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 $497 per night (USD)
VRBO
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 $497 per night (USD)
VRBO
$🌸Home #8 \DEJA⛵BLUE\ Premium WATERFRONT 🌸$
From $958 per night (USD)
Expedia
🌸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 $958 per night (USD)
Expedia
From $1072 per night (USD)
VRBO
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 $1072 per night (USD)
VRBO
From $755 per night (USD)
Expedia
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 $755 per night (USD)
Expedia
From $288 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 $288 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
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VRBO
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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VRBO
From $509 per night (USD)
Expedia
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 $509 per night (USD)
Expedia
From $696 per night (USD)
VRBO
Oceanfront Two-bedroom Gated Condominium adjacent to Marina & 5-Star Restaurant
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
**Perfect Getaway for all ages Imagine this: from the comfort of your bed, you wake up to a beautiful sun rising over ...
From $696 per night (USD)
VRBO
From $336 per night (USD)
Expedia
Moon Bay Key Largo; Water View. Diver's Heaven Contactless check in!
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 $336 per night (USD)
Expedia
From $299 per night (USD)
VRBO
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 $299 per night (USD)
VRBO
From $234 per night (USD)
Expedia
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)
Expedia
From $315 per night (USD)
VRBO
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 $315 per night (USD)
VRBO
From $358 per night (USD)
Expedia
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 $358 per night (USD)
Expedia
Click For Pricing
VRBO
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 ...
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VRBO
From $214 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 $214 per night (USD)
Expedia
$Key Largo Villa, Kawama L1, 3\/3$
From $618 per night (USD)
VRBO
Key Largo Villa, Kawama L1, 3\/3
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Explore the Florida Keys in this central location and have fun with the whole family at this stylish place. Kawama Ya ...
From $618 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 $363 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 $363 per night (USD)
VRBO
$Key Largo Kawama villa K1, 3\/3$
From $641 per night (USD)
Expedia
Key Largo Kawama villa K1, 3\/3
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Have fun with the family at this unique location. Kawama Yacht Club - Private community with 24 hr security. Amenitie ...
From $641 per night (USD)
Expedia
From $920 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 $920 per night (USD)
VRBO
From $528 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 $528 per night (USD)
Expedia
From $364 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 $364 per night (USD)
VRBO
From $396 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 $396 per night (USD)
Expedia
From $472 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 $472 per night (USD)
VRBO
From $433 per night (USD)
Expedia
CONCH RETREAT Truman Annex Condo with 2 decks, Close to Beach, 2 Bikes
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A TRUE CARIBBEAN PARADISE! Location! Location! Location! The Conch Retreat Condo is located in the prestigious Truman An ...
From $433 per night (USD)
Expedia
From $384 per night (USD)
VRBO
Fantasy Fest Special Discount-Beach House Ocean View
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 $384 per night (USD)
VRBO
From $728 per night (USD)
Expedia
**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 30 days prior to your arrival! Spanning an e ...
From $728 per night (USD)
Expedia
From $788 per night (USD)
VRBO
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 $788 per night (USD)
VRBO
From $489 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 $489 per night (USD)
Expedia
From $624 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 $624 per night (USD)
VRBO
From $473 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 $473 per night (USD)
Expedia
From $292 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 $292 per night (USD)
VRBO
$**THE LIME & THE COCONUT @ OLD TOWN** 6BR\/6BA Compound + LAST KEY SERVICES..$
From $4559 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 $4559 per night (USD)
Expedia
From $226 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 $226 per night (USD)
VRBO
From $752 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 $752 per night (USD)
Expedia
From $676 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 $676 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 $687 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 Magnificent Landscape Oasis , That Begins ...
From $687 per night (USD)
VRBO
$Tropical Sunrises from your bed at Oceanfront Paradise 2\/2 with Private Beach$
From $384 per night (USD)
Expedia
Tropical Sunrises from your bed at Oceanfront Paradise 2\/2 with Private Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy our recently renovated Deluxe 2/2 right on the ocean, offering spectacular views of the purple and aquamarine wate ...
From $384 per night (USD)
Expedia
Click For Pricing
VRBO
Gorgeous, Breath-taking Sunsets!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Located on the only cut in Key Largo that connects the bay to the ocean. Great fishing and scuba diving Dive shops and w ...
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VRBO
From $472 per night (USD)
Expedia
Canal-front home with private pool, dock, grill, & balcony - dog-friendly
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Canalside Cabana Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $472 per night (USD)
Expedia
From $1232 per night (USD)
VRBO
Palms Resort at Sugarloaf Beach - Guest House
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
One of a kind beach house with a private sandy beach, dock and boat dockage . Featuring a tropical ambiance and a famil ...
From $1232 per night (USD)
VRBO
From $354 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 $354 per night (USD)
Expedia
From $302 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 $302 per night (USD)
VRBO
$Salt Pond Hideaway | Cute Condo w\/ Pool, Hot Tub$
From $240 per night (USD)
Expedia
Salt Pond Hideaway | Cute Condo w\/ Pool, Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: - Recently updated this spacious, airy rental is the perfect location for your next Key West getaway! - If you ...
From $240 per night (USD)
Expedia
From $883 per night (USD)
VRBO
Snorkel Shack on Sombrero 4 bedrooms 3 baths with pool and 100 Ft of Dockage
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Vaca-21-495 This home is located landside of Sombrero Light. If you take your boat or rent a boat it is a Lighthouse l ...
From $883 per night (USD)
VRBO
From $492 per night (USD)
Expedia
ANOTHER DAY IN PARADISE 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 $492 per night (USD)
Expedia
From $649 per night (USD)
VRBO
513 Mariners Club Key Largo | 3 Bed, 2.5 Bath
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Infinite horizons...from this ground floor, luxury, three-bedroom, two and one-half-bath villa! A peaceful, relaxing ge ...
From $649 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 ...
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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 $1502 per night (USD)
Expedia
A SUNSET BREEZE Beautiful private home with pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy a beautiful private home located in the Historic Truman Gated Community Old Town Key West. Only steps away from Du ...
From $1502 per night (USD)
Expedia
From $450 per night (USD)
VRBO
A SUNSET POOLSIDE in the Truman Annex
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This amazing FIRST FLOOR end unit features two bedrooms and TWO ensuite bathrooms with walk in showers. Each bedroom has ...
From $450 per night (USD)
VRBO
From $588 per night (USD)
Expedia
ARCHIPELAGO ll at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
This newer renovation is a gorgeous 2 bedroom, 2.5 bath townhouse. The kitchen and baths are new and living room, dining ...
From $588 per night (USD)
Expedia
From $279 per night (USD)
VRBO
ALHAMBRA at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $279 per night (USD)
VRBO
From $508 per night (USD)
Expedia
SAILOR'S STORY at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $508 per night (USD)
Expedia
From $441 per night (USD)
VRBO
The Republic- 4 BR KCB Pool Beauty- KCB#19
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
4BR Pool Key Colony Beach Tiki Pool Home with a PRIVATE upstairs & PRIVATE downstairs, two separate living areas. Both l ...
From $441 per night (USD)
VRBO
From $392 per night (USD)
Expedia
AQUA OASIS 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 $392 per night (USD)
Expedia
From $448 per night (USD)
VRBO
CONCH ISLAND 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 $448 per night (USD)
VRBO
$*Casa-Amelia-Key-West* 1\/2 block off Duval Street$
From $587 per night (USD)
Expedia
*Casa-Amelia-Key-West* 1\/2 block off Duval Street
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your home away from home! Casa Amelia is a charming Conch house in the historic Gato Cigar Village. Wake up ...
From $587 per night (USD)
Expedia
From $783 per night (USD)
VRBO
412 Mariners Club Key Largo | 3 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
No need to search further for your perfect vacation home-away-from-home! This sought-after, 3-story corner townhouse is ...
From $783 per night (USD)
VRBO
$Spacious, waterfront condo w\/ a full kitchen, shared pool, & furnished balcony$
From $654 per night (USD)
Expedia
Spacious, waterfront condo w\/ a full kitchen, shared pool, & furnished balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunset at Harbour Place Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $654 per night (USD)
Expedia
From $209 per night (USD)
VRBO
The Marguerite, 603 #3 Elizabeth Street, Old Town Key West monthly Rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
One bedroom, One Bathroom apartment in Old Key West. It is located upstairs with an outside entrance and has dormer ceil ...
From $209 per night (USD)
VRBO
From $1328 per night (USD)
Expedia
Commodore's Cove | Epic Location!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Summary: Commodore's Cove offers the best of Key West: a prime location and all the amenities of home. Up to 12 can stay ...
From $1328 per night (USD)
Expedia
From $2738 per night (USD)
VRBO
Commodore's Compound| HUGE Home!
Bedrooms:
7
Bathrooms:
10
Sleeps:
24
Summary: Welcome to Commodore's Compound, an incredible 8 bed, 7 bath home in prime location situated just one short blo ...
From $2738 per night (USD)
VRBO
From $1458 per night (USD)
Expedia
Seaport Suite | 2nd Story Hideaway!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Summary: Situated in the heart of Old Town Key West, Seaport Suite is the perfect vacation spot for large groups of up t ...
From $1458 per night (USD)
Expedia
From $486 per night (USD)
VRBO
SEASCAPE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $486 per night (USD)
VRBO
From $995 per night (USD)
Expedia
Conch Cove | Heated Pool & Prime Location!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: Conch Cove is a true Key West oasis! Nestled away off of Simonton St, this 3 bed 3 bath home sits just 1 short ...
From $995 per night (USD)
Expedia
From $421 per night (USD)
VRBO
TROPICAL VINEYARD at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $421 per night (USD)
VRBO
From $466 per night (USD)
Expedia
Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Ocean views from living room and master bedroom!! Get your inspiration every morning, directly on the sea from one of t ...
From $466 per night (USD)
Expedia
From $439 per night (USD)
VRBO
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Ocean views from living room and master bedroom!! Get your inspiration every morning, directly on the sea from one of t ...
From $439 per night (USD)
VRBO
$Luxurious Top Floor 2 Bedroom Suite w\/ Unobstructed Ocean Views$
From $319 per night (USD)
Expedia
Luxurious Top Floor 2 Bedroom Suite w\/ Unobstructed Ocean Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
With thoughtful and creative touches, both inside and out, mixed with a keen attention to the smallest of details, this ...
From $319 per night (USD)
Expedia
$Waterfront home w\/ private pool & dock Spectacular views from patio$
From $483 per night (USD)
VRBO
Waterfront home w\/ private pool & dock Spectacular views from patio
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Sombrero Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $483 per night (USD)
VRBO
From $464 per night (USD)
Expedia
Waterfront home with spectacular view, pool, dock, & patio - walk to beach
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Sombrero Siesta Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $464 per night (USD)
Expedia
From $513 per night (USD)
VRBO
🌸Home (#4) ”A WAVE💦 FROM IT ALL” (Partial Ocean View -approximately 150 ft from beach entrance)🌸
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
#4: A WAVE💦 FROM IT ALL (Partial Ocean View Property-approximately 150 ft from beach entrance)🌸 Totally Private😉- Tur ...
From $513 per night (USD)
VRBO
From $404 per night (USD)
VRBO
Boater's Paradise
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
This incredible property in Islamorada is the ultimate getaway, offering a spacious and flexible layout with 9 beds—per ...
From $404 per night (USD)
VRBO
From $1071 per night (USD)
VRBO
311 Mariners Club Key Largo | 4 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
If this villa has come up in your search for that ‘special’ vacation accommodation…you can stop right now. Villa 311 Mar ...
From $1071 per night (USD)
VRBO
From $298 per night (USD)
Expedia
Incredible Views from Ocean Lovers Suite [Ocean Pointe 5413]
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
SEAS THE DAY - OR JUST RELAX - YOU'RE ON ISLAND TIME Classic coastal décor greets you in this one bedroom, one bathroom ...
From $298 per night (USD)
Expedia
From $342 per night (USD)
VRBO
Peachy Keen: October, November, December Specials!
Bedrooms:
4
Bathrooms:
4
Sleeps:
7
This beautiful home has 3 bedrooms and 3 baths in the main house with a bonus cabana. There is a private and heated po ...
From $342 per night (USD)
VRBO
$UNIQUE AND BEAUTIFUL \BONNE-VIE at SEA\<br>$
From $151 per night (USD)
Expedia
UNIQUE AND BEAUTIFUL \"BONNE-VIE at SEA\"<br>
Bedrooms:
1
Bathrooms:
3
Sleeps:
2
Hi there and welcome to our Bonnie -vie! She's anchored about 3/4 mi from the base marina in a beautiful cove. The BOAT ...
From $151 per night (USD)
Expedia
From $342 per night (USD)
VRBO
SPECTACULAR OCEAN VIEWS FROM THIS MODERN BEACH CONDO
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Our property is located on 38 acres surrounded by nature and the ocean. The property is gated with 24 hour security. En ...
From $342 per night (USD)
VRBO
From $375 per night (USD)
Expedia
One Of A Kind Ocean Front With Boat Slip
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This one of a kind ocean front property offers much more than just the view. With 3 bedrooms and 2 bathrooms this 1800 s ...
From $375 per night (USD)
Expedia
From $335 per night (USD)
VRBO
Relax & Recharge at our Quiescent 2 BR Condo with Stunning Ocean Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Delight in a quiet escape, with open ocean views, from our two bedroom condo located in the 3rd building at Ocean Pointe ...
From $335 per night (USD)
VRBO
From $848 per night (USD)
Expedia
Blue Moonshine upgrades throughout modern finishes, close to Smathers Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Great top floor 2 bedroom Condo on the Atlantic ocean with views of the ocean and courtyard. The property has a full siz ...
From $848 per night (USD)
Expedia
From $418 per night (USD)
VRBO
RESERVE QUICKLY! YOU’LL LOVE IT! EVERYONE DOES!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Huge terrace- accessible from every room! Spacious and clean. Peaceful and away from the highway, yet near everything! S ...
From $418 per night (USD)
VRBO
From $1040 per night (USD)
Expedia
Fishermen`s Paradise | Waterfront home with huge pool, 220-foot dock & gorgeous interior
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to your perfect island retreat! This freshly remodeled three-bedroom, four-bathroom vacation home on Big Pine of ...
From $1040 per night (USD)
Expedia
From $215 per night (USD)
VRBO
Sugarloaf Serenity | Spacious, pet-friendly waterfront retreat on Sugarloaf Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Great views of Sugarloaf Sound from this ground-level midcentury-era home that offers expansive sound frontage perfect f ...
From $215 per night (USD)
VRBO
From $3492 per night (USD)
Expedia
**GRAND KEY OASIS @ THE ANNEX** Magnificent Estate & Pool + 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! The vacation ...
From $3492 per night (USD)
Expedia
From $308 per night (USD)
VRBO
Amazing Pool & Canal Ground Level Home, Ocean access
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This is an amazing Ground level Pool and Canal home. With stunning concrete ground pool and Jacuzzi tub. Enjoy the eas ...
From $308 per night (USD)
VRBO
From $448 per night (USD)
Expedia
ADRIFT in Key West at the Truman Annex
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Stunning, Modern Nautical-themed 2 bedroom, 1 bathroom ground floor condo in the Truman Annex Shipyard Complex completel ...
From $448 per night (USD)
Expedia
$Cayman Cottage | 3 bed\/2 bath boating home on Ramrod Key$
From $244 per night (USD)
VRBO
Cayman Cottage | 3 bed\/2 bath boating home on Ramrod Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to Cayman Cottage, a charming three-bedroom, two-bathroom monthly vacation rental in Breezeswept Beach Estates on ...
From $244 per night (USD)
VRBO
From $223 per night (USD)
Expedia
El Paraiso | Canalfront getaway on Cudjoe Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to your charming canalfront retreat on Cudjoe Key! This adorable 3-bedroom, 3-bathroom vacation rental offers th ...
From $223 per night (USD)
Expedia
$Paradise Found | Pet-friendly 3 bed\/2 bath boating home on Cudjoe Key$
From $260 per night (USD)
VRBO
Paradise Found | Pet-friendly 3 bed\/2 bath boating home on Cudjoe Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Canalfront 3 bedroom/2 bathroom home with excellent oceanside boating access. Open floor plan with a large kitchen, stai ...
From $260 per night (USD)
VRBO
From $220 per night (USD)
Expedia
Blackbeard`s Hideaway | Cozy canalfront cottage is an angler's dream on Cudjoe Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Blackbeard's Hideaway, your perfect monthly vacation rental nestled in a quiet neighborhood on the oceanside ...
From $220 per night (USD)
Expedia
From $193 per night (USD)
VRBO
Cedar Cottage | Adorable canalfront cottage, lots of dockage on Big Pine Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Welcome to your perfect slice of paradise in the heart of the Florida Keys! This newly remodeled 2 bed/2 bath home on a ...
From $193 per night (USD)
VRBO
From $304 per night (USD)
Expedia
Foster`s Folly | Gorgeous canalfront pool home close to open water on Cudjoe Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to a slice of paradise on Cudjoe Key, where luxury meets tranquility in this stunning 3-bedroom, 2-bathroom stilt ...
From $304 per night (USD)
Expedia
$OPEN WATER PARADISE ☀️ 2\/2 HALF DUPLEX IN KEY COLONY BEACH (MARATHON, FL) (34)$
From $283 per night (USD)
VRBO
OPEN WATER PARADISE ☀️ 2\/2 HALF DUPLEX IN KEY COLONY BEACH (MARATHON, FL) (34)
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Remodeled! Half Duplex with walk thru layout! Under new ownership as of November 2020. MODERN / CLEAN / SPACIOUS *** ...
From $283 per night (USD)
VRBO
From $228 per night (USD)
Expedia
Luxurious Key West Pool Home block from Duval! Pool & Patio Recently Renovated!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Old Town refuge barely a block from world famous Duval Street with glimpse of Key West Light House! Located in the Histo ...
From $228 per night (USD)
Expedia
$3 BR\/ 2 BA, Canal Front Home, Private Dock for 40' Boat & 1 mi to Beach$
From $320 per night (USD)
VRBO
3 BR\/ 2 BA, Canal Front Home, Private Dock for 40' Boat & 1 mi to Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Kickin' Back Reel Time, Your Home Away from Home in Marathon, FL. This beautifully updated, canal front home ...
From $320 per night (USD)
VRBO
From $690 per night (USD)
Expedia
FOREVER YOUNG at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $690 per night (USD)
Expedia

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