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Florida Keys Rentals

From $1459 per night (USD)
VRBO
**SOUTHERNMOST HOSPITALITY V** 5BR/5BA & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERNMOST ...
From $1459 per night (USD)
VRBO
From $622 per night (USD)
Expedia
Our Nautical Home Key West prime location & amenities. Last minute specials.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $622 per night (USD)
Expedia
From $409 per night (USD)
VRBO
**CAYO CALYPSO @ HIGGS BEACH** Modern Home / Pool + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Upscale islan ...
From $409 per night (USD)
VRBO
From $533 per night (USD)
Expedia
Poolside Breeze Retreat Key West – Your Tropical Getaway Awaits
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $533 per night (USD)
Expedia
From $280 per night (USD)
VRBO
Flamingo Nook. Renovated, Private Pool, Canal & Cabana Club Access!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The ultimate Florida Keys getaway! The Flamingo Nook located at Key Colony Beach near Marathon. Privacy is what separate ...
From $280 per night (USD)
VRBO
From $391 per night (USD)
Expedia
**HAVANA HOUSE @ OLD TOWN** Elegant Cottage Near Duval + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Located on So ...
From $391 per night (USD)
Expedia
From $830 per night (USD)
VRBO
**WINDSWEPT PALMS @ THE BEACH** Oceanfront / Pool & Jacuzzi + LAST KEY SERVICE
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $830 per night (USD)
VRBO
From $1086 per night (USD)
Expedia
**AMERICANA TROPICALE @ OLD TOWN** Home & Pool by Duval + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For the ultim ...
From $1086 per night (USD)
Expedia
From $523 per night (USD)
VRBO
**SHANG-RI-LA @ THE BEACH** Oceanview Condo / Pool & Tennis + LAST KEY SERVICES.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $523 per night (USD)
VRBO
From $594 per night (USD)
Expedia
**ATLANTIC REFLECTIONS @ THE BEACH** Ocean Penthouse / Pool + LAST KEY SERVICES.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $594 per night (USD)
Expedia
From $2467 per night (USD)
VRBO
**THE IBIS & THE CRANE @ OLD TOWN** Compound Near Duval + LAST KEY SERVICES...
Bedrooms:
7
Bathrooms:
6
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Dreaming of a ...
From $2467 per night (USD)
VRBO
From $513 per night (USD)
Expedia
Botanical Island Delight Key West fantastic discounts for Summer & Fall
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $513 per night (USD)
Expedia
From $580 per night (USD)
VRBO
**SALTWATER HARMONY @ THE ANNEX** Charming Condo & Pool + LAST KEY SERVICES...
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SALTWATER HAR ...
From $580 per night (USD)
VRBO
From $687 per night (USD)
Expedia
Atlantic Paradise Found modern luxury Best pool in Key West fine finishes
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $687 per night (USD)
Expedia
From $381 per night (USD)
VRBO
**LA PETITE PENTHOUSE @ THE ANNEX** Elegant Condo & Pool + LAST KEY SERVICES...
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! LA PETITE PEN ...
From $381 per night (USD)
VRBO
From $1925 per night (USD)
Expedia
**CONCH CASA GRANDE @ THE ANNEX** Home+ Pool near Duval + LAST KEY SERVICES...
Bedrooms:
6
Bathrooms:
5
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! CONCH CASA GR ...
From $1925 per night (USD)
Expedia
From $1032 per night (USD)
VRBO
**LA GRANDE REUNION @ OLD TOWN** Estate & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Traveling wit ...
From $1032 per night (USD)
VRBO
From $1023 per night (USD)
Expedia
**RIVIERA AMERICANA @ THE BEACH** Ocean Views + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $1023 per night (USD)
Expedia
From $586 per night (USD)
VRBO
**PROMENADE TO PARADISE @ THE ANNEX** Ocean Condo & Pool + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! If you dream ...
From $586 per night (USD)
VRBO
From $606 per night (USD)
Expedia
Top floor Ocean Views, Spacious 2 Bedroom Condo, Views from every room
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $606 per night (USD)
Expedia
From $273 per night (USD)
VRBO
**SUNSET POINT @ SUNSET MARINA** Condo / Pool & Spa + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SUNSET POINT ...
From $273 per night (USD)
VRBO
From $574 per night (USD)
Expedia
**SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & Pool + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SEA CAPTAIN'S ...
From $574 per night (USD)
Expedia
From $507 per night (USD)
VRBO
**THE MELLOW MACAW** Cozy Condo Near Duval + LAST KEY SERVICES...
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This colorful ...
From $507 per night (USD)
VRBO
From $593 per night (USD)
Expedia
Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $593 per night (USD)
Expedia
From $615 per night (USD)
VRBO
**NEPTUNE'S PENTHOUSE @ THE BEACH** Oceanfront Condo / Pool + LAST KEY SERVICE.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $615 per night (USD)
VRBO
From $414 per night (USD)
Expedia
Best Deals in Duck Key . 2 Bedroom /2 Bath w/40' 'Dock, Trailer Storage Incl,
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
*** This property is completely renovated on the inside and out! We cordially invite you to our property and enjoy the v ...
From $414 per night (USD)
Expedia
From $988 per night (USD)
VRBO
Find Sanity in the Heart of Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Experience the charm of this fantastic Old Town location surrounded by local businesses and restaurants, allowing you to ...
From $988 per night (USD)
VRBO
From $754 per night (USD)
Expedia
**CASITA ANGELITA @ OLD TOWN** Historic Condo by Duval + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This Old Town ...
From $754 per night (USD)
Expedia
From $338 per night (USD)
VRBO
**SUNSET DREAMS @ SUNSET MARINA** Condo / Pool & Spa + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SUNSET DREAMS ...
From $338 per night (USD)
VRBO
From $416 per night (USD)
Expedia
Truman Annex Gem • 2BR Condo • Walk to Beach & Bars
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Best Deal in Truman Annex – Céad Míle Fáilte! 2 Bedroom | 1 Bathroom | Sleeps Up to 5 Guests Welcome to Innis-free, ou ...
From $416 per night (USD)
Expedia
$\Canal-Front Paradise in Big Pine Key-Relax &Explore the keys\$
From $293 per night (USD)
VRBO
\"Canal-Front Paradise in Big Pine Key-Relax &Explore the keys\"
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
-Remodeling house 3 bedroom and 3 bath. -Please note that there is a 28 minimum rental period for this property. - D ...
From $293 per night (USD)
VRBO
From $964 per night (USD)
Expedia
**PUERTA CORALINA @ OLD TOWN** Cottage Near Duval + LAST KEY SERVICE...
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This precious ...
From $964 per night (USD)
Expedia
From $596 per night (USD)
VRBO
High Tide awaits your next visit upgraded condo close to Smathers Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $596 per night (USD)
VRBO
From $2011 per night (USD)
Expedia
**CASA VICTORIA @ OLD TOWN** Historic 5BR Home & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! CASA VICTORIA ...
From $2011 per night (USD)
Expedia
From $543 per night (USD)
VRBO
**FOLLOW THE SUN @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES..
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $543 per night (USD)
VRBO
From $1681 per night (USD)
Expedia
**NOONA'S MANSION @ THE ANNEX** Grand Home & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
6
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Located in Tr ...
From $1681 per night (USD)
Expedia
From $609 per night (USD)
VRBO
Tranquility by Smathers and 10 minute bike downtown Key West value savings
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $609 per night (USD)
VRBO
From $820 per night (USD)
Expedia
Somewhere on the Beach a dream property all amenities included simply amazing
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $820 per night (USD)
Expedia
From $636 per night (USD)
VRBO
**THE ARTISTS' MUSE @ LOVE LANE** Immaculate Home & Pool + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! For many, the ...
From $636 per night (USD)
VRBO
From $1294 per night (USD)
Expedia
**DIAMOND GIRL @ THE ANNEX** Elegant Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Seals & Croft ...
From $1294 per night (USD)
Expedia
From $1333 per night (USD)
VRBO
**THE SMILING IBIS @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Traveling to ...
From $1333 per night (USD)
VRBO
From $458 per night (USD)
Expedia
Waterfront luxury Villa (30) 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 $458 per night (USD)
Expedia
From $465 per night (USD)
VRBO
**NATURES EDGE @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $465 per night (USD)
VRBO
From $567 per night (USD)
Expedia
**OCTOPUS'S GARDEN @ CORAL HAMMOCK** Spacious Home & Pool + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! OCTOPUS'S GAR ...
From $567 per night (USD)
Expedia
From $678 per night (USD)
VRBO
Frost Free at 1800 Atlantic overlooking Smathers Beach top and the sunrise
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $678 per night (USD)
VRBO
From $454 per night (USD)
Expedia
**SUNDRENCHED REFLECTIONS @ SUNSET MARINA** Bayfront Condo + LAST KEY SERVICES..
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SUNDRENCHED R ...
From $454 per night (USD)
Expedia
From $1404 per night (USD)
VRBO
**SWEET HOME ANGELITA @ OLD TOWN** Renovated Home Off Duval + LAST KEY SERVICES
Bedrooms:
4
Bathrooms:
5
Sleeps:
13
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This renovate ...
From $1404 per night (USD)
VRBO
From $955 per night (USD)
Expedia
ROOFTOP PENTHOUSE- | 2 Bed, 1.5 Bath
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The high-end sophisticated Rooftop Penthouse is located directly above the famous Wyland Gallery on Duval Street. Enjoy ...
From $955 per night (USD)
Expedia
From $293 per night (USD)
VRBO
Island Therapy
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautiful 2BD/2BA vacation home features open water views and a full size 35' seawall for docking a boat. Amenities incl ...
From $293 per night (USD)
VRBO
From $433 per night (USD)
Expedia
Truman Annex, two blocks from Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Available for weekly, or longer, rentals (monthly or longer starting in 2026) this three-story townhouse is located on a ...
From $433 per night (USD)
Expedia
From $672 per night (USD)
VRBO
**SOUTHERNMOST PALMS @ THE ANNEX** Villa Near Duval & Beach + LAST KEY SERVICES.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! When you thin ...
From $672 per night (USD)
VRBO
From $328 per night (USD)
Expedia
Stay where you play, On the water w/Boat dock & Trailer parking. Pet friendly!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Stay where you play. The spacious newly refreshed two bedroom vacation rentals are ideal for fishermen and families or ...
From $328 per night (USD)
Expedia
Click For Pricing
VRBO
4 BED DUCK KEY VILLA W/ 35FT DOCK BEHIND IT & CABANA CLUB ACCESS
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
WE HAVE JOINED CABANA CLUB IN KEY COLONY BEACH A SHORT DRIVE AWAY WHICH INCLUDES AN OLYMPIC SIZE POOL. TIKI BAR, RESTAUR ...
Click For Pricing
VRBO
From $391 per night (USD)
Expedia
Dog-Friendly Sunrise Suites Condo with Pool, Hot Tub & Free Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Cayo Coco Suite 208 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $391 per night (USD)
Expedia
From $418 per night (USD)
VRBO
Dog-friendly home with pool & walk to parks & beach - snowbirds welcome
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Casa Atlantic Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $418 per night (USD)
VRBO
From $283 per night (USD)
Expedia
Bright Condo with Homey Feel, Entertainment & Private Parking - Beach Nearby
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Jasmine Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $283 per night (USD)
Expedia
From $593 per night (USD)
VRBO
Newly-Built, Dog-Friendly Home with Shared Pool - Walk to Beach & Dining
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Cabana Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $593 per night (USD)
VRBO
From $357 per night (USD)
Expedia
Cheery Beach Getaway Near Local Attractions - Pool & Easy Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Shipyard Perch Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $357 per night (USD)
Expedia
From $315 per night (USD)
VRBO
Tropical Getaway with Private Balcony, Shared Pool & Hot Tub - Dogs OK
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Antigua Suite 312 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $315 per night (USD)
VRBO
From $599 per night (USD)
Expedia
Sunny Condo with WiFi, Hot Tub, Pool & Tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sunrise Suites - Big Kahuna Suite 202 Our calendar is updated in real-time & our nightly rates are accurately displayed ...
From $599 per night (USD)
Expedia
From $571 per night (USD)
VRBO
Waterfront Duck Key Villa - Sleeps 6
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautiful and spacious 2 bedroom & 2.5 bathrooms Town house in the one and only Duck Key Florida, Harbor Village. In the ...
From $571 per night (USD)
VRBO
From $401 per night (USD)
Expedia
Dog-friendly condo with pool, hot tub, balcony, central AC, W/D, & fitness room
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Saint Lucia Suite 201 Our calendar is updated in real-time & our nightly rates are accurately displaye ...
From $401 per night (USD)
Expedia
From $225 per night (USD)
VRBO
Stunning, Oceanfront Home with Private Pool & Docks - Dog-Friendly
Bedrooms:
3
Bathrooms:
5
Sleeps:
18
Bay Harbor View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $225 per night (USD)
VRBO
From $935 per night (USD)
Expedia
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Hemingway's View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $935 per night (USD)
Expedia
From $439 per night (USD)
VRBO
Sunrise Suites Condo w/ Balcony, Pool & Hot Tub, Tennis & Covered Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Tahiti Suite 104 Our calendar is updated in real-time & our nightly rates are accurately displayed. Si ...
From $439 per night (USD)
VRBO
From $325 per night (USD)
Expedia
Breezy Florida Home with Shared Pool, Dog & Snowbird-Friendly - Walk to Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Conched Out Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $325 per night (USD)
Expedia
From $365 per night (USD)
VRBO
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Barbados Suite 204 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $365 per night (USD)
VRBO
From $394 per night (USD)
Expedia
Dog-Friendly Cottage with Private Hot Tub & Garden - Great Downtown Location
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Windward Isle Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $394 per night (USD)
Expedia
From $477 per night (USD)
VRBO
Cozy, Dog-Friendly Townhome with Shared Pool & Courtyard - Walkable Locale
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Old Town Garden Villas - Abaco Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $477 per night (USD)
VRBO
From $616 per night (USD)
Expedia
Charming cottage with private hot tub - one block to Duvall Street
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Conch Casa Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $616 per night (USD)
Expedia
From $379 per night (USD)
VRBO
Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sunrise Suites - Panama Suite 310 Our calendar is updated in real-time & our nightly rates are accurately displayed. Si ...
From $379 per night (USD)
VRBO
From $293 per night (USD)
Expedia
Newly Furnished Suite with Pool, Hot Tub, Tennis, Balcony, Parking - Dog OK
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Cozumel Suite 112 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $293 per night (USD)
Expedia
From $523 per night (USD)
VRBO
~ 9TH ST BEAUTIFUL HOME W/ PRIVATE POOL ON CANAL ~
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Gorgeous and welcoming ground level home directly on the canal! Located in the renowned city of Key Colony Beach, Mile M ...
From $523 per night (USD)
VRBO
From $317 per night (USD)
Expedia
Cozy Dog-Friendly Condo w/ Shared Pool, Hot Tub, Private Deck & Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Catalina Suite 311 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $317 per night (USD)
Expedia
From $264 per night (USD)
VRBO
Key Largo Paradise
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Key Largo vacation in our slice of paradise. Trailer sleeps 6. Enjoy the amenities of a giant 60" television, outdoor ba ...
From $264 per night (USD)
VRBO
From $546 per night (USD)
Expedia
Elegant home with with patio & community pool - walk to beaches & Duval Street
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Mangrove Lagoon Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $546 per night (USD)
Expedia
From $994 per night (USD)
VRBO
**VILLA ANGELITA @ OLD TOWN** Renovated Condo Off Duval + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This modern O ...
From $994 per night (USD)
VRBO
From $460 per night (USD)
Expedia
**SUZY'S PARROT PERCH @ OLD TOWN** Cozy 2nd Floor Condo + LAST KEY SERVICES...
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SUZY'S PARROT ...
From $460 per night (USD)
Expedia
From $787 per night (USD)
VRBO
Mar Y Sol – Luxury Oceanfront Condo in Key West Breathtaking Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $787 per night (USD)
VRBO
Click For Pricing
Expedia
PARADISE FOR BOATERS AND FISHING
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Private House, 3 BR 2 BATH, CONCRETE 60 Ft dock Avaiable August 1, 2020. Boat shown in Pictures will not be there at tim ...
Click For Pricing
Expedia
From $1455 per night (USD)
VRBO
**PLANTATION TROPICALE @ CASA EAST** Grand Estate & Pool + LAST KEY SERVICES…
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Resembling a ...
From $1455 per night (USD)
VRBO
From $484 per night (USD)
Expedia
Family home in gated community w/great amenities, shared pool, fitness center
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Hemingway Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $484 per night (USD)
Expedia
From $346 per night (USD)
VRBO
Sombrero Beach Villa with Private Pool and Dock
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
This beautiful villa was built in 2017, making it one of the newest and modern homes in the Florida Keys. There are nume ...
From $346 per night (USD)
VRBO
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Expedia
Dog-friendly home w/ large private pool only a short walk to Historic Seaport
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Seaport Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
Click For Pricing
Expedia
From $452 per night (USD)
VRBO
Waterfront Half-Duplex with 30-Ft. Dock, Sitting Pool, and Private Beach Access
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Fantastic Fifth Street Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $452 per night (USD)
VRBO
From $119 per night (USD)
VRBO
Key Largo Waterfront Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The property is located in Pirates Cove (mile marker 99 bayside), which is an early Key Largo development that is quiet ...
From $119 per night (USD)
VRBO
From $252 per night (USD)
VRBO
Comfortable Waterfront Vacation Rental minutes from key west w boat dock 35 ft
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Guests must register at the office unless it is after hours in which you will register at the Guard House. Unit 175 is c ...
From $252 per night (USD)
VRBO
From $554 per night (USD)
Expedia
Little Paradise, Historic Harbor Old Town Key West 2/1.5
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom One and a half bath home is nestl ...
From $554 per night (USD)
Expedia
From $564 per night (USD)
VRBO
208 Mariners Club Key Largo | 3 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Newly renovated! This tri-level townhouse has a laid-back, welcoming Florida Keys vibe, pristine decor, sleek new kitch ...
From $564 per night (USD)
VRBO
From $483 per night (USD)
Expedia
Marina Villa Mariner`s Club 212
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Best vacation rental to explore the Florida keys. Marina Villa 212 (3b/3b) with Marina and ocean views. Escape to ...
From $483 per night (USD)
Expedia
From $385 per night (USD)
VRBO
Fins to the Left in Key Colony Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Enjoy some changes in attitude and latitude in this waterfront beauty! This is a two bedroom, two bath, stilted, one-hal ...
From $385 per night (USD)
VRBO
From $482 per night (USD)
Expedia
Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
You will know you're on vacation when you enter this luxurious townhome! This beautiful home is located in Kawama Yacht ...
From $482 per night (USD)
Expedia
From $485 per night (USD)
VRBO
Vacation Home on Open Gulf with Fantastic Panoramic View
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Our home in Marathon at M.M.51, is located in a tropical setting on the open gulf surrounded by lush palms. Marathon is ...
From $485 per night (USD)
VRBO
From $1377 per night (USD)
Expedia
Gated Vacation Oasis Luxury Home Sunset Point Key Largo
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Escape to a one of a kind gated vacation oasis and experience the relaxing breezes of the bay from every room and around ...
From $1377 per night (USD)
Expedia
From $999 per night (USD)
VRBO
Islamorada Boaters Paradise with 70' Dock and private beach access..
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Calling all boaters and anglers! You will love our home. Nestled on a canal only 3 minutes to the bay and 10 minutes to ...
From $999 per night (USD)
VRBO
Click For Pricing
Expedia
7 Nights - Hyatt Sunset Harbor 2 bed/2bath/Kitchen/Sleeps 6. Fantastic Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Fantastic location!!! Sunday to Sunday 7 night rental at HYATT SUNSET HARBOR 2 bedrooms 2 bath full kitchen and common a ...
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Expedia
From $243 per night (USD)
VRBO
Villa Paradise | 4 bed/2 bath canalfront home on Ramrod Key
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Escape to Villa Paradise – Your Monthly Retreat in the Florida Keys! Discover the ultimate Florida Keys getaway at Vill ...
From $243 per night (USD)
VRBO
From $286 per night (USD)
Expedia
House full of life with pool
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
House in Key Largo. Great Home for a big family, 5 bedrooms and 4 full baths. Jacuzzi. Pool (8x14') with a deck. Can bri ...
From $286 per night (USD)
Expedia
From $297 per night (USD)
VRBO
Keys Kottage: Bayside villa W/ free onsite boat ramp marina & trailer parking.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The Kottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on ...
From $297 per night (USD)
VRBO
From $416 per night (USD)
Expedia
Beautiful Condo with Deck, Patio, & Pool - Walk to Duval Street & Beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Secret Garden Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $416 per night (USD)
Expedia

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