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

$Castaway 2\/2 w\/ 50` Ft. Dock on the Atlantic$
From $295 per night (USD)
VRBO
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 $295 per night (USD)
VRBO
$Palm Point 3bed\/2bath single family with brand new pool, dockage & stunning open$
From $531 per night (USD)
Expedia
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 $531 per night (USD)
Expedia
$Luxurious, Elegant Home, Waterfront\nWith Dockage$
From $993 per night (USD)
VRBO
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 $993 per night (USD)
VRBO
From $406 per night (USD)
Expedia
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 $406 per night (USD)
Expedia
From $784 per night (USD)
VRBO
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 $784 per night (USD)
VRBO
$Ocean View Gem 3\/2.5 Home 70` Dock Cabana Club included, and Jacuzzi on Property$
From $779 per night (USD)
Expedia
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 $779 per night (USD)
Expedia
From $730 per night (USD)
VRBO
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 $730 per night (USD)
VRBO
From $623 per night (USD)
Expedia
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 $623 per night (USD)
Expedia
$A Pirates Great Escape ~ 3bed\/2baths Ocean View Boat Slip included$
From $536 per night (USD)
VRBO
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 $536 per night (USD)
VRBO
$Beachy Keen House 3\/2 Water View Pool Home with Dock$
From $704 per night (USD)
Expedia
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 $704 per night (USD)
Expedia
$Blue Marlin 2\/2 Pool home with 35` Dock Easy Access to Atlantic$
From $369 per night (USD)
VRBO
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 $369 per night (USD)
VRBO
From $506 per night (USD)
Expedia
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 $506 per night (USD)
Expedia
From $171 per night (USD)
VRBO
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 $171 per night (USD)
VRBO
From $1266 per night (USD)
Expedia
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 $1266 per night (USD)
Expedia
From $269 per night (USD)
VRBO
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 $269 per night (USD)
VRBO
From $421 per night (USD)
Expedia
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 $421 per night (USD)
Expedia
From $594 per night (USD)
VRBO
Oceanside home, dock,kayaks,bikes,pool,fishing,111
Bedrooms:
6
Bathrooms:
3
Sleeps:
6
This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built i ...
From $594 per night (USD)
VRBO
$Sea Breeze Cottage 2 Large Decks, pool, free parking\/wifi in Truman Annex$
From $506 per night (USD)
Expedia
Sea Breeze Cottage 2 Large Decks, pool, free parking\/wifi in 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. This is ...
From $506 per night (USD)
Expedia
From $492 per night (USD)
VRBO
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
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 $492 per night (USD)
VRBO
From $526 per night (USD)
Expedia
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 $526 per night (USD)
Expedia
From $834 per night (USD)
VRBO
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)
VRBO
From $484 per night (USD)
Expedia
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 $484 per night (USD)
Expedia
From $490 per night (USD)
VRBO
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 $490 per night (USD)
VRBO
From $518 per night (USD)
Expedia
'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 Hist ...
From $518 per night (USD)
Expedia
From $465 per night (USD)
VRBO
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 $465 per night (USD)
VRBO
From $333 per night (USD)
Expedia
Galleon Resort efficiency
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This unit has a queen size bed. Updated ceramic stand up shower. The unit is an efficiency.It has a small refrigerator, ...
From $333 per night (USD)
Expedia
From $230 per night (USD)
VRBO
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)
VRBO
From $304 per night (USD)
Expedia
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)
Expedia
From $224 per night (USD)
VRBO
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 $224 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
$PLUNGE POOL VILLA ON BLUE WATER LAGOON DUCK Key\/MARATHON, FL$
From $365 per night (USD)
VRBO
PLUNGE POOL VILLA ON BLUE WATER LAGOON DUCK Key\/MARATHON, FL
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
In Duck Key/Marathon, Florida's sun-kissed beaches, you can find total relaxation at our beautiful two-bedroom house. Ne ...
From $365 per night (USD)
VRBO
From $1052 per night (USD)
Expedia
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 $1052 per night (USD)
Expedia
From $654 per night (USD)
VRBO
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 $654 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $1137 per night (USD)
VRBO
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 $1137 per night (USD)
VRBO
From $307 per night (USD)
Expedia
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 $307 per night (USD)
Expedia
From $870 per night (USD)
VRBO
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 $870 per night (USD)
VRBO
From $470 per night (USD)
Expedia
🌸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 $470 per night (USD)
Expedia
From $303 per night (USD)
VRBO
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 $303 per night (USD)
VRBO
$Paradise Awaits: 2 BR Beautiful Condo w\/ Pool, Beach, Marina & Resort Perks$
From $262 per night (USD)
Expedia
Paradise Awaits: 2 BR Beautiful Condo w\/ Pool, Beach, Marina & Resort Perks
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 $262 per night (USD)
Expedia
$Fishing Till Sunset 1bed\/1bath Condo w\/Pool & dock$
From $238 per night (USD)
VRBO
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 $238 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $1055 per night (USD)
VRBO
Steps from Duval with Private Pool – Coconut Palm
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Step into the heart of Key West at Coconut Palm! Just one block from Duval Street, this tropical gem features a ...
From $1055 per night (USD)
VRBO
From $1104 per night (USD)
Expedia
Parking & Shared Pool - Casa Key West
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 $1104 per night (USD)
Expedia
From $688 per night (USD)
VRBO
Private Parking & Near Downtown - Sea Breeze
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 $688 per night (USD)
VRBO
From $284 per night (USD)
Expedia
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 $284 per night (USD)
Expedia
From $416 per night (USD)
VRBO
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 $416 per night (USD)
VRBO
From $1202 per night (USD)
Expedia
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 $1202 per night (USD)
Expedia
From $560 per night (USD)
VRBO
Panoramic Ocean: Beach from every window
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $560 per night (USD)
VRBO
$Luxury waterfront Islamorada Retreat w\/private pool, hot tub, lanai bar& firepit$
From $779 per night (USD)
Expedia
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)
Expedia
$Another Day in Paradise! PRIVATE POOL! Blocks from Duval, 2BR\/2BA in Old Town!$
From $339 per night (USD)
VRBO
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)
VRBO
From $522 per night (USD)
Expedia
Penthouse Beach Ocean Views- Live the Dream
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $522 per night (USD)
Expedia
From $1099 per night (USD)
VRBO
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 $1099 per night (USD)
VRBO
From $508 per night (USD)
Expedia
Beach Penthouse: Ocean Views from every room Tropical Excellence
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 throug ...
From $508 per night (USD)
Expedia
$🌸Home #7 \BEACHY🏖KEEN\ Full WATERFRONT View Property!🌸$
From $859 per night (USD)
VRBO
🌸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 $859 per night (USD)
VRBO
From $608 per night (USD)
Expedia
P55 - Beautiful 3 bedroom, 3 bath home with private pool and hot tub.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This fabulous 3 bedroom, 3 bath, Gulf side home has been remodeled inside and out and the results are perfect! ...
From $608 per night (USD)
Expedia
$🌸Home #8 \DEJA⛵BLUE\ Premium WATERFRONT 🌸$
From $994 per night (USD)
VRBO
🌸Home #8 \"DEJA⛵BLUE\" Premium WATERFRONT 🌸
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
🌸Home #8 "DEJA⛵BLUE" Full Premium WATERFRONT view of Beach, Docks and Ocean🌸 Totally Private😉- Turn-Key and fully Sto ...
From $994 per night (USD)
VRBO
From $1160 per night (USD)
Expedia
Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
"Banana Breeze" is an upscale escape by the sea, and considered by some to be a hidden gem. Tucked away in your own oasi ...
From $1160 per night (USD)
Expedia
From $537 per night (USD)
VRBO
Hemingway Hideaway in the Truman Annex
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Perfectly positioned townhouse in Truman Annex At Historic Foundry building. Hemingway Hideaway in Truman Annex is a de ...
From $537 per night (USD)
VRBO
Click For Pricing
Expedia
NEW LISTING - Cudjoe Key - Canal with Quick Ocean Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Home is located in a very quiet and nice neighborhood! Home is minutes away from Key West or Big Pine for quick access t ...
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Expedia
From $319 per night (USD)
VRBO
Meticulous End Unit Across From Pool - near Local Diving, Fishing & Snorkeling
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Come unwind at our tastefully decorated 2 bedroom, 2 bathroom, condo in Ocean Pointe Suites. Located directly on the Atl ...
From $319 per night (USD)
VRBO
From $144 per night (USD)
Expedia
Key Largo - Sexton Cove (BaySide)
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to "Casa del Agua"!! The property is a Bay-Side Trailer located in the community of Sexton Cove on Mile Marker ...
From $144 per night (USD)
Expedia
From $375 per night (USD)
VRBO
P73 - Charming 4 bedroom duplex with deep water dockage and Cabana Club access.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Beautiful 4 Bedroom, 2 bathroom duplex in Key Colony Beach. Key Colony Beach is a small, friendly, walkable island with ...
From $375 per night (USD)
VRBO
From $237 per night (USD)
Expedia
Oceanside, pet friendly, smart home with plenty of paddle equipment
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
We are offering a nice discount in May of 2023 because we are putting in a new dock. Wonderful, pet-friendly, and beaut ...
From $237 per night (USD)
Expedia
$Key Largo Kawama Villa L1, 3\/3$
From $569 per night (USD)
VRBO
Key Largo Kawama Villa L1, 3\/3
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to paradise! This beautiful and modern unit is located in the highly sought-after Kawama Yacht Club in the heart ...
From $569 per night (USD)
VRBO
Click For Pricing
Expedia
Spacious condo, great location in paradise!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Looking for a tropical getaway that’s easy to get to? This is it! This Condo offers spacious (yes SPACIOUS!) rooms. Newl ...
Click For Pricing
Expedia
From $361 per night (USD)
VRBO
Beach House- Ocean & Beach View-Upgraded-Over 146 Five Star Reviews
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
If you are looking to stay in accommodations of high standards. This is the one for you! As you enter this large one bed ...
From $361 per night (USD)
VRBO
From $703 per night (USD)
Expedia
Oceanfront 2-bdrm Condo next to 5-star Restaurant & Marina
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
*Ocean Memories is the perfect Key West Escape* Wake Up to Amazing Ocean Views Start your day in tranquility, waking u ...
From $703 per night (USD)
Expedia
From $276 per night (USD)
VRBO
Water View. Diver's Heaven. Fishing. Paradise Key Largo, Moonbay
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Our rental is contactless from start to finish. Magnificent top floor end unit suite. Incredible views of the bay/oc ...
From $276 per night (USD)
VRBO
From $387 per night (USD)
Expedia
Outstanding Oceanfront Condo On The Beach With A Pool!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Time to get away! Rent our newest addition! This newly renovated condo with a brand new, high-end, kitchen and updated b ...
From $387 per night (USD)
Expedia
From $234 per night (USD)
VRBO
Canal Front Home in Big Pine Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This two bedroom two bath home open floor concept is very comfortable. Master bedroom has sliding doors to screened in ...
From $234 per night (USD)
VRBO
From $287 per night (USD)
Expedia
Beautiful Key Largo Town Home Fully Renovated Top to Bottom
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Are you looking for a peaceful island vacation with hints of luxury? Look no further. Casa Key Largo is the place for ...
From $287 per night (USD)
Expedia
From $338 per night (USD)
VRBO
OCEANFRONT 2 BDRM, 2 BATH APT, KEY LARGO, TAVERNIER
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This is one of the finest destinations in the Florida Keys. Recently renovated property! Our unit is Oceanfront with a ...
From $338 per night (USD)
VRBO
Click For Pricing
Expedia
Old Town Island House Near a grocery store, beach, bike rental shop, Restaurants
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Two Story Apartment in central Old Town Key West location. Only a 5 min bike ride to Duval. 1 King size bed on 3rd flo ...
Click For Pricing
Expedia
From $380 per night (USD)
VRBO
Amazing Ocean View Condo on the Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Create a memory that will last a lifetime! Rent this 2 bedroom, 2 bath condo with an outstanding View of the beach, pa ...
From $380 per night (USD)
VRBO
$Key Largo Kawama villa K1, 3\/3$
From $795 per night (USD)
Expedia
Key Largo Kawama villa K1, 3\/3
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Experience the charm and relaxation of the Florida Keys at Kawama Yacht Club. Our private community located in the hear ...
From $795 per night (USD)
Expedia
From $853 per night (USD)
VRBO
Sunset Crush- Bayfront property for the perfect sunset, Tavernier
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Do you love sunsets and all things ocean? Sunset Crush is aptly named and will have you crushing HARD over one of the m ...
From $853 per night (USD)
VRBO
From $429 per night (USD)
Expedia
Bahia Vista- Rare Bayfront townhouse at Moon Bay in Key Largo
Bedrooms:
2
Bathrooms:
3
Sleeps:
25
Bahia Vista is a rare end unit within the Moon Bay community, boasting exquisite water bay views from nearly every room ...
From $429 per night (USD)
Expedia
From $292 per night (USD)
VRBO
Beautiful House on Canal - minutes to the Atlantic, no bridges
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
The 3 bed/3 bath canal front home provides quick access to the Atlantic and Looe Key with no bridges. 60' of canal fr ...
From $292 per night (USD)
VRBO
From $364 per night (USD)
Expedia
GREEN SPOT at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to our comfortable and delightful 2nd floor condo in the Shipyard section of Truman Annex. Unit #258 is a tastef ...
From $364 per night (USD)
Expedia
From $364 per night (USD)
VRBO
ANOTHER THREE HOUR TOUR at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $364 per night (USD)
VRBO
From $270 per night (USD)
Expedia
CONCH RETREAT Truman Annex Condo - 2 decks, pool, 2 Bikes, Free parking and WIFI
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A TRUE CARIBBEAN PARADISE! Location! Location! Location! This is a Saturday-Saturday weekly condo for the rest of 2025. ...
From $270 per night (USD)
Expedia
From $395 per night (USD)
VRBO
**MIDTOWN MOSAIC @ MIDTOWN** Modern Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Spanning an e ...
From $395 per night (USD)
VRBO
From $579 per night (USD)
Expedia
Charming Canal-Front House | WiFi+Swim+Kayak+Fish
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
The whole family will enjoy this tranquil, waterfront getaway in Tavernier, adjacent to Key Largo. With four bedrooms, a ...
From $579 per night (USD)
Expedia
From $1025 per night (USD)
VRBO
Beach Getaway in the Florida Keys
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
If you’re reading this, you’re already on the path to paradise! Thank you for considering us for your dream vacation—we ...
From $1025 per night (USD)
VRBO
From $205 per night (USD)
Expedia
Conch House in the Historic District
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Discover a piece of paradise with a beautiful conch home located in the historic district of Key West. 4-bedrooms, 2 ba ...
From $205 per night (USD)
Expedia
From $373 per night (USD)
VRBO
Waterfront House - 30' Dock & Pool at Cabana Club
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Relax in this 3-bedroom, 2-bathroom house in the prestigious Key Colony Beach. It is conveniently located near the end o ...
From $373 per night (USD)
VRBO
Click For Pricing
Expedia
ISLAND SPA in the Truman Annex
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This Shipyard unit has a Queen bed, one bathroom, very sunny, bright condo.It has a very nice large deck balcony facing ...
Click For Pricing
Expedia
$Luxury Galleon Resort & Marina 2 Bed\/2 Bath Marina View$
Click For Pricing
VRBO
Luxury Galleon Resort & Marina 2 Bed\/2 Bath Marina View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Galleon Resort is located in the heart of Old Town Key West and the Marina is one of the most desired harbors in the ...
Click For Pricing
VRBO
From $347 per night (USD)
Expedia
BLUE HEAVEN at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $347 per night (USD)
Expedia
From $459 per night (USD)
VRBO
P46 - Beautiful updated home on the Gulf side with pool and dock!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This is a charming 2 bedroom, 2 bath with a loft, single family home is located on the Gulf side. Offering a private, he ...
From $459 per night (USD)
VRBO
From $327 per night (USD)
Expedia
A Bella Capri in Key West by the Beach! *Monthly rental*
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
This magnificent 5 bedroom Mediterranean villa has a landmark presence, complete privacy and a breathtaking outdoor plaz ...
From $327 per night (USD)
Expedia
From $273 per night (USD)
VRBO
OYSTER'S PEARL at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This 1BR 1BA condo has an extra large living room with a big screen TV. It sits nestled in the back of the Shipyard back ...
From $273 per night (USD)
VRBO
$**THE LIME & THE COCONUT @ OLD TOWN** 6BR\/6BA Compound + LAST KEY SERVICES..$
From $2262 per night (USD)
Expedia
**THE LIME & THE COCONUT @ OLD TOWN** 6BR\/6BA Compound + 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! According to ...
From $2262 per night (USD)
Expedia
From $237 per night (USD)
VRBO
Mariners House @ Landings of Largo
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: Beautiful Landings of Largo townhouse centrally located in Key Largo! The Space: Embark on a truly unique vaca ...
From $237 per night (USD)
VRBO
From $748 per night (USD)
Expedia
🌸Home#6 FANTA🐬SEA Full WATERFRONT Home!🌸
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
🌸Home #6 FANTA🐬SEA WATERFRONT!🌸 Look out on the Ocean in your Totally Private😉- Turn-Key and fully Stocked- Single ...
From $748 per night (USD)
Expedia
From $520 per night (USD)
VRBO
A LATITUDE ADJUSTMENT at the Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
This Foundry townhouse is a Bostonian style 3 level home located in Old Town Key West. This home has been recently renov ...
From $520 per night (USD)
VRBO
From $2805 per night (USD)
Expedia
A Tropical Luxury Getaway, Your own private resort!!
Bedrooms:
7
Bathrooms:
6
Sleeps:
16
For more pictures on this property look us up on Instagram at sterlingbayhouse. This house is located on the open wate ...
From $2805 per night (USD)
Expedia
From $672 per night (USD)
VRBO
Waterfront beautifully renovated 6 Bedrooms 4 Bath , Gated Private Home
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
This Beautifully renovated Compound / Property Comes With A recently completed and Magnificent Landscape Oasis , That Be ...
From $672 per night (USD)
VRBO
$Keys Deal w\/Cafe & Pool Bar! Up to 20% Off Oceanfront 2\/2 with Private Beach$
From $332 per night (USD)
Expedia
Keys Deal w\/Cafe & Pool Bar! Up to 20% Off Oceanfront 2\/2 with Private Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
New Island Grill Pool Bar & Marina Cafe now open! Enjoy our recently renovated Deluxe 2/2 right on the ocean, offering s ...
From $332 per night (USD)
Expedia

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