath gem on a stunning flow-through canal with direc ...
From $415 per night (USD)
VRBO
From $1099 per night (USD)
VRBO
6BR/6BA Pelican's Nest: Oceanfront Home With Pool, Tiki Bar, and 150' Boat Dockage
Bedrooms:
6
Bathrooms:
6
Sleeps:
14
License # VACA-22-277 - Introducing the Pelican's Nest! Nestled against the ocean's edge with water bordering two sides ...
From $1099 per night (USD)
VRBO
From $377 per night (USD)
VRBO
Seas the Day ~ Spacious Waterfront Pool Home, 50` Dock!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Seas the Day Seas the Day beckons you to embrace luxury in Marathon, Florida Keys. This exquisite vacation rental boast ...
From $377 per night (USD)
VRBO
Click For Pricing
Expedia
Beach, 100 Foot Dock, Pool, Near Vaca Cut
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This beautifully furnished and landscaped property is centrally located in the Florida Keys, and features a host of amen ...
Click For Pricing
Expedia
From $182 per night (USD)
VRBO
Beautiful Studio in coco plum with pool, ramp and dockage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Beautiful studio condo in the Heart of the Florida Keys! Located in Coco Plum in Marathon, FL. This condo has a queen s ...
From $182 per night (USD)
VRBO
From $254 per night (USD)
VRBO
Beautiful canal front townhouse w/paradise feel, 3 blocks from Sombrero Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy a little piece of paradise in this beautiful/spacious townhouse located just 3 blocks from Sombrero Beach. This co ...
From $254 per night (USD)
VRBO
From $538 per night (USD)
VRBO
Harbor Hideaway - 3bed,2bath,50' dock, heated pool, tiki with all the amenities.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
VACA-23-42 is a charming romantic villa that serves as your perfect getaway, featuring a private saltwater pool right on ...
From $538 per night (USD)
VRBO
From $914 per night (USD)
VRBO
PS Sandy Beach, Pool View, dock, WiFi, Tennis, Jacuzzi, arrive any day, tropical
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This listing is for a PALM COURT villa, at Cocoplum Beach and Tennis Club and Marina, which is one of the 6 villas (Unit ...
From $914 per night (USD)
VRBO
From $363 per night (USD)
VRBO
FALL Discounts-Blue Ocean Bungalow 3bdr./3ba. updated canal access Sombrero
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Start planning your perfect escape to the Florida Keys! Blue Ocean Bungalow is ideally located on a wide, deep-water can ...
From $363 per night (USD)
VRBO
From $321 per night (USD)
Expedia
Blue Breeze: 3 BR, 2.5 BA House in Grassy Key, Sleeps 8
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Nestled within the tranquil Grassy Key neighborhood, Blue Breeze offers an idyllic escape. This spacious 3-bedroom resid ...
From $321 per night (USD)
Expedia
From $551 per night (USD)
VRBO
Amazing Sombrero Beach house-Pool, Kayaks, Bikes & More, great vacation home!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
New beach house clean and ready for renters. Accessible to beautiful Sombrero Beach via bike, car, kayak or walk. Priv ...
From $551 per night (USD)
VRBO
From $832 per night (USD)
Expedia
Waterfront Home, 200ft Dock, Gulf Access, Kayaks, Bicycles, Mini Golf, Game Room
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
WELCOME TO SOL MATE VACATION HOME - MARATHON, FLORIDA KEYS Welcome to Sol Mate Vacation Home, your private waterfront r ...
From $832 per night (USD)
Expedia
From $1277 per night (USD)
VRBO
Paradise Bay - 4 Bedrooms [with 2 Master Suites] & 4 Bathrooms - sleeps 10
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
NEW : Welcome old Guests. New Turf Grass around Pool. Paradise Bay - A spacious open floor plan located right in the h ...
From $1277 per night (USD)
VRBO
From $229 per night (USD)
VRBO
Oceanfront Sandy Beach Vacation Rental Unit 1
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We have two oversized second story apartments directly on a private Sandy Beach. Both apartments have had complete renov ...
From $229 per night (USD)
VRBO
From $309 per night (USD)
VRBO
Stunning custom home with treehouse setting, deck & neighborhood beach/boat ramp
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hammock House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $309 per night (USD)
VRBO
From $864 per night (USD)
VRBO
Spacious Home, Directly on Gulf , Beautiful Sunsets, 2 Master Suites, 2 Kayaks
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
This spacious property sits directly on the Gulf. Most rooms in the house has views of the Ocean. The deep water dock a ...
From $864 per night (USD)
VRBO
From $395 per night (USD)
VRBO
3 Bedroom 2.5 Bathroom POOL home with Canal Frontage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Fully remodeled home! Everything is brand new and no detail has been spared. This home is the perfect Florida Keys escap ...
From $395 per night (USD)
VRBO
From $301 per night (USD)
VRBO
Waterfront Aviation Florida Keys Vacation Rental 9104
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a beautiful home centrally located in the Florida Keys. It has just been completely renovated and everything is ...
From $301 per night (USD)
VRBO
From $217 per night (USD)
VRBO
Beautiful 2 Bedroom Condo - Private Pool & Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to my spacious and modern 2 bedroom, 2 bathroom condo with a bright and open floor plan! This condo is fully equ ...
From $217 per night (USD)
VRBO
From $681 per night (USD)
VRBO
The Gulf-Front Refuge on Grassy Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Enjoy your own private retreat! Fabulous Home on Morton Street. This three-bedroom, two-bath, private home is tucked aw ...
From $681 per night (USD)
VRBO
From $1591 per night (USD)
VRBO
Private, Gated, Oceanfront, Beachfront 5-Star Estate with dock, putting green.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This Oceanfront, Private Gated Estate is a two story, 3 bedroom/ 3 full bath home with a private beach, peninsula, tiki ...
From $1591 per night (USD)
VRBO
From $569 per night (USD)
VRBO
Villa Casa Cayo.....Ocean Side Canal Sombrero Beach Area
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This very open and airy vacation rental is your home away from home for that once in a lifetime Florida keys vacation! T ...
From $569 per night (USD)
VRBO
From $1133 per night (USD)
VRBO
The Dream House, Fabulous Gulf Front Pool Home with Spa, Dock & Beach
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
The Dream House on Grassy Key (formerly The Gulf House) on the Gulf offers everything you could want ... to have the per ...
From $1133 per night (USD)
VRBO
From $889 per night (USD)
Expedia
Serenity Bay Estate-FL Keys Best Kept Secret! Beautiful, Quiet, Tropical Pardise
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Located in the heart of the fabulous Florida Keys just 50 Miles from Key West, and 100 Miles from Miami International Ai ...
From $889 per night (USD)
Expedia
From $210 per night (USD)
VRBO
Oceanside, Pet Friendly, Smart Home with-SUP, kayak with and 60 ft Dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Great news, we just completed construction of a brand new 60FT dock. We have a kayak launch and plenty of room for your ...
From $210 per night (USD)
VRBO
From $747 per night (USD)
VRBO
Gulffront Waterfront open water views heated private pool,hot tub, kayaks, bikes
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Vista Linda on the Gulf of Mexico with deep water dock and open water views. Nice neighborhood for riding bikes Mid Cent ...
From $747 per night (USD)
VRBO
From $777 per night (USD)
VRBO
Breathtaking big waterfront home with private pool!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Our gorgeous Marathon home is available all year round. This home has 4 bedrooms and three full bathrooms with the maste ...
From $777 per night (USD)
VRBO
From $1000 per night (USD)
Expedia
Waterfront Gated Home—Pool, Spa, Private Dock & Boat Ramp—Gulfside Luxury Stay
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Beautifully furnished and gated home directly on the Gulf waters with a private 12x30' swimming pool & 7' jacuzzi, priva ...
From $1000 per night (USD)
Expedia
From $1037 per night (USD)
VRBO
LAST MINUTE SUMMER DEALS, PRIVATE OASIS! Vacation Home with a place for Everyone
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Guests are sure to enjoy a memorable vacation in this fully furnished, 5 bedroom/4 bath house. The main bedroom has a k ...
From $1037 per night (USD)
VRBO
From $308 per night (USD)
VRBO
Updated Sombrero Beach Canal Home Private Pool-Outdoor Kitchen
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
We REALLY LOVE our Marathon house! UPDATE 2024! We added a mini split AC to the twin bedroom! VERY COOL! Also refinishe ...
From $308 per night (USD)
VRBO
From $469 per night (USD)
VRBO
Open Water views, 100' dock Private Pool Ice machine DIRECT ACCESS open water
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Such a lovely spot for your next Keys "timeout". See the sunset over the Gulf of Mexico. Check for dolphins from your ...
From $469 per night (USD)
VRBO
From $894 per night (USD)
VRBO
Classic Waterfront Estate in Beautiful Sombrero Beach - over 200' of dockspace .
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Weekly rentals in the Keys {and generally elsewhere } are based on a Saturday to Saturday occupancy. Check - in is on Sa ...
From $894 per night (USD)
VRBO
From $840 per night (USD)
VRBO
Ocean Side Waterfront Exclusive Affordable Home - Pool , Tennis, Fishing & Golf
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Discover Villa Sombrero, your cozy waterfront escape in the heart of the Florida Keys. This unique retreat offers: - F ...
From $840 per night (USD)
VRBO
From $987 per night (USD)
Expedia
Custom Built Luxury Home on Canal; Walk to Beach; Close to Everything!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Home Description: Enjoy our large and beautiful custom built luxury home on the water and walking distance to the beach ...
From $987 per night (USD)
Expedia
From $2429 per night (USD)
VRBO
Beachfront 8-bedroom villa
Bedrooms:
5
Bathrooms:
8
Sleeps:
20
Marathon's beautiful beaches are home to our magnificent 8-bedroom oceanview estate where you can have your dream vacati ...
From $2429 per night (USD)
VRBO
From $479 per night (USD)
VRBO
Ground level house with pool and canal to ocean
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
VACA-22-386 This ground level house with two master bedrooms and two full bathroom house is located in a quiet marathon ...
From $479 per night (USD)
VRBO
From $1085 per night (USD)
VRBO
Extraordinary waterfront custom home, pool 56'dock ,ice machine,kayaks,bikes,ect
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Beautiful 6 bedroom 5 bath custom home. too many amenities to list-- 45' t dock,20 ft floating dock, and boat slips, in ...
From $1085 per night (USD)
VRBO
From $306 per night (USD)
Expedia
Key West style waterfront home w/ private pool, modern decor and prime location
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Trout Key Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $306 per night (USD)
Expedia
From $474 per night (USD)
VRBO
🌴 Coco Plum Paradise 🌴 Private Bayfront Home • Pool • Hot Tub • Dock • View
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to Coco Plum Paradise, located in Marathon, FL - the Heart of the Florida Keys. This private Key West-style hom ...
From $474 per night (USD)
VRBO
From $198 per night (USD)
VRBO
Oceanview Retreat w/Pool Steps Away From Beach #14
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover our inviting 1-bedroom condo in Marathon, a serene retreat with stunning ocean views from a screened balcony. F ...
From $198 per night (USD)
VRBO
From $813 per night (USD)
VRBO
Extra Lux Grouper House w/ 4 Master Suites, 6 BA, Pool, Dock & Private Boat Ramp
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Grouper House — Your Private Ultra Luxury Retreat in the Heart of the Florida Keys Step into Grouper House, ...
From $813 per night (USD)
VRBO
From $266 per night (USD)
Expedia
Canal Home with Direct Ocean Access, 75' dock, Hammock, Coconut Trees & More🌴
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
LICENSE: VACA020-937. Write to me with any questions, under the MESSAGE OWNER SECTION and I will be happy to chat with ...
From $266 per night (USD)
Expedia
From $753 per night (USD)
VRBO
PARADISE HOME ON THE ATLANTIC WITH HEATED POOL
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
***PROPERTY IS PERMASAFE PROTECTED AGAINST COVID-19, MOST BACTERIAS AND VIRUSES*** www.Permasafe.com/home-2/ ...
From $753 per night (USD)
VRBO
From $701 per night (USD)
Expedia
Sunset Catch- Gulf Front, Open Water Views, Private Pool and Dock, Kayaks.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Whether an avid adventurer or a family seeking to relax and enjoy the expansive view, Sunset Catch is the place for you. ...
From $701 per night (USD)
Expedia
From $530 per night (USD)
VRBO
Waterfront Pool home with Quick Access to Gulf
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Enjoy your relaxing Keys Vacation in YELLOWTAIL BUNGALOW (PLR2019-00357) This newly rebuilt / renovated CBS private home ...
From $530 per night (USD)
VRBO
From $353 per night (USD)
VRBO
3 Bedroomed Ocean View Condo, Lovely View #33
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This is a 1200 sqare foot, newly refurbished spacious 3 bed, 2 bath condo (see video above)with a 2nd floor uninterrupte ...
From $353 per night (USD)
VRBO
From $488 per night (USD)
VRBO
IB50 Relax & Renew | 3 Bed, 2 Bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This canal-front home offers 3 bedrooms, 2 baths, a screened-in porch, and a covered veranda, perfect for relaxing in th ...
From $488 per night (USD)
VRBO
From $393 per night (USD)
VRBO
Gulf Open Water, Stunning Views, Protected Boat Dock, Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Media Luna is located on the Gulf of Mexico, this island home has 55 feet of sliding glass doors opening onto the Gulf, ...
From $393 per night (USD)
VRBO
From $400 per night (USD)
VRBO
SPECTACULAR! PRIVATE POOL, OCEAN FRONT, & DOCK Sister house nextdoor VRBO#770357
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
From the moment that you arrive you will be swept away by the views this house offers. Perfect for a family, or friends ...
From $400 per night (USD)
VRBO
From $393 per night (USD)
VRBO
Waterfront, dock, easy ocean access, heated pool, walk to beach! Great location!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
One room with a king sized bed and the other has a queen sized bed – both with cool comfort memory foam mattresses. Pull ...
From $393 per night (USD)
VRBO
From $418 per night (USD)
VRBO
Amazing Views! Dockage on the open water! Brand New 4 Bedrooms, Cabana Club!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Sweeping views of the Open Atlantic Ocean and just seconds to Vaca Cut! Boating hot spot as well as a comfortable home t ...
From $418 per night (USD)
VRBO
From $496 per night (USD)
Expedia
P39 - 3 bed, 3 bath home with spectacular open wat
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This 3 bedroom, 3 bath home boasts a magnificent open water view and spectacular infinity pool! Boating guests ar ...
From $496 per night (USD)
Expedia
From $421 per night (USD)
VRBO
Kon Tiki ~ Private Waterfront Pool Home, 30' Dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Kon Tiki at Sombrero Beach Kon Tiki at Sombrero Beach is a charming 2-story on stilts A-frame vacation rental in Maratho ...
From $421 per night (USD)
VRBO
From $616 per night (USD)
Expedia
Reel Relaxin` ~ Luxury Waterfront Pool Home
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Reel Relaxin' Experience luxury living at Reel Relaxin', a coastal chic decorated vacation rental in Marathon, Florida. ...
From $616 per night (USD)
Expedia
From $402 per night (USD)
VRBO
Island Time~ Pool Home Seconds to Open Ocean! 32' Dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Property Highlights: • Sleeps: 8 • Bedrooms: 3 • Bathrooms: 2 • Dock: 32' seawall dockage, 5-7' depth, with direct acce ...
From $402 per night (USD)
VRBO
From $744 per night (USD)
Expedia
Casa Playa~ Luxury Pool Home Amazing Outdoor Area!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
4BR 4.5BA Home w/ Fantastic Outdoor Entertainment Area w/ Full Kitchen, Yard Games, Bikes, Kayaks, Paddleboards! ...
From $744 per night (USD)
Expedia
From $562 per night (USD)
VRBO
Angler & Ale~ Waterfront Pool Home, Hot Tub & 60' Dock!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Angler and Ale Escape to luxury at Angler and Ale, a 4-bed, 3-bath private pool split-level home located near Sombrero ...
From $562 per night (USD)
VRBO
From $292 per night (USD)
Expedia
Sunset Bay ~ Luxury Waterfront Villa, 31' Boat Slip
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
••• Property Highlights: • Sleeps: 8 • Bedrooms: 3 • Bathrooms: 2.5 • Master Bedroom: Indulge in the ultimate retreat i ...
From $292 per night (USD)
Expedia
From $270 per night (USD)
VRBO
Seaside Villa~ Charming Beachfront Condo w/ Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Seaside Villa at Coco Plum Beach Welcome to Seaside Villa, a charming 2-bedroom, 2-bathroom condo nestled in the heart ...
From $270 per night (USD)
VRBO
From $433 per night (USD)
Expedia
Indigo Reef #50 ~ The Palms, Sunset Views & 31' Boat Slip
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Property Highlights: • Sleeps: 6 • Bedrooms: 3 • Bathrooms: 2.5 • Dock: 35' dock (boat length max is 31'), slip number ...
From $433 per night (USD)
Expedia
From $1156 per night (USD)
VRBO
Sunsets in Paradise~ Gulf Front Pool Home, 22' Dock, Kayaks, Bikes & Paddleboards
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Sunsets in Paradise Escape to an indulgent private 5-bedroom gulfside split-level retreat in the Florida Keys, where lu ...
From $1156 per night (USD)
VRBO
From $398 per night (USD)
Expedia
One Particular Harbor ~ Waterfront Pool Home Near the Beach!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
One Particular Harbor Nestled in the peaceful Coco Plum Beach neighborhood, this 3BR, 3BA home features a private, heat ...
From $398 per night (USD)
Expedia
From $407 per night (USD)
VRBO
Sombrero Chic~ Waterfront Pool Home Near Sombrero Beach, 40' Dock!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Sombrero Chic at Sombrero Beach Perched on stilts, this tropical retreat, Sombrero Chic, seamlessly combines classic Fl ...
From $407 per night (USD)
VRBO
From $310 per night (USD)
Expedia
Turtle Cove at Indigo Reef~ Pet-friendly Townhome, 31' Boat Slip!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Property Highlights: • Sleeps: 8 • Bedrooms: 3 • Bathrooms: 2.5 • Dock: 35' dock (boat length max is 31'), slip number ...
From $310 per night (USD)
Expedia
From $365 per night (USD)
VRBO
Sunset House at Indigo Reef ~ Open Water Views, 31' Slip!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
The Sunset House at Indigo Reef Spacious and like new 3 BR 2.5 BA at one of Marathon, Florida Keys most prestigious res ...
From $365 per night (USD)
VRBO
From $541 per night (USD)
Expedia
Tropical Seahorse at Coral Lagoon ~ Waterfront Villa w Resort Pool & Slip
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
IMPORTANT: If you are planning to bring a boat, there are additional documents you will need to complete for us to submi ...
From $541 per night (USD)
Expedia
From $736 per night (USD)
VRBO
Pier Pressure~ Luxury Waterfront Pool Home, 100' Dock
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Pier Pressure Welcome to Pier Pressure, your luxurious waterfront oasis in Marathon, Florida! This stunning, newly remo ...
From $736 per night (USD)
VRBO
From $418 per night (USD)
Expedia
2BR Condo with Pool & Marina in Marathon
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Spacious and well-equipped, this 2-bedroom, 2-bath condo offers a convenient home base for exploring the area. ...
From $418 per night (USD)
Expedia
From $1252 per night (USD)
VRBO
Luxury Waterfront Estate—Pool, Spa, Game Lounge, 2 Docks & Ramp Access—Gulfside
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Welcome to The Azul Sea Estate, adventure awaits you.. 5 Beds | 5 Baths | Separate Guest Quarters | 3219 Square Feet Un ...
From $1252 per night (USD)
VRBO
From $479 per night (USD)
VRBO
Close to Sombrero Beach! Open Water Views, POOL and Dockage!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Privacy galore at this great location on Sombrero Beach Rd WITH A BRAND NEW POOL! Famous Sombrero Beach is approximately ...
From $479 per night (USD)
VRBO
From $623 per night (USD)
VRBO
Refuge on the Reef~ Waterfront Pool Home, 75' Dock
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Refugee on the Reef Relax your cares away at Refuge on the Reef! Read a book in the shady outdoor hammock, take a lazy d ...
From $623 per night (USD)
VRBO
From $334 per night (USD)
Expedia
Indigo Reef #17~ Plane Fun ~ 31' Boat Slip!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
••• Property Highlights: • Sleeps: 8 • Bedrooms: 3 • Bathrooms: 2.5 • Dock: 35' dock (boat length max is 31'), slip num ...
From $334 per night (USD)
Expedia
From $586 per night (USD)
VRBO
Waterfront luxury Villa (13) with 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 $586 per night (USD)
VRBO
From $346 per night (USD)
Expedia
Pet Friendly Home on the Canal
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located in the heart of the middle Keys - Marathon, FL this three bedroom, two bath bungalow on the water has a 50 foot ...
From $346 per night (USD)
Expedia
From $677 per night (USD)
VRBO
Casa del Mar, Open waterfront pool home in the Sombrero Beach area
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Fabulous location in the Sombrero Beach area of the Middle Keys. Sombrero Beach is one of the Florida Keys jewels, ocean ...
From $677 per night (USD)
VRBO
From $186 per night (USD)
Expedia
Cozy Conch - oceanside charmer 10 minutes from beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The Cozy Conch is ideally located, just walking distance from the historic 7 mile bridge. Take a bike ride along Overse ...
From $186 per night (USD)
Expedia
From $987 per night (USD)
VRBO
Brand New Build! Krakens Cove, Marathon FL
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Spacious, tropical home features 4 king bedrooms, each with ensuite bath. Open concept living area with state of the ar ...
From $987 per night (USD)
VRBO
From $232 per night (USD)
Expedia
Oceanside waterfront 2/2 home with 55ft dock and paddle equipment
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Our wonderful Oceanside waterfront home is just two minutes from the Atlantic Ocean and Vaca Cut. There are no bridges t ...
From $232 per night (USD)
Expedia
From $188 per night (USD)
VRBO
Pet Friendly Half-Duplex Cottage with kayaks and 40' Slip Option at Marina
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We have a lovely oceanside cottage in Marathon Key, Florida, close to everything with hidden amenities. The cottage has ...
From $188 per night (USD)
VRBO
From $538 per night (USD)
VRBO
Calm Palms- Corner of Canal, Heated Pool, Kayaks and Privacy!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Calm Palms is the place to book if you want a conveniently located vacation home with privacy, a heated pool to relax in ...
From $538 per night (USD)
VRBO
From $239 per night (USD)
VRBO
Sailor's Delight in Marathon
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
This condominium at The Reef in Marathon, Middle Keys is a true resort setting with a home away from home feel. This uni ...
From $239 per night (USD)
VRBO
From $338 per night (USD)
VRBO
Resort, beaches, restaurants, apartments,
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
square ft. - 864 sleeps 6; kitchen - 1 full; bedding includes 1 king, 2 twin beds,1 sofa bed most comfortable for 2 chil ...
From $338 per night (USD)
VRBO
From $876 per night (USD)
VRBO
NEW Waterfront Home w/ Heated POOL & Private Dock
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
New 4-bedroom spacious home with 2 master suites, a heated pool, 160' of dock, and a covered outdoor bar. Large kitchen ...
From $876 per night (USD)
VRBO
From $852 per night (USD)
Expedia
Casa De La Playa Oceanfront the Key to the Beach a
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
VACA-22-368Welcome to the beach house! Enjoy the Southeast Exposure with the sun all day, while having your toes in the ...
From $852 per night (USD)
Expedia
From $324 per night (USD)
VRBO
Renovated waterfront duplex with canal access, covered patio, deck, & central AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Conch Cabana Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $324 per night (USD)
VRBO
From $425 per night (USD)
Expedia
Private 174ft dock & ramp, 3br, 3 mins to Sombrero Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
****7 Day Minimum Per City Ordinance**** Vacation Rental Permit# VACA-22-404 This 3bed, 3 bath sleeps 8. Stunning wate ...
From $425 per night (USD)
Expedia
From $412 per night (USD)
VRBO
2BR Condo Overlooking the Marina
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Located between Key Largo and Key West, this waterfront condo is nestled within a peaceful resort overlooking t ...
From $412 per night (USD)
VRBO
From $673 per night (USD)
Expedia
Sombrero Beach Beauty~ 50` Dock Private Pool Home!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Property Highlights: • Sleeps: 12 • Bedrooms: 5 • Bathrooms: 3 • Master Bedroom: Experience the epitome of relaxation i ...
From $673 per night (USD)
Expedia

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