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 $800 per night (USD)
VRBO
Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This house is a 3 bedroom stand alone unit with 2 king bedrooms upstairs with balconies and own bathrooms and the b ...
From $800 per night (USD)
VRBO
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Expedia
Studio in the heart of the Florida Keys, snowbird community
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
400 sq ft fully equipped studio,full bathroom & kitchenette. Chase sofa with sleeper. On wide private canal to the Ocea ...
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Expedia
From $793 per night (USD)
VRBO
AFTERNOON DELIGHT at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This amazing 2 bedroom/2 bath condo has one of the best views in Key West. Located in the historic Mills Place in Truman ...
From $793 per night (USD)
VRBO
From $297 per night (USD)
Expedia
Oceanfront, Snowbird-Friendly Home with High-Speed WiFi, Ocean Views, and Dock
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Humpty Dumpty Hacienda Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $297 per night (USD)
Expedia
$3BR\/3BA Duck Key Island Retreat With Private Pool$
From $260 per night (USD)
VRBO
3BR\/3BA Duck Key Island Retreat With Private Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
In the Heart of the Florida Keys, this three bedroom and three bath Duck Key retreat is located within just minutes of t ...
From $260 per night (USD)
VRBO
From $1143 per night (USD)
Expedia
The Real Liveaboard Experience. Lets go cruising!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This is a private yacht charter. Only your family and friends aboard along with your captains. License To Chill is back ...
From $1143 per night (USD)
Expedia
$3BR\/2BA Canalside Flamingo Island Home With Heated Pool, Jacuzzi, and 60' Boat Slip$
From $428 per night (USD)
VRBO
3BR\/2BA Canalside Flamingo Island Home With Heated Pool, Jacuzzi, and 60' Boat Slip
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
License # VACA-23-219 - Discover paradise at this Flamingo Island retreat in Marathon boasting everything you'll need fo ...
From $428 per night (USD)
VRBO
$**SWEET AMERICANA @ OLD TOWN** 8BR\/8BA Compound + 2 Pools + LAST KEY SERVICES…$
From $5557 per night (USD)
Expedia
**SWEET AMERICANA @ OLD TOWN** 8BR\/8BA Compound + 2 Pools + LAST KEY SERVICES…
Bedrooms:
10
Bathrooms:
8
Sleeps:
20
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! It doesn't ge ...
From $5557 per night (USD)
Expedia
$Dog-friendly home on a wide canal w\/ WiFi & amazing water views$
From $317 per night (USD)
VRBO
Dog-friendly home on a wide canal w\/ WiFi & amazing water views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Tarpon Cove Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $317 per night (USD)
VRBO
$2BR\/1BA Serene Cozy Cottage of Shady Palms in Islamorada With Heated Pool$
From $365 per night (USD)
VRBO
2BR\/1BA Serene Cozy Cottage of Shady Palms in Islamorada With Heated Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy a unique and secluded vacation experience in the heart of Islamorada at Shady Palms! Our charming cottage features ...
From $365 per night (USD)
VRBO
From $315 per night (USD)
VRBO
Airy Top Floor Blue Heron Suite [Ocean Pointe 3407]
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
With thoughtful and creative touches both inside and out mixed with a keen attention to the smallest of details, this oc ...
From $315 per night (USD)
VRBO
From $240 per night (USD)
VRBO
Julia's Secret
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Best location in Key West! Just steps from the world class shops and restaurants of world famous Duval Street. There are ...
From $240 per night (USD)
VRBO
From $329 per night (USD)
VRBO
**BIRD of PARADISE** Elegant Home & Pool + 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! Like witnessi ...
From $329 per night (USD)
VRBO
From $2754 per night (USD)
Expedia
**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + 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! Key West has ...
From $2754 per night (USD)
Expedia
$Waterfront Vacation Home w\/Stunning Bay\/Canal Views, Private Dock, Private Beach$
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VRBO
Waterfront Vacation Home w\/Stunning Bay\/Canal Views, Private Dock, Private Beach
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Casa Koto Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
Click For Pricing
VRBO
From $3049 per night (USD)
Expedia
Bananas Foster, Downtown | Epic Guesthouse!
Bedrooms:
8
Bathrooms:
9
Sleeps:
19
Summary: Palm trees, sunsets, and the blissful pace of island time will all be yours when you stay at this large histori ...
From $3049 per night (USD)
Expedia
From $681 per night (USD)
VRBO
Fully renovated Condo with Private Balcony, Shared Pool, Hot Tub and Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
*Brand New Listing* Welcome to Captains Choice The NICEST Unit at Sunrise Suites Resort in Key West- Unit 302. Tropical ...
From $681 per night (USD)
VRBO
From $715 per night (USD)
Expedia
Spectacular Ocean Front Home In Beautiful Islamorada!>Dock,Com Pool, & Prv Bch
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
VRL# 24-0132 we are one of Islamorada’s limited number of licensed weekly vacation homes. This magnificent home with d ...
From $715 per night (USD)
Expedia
From $505 per night (USD)
VRBO
VOTED TRIPADVISOR'S #1 KEY LARGO DESTINATION: 2 KING SUITES, POOLS TENNIS
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Please check out our other properties in Kawama by entering the following property numbers in the section "where do you ...
From $505 per night (USD)
VRBO
From $324 per night (USD)
Expedia
~Bahari House, Seaport~Walk to the harbor from this quintessential conch home
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $324 per night (USD)
Expedia
$Luxury Key Largo Home w\/ Guest House & Pool!$
From $439 per night (USD)
VRBO
Luxury Key Largo Home w\/ Guest House & Pool!
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Total relaxation awaits you at this Key Largo vacation rental. Located in prestigious Buccaneer Point, this 3-bedroom, 4 ...
From $439 per night (USD)
VRBO
From $276 per night (USD)
Expedia
Upscale end unit home @ Truman Annex close to Duval St
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $276 per night (USD)
Expedia
From $253 per night (USD)
VRBO
Keys Paradise Stay
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Fully furnished, 2 bedroom/ 1 bath mobile home featuring 1 master bedroom with Queen size bed + 1 bedroom with bunk bed ...
From $253 per night (USD)
VRBO
From $1314 per night (USD)
VRBO
Dream Vacation! 3 Awesome Units, Pool, On-Site Bar, Gym, Parking!
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $1314 per night (USD)
VRBO
From $444 per night (USD)
VRBO
King Bed Accommodation at The Gates Hotel Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $444 per night (USD)
VRBO
From $525 per night (USD)
VRBO
Pool View Two Queen Beds at The Gates Hotel Key West, Swimming Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $525 per night (USD)
VRBO
From $461 per night (USD)
VRBO
Pool View King at The Gates Hotel Key West, Onsite Swimming Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $461 per night (USD)
VRBO
From $229 per night (USD)
Expedia
**DRIFTWOOD DREAMS @ 1800 ATLANTIC** Beachside 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 $229 per night (USD)
Expedia
From $424 per night (USD)
VRBO
Breezy Beach Waterfront home in Port Antigua
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Relax in this beautiful and comfortably updated bayside home in Port Antigua. Port Antigua is the Lower Keys best kept ...
From $424 per night (USD)
VRBO
From $510 per night (USD)
Expedia
Villa 5053 on Duck Key BOAT SLIP available
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Boat slip available for additional $100 a night. Largest boat that can fit is 33 ft. Ask for availability. This villa b ...
From $510 per night (USD)
Expedia
From $662 per night (USD)
VRBO
403 Mariners Club | 3 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Starlight star bright...first star I see tonight...I wish I may I wish I might have the wish I wish tonight… And I wish ...
From $662 per night (USD)
VRBO
From $1168 per night (USD)
Expedia
Poolside Paradise | Private Oasis, 1 Block to Duval!
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Summary: This 3 bed 2 bath home with an amazing HEATED pool is located right off the quieter end of Duval St. The home c ...
From $1168 per night (USD)
Expedia
From $450 per night (USD)
VRBO
Waterfront 75’Dock POOL Kayaks Bikes SombreroBeach2mi OutdoorSpace WalkToStores
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
OUTDOORS @ LUNA BAY BREEZE We invite you to enjoy tropical tranquil breezes from the Atlantic Ocean side of Marathon an ...
From $450 per night (USD)
VRBO
$Poolside Retreat | Cottage w\/ Pool$
From $374 per night (USD)
Expedia
Poolside Retreat | Cottage w\/ Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Poolside Retreat is the PERFECT vacation home for a couple or small group of friends looking for a fun-filled g ...
From $374 per night (USD)
Expedia
$Lou & Mary`s Getaway ~ 2 bed 2 Bath home W\/Dock, Inch Beach & Cabana Club$
From $276 per night (USD)
VRBO
Lou & Mary`s Getaway ~ 2 bed 2 Bath home W\/Dock, Inch Beach & Cabana Club
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Relax, Fish and Enjoy your stay in this ground level 2 bedroom, 2 bath half-duplex. This Home has easy access to the bay ...
From $276 per night (USD)
VRBO
$Reel Sunset 3\/2 with Pool and Canalfront in Duck Key$
From $763 per night (USD)
Expedia
Reel Sunset 3\/2 with Pool and Canalfront in Duck Key
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Beautiful 3 bedroom 2.5 bath canal front home with private pool. Seaside decor and casual elegance define this comforta ...
From $763 per night (USD)
Expedia
From $390 per night (USD)
VRBO
Updated home with private pool, patio, & grill in enclosed tropical backyard
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Margaret Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $390 per night (USD)
VRBO
From $424 per night (USD)
VRBO
Keys Escape! Lovely Hammock View, Pools, Beach Access, Free Parking!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We are about getting out there and having fun in the unmatched beauty of bayside Key Largo. Take an early morning swim i ...
From $424 per night (USD)
VRBO
From $327 per night (USD)
VRBO
Oceanview Condo 2bed 2bath second floor with elevator & ocean views!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Oceanview Condo is fully furnished and features two bedrooms, two bathrooms, a dining area, full kitchen, washer/dryer, ...
From $327 per night (USD)
VRBO
From $616 per night (USD)
Expedia
Yellowtail For Dinner 3bed 3bath updated single family home with private pool &
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Yellowtail For Dinner is a stunning 3bed/3bath that is it is only one house away from the mouth of a deep-water canal th ...
From $616 per night (USD)
Expedia
From $967 per night (USD)
VRBO
Sunrise Paradise on Sombrero Brand New 4 bed 5 bath Pool Jacuzzi Kayaks
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Plr2019-00051 Are you looking for an upscale, top-of-the-line, out of this world property? Then look no further than Sun ...
From $967 per night (USD)
VRBO
$Casa De Tiki 4bed\/3bath half duplex w\/ heated pool, dockage & more!$
From $479 per night (USD)
Expedia
Casa De Tiki 4bed\/3bath half duplex w\/ heated pool, dockage & more!
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Casa De Tiki is a spacious 4-bedroom, 3-bathroom half duplex located just minutes from the stunning Sombrero Beach. Insi ...
From $479 per night (USD)
Expedia
From $262 per night (USD)
VRBO
Boot Key Harbor Comfy Condo 1bed 1bath
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This updated one-bedroom condo, centrally located in Marathon, offers convenient access to historical sites such as Cran ...
From $262 per night (USD)
VRBO
From $777 per night (USD)
Expedia
Sweet Retreat! 4 bedroom 2.5 Baths Sombrero Beach w Pool Jacuzzi, 37` dock 2
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Plr2019-00281 Do you love the Tropical Waters of the Florida Keys? This vacation home is calling to you. Located on the ...
From $777 per night (USD)
Expedia
From $313 per night (USD)
VRBO
Tropical Oasis Home in Key Colony 3 bedrooms 2 Baths
Bedrooms:
2
Bathrooms:
4
Sleeps:
5
Rentals are Saturday – Saturday unless prior agent and guest agreement made or calendar matched to other reservations a ...
From $313 per night (USD)
VRBO
$Castaway 2\/2 w\/ 50` Ft. Dock on the Atlantic$
From $356 per night (USD)
Expedia
Castaway 2\/2 w\/ 50` Ft. Dock on the Atlantic
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
VACA-22-419 7-night minimum, NO Exceptions Max Occupancy: 5 (No Matter the age) Per the city of Marathon's rule. ***Ask ...
From $356 per night (USD)
Expedia
$Palm Point 3bed\/2bath single family with brand new pool, dockage & stunning open$
From $675 per night (USD)
VRBO
Palm Point 3bed\/2bath single family with brand new pool, dockage & stunning open
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Palm Point presents a breathtaking 3-bedroom, 2-bathroom single-family residence located in Marathon on the gulf side of ...
From $675 per night (USD)
VRBO
$Luxurious, Elegant Home, Waterfront\nWith Dockage$
From $1107 per night (USD)
Expedia
Luxurious, Elegant Home, Waterfront\nWith Dockage
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Oasis getaway, 3 bedroom, 3 bath, including chefs kitchen. This home has all the amenities on the water, located in a q ...
From $1107 per night (USD)
Expedia
From $499 per night (USD)
VRBO
Waves of the Sea, Ocean View Home with Dock, Private Pool
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
VACA-22-260 Booking Min age is 25 and must be present for the duration of the reservation. Max occupancy is 8 no matter ...
From $499 per night (USD)
VRBO
From $1084 per night (USD)
Expedia
Mariners Club # 314 3 Bed 2.5 Bath Key Largo Beachfront Luxury Ocean views and
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Every one will love this luxurious and spacious 3 bedroom and 2.5 bathroom condo in the exclusive Mariner's Club gated c ...
From $1084 per night (USD)
Expedia
$Ocean View Gem 3\/2.5 Home 70` Dock Cabana Club included, and Jacuzzi on Property$
From $799 per night (USD)
VRBO
Ocean View Gem 3\/2.5 Home 70` Dock Cabana Club included, and Jacuzzi on Property
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Easy Breezy Oceanside home on the Atlantic Ocean, just one house in from open water, with easy deep water access by boat ...
From $799 per night (USD)
VRBO
From $747 per night (USD)
Expedia
Shangri-La 3 Bedroom 3 Baths Gulf Front Estate
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
VACA-22-258 Rentals would be Saturday – Saturday unless prior agent and guest agreement made or calendar matched to othe ...
From $747 per night (USD)
Expedia
From $735 per night (USD)
VRBO
Coral Lagoon#8 3 Bed 2.5 bath 35` optional boat slip MKB~Blanco
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This Coral Lagoon Resort & Marina townhome in a quaint Key West village style atmosphere. 1450 sq ft and Built in 200 ...
From $735 per night (USD)
VRBO
$A Pirates Great Escape ~ 3bed\/2baths Ocean View Boat Slip included$
From $621 per night (USD)
Expedia
A Pirates Great Escape ~ 3bed\/2baths Ocean View Boat Slip included
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Oceanfront Penthouse Condo with a Private Boat slip. Small Gated Community on the southern tip of Islamorada. The condo ...
From $621 per night (USD)
Expedia
$Beachy Keen House 3\/2 Water View Pool Home with Dock$
From $763 per night (USD)
VRBO
Beachy Keen House 3\/2 Water View Pool Home with Dock
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Vaca-21-258 Beachy Keen House! This home is just one house up from the white sands of Sombrero Beach. Three bedrooms, tw ...
From $763 per night (USD)
VRBO
$Blue Marlin 2\/2 Pool home with 35` Dock Easy Access to Atlantic$
From $317 per night (USD)
Expedia
Blue Marlin 2\/2 Pool home with 35` Dock Easy Access to Atlantic
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
VACA-21-25 7-night minimum, NO Exceptions Friday to Friday booking Only (for alternate dates message agent) We can do M ...
From $317 per night (USD)
Expedia
From $488 per night (USD)
VRBO
Compelling Canal Home with Pool & Large Dock on each side-Cabana Club Included
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
DUPLEX, THIS LISTING NUMBER IS 561552 OTHER SIDE LISTING IS 1275459. EACH SIDE HAS 4 BEDROOMS 3 BATHS, YOUR OWN POOL AND ...
From $488 per night (USD)
VRBO
From $176 per night (USD)
Expedia
Escape to Eden | Canalfront half-duplex with short run to channel on Big Pine Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Newly renovated, tranquil half-duplex nestled among the natural beauty of Big Pine Key! Enjoy an immaculately clean spac ...
From $176 per night (USD)
Expedia
From $1531 per night (USD)
VRBO
Old Town Retreat near Upper Duval St
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Casa Caribe! When you think of the Caribbean, you think of tranquil blue green waters and a fun vibe. That's the feel wh ...
From $1531 per night (USD)
VRBO
From $259 per night (USD)
Expedia
Canal-front condo with amazing views & convenient location
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Sombrero Siesta Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $259 per night (USD)
Expedia
From $432 per night (USD)
VRBO
Dog-friendly condo with pool & hot tub - walk or bike to beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Suites - Paradise Escape 407 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $432 per night (USD)
VRBO
From $546 per night (USD)
Expedia
Oceanside home, dock,kayaks,bikes,pool,fishing,111
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built i ...
From $546 per night (USD)
Expedia
From $518 per night (USD)
VRBO
Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sea Breeze Cottage Cottage is a private, tropical, stand alone cottage located in the prestigious Truman Annex. 3 bedro ...
From $518 per night (USD)
VRBO
From $399 per night (USD)
Expedia
Hip Studio in Old Town - Walk to the Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in ...
From $399 per night (USD)
Expedia
From $514 per night (USD)
VRBO
Oceanside home, dock,kayaks,bikes,pool,fishing,109
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built i ...
From $514 per night (USD)
VRBO
From $834 per night (USD)
Expedia
3 bedroom 2 bath Ocean front condo on marina with opt boat slip.
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
3 bedroom 2 bathroom Ocean front condo. Full service marina on site. Restaurant/bar on site. Pool and spa Optional 50 ...
From $834 per night (USD)
Expedia
From $470 per night (USD)
VRBO
Oceanside home, dock,kayaks,bikes,pool,fishing,107
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built i ...
From $470 per night (USD)
VRBO
From $517 per night (USD)
Expedia
Ocean Front Modern Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
This luxurious cozy and comfortable, three-story home, overlooks the blue Atlantic, punctuated by small tropical islands ...
From $517 per night (USD)
Expedia
From $413 per night (USD)
VRBO
'LA DOLCE VITA' OLD TOWN, STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
La Dolce Vita is located in the heart of Old Town Key West and just steps to Duval Street in the heart of the Historic ...
From $413 per night (USD)
VRBO
From $437 per night (USD)
Expedia
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Here in Key West we believe in One Human Family where everyone is welcome and treated like family. Key West! .....it’s ...
From $437 per night (USD)
Expedia
From $362 per night (USD)
VRBO
Galleon Resort available Jan 4-18 2025
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
You can book 1 or both weeks. Saturday-Saturday. This unit has a queen size bed. Updated ceramic stand up shower. The un ...
From $362 per night (USD)
VRBO
From $230 per night (USD)
Expedia
Key Largo Oasis.
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Relax with the whole family at this peaceful place to stay. The upstairs of the home features 3 bedrooms, 1 and half bat ...
From $230 per night (USD)
Expedia
From $304 per night (USD)
VRBO
Beautiful Key Largo awaits
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy this lavishly decorated 2 bedroom 2 bathroom ground floor unit in beautiful Buttonwood Bay. Unit is a smoke free, ...
From $304 per night (USD)
VRBO
From $304 per night (USD)
Expedia
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cottage #14 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. Located on a compound wi ...
From $304 per night (USD)
Expedia
Click For Pricing
VRBO
3 blocks from waterfront and 1 block off Duval in heart of Old Town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Want to “ Get away from it all” but still be in the heart of Olde Town Key West with everything you need right there? Th ...
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VRBO
From $641 per night (USD)
Expedia
Relax by Sombrero Beach 21 mins away at our 2-bedroom Marathon Villa
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
In Marathon, Florida's sun-kissed beaches, you can find total relaxation at our beautiful two-bedroom house. Nestled jus ...
From $641 per night (USD)
Expedia
From $1165 per night (USD)
VRBO
Seaside Retreat: Waterfront Home with private heated pool & lush landscaping
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $1165 per night (USD)
VRBO
From $660 per night (USD)
Expedia
Marathon Keys Coral Lagoon Unit 2 Waterfront Villa
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
*Currently the seawall repair is not affecting our side of the property, our view is unobstructed and not affected. Also ...
From $660 per night (USD)
Expedia
From $342 per night (USD)
VRBO
Key Largo Getaway [ Ocean Pointe 1316 ]
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
In beautiful Tavernier, you'll find our impressive 2-bedroom condo waiting for your escape. Nestled just a short 19-minu ...
From $342 per night (USD)
VRBO
From $647 per night (USD)
Expedia
Hidden Gem Sunset Views-Marlin Bay Resort & Marina
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort fea ...
From $647 per night (USD)
Expedia
From $399 per night (USD)
VRBO
🌸Home #1: “ANCHORS ⚓ AWAY” (Off Water-approximately 300 ft from beach entrance)- 🌸
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Home #1: “ANCHORS ⚓ AWAY” (Off Water-approximately 300 ft from beach entrance)- 🌸 Totally Private😉- Turn-Key and fully ...
From $399 per night (USD)
VRBO
From $543 per night (USD)
Expedia
Historic House, Gorgeous Porch, Great Location, See 5 Star Reviews
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderfu ...
From $543 per night (USD)
Expedia
From $371 per night (USD)
VRBO
Happiness is the sand between your toes and the sunburn on your nose!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nautical 2 bedroom & 2 bath inspired getaway in a gated and professionally managed community/resort with an abundance of ...
From $371 per night (USD)
VRBO
$Fishing Till Sunset 1bed\/1bath Condo w\/Pool & dock$
From $329 per night (USD)
Expedia
Fishing Till Sunset 1bed\/1bath Condo w\/Pool & dock
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Vaca-21-257 Located on Coco Plum at the Coco Plum Terraces. Shared Pool and private dock. The adorable one bedroom one ...
From $329 per night (USD)
Expedia
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VRBO
3 blocks from waterfront and 1 block off Duval in Old Town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Want to “ Get Away from it all” but still in the heart of Old Town Key West with everything you need within walking dist ...
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VRBO
From $1044 per night (USD)
Expedia
W08 - New Luxury Property! Stunning Canal Front Pool Home - Sleeps 14
Bedrooms:
7
Bathrooms:
6
Sleeps:
14
Welcome to paradise! Escape to this luxurious 6 bedroom/6.5 bathroom home designed for VIP guests. Each bedroom i ...
From $1044 per night (USD)
Expedia
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VRBO
Key Largo Paradise Home in Calusa Campground
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Fully furnished, 2 bedroom/1 bath mobile home featuring 2 bedrooms with bunk beds Full over Full. The property has an o ...
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VRBO
From $576 per night (USD)
Expedia
Sea Breeze, Near Downtown!| Off-Street Parking!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Sea Breeze is the perfect location for your tropical getaway. This two bedroom condo is located in the heart of ...
From $576 per night (USD)
Expedia
From $294 per night (USD)
VRBO
Breeze On Inn: A Waterfront Retreat with 2 Bedrooms 2 bathrooms and Dockage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This 2-bedroom, 2-bath mobile home is located on Grassy Key, in the Florida Keys, on the Gulf side. It sits on a canal, ...
From $294 per night (USD)
VRBO
From $443 per night (USD)
Expedia
Anglers Reef Islamorada home with ocean views, private marina, beach & pool
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Angler's Retreat is a 2 bedroom, 2.5 bathroom single-family home with picturesque ocean views, privacy, and space. The p ...
From $443 per night (USD)
Expedia
From $1343 per night (USD)
VRBO
Coastal Comfort; Waterfront Luxury Home with private pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $1343 per night (USD)
VRBO
From $702 per night (USD)
Expedia
Panoramic Ocean: Beach from every window
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Key West Paradise Found is perched on the top floor with breathtaking Ocean Views, Reconfigured Master Bedroom and Rem ...
From $702 per night (USD)
Expedia
$Luxury waterfront Islamorada Retreat w\/private pool, hot tub, lanai bar& firepit$
From $779 per night (USD)
VRBO
Luxury waterfront Islamorada Retreat w\/private pool, hot tub, lanai bar& firepit
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to "Casa de Karma", your own private, resort style paradise! Enjoy your large heated pool (with sun shelf and s ...
From $779 per night (USD)
VRBO
$Another Day in Paradise! PRIVATE POOL! Blocks from Duval, 2BR\/2BA in Old Town!$
From $339 per night (USD)
Expedia
Another Day in Paradise! PRIVATE POOL! Blocks from Duval, 2BR\/2BA in Old Town!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
*** Located in the Old Town neighborhood. This exclusive residential area of Old Town Key West is really an extension of ...
From $339 per night (USD)
Expedia
From $845 per night (USD)
VRBO
Penthouse Beach Ocean Views- Live the Dream
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
You feel the excitement the moment you arrive. The warm tropical breezes, the blue green water. It's a rhythm. A rhythm ...
From $845 per night (USD)
VRBO
From $1129 per night (USD)
Expedia
Havana Daydream; Spacious Waterfront 4 Bedroom Home With Private Heated Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
If you’re looking for an upscale escape by the sea, Havana Daydream is your Key West hidden gem. Enjoy the island life i ...
From $1129 per night (USD)
Expedia
From $674 per night (USD)
VRBO
Beach Penthouse: Ocean Views from every room Tropical Excellence
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Ocean views from every room with floor to ceiling windows. Feel the warm tropical breezes as the palm trees sway to the ...
From $674 per night (USD)
VRBO
$🌸Home #7 \BEACHY🏖KEEN\ Full WATERFRONT View Property!🌸$
From $923 per night (USD)
Expedia
🌸Home #7 \"BEACHY🏖KEEN\" Full WATERFRONT View Property!🌸
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
🌸Home #7 "BEACHY🏖KEEN" Full WATERFRONT View over the docks and beach and Ocean!🌸 Totally Private😉- Turn-Key and full ...
From $923 per night (USD)
Expedia
$Coconut Palm, Great Location | Island Home w\/ Pool$
From $1080 per night (USD)
VRBO
Coconut Palm, Great Location | Island Home w\/ Pool
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Coconut Palm is the perfect place for your beautiful tropical getaway in Key West. It is located just one block ...
From $1080 per night (USD)
VRBO
From $1039 per night (USD)
Expedia
Casa Key West | Pool & Free Parking
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: - Located on the south end of Duval Street steps from the Southernmost Point! - Large open-concept condo with p ...
From $1039 per night (USD)
Expedia

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