Monroe Area Rentals
From $275 per night (USD)VRBO
Coo Coo's Nest ~ Key Largo canal front 2/3 with pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Beautiful pool home with dockage in the heart of Key Largo! The Space: Step into the enchanting Coo Coo's Nest ...
From $275 per night (USD)VRBO
From $346 per night (USD)Expedia
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 $346 per night (USD)Expedia
From $500 per night (USD)VRBO
Waterfront Private Home w/Pool-Family&Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Welcome to Casa Pina! Located right in the heart of Marathon. Enjoy your trip to the keys in this stunning cus ...
From $500 per night (USD)VRBO
From $231 per night (USD)Expedia
Tiny House RV, Kayak, Canoe, Beach, Marina, Pool, Near Restaurant's & State park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
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 $231 per night (USD)Expedia
From $338 per night (USD)VRBO
Snorkel & Dive Legendary Coral Reefs - Then Relax Poolside with a Drink!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Enjoy a beautifully designed 2-bedroom, 2-bathroom oceanfront condo in Key Largo, perfectly positioned beside ...
From $338 per night (USD)VRBO
From $644 per night (USD)Expedia
4 bed & 4 bath Unit 906 @Mariners Club - Sleeps 10!! Ohana Cay
- Bedrooms:
- 4
- 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 $644 per night (USD)Expedia
From $307 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 $307 per night (USD)VRBO
From $288 per night (USD)Expedia
**CARIBBEAN CHARM** Villa Near Duval & Beach + Last Key White Glove Service...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! The sound of ...
From $288 per night (USD)Expedia
From $515 per night (USD)VRBO
P00 - 4 Bedroom Pool Home overlooking Sombrero Beach!
- 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 $515 per night (USD)VRBO
From $367 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 $367 per night (USD)Expedia
From $508 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 $508 per night (USD)VRBO
From $352 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 condo unit offers 1,280 sq feet of living space ...
From $352 per night (USD)Expedia
From $456 per night (USD)VRBO
P78 - Charming 3 bedroom 2 bath home in Sombrero Beach with dock and pool
- 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 $456 per night (USD)VRBO
From $395 per night (USD)Expedia
P22 - Lovely 3 bedroom 2 bath duplex with private pool, dockage and Cabana Club
- 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 $395 per night (USD)Expedia
From $1148 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 $1148 per night (USD)VRBO
From $699 per night (USD)Expedia
P28 - Luxury 4 bedroom, single family home with pool and dock in Key Colony Beach
- 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 $699 per night (USD)Expedia
From $656 per night (USD)VRBO
P02 - 5 bed, 3.5 bath home with large private pool in Sombrero Beach!
- 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 $656 per night (USD)VRBO
From $471 per night (USD)Expedia
P43 - Spacious 3 bedroom 3 bath home with Pool in the Sombrero Beach Area
- 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 $471 per night (USD)Expedia
From $801 per night (USD)VRBO
Swept Away – 3BR/2BA Keys Retreat with Pool, Dock & Stunning Open Water Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Swept Away, an exquisite and newly crafted luxury single-family residence boasting three bedrooms and two bathrooms. Thi ...
From $801 per night (USD)VRBO
From $586 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 $586 per night (USD)Expedia
From $3780 per night (USD)VRBO
**ALL TOGETHER NOW @ OLD TOWN** 3 Home Compound + Last Key White Glove Service…
- Bedrooms:
- 14
- Bathrooms:
- 13
- Sleeps:
- 32
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Coordinating ...
From $3780 per night (USD)VRBO
From $593 per night (USD)Expedia
4 BR 4 BA, Private Pool, Paddleboards, Bikes, Lots of Great Amenities!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
The Blue Turtle Villa, located in Key Colony Beach, in the Marathon area, is a gorgeous, brand new, designer decorated c ...
From $593 per night (USD)Expedia
From $540 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 $540 per night (USD)VRBO
From $334 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 $334 per night (USD)Expedia
From $1081 per night (USD)VRBO
**MAYA’S SECRET TREASURE** Pool & Balcony + Last Key White Glove Service...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Walking along ...
From $1081 per night (USD)VRBO
From $1371 per night (USD)Expedia
Duval's Duet - Double Balconies Duval Street
- 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' ...
From $1371 per night (USD)Expedia
From $440 per night (USD)VRBO
BOAT SLIP INCLUDED AUGUST-NOVEMBER 2026!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
- VR#258 - Saturday check-in. 2 bedroom and 2.5 bath at 117 Anglers Way with Boat Slip #36 available. Awesome family ge ...
From $440 per night (USD)VRBO
From $1029 per night (USD)Expedia
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 $1029 per night (USD)Expedia
From $505 per night (USD)VRBO
Open Water View from porch , golf cart, dock, bikes, kayaks, trailer parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Waterfront Modern Home w/ Dock, Ocean Access + Golf Cart | Fishing Paradise | Resort Amenities Stay at this beautifully ...
From $505 per night (USD)VRBO
From $578 per night (USD)Expedia
122 Mariners Club - An exceptional 2 bedroom luxury condo with ocean and marina views
- 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 $578 per night (USD)Expedia
From $328 per night (USD)VRBO
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball
- 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 $328 per night (USD)VRBO
From $874 per night (USD)Expedia
FULL TIME LIC MGR - INDOOR/OUTDOOR PICKLEBALL - SPEAKEASY - OCEANFRONT RESORT!
- 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 $874 per night (USD)Expedia
From $360 per night (USD)VRBO
5 STAR HOME 4 BR 3/1/2 baths, pool. Extremely discounted for 28 day rental.
- 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 $360 per night (USD)VRBO
From $718 per night (USD)Expedia
Oceanfront 4 bedroom, 3 Bath House, Private Pool and Deep Water Concrete Dock!!
- 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 $718 per night (USD)Expedia
From $427 per night (USD)VRBO
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Community 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 $427 per night (USD)VRBO
From $389 per night (USD)Expedia
COCONUT PALM SUITE ~ Adult Only, 1 BR, 1 Ba w/ Kitchen and Community 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 $389 per night (USD)Expedia
From $670 per night (USD)VRBO
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 $670 per night (USD)VRBO
From $389 per night (USD)Expedia
ROYAL PALM SUITE ~ Adult Only, 1 BR, 1 Ba w/ Kitchen and Community 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 $389 per night (USD)Expedia
From $391 per night (USD)VRBO
Waterfront Sunway Lagoon *Huge Private Dock*
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
<p>Welcome to Marathon, home of the best fishing town in the Middle Keys. This home has an incredible 120ft boat dockage ...
From $391 per night (USD)VRBO
From $195 per night (USD)Expedia
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 $195 per night (USD)Expedia
From $410 per night (USD)VRBO
~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 $410 per night (USD)VRBO
From $391 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 $391 per night (USD)Expedia
From $454 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 $454 per night (USD)VRBO
From $1005 per night (USD)Expedia
PARADISE FOUND!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Paradise Found at Mariners Club resort in Key Largo, FL is a spacious 3-story 3bed/3bath townhome overlooking a beautif ...
From $1005 per night (USD)Expedia
From $707 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 $707 per night (USD)VRBO
From $765 per night (USD)Expedia
4 Bedroom,4 Bath with private pool and 37 and 1/2 foot boat dock
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This home has 2 levels and is located at 401 9th Street in Key Colony Beach. Private Boat dock that is 37 and half feet ...
From $765 per night (USD)Expedia
From $296 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 b ...
From $296 per night (USD)VRBO
From $317 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 b ...
From $317 per night (USD)Expedia
From $326 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 b ...
From $326 per night (USD)VRBO
From $498 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 $498 per night (USD)Expedia
From $452 per night (USD)VRBO
Angler's Retreat updated 3-bedroom, 2-bath home just minutes from Sombrero Beach!
- 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 $452 per night (USD)VRBO
From $473 per night (USD)Expedia
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come stay with us at VENTURE OUT, a fantastic gated, activity filled community in Cudjoe Key, Fl- only 20 miles north of ...
From $473 per night (USD)Expedia
From $417 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 $417 per night (USD)VRBO
From $412 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 $412 per night (USD)Expedia
From $498 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 $498 per night (USD)VRBO
From $607 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 $607 per night (USD)Expedia
From $4327 per night (USD)VRBO
Beautiful Florida Keys Oasis, private beach with magnificent sunsets
- Bedrooms:
- 11
- Bathrooms:
- 10
- Sleeps:
- 44
Nestled along the picturesque shores of Key Largo, Florida, Bahia Bay is a luxurious waterfront estate offering an unpar ...
From $4327 per night (USD)VRBO
From $181 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 $181 per night (USD)Expedia
From $548 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 $548 per night (USD)VRBO
From $244 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 Duva ...
From $244 per night (USD)Expedia
From $1935 per night (USD)VRBO
6 BR 6 BA Duval Street Suites free parking & pool
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 24
Summary: This can accommodate 24 people, each apartment has 2 beds. You'll have privacy with six individual suites each ...
From $1935 per night (USD)VRBO
From $1167 per night (USD)Expedia
Sombrero Beach house with private dock and pool
- Bedrooms:
- 4
- Bathrooms:
- 2
- Sleeps:
- 8
Casa MarBella @ Sombrero Beach offers plenty of indoor and outdoor space. Enjoy our beautiful pool with flowing waterfal ...
From $1167 per night (USD)Expedia
From $880 per night (USD)VRBO
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 $880 per night (USD)VRBO
From $195 per night (USD)Expedia
MONTHLY Rental, JAN, FEB, MAR 2027 just opened, Old Town, pets ok
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Sea Monkey and The Mermaid! Our home is a duplex located in Old Town and full of Key West charm. Both unit ...
From $195 per night (USD)Expedia
From $552 per night (USD)VRBO
Sunset Villas: Bayfront Beach Compound<br>**28 Night Min**
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Sunset Villas is a boutique resort boasting 4 private villas on a Bayfront acre with one of the few swimmable sandy beac ...
From $552 per night (USD)VRBO
From $593 per night (USD)Expedia
Peaceful canal-front 3/3 Single-Family Home w/ Private Pool & Cabana Club Access
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Blue Heron House, your private canal-front escape in the heart of Key Colony Beach. This ground-level, single ...
From $593 per night (USD)Expedia
From $204 per night (USD)VRBO
Easy Ocean Access House 30' Dock & Pool at Cabana Club
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our Beach House in the prestigious Key Colony Beach. 30 FT dock house in a 90 FT canal with easy access to th ...
From $204 per night (USD)VRBO
From $665 per night (USD)Expedia
Amazing Sunsets, Bay Breezes in the beautiful Florida Keys
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience ultimate relaxation at Anchors Aweigh, a modern 3-bedroom Key Largo home in the beautiful Florida Keys. Co ...
From $665 per night (USD)Expedia
From $610 per night (USD)VRBO
115 Mariners Club Spacious Villa with Resort Pools
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
As you enter this marina-front villa in Key Largo, the coastal view captivates you, showcasing the private yacht harbor ...
From $610 per night (USD)VRBO
From $490 per night (USD)Expedia
Poolside Suite - Pool & Close to Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Poolside Suite is the PERFECT vacation home for family and friends looking for a fun-filled getaway in the hea ...
From $490 per night (USD)Expedia
From $354 per night (USD)VRBO
Cozy Home!!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Newly renovated half duplex on a quiet street in Marathon. Conveniently located in the heart of Marathon, on a canal jus ...
From $354 per night (USD)VRBO
From $209 per night (USD)Expedia
Away From It All @ The Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $209 per night (USD)Expedia
From $555 per night (USD)VRBO
Coral Lagoon #13: Heated Pool, Views, easy Gulf & Atlantic Access via Vaca Cut
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Coral Lagoon #13: Pool, Water Views, Located just off Vaca Cut with easy Gulf & Atlantic Access. ** CHECK OUT OUR REVIE ...
From $555 per night (USD)VRBO
From $596 per night (USD)Expedia
Galleon Resort beach hotel luxury in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It ...
From $596 per night (USD)Expedia
From $440 per night (USD)VRBO
Waterfront Sunset View Aqua Villa at Conch Shell @ Mangrove Resort LLC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
The Conch Shell houseboat has 1 Queen bed, 1 Queen sofa sleeper and 2 Twin beds in the loft. Each houseboat has flat-scr ...
From $440 per night (USD)VRBO
From $1636 per night (USD)Expedia
NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Seaside Place welcomes guests from all states and follows all cleanliness and safety guidelines. Your safety and comfor ...
From $1636 per night (USD)Expedia
From $157 per night (USD)VRBO
Enjoy this relaxing beachy house on a canal flowing into sexton cove bay.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy this cozy home with a beautiful water front terrace. Conveniently located close to grocery stores, great restaura ...
From $157 per night (USD)VRBO
From $337 per night (USD)Expedia
Vibrant Family Condo with Pool & Ocean Panorama U3
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Enjoy vibrant living at our 2-bedroom Colourful Keys Condo, where fun meets relaxation. Boasting pool and ocea ...
From $337 per night (USD)Expedia
From $633 per night (USD)VRBO
P82 - Sombrero Beach - 4 bedroom pool home with dock and private ramp.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Sombrero Beach Sea-clusion awaits our guests! Get ready to create great vacation memories! This spacious 4-bedroom, 3 a ...
From $633 per night (USD)VRBO
From $859 per night (USD)Expedia
3bed vacation ocean side townhome 2pools,marina,lagoon,golf cart,bikes,kayaks
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Family and Friends vacation in mind - beautiful Key Largo townhouse with 2 separate living rooms which that offers a un ...
From $859 per night (USD)Expedia
From $940 per night (USD)VRBO
**THE ZESTY LIME @ OLD TOWN** Restored Home + Last Key White Glove Service...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West is k ...
From $940 per night (USD)VRBO
From $370 per night (USD)Expedia
Sunsets on the bay at Villa Mia
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Come and enjoy sunsets on the bay at Villa Mia! We created a peaceful retreat for our family and friends to enjoy. It is ...
From $370 per night (USD)Expedia
From $486 per night (USD)VRBO
Reel Paradise I - 2bed/2bath half duplex with private pool & dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Reel Paradise 1, a charming 2-bedroom, 2-bath half duplex designed for the perfect Florida Keys getaway. This ...
From $486 per night (USD)VRBO
From $853 per night (USD)Expedia
P87 - Modern 4 bedroom, 4 bath home on open water in Sombrero Beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Stunning views with premier Sombrero Beach location sets this home apart from all others! This ocean front home is spect ...
From $853 per night (USD)Expedia
From $1398 per night (USD)VRBO
Elev • 5BR/8BA • Game Room • 75’ Deep Canal Dock • Ice Maker • Kayaks • Bikes
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to your private Mediterranean-style paradise in Key Colony Beach, proudly known as the Gem of the Keys. This lux ...
From $1398 per night (USD)VRBO
From $413 per night (USD)VRBO
Waterfront Community in Key Largo, Florida - Moon Bay Condo A210 Sunsets
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Moon Bay, a piece of paradise! It is located on Blackwater Sound in Key Largo, Florida. Unit A210 is an end ...
From $413 per night (USD)VRBO
From $256 per night (USD)VRBO
Duval Street Suites full kitchen Old Town with heated pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Key Lime Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and full kitchen complete ...
From $256 per night (USD)VRBO
From $628 per night (USD)Expedia
Oceanside Kawama Villa R5
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Come experience ultimate relaxation and comfort in this stunning three-story vacation home. On the first floor, you will ...
From $628 per night (USD)Expedia
From $2112 per night (USD)VRBO
Thompson Island - Private Island Estate in Key West
- Bedrooms:
- 8
- Bathrooms:
- 9
- Sleeps:
- 20
Thompson Island is the only private island in Key West with direct bridge access. Guests drive across a private bridge, ...
From $2112 per night (USD)VRBO
From $237 per night (USD)VRBO
Keys Life Cottage ~ Downtown Islamorada Cottage with Pool Access!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Keys Life Cottage! Experience the laid-back charm of Islamorada at Keys Life Cottage, a beautifully coastal- ...
From $237 per night (USD)VRBO
From $492 per night (USD)VRBO
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Oceanfront Oasis in Key West – Steps from Smathers Beach Escape to paradise in this spacious 2-bedroom, 2-bath condo wi ...
From $492 per night (USD)VRBO
From $405 per night (USD)Expedia
Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Caribbean Conch – Your Island Retreat Awaits Escape to the serene beauty of Caribbean Conch, a spacious and ...
From $405 per night (USD)Expedia
From $596 per night (USD)VRBO
Key Largo Ocean Shore Villa 3 with pool & boat slip
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This centrally located boater`s paradise is the perfect place to relax. Walk to restaurants, cook in kitchen or grill do ...
From $596 per night (USD)VRBO
From $900 per night (USD)Expedia
Beautiful Oceanside Mariner`s 3 Bedroom Townhome
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Best vacation rental to explore the Florida keys. Marina Villa 210 (3b/3b) with Marina and ocean views. Escape to pa ...
From $900 per night (USD)Expedia
From $1125 per night (USD)VRBO
Waterfront, 100ft Dock, Kayaks, Bikes, Pool, Hot Tub, Basketball & Pickleball
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
WELCOME TO COCO PLUM ON THE BAY - MARATHON, FLORIDA KEYS Welcome to Coco Plum on the Bay, your private waterfront retre ...
From $1125 per night (USD)VRBO
From $395 per night (USD)Expedia
Rent a Piece of Paradise, Best Location on the Island!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Rent a piece of paradise right in the heart of beautiful Old Town Key West. Walking distance to all major attraction (r ...
From $395 per night (USD)Expedia
From $459 per night (USD)VRBO
**TIDEWATER VIEWS** Cottage + Boat Slip + Pool + Last Key White Glove Service...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! TIDEWATER VIE ...
From $459 per night (USD)VRBO
From $783 per night (USD)Expedia
Beautiful 4 Bedroom, 3 Bath, Spacious Pool/SPA Home with 200' wide Canal.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Casa del Cielo. Enjoy breathtaking views of the Gulf and Ocean from this beautiful canal front home. Bring y ...
From $783 per night (USD)Expedia
From $438 per night (USD)VRBO
Little Island Pearl
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Paradise in Key Colony Beach, Florida Keys Dreaming of a relaxing getaway in the beautiful Florida Keys? Welc ...
From $438 per night (USD)VRBO
From $384 per night (USD)Expedia
B105 Moon Bay - 3 bedroom townhouse includes studio apartment and boat dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Lovely bayside townhouse with 2 bedrooms, 1 1/2 baths on the main floor, and a studio apartment on the ground floor with ...
From $384 per night (USD)Expedia