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 $305 per night (USD)
VRBO
Sumptuous Home with Private Pool, Central AC, WiFi, and Private Washer/Dryer
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Flagler Station Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $305 per night (USD)
VRBO
From $334 per night (USD)
Expedia
W04 - 209 Sombrero Beach Rd.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Newer built canal front townhouse in the Anglers area of the Sombrero Beach neighborhood. This home features a private h ...
From $334 per night (USD)
Expedia
From $559 per night (USD)
VRBO
Keys Cottage with Beach and Dockage! Bayfront Property!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
"Deckhouse" is the perfect beachy cottage for your Keys vacation! It has a full-size kitchen with granite countertops an ...
From $559 per night (USD)
VRBO
From $205 per night (USD)
Expedia
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
water front home is located on 100 foot wide canal with your own 30 feet of Free dockage. We are pet friendly. Furnished ...
From $205 per night (USD)
Expedia
From $430 per night (USD)
VRBO
Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
We are moving to a monthly rental model and passing on the savings to you. Here in Key West we believe in One Human Fam ...
From $430 per night (USD)
VRBO
From $399 per night (USD)
Expedia
Waterfront Cottage - Beach and Dockage! Open Water Views!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
In a world of chain hotels and paved over paradise, experience the Florida Keys the way they used to be! Sitting on a pr ...
From $399 per night (USD)
Expedia
$\Your own private resort\ - Mockingbird Pointe - Waterfront, pool and dockage$
From $478 per night (USD)
VRBO
\"Your own private resort\" - Mockingbird Pointe - Waterfront, pool and dockage
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Mockingbird Pointe is a quiet secluded 1/2 acre tropical waterfront paradise in the heart of the Florida Keys with priva ...
From $478 per night (USD)
VRBO
From $427 per night (USD)
Expedia
Nader Vacation Rental
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
We have our 3 bedroom 2 bathroom home in Little Torch Key available for anyone looking to take a vacation in the lower ...
From $427 per night (USD)
Expedia
From $272 per night (USD)
VRBO
P64 - Spacious 3 bedroom duplex in Key Colony with dockage and Cabana Club...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Beautiful duplex home in Key Colony Beach. Key Colony Beach is a small, friendly, walkable island with easy access to lo ...
From $272 per night (USD)
VRBO
From $282 per night (USD)
Expedia
Manatee Bay , Pool table, Jacuzzi, Pool, Kayaks, REDUCED RATES AVAIL NOW<br>
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
The Manatee Bay has the best of all worlds. It has a large custom fiberglass pool situated next to a 20 ft+ deep and bea ...
From $282 per night (USD)
Expedia
From $279 per night (USD)
VRBO
Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Lobstering paradise is just 2 houses down from open water on a deep 60 foot wide canal, gorgeous open water views, ...
From $279 per night (USD)
VRBO
From $654 per night (USD)
Expedia
A Taste of Vitamin Sea
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
STR21-000361Welcome to A Taste of Vitamin Sea Your Key Colony Beach Escape! Discover the best of the Florida Keys at th ...
From $654 per night (USD)
Expedia
From $1129 per night (USD)
VRBO
Elegant Home with Beach & Dockage! Spectacular Sunsets!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
This elegant home is located on a beautiful 2.5 acre gated beachfront estate with amazing views of our beautiful island ...
From $1129 per night (USD)
VRBO
From $435 per night (USD)
Expedia
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This wonderful 2 bedroom downstairs unit is owner's second home and has just been beautifully and professionally decorat ...
From $435 per night (USD)
Expedia
From $2234 per night (USD)
VRBO
~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
THE PROPERTY: Dreams do come true in Key West! As you enter the front gate of this luxury property, you arrive in a priv ...
From $2234 per night (USD)
VRBO
From $605 per night (USD)
Expedia
Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Spectacular ocean views from this condo located on the top floor with 1350 sq ft of fabulous living space and a 45 ft pr ...
From $605 per night (USD)
Expedia
From $667 per night (USD)
VRBO
**OLD TOWN OASIS @ THE ANNEX** Oceanside 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! OLD TOWN OASI ...
From $667 per night (USD)
VRBO
From $477 per night (USD)
Expedia
Waterfront home with dock, pool table & private pool - walk to Sombrero Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Anchor House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $477 per night (USD)
Expedia
From $586 per night (USD)
VRBO
Luxury 3BR/3BA Cottage with the Best Sunset Views in the Florida Keys!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Professionally decorated, fully renovated Cottage with 3 Bedrooms & 3 Bathroom Cottage located in the Village at Hawks ...
From $586 per night (USD)
VRBO
From $313 per night (USD)
Expedia
Luxurious 2BR Beachfront Condo | Steps to Pool & Ocean | Ocean Pointe Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Welcome to Island Time 🏝️—your beachfront escape in beautiful Key Largo. Wake up to gentle ocean breezes, step ...
From $313 per night (USD)
Expedia
From $318 per night (USD)
VRBO
Spectacular Open-Water Sunset Views w/Boat Slip & Trailer Parking. Pet Friendly!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This beautiful newly refreshed vacation rental is all about the view. It is upstairs with an unobstructed view of the Fl ...
From $318 per night (USD)
VRBO
From $311 per night (USD)
Expedia
Canal-front home remodeled for HGTV with private swimming pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
La Pirata Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $311 per night (USD)
Expedia
Click For Pricing
VRBO
Waterfront Duck Key Villa
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Come and enjoy Duck Key in the Florida Keys, known as America's Caribbean, a lush shangri-la with tropical vegetation an ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Vacation like a local
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Newly renovated 3 bedroom/ 2 bathroom + loft, corner canal lot. Fully equipped home. Plenty of room for boat and great ...
Click For Pricing
Expedia
From $665 per night (USD)
VRBO
TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
We are proud to announce- Castaway Island has been named for 2024’s KW people’s choice awards as a FINALIST for Best Va ...
From $665 per night (USD)
VRBO
From $350 per night (USD)
Expedia
COCONUT Adorable cottage in Old Town
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The 'Coconut' as it's so lovingly referred to is the perfect Pied A Terre for your vacation in the Florida Keys. Open l ...
From $350 per night (USD)
Expedia
From $217 per night (USD)
VRBO
Ocean Shores Home Key Largo
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Oceanside single family home in one of Key largo most desirable neighborhoods with waterview and private pool. Large lot ...
From $217 per night (USD)
VRBO
From $253 per night (USD)
Expedia
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cottage #11 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. Located on a compound wi ...
From $253 per night (USD)
Expedia
From $184 per night (USD)
VRBO
Snowbird-Friendly Home with Central AC, High-Speed WiFi, and Washer/Dryer
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
White Palm Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $184 per night (USD)
VRBO
From $434 per night (USD)
Expedia
**COASTLINE COMFORT @ COCONUT MALLORY** Condo + 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! When your vac ...
From $434 per night (USD)
Expedia
From $402 per night (USD)
VRBO
**SET SAIL @ COCONUT MALLORY** Condo + 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! SET SAIL cele ...
From $402 per night (USD)
VRBO
Click For Pricing
Expedia
Cozy studio cottage in Old Town Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cute Studio cottage with additional sleeping loft. Nicely landscaped shared pool and outside area. Walking distance to ...
Click For Pricing
Expedia
From $1139 per night (USD)
VRBO
Sun of a Beach in Marathon
Bedrooms:
5
Bathrooms:
7
Sleeps:
16
Indulge in the charm of this splendid split-level residence nestled in the heart of the captivating Florida Keys. This d ...
From $1139 per night (USD)
VRBO
From $270 per night (USD)
Expedia
Work remote, or not at all, in paradise at this cozy, beachy condo!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Flexible cancellation policy. Futura Yacht Club is an exclusive private, gated resort community. Not like a hotel, FYC ...
From $270 per night (USD)
Expedia
From $217 per night (USD)
VRBO
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cottage #15 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. Located on a compound wi ...
From $217 per night (USD)
VRBO
From $656 per night (USD)
Expedia
136 Mariners Club | 3 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This spectacular 2600 square foot villa boasts a blissful atmosphere and breathtaking view of the harbor and the Atlanti ...
From $656 per night (USD)
Expedia
From $650 per night (USD)
VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $650 per night (USD)
VRBO
From $225 per night (USD)
Expedia
Canal-front Keys escape with amazing view, boat access, firepit, gril, AC, & W/D
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Torchbearer - Lower Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $225 per night (USD)
Expedia
From $349 per night (USD)
VRBO
Waterfront escape with dock, furnished deck & patio, grill & central AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Dockside Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired d ...
From $349 per night (USD)
VRBO
From $305 per night (USD)
Expedia
Pristine Waterfront Charmer - Outdoor Living & Dining, Dock, AC - Snowbirds OK
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Tradewinds Treat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $305 per night (USD)
Expedia
From $574 per night (USD)
VRBO
Welcome to the Shady Palms - Private Pool - RealKeyWest
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Step into this beautifully restored and redecorated 1933 Key West home. This first-floor home has Bahama shutters throug ...
From $574 per night (USD)
VRBO
From $875 per night (USD)
Expedia
**ENVY OF THE ISLAND @ OLD TOWN** Pristine Home & Pool + LAST KEY SERVICES...
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! While Old Tow ...
From $875 per night (USD)
Expedia
From $301 per night (USD)
VRBO
Doc's Holiday in Key Colony Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This half dupex in Key Colony Beach is situated on the East side of the island, just a short stroll away from the Cabana ...
From $301 per night (USD)
VRBO
From $394 per night (USD)
Expedia
Oceanfront! Oceanfront! Oceanfront!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
License # 25-0123 - Completely Renovated - 2 Bedroom, 2 Bath, condominium unit. Just steps from the elevator on the 5th ...
From $394 per night (USD)
Expedia
From $325 per night (USD)
VRBO
Stay & Play; Enjoy Scenic Views Ocean Pointe 5312
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Upon entering the home you’ll be greeted by laidback island decor and vast ocean views. The Tommy Bahama Tiki inspired a ...
From $325 per night (USD)
VRBO
From $549 per night (USD)
Expedia
SOUTHERNMOST SWIM AND SOCIAL CLUB
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your Home Away from Home in Beautiful Key West Welcome to Southernmost Swim & Social Club — where you and your loved on ...
From $549 per night (USD)
Expedia
From $203 per night (USD)
VRBO
Enjoy a Fun in the Sun getaway 3 Bedroom House, Tiki Hut, Boat Ramp, & Dockage!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come relax in Florida Keys Paradise while you enjoy the comforts of a clean 3 bedroom house (not a mobile home). Central ...
From $203 per night (USD)
VRBO
From $365 per night (USD)
VRBO
Quiet Lane in the Heart of Old Town, Sleeps 4 + 🐶🐾
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Unbeatable location just 1 block from the iconic Green Parrot Bar and 2 blocks from world famous Duval Street. Blue Heav ...
From $365 per night (USD)
VRBO
From $234 per night (USD)
VRBO
Luxury cottage in the heart of paradise
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
WELCOME ABOARD TO ONE OF LARGER COTTAGES ON THE CAMPGROUND. Comfortable and spacious cottage in the center of KEY LARG ...
From $234 per night (USD)
VRBO
From $298 per night (USD)
Expedia
Oceanfront Community, Luxury,Beach,Pools, TOP AMENITIES & VALUE in FLORIDA KEYS
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Everything you need to Stay, Love, and Relax..... Our featured home is a modern, updated condo in Key Largo's Oceanside ...
From $298 per night (USD)
Expedia
$Blue Home - Receive 400 dollars \ntowards a BOAT RENTAL!$
From $464 per night (USD)
VRBO
Blue Home - Receive 400 dollars \ntowards a BOAT RENTAL!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Receive a $400 boat rental gift certificate from Nothing Better Boat Rentals, LLC. when you book a full week at one o ...
From $464 per night (USD)
VRBO
From $239 per night (USD)
Expedia
One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience Paradise at One of the Best Private Beaches! Let me assist you in finding the best and most affordable fligh ...
From $239 per night (USD)
Expedia
From $608 per night (USD)
VRBO
Waterfront luxury Villa (54) with sunset views and boat slip
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This spacious 3BD, 2.5BA Villa is the perfect blend of comfort and coastal charm. Each bedroom features its own televisi ...
From $608 per night (USD)
VRBO
From $608 per night (USD)
Expedia
Waterfront luxury Villa (43) with spectacular sunset views and boat slip
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This beautifully remodeled, spacious 3BD, 2.5BA Villa is the perfect blend of comfort and coastal charm. Each bedroom fe ...
From $608 per night (USD)
Expedia
From $784 per night (USD)
VRBO
ISLAND TIME - 5 Bed/3 Bath OldTown Complex - MONTHLY - Private pool
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
WELCOME TO ISLAND TIME! Key West Island Time is a rare find in old town Key West. It is a total of 5 bedrooms and three ...
From $784 per night (USD)
VRBO
From $585 per night (USD)
Expedia
Beautiful Waterfront Gulf of America Great location.
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
This property is like having your own private resort. On the Gulf of Mexico. Million-dollar waterfront views & sunsets. ...
From $585 per night (USD)
Expedia
Click For Pricing
VRBO
A great place to relax, fish, or even work from. 2/2 , 66 ft
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
2 Master suites with great screened in porch overlooking Bayside canal. 66 dock, fully furnished. Large family room with ...
Click For Pricing
VRBO
$White Home - Receive 400 dollars \ntowards a BOAT RENTAL!$
From $708 per night (USD)
VRBO
White Home - Receive 400 dollars \ntowards a BOAT RENTAL!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Receive a $400 boat rental gift certificate from Nothing Better Boat Rentals, LLC. when you book a full week at one o ...
From $708 per night (USD)
VRBO
From $587 per night (USD)
VRBO
TROPICAL PROPERTIES VACATION RENTAL - KEY WEST
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
****This property requires a minimum stay of 28 nights in the same calendar month**** ***Brand New Pool with waterfall, ...
From $587 per night (USD)
VRBO
$Yellow Home - Receive 400 dollars \ntowards a BOAT RENTAL!$
From $461 per night (USD)
VRBO
Yellow Home - Receive 400 dollars \ntowards a BOAT RENTAL!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Receive a $400 boat rental gift certificate from Nothing Better Boat Rentals, LLC. when you book a full week at one o ...
From $461 per night (USD)
VRBO
From $278 per night (USD)
VRBO
Tropical Jewel: Historic Seaport Oldtown - 2BR/2BA - Pool - RealKeyWest
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
WELCOME TO TROPICAL JEWEL! Near all the action of the historic seaport and Duval Street, you can get out into the cit ...
From $278 per night (USD)
VRBO
From $485 per night (USD)
Expedia
Waterfront luxury Villa (34) with sunset views and boat slip
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This spacious 3BD, 2.5BA Villa is the perfect blend of comfort and coastal charm. Each bedroom features its own televisi ...
From $485 per night (USD)
Expedia
From $229 per night (USD)
VRBO
Huge Oct savings! Sea-Esta! condo, Beach, Pool, Key Colony Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sea-Esta is located on the Atlantic Ocean with a private white sandy beach. If the ocean isn’t calling you, Sea-Esta by ...
From $229 per night (USD)
VRBO
From $290 per night (USD)
Expedia
Lazy Tortuga in Key Colony Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Lazy Tortuga is a ground level luxurious half duplex! This property features 2 bedrooms and 2 bathrooms. The master bedr ...
From $290 per night (USD)
Expedia
From $578 per night (USD)
VRBO
MAJESTIC PARADISE II Luxury living in Truman Annex. Downtown, pool, 2 blks
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Featured in The Key West Citizen Home of the Week. Perfect location, and newly renovated with fresh paint, new kitchen w ...
From $578 per night (USD)
VRBO
From $469 per night (USD)
Expedia
BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
2 POOLS, FAST FREE WIFI, SALTWATER SWIMMING LAGOON, 2 KIDS AND 2 JUNIOR KAYAKS, FREE DOUBLE GOLF CART, 2 FREE BICYCLES, ...
From $469 per night (USD)
Expedia
From $1116 per night (USD)
VRBO
Pirate Point, Luxe 5BR Escape w/ Pool, Tiki, & Dock Minutes from the Beach
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Welcome to Pirate Point – your private slice of paradise. Tucked away at the end of a peaceful canal street on lush, lan ...
From $1116 per night (USD)
VRBO
From $323 per night (USD)
Expedia
Sirena Key Cottage in Venture Out
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
VO365 Sirena Key Cottage 35' Seawall It's a wonderful time to enjoy Paradise! Quick ocean side access to gulf a ...
From $323 per night (USD)
Expedia
From $229 per night (USD)
VRBO
Another Day in Paradise Best Waterfront and Poolside Views.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Our Moon Bay Luxury Condominium unit # B403, 4th floor, is located directly on the scenic Blackwater Sound near Florida ...
From $229 per night (USD)
VRBO
From $1060 per night (USD)
Expedia
**JASMINE JEWEL @ THE ANNEX** Lush Private Home & 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! Hidden amongs ...
From $1060 per night (USD)
Expedia
From $548 per night (USD)
VRBO
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy the nicest Fully Renovated Villa on Duck Key. Boat slip available for additional $100 a night. Largest boat that ...
From $548 per night (USD)
VRBO
From $542 per night (USD)
Expedia
Kelly's Kabin - Adorable Private Summerland Key Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Kelly's Kabin is a recently renovated property freshly painted in tropical blues. It's a private home without neighbors ...
From $542 per night (USD)
Expedia
From $385 per night (USD)
VRBO
Paradise in Beautiful Key Largo!! Amazing Views!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Your dream vacation awaits you at Kawama Yacht Club! A unique gated townhome community located in the heart of Key Larg ...
From $385 per night (USD)
VRBO
From $277 per night (USD)
VRBO
Sugar Cane - Florida Keys tropical retreat. Newly renovated!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We have just completely renovated this condo at Ocean Pointe and it's Insta-worthy. Every detail has been designed and c ...
From $277 per night (USD)
VRBO
From $586 per night (USD)
VRBO
Absolutely Perfect! Reel Vacation Villa w/Pool, Dock, Close to Beach w/Extras!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This stunning home on the Intracoastal Waterway is loaded with amenities including a private pool and patio with boat do ...
From $586 per night (USD)
VRBO
Click For Pricing
Expedia
Cozy 2 Bedroom home in Summerland Key
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Our home is located in a quiet and cozy area 5 minutes away from the famous Ramrod Swim Hole; a local treasure. It is al ...
Click For Pricing
Expedia
From $731 per night (USD)
VRBO
ADMIRAL'S PARADISE in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Newly renovated town home located on a charming lane in the Truman Annex. The generous open floor plan features 10 foot ...
From $731 per night (USD)
VRBO
From $1591 per night (USD)
Expedia
Balcony - Sky Suites Retreat, on Duval
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Summary: This elegant, elevated 2nd story loft with vaulted ceilings has been designed for your next dream Key West geta ...
From $1591 per night (USD)
Expedia
From $496 per night (USD)
VRBO
Bright & Cheery Pool Front Home w/ Optional Boat Slip at Anglers Reef Islamorada
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Angler’s Reef Villas & Marina, a stunning Islamorada vacation destination. Quaint streets and walking paths w ...
From $496 per night (USD)
VRBO
From $393 per night (USD)
Expedia
50% OFF weekly fall rentals. Head to tropical weather and waters this fall!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Sea Salt Cottage is a spacious 3 bedroom 2 bath open concept home on a wide canal with direct access to the ocean. Gues ...
From $393 per night (USD)
Expedia
From $318 per night (USD)
VRBO
Modern-Coastal Spacious Suite [Ocean Pointe 3301]
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Come enjoy this 2 bedroom, 2 bath spacious end suite overlooking the Atlantic Ocean at Ocean Pointe Suites; an ideal des ...
From $318 per night (USD)
VRBO
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Expedia
Amazing Water Front Pool House & Dock in a very exclusive area!
Bedrooms:
3
Bathrooms:
4
Sleeps:
17
Spectacular home! find the perfect Vacation Rental, two homes in one, with two private entrances , escape to the Flori ...
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Expedia
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VRBO
Oceanfront Duck Key Townhouse - Sleeps 6
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Come and enjoy Duck Key in the Florida Keys, known as America's Caribbean, a lush shangri-la with tropical vegetation an ...
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VRBO
From $196 per night (USD)
Expedia
Amazing Ocean view condo
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Newly Renovated Beach Décor unit! Breathtaking views of the Atlantic ocean and protected Florida Keys mangroves. Heated ...
From $196 per night (USD)
Expedia
From $626 per night (USD)
VRBO
Pet Friendly, Pool, Private Balcony-Tortuga Suite
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Welcome to Sunrise Suites, a peaceful community on Key West's southeast side. Just 1 mile from the beach and 10 ...
From $626 per night (USD)
VRBO
From $556 per night (USD)
Expedia
TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Tortuga Hammock Townhouse Highlights: Location: Stock Island, within the gated Coral Hammock community, close to Key Wes ...
From $556 per night (USD)
Expedia
From $380 per night (USD)
VRBO
Waterfront Property - Marina Access - Spacious - Excellent Key West Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located just two miles from picturesque Smathers Beach, this well appointed two bedroom, two bath condo is ideally situa ...
From $380 per night (USD)
VRBO
From $667 per night (USD)
Expedia
★Beautiful Modern gated Vacation Oasis★ Private pool & patio close to activities
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Stay in a beautifully modern decorated comfortable gated house with private pool and patio, Carport, large 4K Smart TV ...
From $667 per night (USD)
Expedia
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VRBO
Beautiful Keys Getaway! Located on deep water canal for quick access to
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a 2 bedroom, 2 bathroom concrete block house. It is located on a clean swimming canal right off Pine Channel. ...
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VRBO
From $684 per night (USD)
Expedia
★Welcoming Family Vacation Gated home★with private heated pool and Patio
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy a great family vacation in this comfortable gated home offering a private pool and patio, 4K Smart TV's, high spee ...
From $684 per night (USD)
Expedia
From $861 per night (USD)
VRBO
Key West's Crown Jewel
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Key West's Crown Jewel is a penthouse condominium at 1800 Atlantic Condominium development with two-bedroom, two-bath wi ...
From $861 per night (USD)
VRBO
From $332 per night (USD)
Expedia
Ocean Front 2/2 Condo,OCEAN FRONT/MARINA VIEW,Tavernier/Key Largo Fl. Fla.Keys
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Paradise! Discover the pinnacle of luxury at Ocean Pointe, a premier resort nestled in Tavernier, Florida Key ...
From $332 per night (USD)
Expedia
From $575 per night (USD)
VRBO
Life in Paradise at #1 Rated Resort in Marathon - Coral Lagoon - Boat Slip Avail
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
** The Marina is repairing all of the canal boat slips currently BUT you can reserve a slip at the marina right there fo ...
From $575 per night (USD)
VRBO
From $520 per night (USD)
Expedia
Beautiful Updated Kawama Townhouse. Marina, boat ramp, lagoon and pools.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This gorgeous 3 bedroom 3 full bath townhouse is located in the tropical neighborhood of Kawama. This unit underwent a f ...
From $520 per night (USD)
Expedia
From $520 per night (USD)
VRBO
Beautiful updated Kawama Townhouse. Two units available. Second unit #1306961.
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
This gorgeous 3 bedroom 3 full bath townhouse is located in the tropical neighborhood of Kawama. This unit underwent a ...
From $520 per night (USD)
VRBO
From $629 per night (USD)
Expedia
Manatee Watch | Gorgeous pool, 5 bedrooms, easy ocean access on Big Pine Key
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Discover your dream waterfront getaway on Big Pine Key! This impeccably updated 5-bedroom, 4-bathroom boating home offer ...
From $629 per night (USD)
Expedia
From $268 per night (USD)
VRBO
P23 - New 3 bedroom 2 bath duplex with private pool and deep water dockage.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This all ground level home boasts ease of access inside and out, with an open floor plan and a large, fully equipped kit ...
From $268 per night (USD)
VRBO
From $201 per night (USD)
Expedia
Serene Sunsets Await - Tropical Island Getaway Without The Extensive Travel
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
BOAT SLIP Available for ALL Lobster Seasons..! January 2025 Updates: Unbelievable...! Word to describe the upgrades ...
From $201 per night (USD)
Expedia
From $318 per night (USD)
VRBO
Ground floor no stairs close to everything Atlantic side
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
A fisherman's dream boat dock freezers for your catch commercial icemaker fish cleaning station backyard grill fully s ...
From $318 per night (USD)
VRBO
From $839 per night (USD)
Expedia
Villa Jekjak | 4 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Enjoy the unobstructed 270-degree ocean view in this newly renovated beachfront residence. Located in the most exclusive ...
From $839 per night (USD)
Expedia

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