Florida Keys Rentals
From $178 per night (USD)VRBO
Quiet & Stress Free canal home with private dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The home has 3 bedrooms and 2 bath. The dock has space for a boat up to 30’. Come and enjoy the beautiful surroundings ...
From $178 per night (USD)VRBO
From $269 per night (USD)Expedia
Southernmost View - Private Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Southernmost View is a modern, luxurious waterfront home in a private seven-home gated community just steps fr ...
From $269 per night (USD)Expedia
From $400 per night (USD)VRBO
Beautiful vacation home in the heart of Islamorada , Florida Keys
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A perfect Keys home located in the heart of Islamorada in the sought-after Port Antigua community with access to the hom ...
From $400 per night (USD)VRBO
From $252 per night (USD)Expedia
BOOK YOUR DREAM VACATION at BEACON REEF - SPECIAL SUMMER DEAL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
August to November, take $500 off regular price! World Famous Beacon Reef Condo (a gated community) Oceanfront Islamorad ...
From $252 per night (USD)Expedia
From $331 per night (USD)VRBO
Imagine in the Keys - Venture Out Unit 073
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Imagine in the Keys VO073 35' Dockage Canal front 2Bd/2Ba This home features 2Bd/2Ba and is located only 3 lots from op ...
From $331 per night (USD)VRBO
From $572 per night (USD)Expedia
Key Largo Villa, Kawama K5, 3/3
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Keys Relaxing Getaway....Have fun with the whole family at this stylish place. Explore the Florida Keys from this centr ...
From $572 per night (USD)Expedia
From $401 per night (USD)VRBO
★Remodeled tropical delight townhome★private plunge pool close to fun activities
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This beautiful townhouse was remodeled in late 2021 with a modern tropical inspired scheme. High speed internet -1,000m ...
From $401 per night (USD)VRBO
From $361 per night (USD)Expedia
Conch Get Enough at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy an early morning cup of coffee on your private bedroom balcony after being gently woken by the crowing of a wild r ...
From $361 per night (USD)Expedia
From $1723 per night (USD)VRBO
Key West Oasis - Truman Annex Estate
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to Key West Oasis Luxury | Privacy | Iconic Location in Truman Annex Tucked away on one of the most exclusive ...
From $1723 per night (USD)VRBO
From $742 per night (USD)Expedia
Bayside Boaters Paradise w/Pool – Marlin Bay
- 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 $742 per night (USD)Expedia
From $300 per night (USD)VRBO
Executive Bay Club Bayfront/Beachfront paradise
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Watch the sunset from your private balcony from this bay front , beach front townhouse/condo. Recently remodeled and ful ...
From $300 per night (USD)VRBO
From $238 per night (USD)VRBO
Modern 2BR Condo Old Town/Balcony & Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
*28 day min stay* Come enjoy this fully updated 2/BR condo in the heart of Old Town. The perfect balance of being close ...
From $238 per night (USD)VRBO
From $465 per night (USD)VRBO
Green Goddess - Sunsets Included - 4BD/3Bath - 360° Rooftop - Private Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the beauty of Key West's famous sunsets from the comfort of your own vacation home at The Green Goddess. This ...
From $465 per night (USD)VRBO
From $387 per night (USD)Expedia
BeachHouse @ Sombrero & Ocean access w/45’ Dock, kayaks and Bikes.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Your family will be close to everything when you stay at this centrally-located place. Our home is close to grocery stor ...
From $387 per night (USD)Expedia
From $794 per night (USD)VRBO
Sky Suite with Balcony Overlooking Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Welcome to Sky Suite On Duval Street - a newly remodeled masterpiece that overlooks world famous Duval Street. ...
From $794 per night (USD)VRBO
From $538 per night (USD)Expedia
Kawama Yacht Club-Oceanfront Resort-Private Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Kawama Yacht Club, a Tropical Oceanside Resort in the heart of the Florida Keys (Oceanside Key Largo at Mile ...
From $538 per night (USD)Expedia
From $1248 per night (USD)VRBO
**ENDLESS SUMMER @ OLD TOWN** New Villa & Pool + Last Key White Glove Service...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! All year long ...
From $1248 per night (USD)VRBO
From $859 per night (USD)Expedia
Historic Old Town Key West Cigarmaker's Cottage - Cigar House, Sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
OVERVIEW The Cigar House is a 100+ year old “Cigar maker’s house”. The recently completely renovated house is charming, ...
From $859 per night (USD)Expedia
From $990 per night (USD)VRBO
525 Mariners Club - Luxury 4 bedroom ocean-front villa perfect for family and friends
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Discover an extraordinary oceanfront sanctuary where sophistication meets serenity in the heart of the Florida Keys. Thi ...
From $990 per night (USD)VRBO
From $383 per night (USD)Expedia
Luxury Condominium In Key Largo... Sunsets, Marina
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
From your balcony in the Kawama Tower, you get stunning vistas of ocean and palm trees. Enjoy the view from this complet ...
From $383 per night (USD)Expedia
From $676 per night (USD)VRBO
Duval Dream Loft - On Duval street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Located in the heart of world-famous Duval Street, this unique property offers an authentic downtown Key West ...
From $676 per night (USD)VRBO
From $677 per night (USD)Expedia
The Collins - On Duval Street
- 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 Co ...
From $677 per night (USD)Expedia
From $273 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 $273 per night (USD)VRBO
From $267 per night (USD)Expedia
Enjoy Caribbean weather in the USA. Openings August 2026 forward!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
We have a big bright eat in fully stocked kitchen. Kitchen has many pots and pans, keurig, blender, glassware and most t ...
From $267 per night (USD)Expedia
From $859 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 $859 per night (USD)VRBO
From $372 per night (USD)Expedia
Mermaid Magic ground level 3bed/3bath half duplex in Kcb with dockage & cabana club
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Mermaid Magic, a beautiful and spacious ground-level 3-bedroom, 3-bath duplex in the heart of the Florida Key ...
From $372 per night (USD)Expedia
From $436 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 $436 per night (USD)VRBO
From $643 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 $643 per night (USD)Expedia
From $767 per night (USD)VRBO
Sunrise Escape - Ocean Front Villa - Sleeps 10
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Wake up to the sunrise over the ocean and unwind with sunset views from your private jetty. This marina-front, ocean-vie ...
From $767 per night (USD)VRBO
From $393 per night (USD)Expedia
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 $393 per night (USD)Expedia
From $752 per night (USD)VRBO
Latitude Adjustment FLKeys
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Latitude Adjustment, Islamorada, Florida This home is our families' paradise in the Florida Keys and we want to share it ...
From $752 per night (USD)VRBO
From $742 per night (USD)Expedia
612 Mariners Club - 4 bedroom Tri-level townhome with room for the whole family
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Three-story townhouse with over 2600 sq of living space...room for the whole family! Ground floor 1-bedroom (king bed) ...
From $742 per night (USD)Expedia
From $316 per night (USD)VRBO
Ocean Point Retreat ~ Immaculate Ocean Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Private Beach, Fishing Pier, Fish Cleaning Station, Jr. Olympic pool, Spa, Pickleball Court, BBQ grills, nature ...
From $316 per night (USD)VRBO
From $275 per night (USD)Expedia
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)Expedia
From $346 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 $346 per night (USD)VRBO
From $500 per night (USD)Expedia
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)Expedia
From $231 per night (USD)VRBO
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)VRBO
From $338 per night (USD)Expedia
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)Expedia
From $439 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 $439 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 $494 per night (USD)Expedia
By The Sea ~ Islamorada Home with Ocean Views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Canal front 2/2 with ocean views and relaxing breezes! The Space: This canal front two bedroom two bathroom ho ...
From $494 per night (USD)Expedia
From $367 per night (USD)VRBO
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)VRBO
From $508 per night (USD)Expedia
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)Expedia
From $352 per night (USD)VRBO
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)VRBO
From $456 per night (USD)Expedia
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)Expedia
From $512 per night (USD)VRBO
P27 - Private Beach Access! Pool home with everything you need for an unforgettable vacation. 3 bedroom 2 baths with deep water dockage.
- 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 $512 per night (USD)VRBO
From $299 per night (USD)Expedia
P29 - Charming 3 bedroom 2 bath duplex with deep water dockage and Cabana Club membership
- 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 $299 per night (USD)Expedia
From $418 per night (USD)VRBO
P67 - Spacious 3 bedroom 4 bath with private pool, dock and beach membership!
- 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 $418 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 $392 per night (USD)VRBO
P17 - Charming 3 bedroom 2 bath duplex with Private pool and deep water dockage. Ground level and completely updated!
- 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 $392 per night (USD)VRBO
From $339 per night (USD)Expedia
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 plenty of space, ...
From $339 per night (USD)Expedia
From $374 per night (USD)VRBO
P62 - 3 Bedroom 2 bath, private pool and beach membership
- 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 $374 per night (USD)VRBO
From $455 per night (USD)Expedia
P34 - Beautiful 4 bedroom 2 bath, single family home with private pool and deep water dockage.
- 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 $455 per night (USD)Expedia
From $378 per night (USD)VRBO
P51 - 2 bedroom 2 bath, single family pool home with dock
- 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 $378 per night (USD)VRBO
From $1148 per night (USD)Expedia
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)Expedia
From $699 per night (USD)VRBO
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)VRBO
From $368 per night (USD)Expedia
P21 - Charming 3 bedroom 3.5 bath duplex with dockage and Cabana Club.
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 7
This beautiful 3 bedroom, 3.5 bath duplex is located in Key Colony Beach. This home comes with access to The Cabana Club ...
From $368 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 $327 per night (USD)Expedia
P10 - Charming 2 bedroom, 2 bath duplex with private pool and deep water dockage.
- 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 $327 per night (USD)Expedia
From $347 per night (USD)VRBO
P72 - Charming 4 bedroom, 2 bath duplex with deep water dockage and Cabana Club access.
- 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 $347 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 $685 per night (USD)VRBO
P58 - Gulf Front Luxury 4 bedroom 4 bath with private pool and deep water dockage?
- 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 $685 per night (USD)VRBO
From $801 per night (USD)Expedia
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)Expedia
From $586 per night (USD)VRBO
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)VRBO
From $3780 per night (USD)Expedia
**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)Expedia
From $593 per night (USD)VRBO
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)VRBO
From $540 per night (USD)Expedia
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)Expedia
From $334 per night (USD)VRBO
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)VRBO
From $1081 per night (USD)Expedia
**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)Expedia
From $1371 per night (USD)VRBO
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)VRBO
From $440 per night (USD)Expedia
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)Expedia
From $1029 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 $1029 per night (USD)VRBO
From $505 per night (USD)Expedia
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)Expedia
From $578 per night (USD)VRBO
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)VRBO
From $328 per night (USD)Expedia
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)Expedia
From $874 per night (USD)VRBO
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)VRBO
From $360 per night (USD)Expedia
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)Expedia
From $718 per night (USD)VRBO
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)VRBO
From $427 per night (USD)Expedia
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)Expedia
From $389 per night (USD)VRBO
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)VRBO
From $389 per night (USD)Expedia
Oceanside Anglers Reef Home+Beach, Pool and Kayaks
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Experience the ultimate island getaway at this charming oceanfront villa in the heart of Islamorada. Nestled w ...
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 $432 per night (USD)Expedia
GORGEOUS SEA THEMED 2 STORY HOME W/ PRIVATE POOL AND BEACH ACCESS
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Beautiful new 2-Story home with balcony patio. Perfect to do some grilling and feel the salt in the air. Home was finali ...
From $432 per night (USD)Expedia
From $390 per night (USD)VRBO
Charming 'Boho Breeze' Retreat w/ Pool Access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience crystal clear waters, picturesque beaches, and famous historic sites with a stay at 'Boho Breeze!' This 2-bed ...
From $390 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 $432 per night (USD)VRBO
Island Oasis at the Truman Annex in Key West
- 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 $432 per night (USD)VRBO
From $391 per night (USD)Expedia
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)Expedia
From $195 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 $195 per night (USD)VRBO
From $410 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 $410 per night (USD)Expedia
From $949 per night (USD)VRBO
P44 - 4 bed, 3 bath estate home with Southern Charm and private pool
- 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 $949 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 $495 per night (USD)VRBO
Rx: Paradise updated 2bed/2.5bath townhouse style condo with open water views, shared pool & dockage
- 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 $495 per night (USD)VRBO
From $296 per night (USD)Expedia
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)Expedia