Monroe Area, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Monroe Area, Florida on RentalSaver.com!

Monroe Area Rentals

From $212 per night (USD)
VRBO
Crystal blue seas, Island Breezes, Morning Sunrises & Key West Island days.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Lovely 2nd floor unit. Beautifully renovated, This unit has luxurious finishes. Both bedrooms and the living room open o ...
From $212 per night (USD)
VRBO
From $2722 per night (USD)
Expedia
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
THE PROPERTY: Come enjoy the Key West cottage lifestyle where you can people watch from your front porch or take a dip ...
From $2722 per night (USD)
Expedia
From $416 per night (USD)
VRBO
No Stairs-Private Tropical Beach-steps from condo-Hi-Speed WIFI-It's Loaded!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Ask me about Covid-19 my cancellation policy. Our White Sandy Tropical Private is Beautiful and Private! I also own 3 o ...
From $416 per night (USD)
VRBO
From $216 per night (USD)
Expedia
Island Style, Morning Sunrises, Salty Ocean Breezes & Downtown Key West days.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a lovely 3rd floor partial ocean-view unit. You will love the spacious 50 ft private balcony that runs the lengt ...
From $216 per night (USD)
Expedia
$NEW!! Thirsty Mermaid - Large 4\/3 Pool Home - RealKeyWest$
From $572 per night (USD)
VRBO
NEW!! Thirsty Mermaid - Large 4\/3 Pool Home - RealKeyWest
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Thirsty Mermaid is located in the Casa Marina area just minutes from the Atlantic Ocean. This beautiful property has 2 f ...
From $572 per night (USD)
VRBO
From $468 per night (USD)
Expedia
Duck Key Darling: 2-Bedroom, 2-Bath Townhouse with Exclusive Cabana Club Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Experience the epitome of luxury at Duck Key Darling, a splendid 2-bedroom, 2-bath Townhouse Villa nestled within Hawks ...
From $468 per night (USD)
Expedia
$Couples paradise-king bed\/AC\/kayaks for your use\/fishing\/snorkeling\/diving$
From $242 per night (USD)
VRBO
Couples paradise-king bed\/AC\/kayaks for your use\/fishing\/snorkeling\/diving
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Comforting king size bed with an extra room for storage or office, and perfect outdoor living space make for a great cou ...
From $242 per night (USD)
VRBO
$Old Town! Spacious Condo in Historic Home w\/Pool!$
From $266 per night (USD)
Expedia
Old Town! Spacious Condo in Historic Home w\/Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into ...
From $266 per night (USD)
Expedia
$Deep\/Wide\/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise$
From $240 per night (USD)
VRBO
Deep\/Wide\/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Amazing canal front 3 bed 3 bath open concept house located in prestigious community of Summerland Key Cove. It is the ...
From $240 per night (USD)
VRBO
From $285 per night (USD)
Expedia
Breezy Half-Duplex with 35 Ft. Dock. - Cabana Club Access with Pool and Beach
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Breezy Palms Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $285 per night (USD)
Expedia
From $316 per night (USD)
VRBO
Dog-friendly waterfront home with dock, pool, gas grill, & beach access
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Ninth Street Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $316 per night (USD)
VRBO
From $346 per night (USD)
Expedia
Gulf Pointe Paradise
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Gulf Pointe Paradise is a tranquil townhouse featuring a balcony with sweeping Gulf of Mexico views. Dockage is availabl ...
From $346 per night (USD)
Expedia
From $664 per night (USD)
VRBO
Oceanfront Duplex with Beautiful Beach & Dock for Boat Access - Dogs OK
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
The Zane Grey Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $664 per night (USD)
VRBO
From $279 per night (USD)
Expedia
Waterfront home with 24-foot dock, shared pool, & beach access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Key Lime on Fifth Street Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $279 per night (USD)
Expedia
From $284 per night (USD)
VRBO
Waterfront Home with 35-Foot Dock, Bay Views, WiFi, and Shared Pool and Beach
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Tropical Charm Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $284 per night (USD)
VRBO
From $435 per night (USD)
Expedia
Breezy waterfront home with pool, 35-foot dock & cabana club access
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Captain's Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $435 per night (USD)
Expedia
From $705 per night (USD)
VRBO
Waterfront Duplex with Shared Pool & Beach Access, 35-ft Dock
Bedrooms:
8
Bathrooms:
7
Sleeps:
17
Breezy Palms & Tropical Charm Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $705 per night (USD)
VRBO
From $303 per night (USD)
Expedia
Dog-Friendly Home with 60-Ft. Dock and Access to Cabana Club and Shared Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Downhome Cabin by the Canal Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply e ...
From $303 per night (USD)
Expedia
From $362 per night (USD)
VRBO
Waterfront Home with 35-Foot Dock and Access to Private Beach and Shared Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Ninth Street Utopia Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $362 per night (USD)
VRBO
From $349 per night (USD)
Expedia
Waterfront home with 35-ft dock & access to Cabana Club pool & beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Canal-side Charisma Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $349 per night (USD)
Expedia
$Cozy Canal-Front House w\/ Free WiFi and Deck - Close to Beaches & State Park$
From $282 per night (USD)
VRBO
Cozy Canal-Front House w\/ Free WiFi and Deck - Close to Beaches & State Park
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Anchors Aweigh Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $282 per night (USD)
VRBO
From $675 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 $675 per night (USD)
Expedia
From $681 per night (USD)
VRBO
Oceanfront Paradise w Dock for your 35' boat and Huge Tiki and Firepit. Dogs OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Direct Oceanfront Home with plenty of outdoor living space. Huge Tiki Hut with ice maker, 50" TV, refridgerator, fire p ...
From $681 per night (USD)
VRBO
From $407 per night (USD)
Expedia
Waterfront Tiny House w Pool, Beach, and Boat Dock
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Private community with 2 private beach areas, boat ramp, heated swimming pool, beach volleyball, children's area with pl ...
From $407 per night (USD)
Expedia
From $1328 per night (USD)
VRBO
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 has its own private beach located in the heart of Su ...
From $1328 per night (USD)
VRBO
From $493 per night (USD)
Expedia
**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 $493 per night (USD)
Expedia
From $456 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 30 days prior to your arrival! Imagine a tra ...
From $456 per night (USD)
VRBO
From $818 per night (USD)
Expedia
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 $818 per night (USD)
Expedia
From $2276 per night (USD)
VRBO
**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 $2276 per night (USD)
VRBO
From $589 per night (USD)
Expedia
**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 $589 per night (USD)
Expedia
$**SMOOTH SAILING @ THE BEACH** Ocean Condo \/ Pool & Tennis + LAST KEY SERVICES..$
From $1295 per night (USD)
VRBO
**SMOOTH SAILING @ THE BEACH** Ocean Condo \/ Pool & Tennis + 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! Formerly La B ...
From $1295 per night (USD)
VRBO
From $514 per night (USD)
Expedia
**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 $514 per night (USD)
Expedia
From $1856 per night (USD)
VRBO
**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 $1856 per night (USD)
VRBO
From $371 per night (USD)
Expedia
Sombrero Beach Home on Canal with Private Dock and Heated Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This beautiful villa was built in 2018, making it one of the newest and modern homes in the Florida Keys. There are nume ...
From $371 per night (USD)
Expedia
From $5147 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 $5147 per night (USD)
VRBO
$**SOUTHERNMOST HOSPITALITY VII** 7BR\/7BA & Pool + LAST KEY SERVICES...$
From $4751 per night (USD)
Expedia
**SOUTHERNMOST HOSPITALITY VII** 7BR\/7BA & Pool + LAST KEY SERVICES...
Bedrooms:
8
Bathrooms:
7
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERNMOST ...
From $4751 per night (USD)
Expedia
From $1098 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 $1098 per night (USD)
VRBO
From $3278 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 $3278 per night (USD)
Expedia
From $735 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 $735 per night (USD)
VRBO
From $667 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 $667 per night (USD)
Expedia
From $801 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 $801 per night (USD)
VRBO
$**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo \/ Pool + LAST KEY SERVICES$
From $944 per night (USD)
Expedia
**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach 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! This freshly ...
From $944 per night (USD)
Expedia
$**CASA SUITE CASA @ CASA MARINA** Lush Home \/ Pool + LAST KEY SERVICE...$
From $517 per night (USD)
VRBO
**CASA SUITE CASA @ CASA MARINA** Lush Home \/ Pool + LAST KEY SERVICE...
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Imagine your ...
From $517 per night (USD)
VRBO
$**SOUTHERNMOST HOSPITALITY V** 5BR\/5BA & Pool + LAST KEY SERVICES...$
From $3739 per night (USD)
Expedia
**SOUTHERNMOST HOSPITALITY V** 5BR\/5BA & 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! SOUTHERNMOST ...
From $3739 per night (USD)
Expedia
From $665 per night (USD)
VRBO
Our Nautical Home in Key West is available for amazing prices Summer of 2023
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
1st floor garden-view unit, King in the master bedroom, A double and a single in the guest bedroom and a queen sleeper ...
From $665 per night (USD)
VRBO
$**CAYO CALYPSO @ HIGGS BEACH** Modern Home \/ Pool + LAST KEY SERVICES...$
From $436 per night (USD)
Expedia
**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 30 days prior to your arrival! Upscale islan ...
From $436 per night (USD)
Expedia
From $774 per night (USD)
VRBO
Poolside Breeze a Tropical Retreat has a wrap around Balcony best location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Poolside Breeze! Discover a beautifully decorated two-bedroom condominium on the first floor, ideally locate ...
From $774 per night (USD)
VRBO
From $333 per night (USD)
Expedia
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)
Expedia
From $383 per night (USD)
VRBO
**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 30 days prior to your arrival! Located on So ...
From $383 per night (USD)
VRBO
$**WINDSWEPT PALMS @ THE BEACH** Oceanfront \/ Pool & Jacuzzi + LAST KEY SERVICE$
From $1659 per night (USD)
Expedia
**WINDSWEPT PALMS @ THE BEACH** Oceanfront \/ Pool & Jacuzzi + LAST KEY SERVICE
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Imagine a hom ...
From $1659 per night (USD)
Expedia
From $2769 per night (USD)
VRBO
**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 $2769 per night (USD)
VRBO
$**SHANG-RI-LA @ THE BEACH** Oceanview Condo \/ Pool & Tennis + LAST KEY SERVICES.$
From $954 per night (USD)
Expedia
**SHANG-RI-LA @ THE BEACH** Oceanview Condo \/ Pool & Tennis + 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! SHANG-RI-LA i ...
From $954 per night (USD)
Expedia
$**ATLANTIC REFLECTIONS @ THE BEACH** Ocean Penthouse \/ Pool + LAST KEY SERVICES.$
From $1425 per night (USD)
VRBO
**ATLANTIC REFLECTIONS @ THE BEACH** Ocean Penthouse \/ 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! ATLANTIC REFL ...
From $1425 per night (USD)
VRBO
From $4141 per night (USD)
Expedia
**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 $4141 per night (USD)
Expedia
From $638 per night (USD)
VRBO
Botanical Island Delight Key West fantastic discounts for Summer & Fall
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This unit has a king in both bedrooms. 1800 Atlantic is directly on the Atlantic ocean in Key West, adjacent to Smather ...
From $638 per night (USD)
VRBO
From $709 per night (USD)
Expedia
**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 $709 per night (USD)
Expedia
From $1045 per night (USD)
VRBO
Atlantic Paradise Found modern luxury Best pool in Key West fine finishes
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Atlantic Paradise Found C232 at 1800 Atlantic Condominiums is a beautifully appointed spacious condominium with a lovely ...
From $1045 per night (USD)
VRBO
From $702 per night (USD)
Expedia
**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 $702 per night (USD)
Expedia
From $3815 per night (USD)
VRBO
**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 $3815 per night (USD)
VRBO
From $983 per night (USD)
Expedia
3 bed 2.5 bath at Coral Lagoon Resort with boat slip directly behind villa!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
We are the No. 1 rated resort in Marathon! Enjoy our renovated luxury villa with boat slip right behind the villa! We ...
From $983 per night (USD)
Expedia
From $738 per night (USD)
VRBO
**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 30 days prior to your arrival! Traveling wit ...
From $738 per night (USD)
VRBO
From $1668 per night (USD)
Expedia
**RIVIERA AMERICANA @ THE BEACH** Ocean Views + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! A stay in Key ...
From $1668 per night (USD)
Expedia
From $1017 per night (USD)
VRBO
**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 $1017 per night (USD)
VRBO
From $890 per night (USD)
Expedia
Top floor Ocean Views, Spacious 2 Bedroom Condo, Views from every room
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Top floor penthouse ocean-view condominium at 1800 Atlantic in the highly desirable B building. This unit has recently b ...
From $890 per night (USD)
Expedia
From $559 per night (USD)
VRBO
**BLUE HERON'S COVE @ THE ANNEX** Luxury Villa by Duval + 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! BLUE HERON'S ...
From $559 per night (USD)
VRBO
$**SUNSET POINT @ SUNSET MARINA** Condo \/ Pool & Spa + LAST KEY SERVICES...$
From $322 per night (USD)
Expedia
**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 30 days prior to your arrival! SUNSET POINT ...
From $322 per night (USD)
Expedia
From $983 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 21 days prior to your arrival! This colorful ...
From $983 per night (USD)
VRBO
From $729 per night (USD)
Expedia
Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This wonderful property has just received a major face lift and has been beautifully renovated. King bed in the master b ...
From $729 per night (USD)
Expedia
$**NEPTUNE'S PENTHOUSE @ THE BEACH** Oceanfront Condo \/ Pool + LAST KEY SERVICE.$
From $1273 per night (USD)
VRBO
**NEPTUNE'S PENTHOUSE @ THE BEACH** Oceanfront Condo \/ Pool + LAST KEY SERVICE.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! As Neptune wa ...
From $1273 per night (USD)
VRBO
$Best Deals in Duck Key . 2 Bedroom \/2 Bath w\/40' 'Dock, Trailer Storage Incl,$
From $416 per night (USD)
Expedia
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 $416 per night (USD)
Expedia
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VRBO
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
VRBO
From $1112 per night (USD)
Expedia
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 $1112 per night (USD)
Expedia
From $1520 per night (USD)
VRBO
**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 $1520 per night (USD)
VRBO
$**SUNSET DREAMS @ SUNSET MARINA** Condo \/ Pool & Spa + LAST KEY SERVICES...$
From $287 per night (USD)
Expedia
**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 30 days prior to your arrival! SUNSET DREAMS ...
From $287 per night (USD)
Expedia
From $367 per night (USD)
VRBO
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 $367 per night (USD)
VRBO
From $293 per night (USD)
Expedia
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 $293 per night (USD)
Expedia
From $1626 per night (USD)
VRBO
**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 $1626 per night (USD)
VRBO
From $722 per night (USD)
Expedia
High Tide awaits your next visit upgraded condo close to Smathers Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
1800 Atlantic Condominiums Unit B117 2 Bedroom Garden-View Condo at 1800 Atlantic Perfect for a family get-away or a gr ...
From $722 per night (USD)
Expedia
From $4168 per night (USD)
VRBO
**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 $4168 per night (USD)
VRBO
$**FOLLOW THE SUN @ THE BEACH** Ocean Condo \/ Pool & Tennis + LAST KEY SERVICES..$
From $890 per night (USD)
Expedia
**FOLLOW THE SUN @ THE BEACH** Ocean Condo \/ Pool & Tennis + 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! FOLLOW THE SU ...
From $890 per night (USD)
Expedia
From $2990 per night (USD)
VRBO
**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 $2990 per night (USD)
VRBO
From $703 per night (USD)
Expedia
Tranquility by Smathers and 10 minute bike downtown Key West value savings
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
2 Bedroom 2 bath Island View King in the master bedroom, king in the the guest bedroom and a queen sleeper sofa in the ...
From $703 per night (USD)
Expedia
From $1221 per night (USD)
VRBO
Somewhere on the Beach a dream property all amenities included simply amazing
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Somewhere on the Beach has amazing views of the Atlantic Ocean and White Street Pier. The property was completely remode ...
From $1221 per night (USD)
VRBO
$4 Bed 3 Bath Duck Key Sanctuary Villa W\/ Private Pool & 35 Foot Dock - Sleeps 10$
From $1235 per night (USD)
Expedia
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 $1235 per night (USD)
Expedia
From $567 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 30 days prior to your arrival! For many, the ...
From $567 per night (USD)
VRBO
From $2547 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 $2547 per night (USD)
Expedia
From $2206 per night (USD)
VRBO
**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 $2206 per night (USD)
VRBO
From $546 per night (USD)
Expedia
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 $546 per night (USD)
Expedia
$**NATURES EDGE @ THE BEACH** Ocean Condo \/ Pool & Tennis + LAST KEY SERVICES...$
From $921 per night (USD)
VRBO
**NATURES EDGE @ THE BEACH** Ocean Condo \/ Pool & Tennis + 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! NATURE'S EDGE ...
From $921 per night (USD)
VRBO
From $888 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 $888 per night (USD)
Expedia
From $976 per night (USD)
VRBO
Frost Free at 1800 Atlantic overlooking Smathers Beach top and the sunrise
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
1800 Atlantic 4th floor condominiums unit C439. Overlooking Smathers Beach and the Atlantic Ocean, this two bedroom, tw ...
From $976 per night (USD)
VRBO
From $295 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 30 days prior to your arrival! SUNDRENCHED R ...
From $295 per night (USD)
Expedia
From $3095 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 $3095 per night (USD)
VRBO
From $1064 per night (USD)
Expedia
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 $1064 per night (USD)
Expedia
From $276 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 $276 per night (USD)
VRBO
From $412 per night (USD)
Expedia
Truman Annex, two blocks from Duval
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Available for weekly, or longer, rentals this three-story townhouse is located on a picturesque street in the beautiful ...
From $412 per night (USD)
Expedia
From $766 per night (USD)
VRBO
**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 $766 per night (USD)
VRBO
From $332 per night (USD)
Expedia
Judy's place at Venture Out
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Judy's Place is located in the Venture Out Resort. A quiet little secret escape just 20 miles from Key West. Judy's Plac ...
From $332 per night (USD)
Expedia
$Stay where you play, On the water w\/Boat dock & Trailer parking. Pet friendly!$
From $328 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 $328 per night (USD)
VRBO
$4 BED DUCK KEY VILLA W\/ 35FT DOCK BEHIND IT & CABANA CLUB ACCESS$
From $1140 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 $1140 per night (USD)
Expedia

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