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Florida Keys Rentals

$Group Therapy | 3 bed, 2 bath home w\/ new pool, quick ocean access$
From $333 per night (USD)
VRBO
Group Therapy | 3 bed, 2 bath home w\/ new pool, quick ocean access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your dream escape! This beautifully remodeled 3-bedroom, 2-bathroom pool home on Cudjoe Key's oceanside is th ...
From $333 per night (USD)
VRBO
From $1391 per night (USD)
Expedia
One of the very few beach houses with a daily, rental license in the Keys.
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
This is a newly remodeled four bedrooms elegant house. The property located in the heart of Summerland Key. It is the ...
From $1391 per night (USD)
Expedia
From $720 per night (USD)
VRBO
W10 - 4 Bedroom Sombrero Isle Beauty on Crystal Lagoon!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This spacious 4-bedroom, 3-bath home is a half a mile from the picturesque Sombrero Beach. Located on Sombrero Is ...
From $720 per night (USD)
VRBO
From $1181 per night (USD)
Expedia
**BRISA FRESCA @ THE ANNEX** Airy Home by Duval & Beach + 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! A trip to Key ...
From $1181 per night (USD)
Expedia
From $354 per night (USD)
VRBO
**VILLA OLIVIETTA @ SOLARES HILL** Upscale 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! This ultimate ...
From $354 per night (USD)
VRBO
$**SMOOTH SAILING @ THE BEACH** Ocean Condo \/ Pool & Tennis + LAST KEY SERVICES..$
From $656 per night (USD)
Expedia
**SMOOTH SAILING @ THE BEACH** Ocean Condo \/ Pool & Tennis + LAST KEY SERVICES..
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $656 per night (USD)
Expedia
From $513 per night (USD)
VRBO
**VILLA BAHAMA @ THE ANNEX** Villa Near Duval & Beach + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! VILLA BAHAMA ...
From $513 per night (USD)
VRBO
From $837 per night (USD)
Expedia
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Traveling to ...
From $837 per night (USD)
Expedia
From $2243 per night (USD)
VRBO
**THE ROYAL COMPOUND @ THE ANNEX** Lush Estate & Pool + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Located in th ...
From $2243 per night (USD)
VRBO
From $755 per night (USD)
Expedia
Oceanfront Duplex with Spectacular Views, Beach, & Dock
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
The Henry Flagler Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $755 per night (USD)
Expedia
From $522 per night (USD)
VRBO
**VILLA CUBANA @ OLD TOWN** Comfy Cottage Near Duval + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This colorful ...
From $522 per night (USD)
VRBO
$**SOUTHERNMOST HOSPITALITY VII** 7BR\/7BA & Pool + LAST KEY SERVICES...$
From $2073 per night (USD)
Expedia
**SOUTHERNMOST HOSPITALITY VII** 7BR\/7BA & Pool + LAST KEY SERVICES...
Bedrooms:
8
Bathrooms:
8
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERNMOST ...
From $2073 per night (USD)
Expedia
From $706 per night (USD)
VRBO
**GULFSIDE VISTAS @ THE ANNEX** Condo & Pool + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! GULFSIDE VIST ...
From $706 per night (USD)
VRBO
From $1808 per night (USD)
Expedia
**STAR OF THE SEAPORT @ OLD TOWN** Huge 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! For a truly o ...
From $1808 per night (USD)
Expedia
From $429 per night (USD)
VRBO
**CASA OLIVIANA @ SOLARES HILL** Grand Home & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Finally, a la ...
From $429 per night (USD)
VRBO
From $576 per night (USD)
Expedia
Beautiful Modern House in Key Largo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Open layout of the living area, dining room and kitchen. Large, screened patio offers the tropical 'out of doors and fre ...
From $576 per night (USD)
Expedia
From $545 per night (USD)
VRBO
Coral Hammock Poolside Home 3 bdrm 3 bath10 minute drive to Old Town Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
3 Bedrooms, 3 Full Bathrooms, Backs to Community Pool, Sleeps up to 6 This home was built in 2004. It has been well ma ...
From $545 per night (USD)
VRBO
$**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo \/ Pool + LAST KEY SERVICES$
From $602 per night (USD)
Expedia
**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo \/ Pool + LAST KEY SERVICES
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $602 per night (USD)
Expedia
From $313 per night (USD)
VRBO
**MAISON TROPICALE @ OLD TOWN** Historic Home + 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! Imagine a tra ...
From $313 per night (USD)
VRBO
$**CASA SUITE CASA @ CASA MARINA** Lush Home \/ Pool + LAST KEY SERVICE...$
From $421 per night (USD)
Expedia
**CASA SUITE CASA @ CASA MARINA** Lush Home \/ Pool + LAST KEY SERVICE...
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Imagine your ...
From $421 per night (USD)
Expedia
$**SOUTHERNMOST HOSPITALITY V** 5BR\/5BA & Pool + LAST KEY SERVICES...$
From $1757 per night (USD)
VRBO
**SOUTHERNMOST HOSPITALITY V** 5BR\/5BA & Pool + LAST KEY SERVICES...
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERNMOST ...
From $1757 per night (USD)
VRBO
From $449 per night (USD)
Expedia
Our Nautical Home Key West prime location & amenities. Last minute specials.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $449 per night (USD)
Expedia
$**CAYO CALYPSO @ HIGGS BEACH** Modern Home \/ Pool + LAST KEY SERVICES...$
From $312 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 $312 per night (USD)
VRBO
From $421 per night (USD)
Expedia
Poolside Breeze a Tropical Retreat has a wrap around Balcony best location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $421 per night (USD)
Expedia
From $333 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 $333 per night (USD)
VRBO
From $340 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 $340 per night (USD)
Expedia
$**WINDSWEPT PALMS @ THE BEACH** Oceanfront \/ Pool & Jacuzzi + LAST KEY SERVICE$
From $1107 per night (USD)
VRBO
**WINDSWEPT PALMS @ THE BEACH** Oceanfront \/ Pool & Jacuzzi + LAST KEY SERVICE
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $1107 per night (USD)
VRBO
From $1094 per night (USD)
Expedia
**AMERICANA TROPICALE @ OLD TOWN** Home & Pool by Duval + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For the ultim ...
From $1094 per night (USD)
Expedia
$**SHANG-RI-LA @ THE BEACH** Oceanview Condo \/ Pool & Tennis + LAST KEY SERVICES.$
From $631 per night (USD)
VRBO
**SHANG-RI-LA @ THE BEACH** Oceanview Condo \/ Pool & Tennis + LAST KEY SERVICES.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $631 per night (USD)
VRBO
$**ATLANTIC REFLECTIONS @ THE BEACH** Ocean Penthouse \/ Pool + LAST KEY SERVICES.$
From $655 per night (USD)
Expedia
**ATLANTIC REFLECTIONS @ THE BEACH** Ocean Penthouse \/ Pool + LAST KEY SERVICES.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $655 per night (USD)
Expedia
From $2083 per night (USD)
VRBO
**THE IBIS & THE CRANE @ OLD TOWN** Compound Near Duval + LAST KEY SERVICES...
Bedrooms:
8
Bathrooms:
6
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Dreaming of a ...
From $2083 per night (USD)
VRBO
From $393 per night (USD)
Expedia
Botanical Island Delight Key West fantastic discounts for Summer & Fall
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $393 per night (USD)
Expedia
From $431 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 $431 per night (USD)
VRBO
From $545 per night (USD)
Expedia
Atlantic Paradise Found modern luxury Best pool in Key West fine finishes
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $545 per night (USD)
Expedia
From $390 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 $390 per night (USD)
VRBO
From $1948 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 $1948 per night (USD)
Expedia
Click For Pricing
VRBO
3 bed 2.5 bath at Coral Lagoon Resort with boat slip directly behind villa!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
We are the No. 1 rated resort in Marathon! Enjoy our renovated luxury villa with boat slip right behind the villa! We ...
Click For Pricing
VRBO
From $627 per night (USD)
Expedia
**LA GRANDE REUNION @ OLD TOWN** Estate & Pool + LAST KEY SERVICES...
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Traveling wit ...
From $627 per night (USD)
Expedia
From $1059 per night (USD)
VRBO
**RIVIERA AMERICANA @ THE BEACH** Ocean Views + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $1059 per night (USD)
VRBO
From $467 per night (USD)
Expedia
Top floor Ocean Views, Spacious 2 Bedroom Condo, Views from every room
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $467 per night (USD)
Expedia
$**SUNSET POINT @ SUNSET MARINA** Condo \/ Pool & Spa + LAST KEY SERVICES...$
From $202 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 $202 per night (USD)
VRBO
From $460 per night (USD)
Expedia
**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 $460 per night (USD)
Expedia
From $509 per night (USD)
VRBO
Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $509 per night (USD)
VRBO
$**NEPTUNE'S PENTHOUSE @ THE BEACH** Oceanfront Condo \/ Pool + LAST KEY SERVICE.$
From $755 per night (USD)
Expedia
**NEPTUNE'S PENTHOUSE @ THE BEACH** Oceanfront Condo \/ Pool + LAST KEY SERVICE.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $755 per night (USD)
Expedia
$Best Deals in Duck Key . 2 Bedroom \/2 Bath w\/40' 'Dock, Trailer Storage Incl,$
From $414 per night (USD)
VRBO
Best Deals in Duck Key . 2 Bedroom \/2 Bath w\/40' 'Dock, Trailer Storage Incl,
Bedrooms:
3
Bathrooms:
3
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)
VRBO
Click For Pricing
Expedia
Luxury Waterfront Pool Home Canal Front Direct Ocean Access Fisherman's Paradise
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Come relax in our Marathon Oasis...This calm, comfortable and modern updated home is a 2/2 with a great open room floor ...
Click For Pricing
Expedia
From $878 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 $878 per night (USD)
VRBO
From $644 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 $644 per night (USD)
Expedia
$**SUNSET DREAMS @ SUNSET MARINA** Condo \/ Pool & Spa + LAST KEY SERVICES...$
From $273 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 $273 per night (USD)
VRBO
From $370 per night (USD)
Expedia
Irish in Truman Annex Shipyard close to Historic Duval & Ft Zach State Park
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Best Deal in Truman Annex - Céad Míle Fáilte (Irish) 2 Bedroom 1 bathroom Condo - sleeps up to 5 Here's Céad Míle Fáilt ...
From $370 per night (USD)
Expedia
From $237 per night (USD)
VRBO
New Listing! Beautiful Canal front , Key Deer and jacuzzi.
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 $237 per night (USD)
VRBO
From $737 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 $737 per night (USD)
Expedia
From $422 per night (USD)
VRBO
High Tide awaits your next visit upgraded condo close to Smathers Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $422 per night (USD)
VRBO
From $1607 per night (USD)
Expedia
**CASA VICTORIA @ OLD TOWN** Historic 5BR Home & Pool + LAST KEY SERVICES...
Bedrooms:
6
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! CASA VICTORIA ...
From $1607 per night (USD)
Expedia
$**FOLLOW THE SUN @ THE BEACH** Ocean Condo \/ Pool & Tennis + LAST KEY SERVICES..$
From $517 per night (USD)
VRBO
**FOLLOW THE SUN @ THE BEACH** Ocean Condo \/ Pool & Tennis + LAST KEY SERVICES..
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $517 per night (USD)
VRBO
From $2436 per night (USD)
Expedia
**NOONA'S MANSION @ THE ANNEX** Grand Home & Pool + LAST KEY SERVICES...
Bedrooms:
6
Bathrooms:
6
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Located in Tr ...
From $2436 per night (USD)
Expedia
From $416 per night (USD)
VRBO
Tranquility by Smathers and 10 minute bike downtown Key West value savings
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $416 per night (USD)
VRBO
From $740 per night (USD)
Expedia
Somewhere on the Beach a dream property all amenities included simply amazing
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $740 per night (USD)
Expedia
$4 Bed 3 Bath Duck Key Sanctuary Villa W\/ Private Pool & 35 Foot Dock - Sleeps 10$
From $1266 per night (USD)
VRBO
4 Bed 3 Bath Duck Key Sanctuary Villa W\/ Private Pool & 35 Foot Dock - Sleeps 10
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
We offer a unique Sanctuary Villa located on the island of Duck Key. This 4 bedroom 3 bath villa sleeps 10 people comfor ...
From $1266 per night (USD)
VRBO
From $448 per night (USD)
Expedia
**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 $448 per night (USD)
Expedia
From $1234 per night (USD)
VRBO
**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 $1234 per night (USD)
VRBO
From $830 per night (USD)
Expedia
**THE SMILING IBIS @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Traveling to ...
From $830 per night (USD)
Expedia
From $563 per night (USD)
VRBO
Waterfront luxury Villa (30) with sunset views and boat slip
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse y ...
From $563 per night (USD)
VRBO
$**NATURES EDGE @ THE BEACH** Ocean Condo \/ Pool & Tennis + LAST KEY SERVICES...$
From $536 per night (USD)
Expedia
**NATURES EDGE @ THE BEACH** Ocean Condo \/ Pool & Tennis + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $536 per night (USD)
Expedia
From $450 per night (USD)
VRBO
**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 $450 per night (USD)
VRBO
From $519 per night (USD)
Expedia
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 $519 per night (USD)
Expedia
From $202 per night (USD)
VRBO
**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 $202 per night (USD)
VRBO
From $1275 per night (USD)
Expedia
**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 $1275 per night (USD)
Expedia
From $1096 per night (USD)
VRBO
ROOFTOP PENTHOUSE- | 2 Bed, 1.5 Bath
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The high-end sophisticated Rooftop Penthouse is located directly above the famous Wyland Gallery on Duval Street. Enjoy ...
From $1096 per night (USD)
VRBO
From $663 per night (USD)
Expedia
**PROMENADE TO PARADISE @ THE ANNEX** Ocean Condo & Pool + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! If you dream ...
From $663 per night (USD)
Expedia
From $283 per night (USD)
VRBO
Island Therapy
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful 2BD/2BA vacation home features open water views and a full size 35' seawall for docking a boat. Amenities incl ...
From $283 per night (USD)
VRBO
From $579 per night (USD)
Expedia
**SOUTHERNMOST PALMS @ THE ANNEX** Villa Near Duval & Beach + LAST KEY SERVICES.
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! When you thin ...
From $579 per night (USD)
Expedia
$Stay where you play, On the water w\/Boat dock & Trailer parking. Pet friendly!$
From $315 per night (USD)
VRBO
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 $315 per night (USD)
VRBO
$4 BED DUCK KEY VILLA W\/ 35FT DOCK BEHIND IT & CABANA CLUB ACCESS$
From $1520 per night (USD)
Expedia
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 ...
From $1520 per night (USD)
Expedia
From $376 per night (USD)
VRBO
Dog-Friendly Sunrise Suites Condo with Pool, Hot Tub & Free Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Suites - Cayo Coco Suite 208 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $376 per night (USD)
VRBO
From $551 per night (USD)
Expedia
Waterfront Duck Key Villa - Sleeps 6
Bedrooms:
3
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 $551 per night (USD)
Expedia
$Dog-friendly condo with pool, hot tub, balcony, central AC, W\/D, & fitness room$
From $452 per night (USD)
VRBO
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 $452 per night (USD)
VRBO
From $849 per night (USD)
Expedia
Stunning, Oceanfront Home with Private Pool & Docks - Dog-Friendly
Bedrooms:
3
Bathrooms:
7
Sleeps:
18
Bay Harbor View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $849 per night (USD)
Expedia
From $791 per night (USD)
VRBO
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Hemingway's View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $791 per night (USD)
VRBO
Click For Pricing
Expedia
Updated Corner Condo with Pool, Hot Tub, WiFi, Covered Parking - Dogs OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Suites - Sea Breeze Suite 101 Our calendar is updated in real-time & our nightly rates are accurately displayed ...
Click For Pricing
Expedia
$Sunrise Suites Condo w\/ Balcony, Pool & Hot Tub, Tennis & Covered Parking$
From $558 per night (USD)
VRBO
Sunrise Suites Condo w\/ Balcony, Pool & Hot Tub, Tennis & Covered Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Suites - Tahiti Suite 104 Our calendar is updated in real-time & our nightly rates are accurately displayed. Si ...
From $558 per night (USD)
VRBO
From $191 per night (USD)
Expedia
Breezy Florida Home with Shared Pool, Dog & Snowbird-Friendly - Walk to Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Headquarters Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $191 per night (USD)
Expedia
From $381 per night (USD)
VRBO
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Suites - Barbados Suite 204 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $381 per night (USD)
VRBO
From $682 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 $682 per night (USD)
Expedia
From $540 per night (USD)
VRBO
Cozy, Dog-Friendly Townhome with Shared Pool & Courtyard - Walkable Locale
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Old Town Garden Villas - Abaco Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $540 per night (USD)
VRBO
From $651 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 $651 per night (USD)
Expedia
From $375 per night (USD)
VRBO
Dog-friendly home with pool & walk to parks & beach - snowbirds welcome
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Casa Atlantic Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $375 per night (USD)
VRBO
From $364 per night (USD)
Expedia
Bright Condo with Homey Feel, Entertainment & Private Parking - Beach Nearby
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Jasmine Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $364 per night (USD)
Expedia
From $590 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 $590 per night (USD)
VRBO
From $460 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 $460 per night (USD)
Expedia
From $396 per night (USD)
VRBO
Tropical Getaway with Private Balcony, Shared Pool & Hot Tub - Dogs OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Suites - Antigua Suite 312 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $396 per night (USD)
VRBO
From $629 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 $629 per night (USD)
Expedia
From $391 per night (USD)
VRBO
Truman Annex, two blocks from Duval
Bedrooms:
3
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 $391 per night (USD)
VRBO
$Watch Sunsets from Your Deck, Shared Pool\/Hot Tub - Perfect for the Whole Family$
From $367 per night (USD)
Expedia
Watch Sunsets from Your Deck, Shared Pool\/Hot Tub - Perfect for the Whole Family
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Panama Suite 310 Our calendar is updated in real-time & our nightly rates are accurately displayed. Si ...
From $367 per night (USD)
Expedia
From $451 per night (USD)
VRBO
Newly Furnished Suite with Pool, Hot Tub, Tennis, Balcony, Parking - Dog OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Suites - Cozumel Suite 112 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $451 per night (USD)
VRBO
From $690 per night (USD)
Expedia
811 Mariners Club Key Largo | 4 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Flawless describes to the T this immaculate townhouse. Oh-so-thoughtful floor plan, exquisite decor and furnishing...top ...
From $690 per night (USD)
Expedia
$Cozy Dog-Friendly Condo w\/ Shared Pool, Hot Tub, Private Deck & Parking$
From $567 per night (USD)
VRBO
Cozy Dog-Friendly Condo w\/ Shared Pool, Hot Tub, Private Deck & Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Suites - Catalina Suite 311 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $567 per night (USD)
VRBO
From $309 per night (USD)
Expedia
Key Largo Paradise
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Key Largo vacation in our slice of paradise. Trailer sleeps 6. Enjoy the amenities of a giant 60" television, outdoor ba ...
From $309 per night (USD)
Expedia
From $624 per night (USD)
VRBO
Elegant home with with patio & community pool - walk to beaches & Duval Street
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Mangrove Lagoon Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $624 per night (USD)
VRBO
From $658 per night (USD)
Expedia
**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 $658 per night (USD)
Expedia

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