Monroe Area Rentals
From $440 per night (USD)VRBO
W04 - Spacious 4 bed, 3 bath home in Sombrero with private pool
- 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 $440 per night (USD)VRBO
From $193 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 $193 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 $588 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 $588 per night (USD)Expedia
From $485 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 $485 per night (USD)VRBO
From $364 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 $364 per night (USD)Expedia
From $379 per night (USD)VRBO
Manatee Bay , Pool table, Pool, Kayaks, Jacuzzi not working.
- 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 $379 per night (USD)VRBO
From $232 per night (USD)Expedia
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 $232 per night (USD)Expedia
From $702 per night (USD)VRBO
Welcome to A Taste of Vitamin Sea – Your Key Colony Beach Escape!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to A Taste of Vitamin Sea – Your Key Colony Beach Escape! Discover the best of the Florida Keys at this spacio ...
From $702 per night (USD)VRBO
From $1204 per night (USD)Expedia
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 $1204 per night (USD)Expedia
From $305 per night (USD)VRBO
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 $305 per night (USD)VRBO
From $1952 per night (USD)Expedia
~DREAMING ON DUVAL~ 5 bedroom, 4.5 bath home with private pool and 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 $1952 per night (USD)Expedia
From $707 per night (USD)VRBO
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 $707 per night (USD)VRBO
From $652 per night (USD)Expedia
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 $652 per night (USD)Expedia
From $217 per night (USD)VRBO
Island Time | Ocean Pointe 1207 | Oceanfront 2BR Condo in Key Largo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to Island Time — a 2-bedroom oceanfront condo at Ocean Pointe Resort in Tavernier, the heart of Key La ...
From $217 per night (USD)VRBO
From $402 per night (USD)Expedia
Spectacular Open-Water Sunset Views w/Boat Slip & Trailer Parking. Pet Friendly!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Our 2-bedroom Vacation Rental is newly renovated with an awe-inspiring view of Florida Bay. The Vacation Rental includes ...
From $402 per night (USD)Expedia
From $772 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 KW people’s choice awards as a FINALIST for Best Vacation ...
From $772 per night (USD)VRBO
From $208 per night (USD)Expedia
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 $208 per night (USD)Expedia
From $438 per night (USD)VRBO
**SET SAIL @ COCONUT MALLORY** Condo + Last Key White Glove Service...
- 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 $438 per night (USD)VRBO
From $1134 per night (USD)Expedia
Sun of a Beach – Waterfront 7BR Home with Pool, Spa & Dock Minutes from Sombrero Beach
- 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 $1134 per night (USD)Expedia
From $213 per night (USD)VRBO
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 $213 per night (USD)VRBO
From $515 per night (USD)VRBO
Prime Waterfront! Steps to Duval & Sunset Pier! 2BR with Pool & Tiki Bar at 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 $515 per night (USD)VRBO
From $367 per night (USD)VRBO
610 Mariners Club - 1 bedroom island style ground floor apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sweet studio apartment in the coveted Mariners Club on the island of Key Largo. This is a duplex-style, ground-floor ...
From $367 per night (USD)VRBO
From $391 per night (USD)Expedia
Shady Palms | Historic Charm Private Pool & Effortless Island Style 2BD/2.5BA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Shady Palms, a polished private retreat where historic Key West character meets relaxed island luxury. Though ...
From $391 per night (USD)Expedia
From $321 per night (USD)VRBO
Doc's Holiday updated 2bed/2bath half duplex with Cabana Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This half duplex in Key Colony Beach is situated on the East side of the island, just a short stroll away from the Caban ...
From $321 per night (USD)VRBO
From $326 per night (USD)Expedia
Stay and Play, Enjoy Scenic Views at Ocean Pointe 5312
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Enjoy coastal comfort at our oceanfront property nestled on 60 lush acres, part of a protected mangrove forest ...
From $326 per night (USD)Expedia
From $480 per night (USD)VRBO
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 $480 per night (USD)VRBO
From $219 per night (USD)Expedia
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 $219 per night (USD)Expedia
From $266 per night (USD)VRBO
It's a Salt Life After All at the Golf Club in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This 2 bedroom 2 bath town-home is just what you are looking for. The amenities include two community pools, a gym, and ...
From $266 per night (USD)VRBO
From $242 per night (USD)Expedia
Quiet Lane in the Heart of Old Town, Sleeps 4, Dog Friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our Key West retreat — a home we cherish and live in part of the year, now open for guests who appreciate com ...
From $242 per night (USD)Expedia
From $340 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 $340 per night (USD)VRBO
From $383 per night (USD)Expedia
Key Largo Oceanfront Escape: Pools, Beach, Fishing Pier, No Steps ! 🏝️
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Everything You Need to Stay, Play, and Relax...🏝️ Experience our lovely Modern Oasis Condo in Key Largo’s Premier Ocea ...
From $383 per night (USD)Expedia
From $546 per night (USD)VRBO
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 $546 per night (USD)VRBO
From $535 per night (USD)Expedia
Beautiful Waterfront Large Private Gulfside Home Family Friendly.
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
This property is like having your own private resort. On the Gulfside. Million-dollar waterfront views & sunsets. Next t ...
From $535 per night (USD)Expedia
From $413 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 $413 per night (USD)VRBO
Click For PricingExpedia
Tropical Jewel - Stay Where The Vacation Never Ends- 2BD/2Bath - Private Pool
- 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 city ...
Click For PricingExpedia
From $535 per night (USD)VRBO
Indigo Reef #34 | Waterfront + Boat Slip +Sunset
- 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 $535 per night (USD)VRBO
From $278 per night (USD)Expedia
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 $278 per night (USD)Expedia
From $302 per night (USD)VRBO
Lazy Tortuga ground level 2bed/2bath half duplex with dockage & cabana club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Lazy Tortuga is a luxurious ground-level half duplex offering the perfect blend of comfort and coastal charm. This beaut ...
From $302 per night (USD)VRBO
From $217 per night (USD)Expedia
COZY FAMILY HOME-POOL-SPA -5 minute drive to sombrero beach-private property
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Your Marathon Paradise! This beautiful home features 2 bedrooms, 2 bathrooms, and a spacious open-concept li ...
From $217 per night (USD)Expedia
From $410 per night (USD)VRBO
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 $410 per night (USD)VRBO
From $1072 per night (USD)Expedia
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 $1072 per night (USD)Expedia
From $238 per night (USD)VRBO
Another Day in Paradise Best Waterfront and Poolside Views.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy this stunning Moon Bay Luxury Condo located directly on the scenic Blackwater Sound near Florida Bay with a the be ...
From $238 per night (USD)VRBO
From $396 per night (USD)Expedia
**JASMINE JEWEL @ THE ANNEX** Lush Home & Pool + Last Key White Glove Service...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Hidden amongs ...
From $396 per night (USD)Expedia
From $524 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. Ask for availabil ...
From $524 per night (USD)VRBO
From $538 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 $538 per night (USD)Expedia
From $482 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 $482 per night (USD)VRBO
From $404 per night (USD)Expedia
Charming Half Duplex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Charming Half Duplex offering 2 bedrooms 2 bathrooms. The home is on a quiet street in a residential neighborhood on a c ...
From $404 per night (USD)Expedia
From $1335 per night (USD)VRBO
Sky Suites Retreat - Balcony Overlooking 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 get ...
From $1335 per night (USD)VRBO
From $550 per night (USD)Expedia
Pristine Islamorada Pool Home with Ocean View and Dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Summary: Welcome to Angler’s Reef 148 - a stunning Islamorada vacation destination. This two bedroom, two and a half ba ...
From $550 per night (USD)Expedia
From $406 per night (USD)VRBO
Escape the cold, dreary winter days and head to tropical weather and waters!
- 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 $406 per night (USD)VRBO
From $344 per night (USD)Expedia
Amazing Ocean view condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Newly Renovated Beach Décor unit! Breathtaking views of the Atlantic ocean and protected Florida Keys mangroves. Heated ...
From $344 per night (USD)Expedia
From $409 per night (USD)VRBO
The Tortuga at Sunrise Suites - Balcony & Pool
- 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 1 ...
From $409 per night (USD)VRBO
From $479 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 $479 per night (USD)Expedia
From $516 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 $516 per night (USD)VRBO
From $513 per night (USD)Expedia
Ocean view house
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
ocean front, Beautiful island views and sunrise 🌅 view in the morning, had access for the boat , kayaking, paddle ...
From $513 per night (USD)Expedia
From $445 per night (USD)VRBO
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 $445 per night (USD)VRBO
From $595 per night (USD)Expedia
Gorgeous Waterfront 3 Bedroom Coral Lagoon Villa, Sleeps 8, with 40' Boat Slip!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
ALL CANAL BOAT SLIP CONSTRUCTION IS NOW COMPLETE & CORAL LAGOON RESORT IS BETTER THAN EVER! Thank you for your interest ...
From $595 per night (USD)Expedia
From $478 per night (USD)VRBO
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 $478 per night (USD)VRBO
From $442 per night (USD)Expedia
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 $442 per night (USD)Expedia
From $500 per night (USD)VRBO
Manatee Watch | 5 bedrooms, pool, ocean access
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Summary: Gorgeous pool, big dock & easy ocean access from this 5 bed/4 bath home on Big Pine Key The Space: Discove ...
From $500 per night (USD)VRBO
From $245 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 $245 per night (USD)Expedia
From $314 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 $314 per night (USD)VRBO
From $664 per night (USD)Expedia
Beautiful Coral Lagoon #12 - Waterfront - With 40' Boat Slip right out back!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
ALL CANAL BOAT SLIP CONSTRUCTION IS NOW COMPLETE & CORAL LAGOON RESORT IS BETTER THAN EVER! NEWLY RENOVATED AND...… GOR ...
From $664 per night (USD)Expedia
From $549 per night (USD)VRBO
Spectacular Water Front Home! Key Largo, Ocean side, Sea Breeze
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Breathtaking concrete home with 2,200SF A/C and 6,900SF lot, freshly remodeled with elegance having large impact windows ...
From $549 per night (USD)VRBO
From $626 per night (USD)Expedia
Aqua Lodge Houseboat \"The Grey Lady\"
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
This houseboat has 2 Queen beds, 1 Double bed and 1 Twin bed. The houseboat has a flat-screen TV with cable in the livin ...
From $626 per night (USD)Expedia
From $596 per night (USD)VRBO
The Dancing Rooster: 2 Blocks from Duval in Old Town.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located just 2 short blocks from Duval and in the center of downtown, the Southernmost Retreat is a recently renovated a ...
From $596 per night (USD)VRBO
From $257 per night (USD)Expedia
Cudjoe Bay Getaway In Paradise
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our house in paradise! This elevated canal house is the fourth property away from Cudjoe Bay and the Atlantic ...
From $257 per night (USD)Expedia
From $602 per night (USD)VRBO
Aqua Lodge Houseboat \"Calypso\"
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
It doesn’t get much more unique than the Aqua Villas at Mangrove Marina. Come experience the adventure of living on the ...
From $602 per night (USD)VRBO
From $546 per night (USD)Expedia
Aqua Lodge Houseboat \"Captain's Quarters\"
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Aqua Villas at Mangrove Marina Resorts “Captain’s Quarters” houseboat, located between Key Largo and Isla ...
From $546 per night (USD)Expedia
From $212 per night (USD)VRBO
Tarpon Tales | Fantastic boating, pet-friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Boater’s Dream: Double Dockage, Quick Channel Access, Fenced Yard The Space: Welcome to your ideal Florida ...
From $212 per night (USD)VRBO
From $269 per night (USD)VRBO
Casa Playa | 4 bed/2 bath canalfront getaway
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 4 bed/2 bath canalfront getaway on Ramrod Key The Space: Welcome to Casa Playa, your spacious 4-bedroom, 2 ...
From $269 per night (USD)VRBO
From $406 per night (USD)VRBO
Key West Beach House with heated pool, tiki, and dock.♿︎
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Key West. Located on this beautiful island 13 miles from downtown is this quaint 2-level beach home. With sle ...
From $406 per night (USD)VRBO
From $471 per night (USD)Expedia
Aqua Lodge Houseboat \"Yellow Tail \"
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Are you ready to be adventurous , do something unique and fun? Well, it doesn’t get Yellow Tail houseboat, is a 1 bedro ...
From $471 per night (USD)Expedia
From $765 per night (USD)VRBO
KEY LARGO BRAND NEW HOUSE WITH POOL & DOCKAGE
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to paradise! This home is a new listing to VRBO. If you are looking for a large beautiful home with a pool in a ...
From $765 per night (USD)VRBO
From $548 per night (USD)Expedia
**SEAPORT SENSATION @ OLD TOWN** Condo & Pool + Last Key White Glove Service...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! It is not so ...
From $548 per night (USD)Expedia
From $602 per night (USD)VRBO
**COASTAL LOVING @ OLD TOWN** 4BR Home & Pool + Last Key White Glove Service...
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! If you’re loo ...
From $602 per night (USD)VRBO
From $449 per night (USD)Expedia
Flirty Flamingo Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Flirty Flamingo is luxurious and in a prime Key West location. Built in 1998 and meticulously cared for this spacious 3 ...
From $449 per night (USD)Expedia
From $546 per night (USD)VRBO
Waterfront luxury Villa (29) 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 $546 per night (USD)VRBO
From $343 per night (USD)Expedia
Key Largo Treasure – End-Unit w/ Pools, Lagoon, Marina & Ocean Views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Key Largo Treasure, your tropical retreat in the heart of the Upper Florida Keys. This charming, two-bedroom, ...
From $343 per night (USD)Expedia
From $642 per night (USD)VRBO
Key Largo Villa, Kawama P6, 3/3
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful Kawama Townhouse...Relax with the whole family at this peaceful place to stay. This fully renovated town ho ...
From $642 per night (USD)VRBO
From $789 per night (USD)Expedia
406 Mariners Club - 3 bedroom elegant tri-level townhome with views of the ocean
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to this elegant island townhome in Mariner's Club, Key Largo's premier resort. Updated and upgraded! This is a ...
From $789 per night (USD)Expedia
From $754 per night (USD)VRBO
411 Mariners Club - This 4-bedroom tri-level townhouse is perfect for couples, family & friends
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Spend tranquil days on the sun-kissed balcony with ocean views! Cool down with a plunge in the pool, then make plans to ...
From $754 per night (USD)VRBO
From $275 per night (USD)Expedia
Paradise for Rent (Condo and Private Boat Slip) monthly discount for sept & oct
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
We are happy to answer all questions! Tropical settings, beautiful sunset views, do as much as you want to do. Just lay ...
From $275 per night (USD)Expedia
From $596 per night (USD)VRBO
Henry's Piece of Paradise on the Ocean in Key West - Weekly / Nightly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Thirteen-hundred-fifty square feet of fabulous living space located on the second floor with garden and partial ocean vi ...
From $596 per night (USD)VRBO
From $860 per night (USD)Expedia
131 Mariners Club - Breathtaking harbor and ocean view! Room for the whole family
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Framed by stunning ocean views, this residence has been recently refreshed with elegant new paint, appliances, furnishin ...
From $860 per night (USD)Expedia
From $284 per night (USD)VRBO
Deep Water Canal, Swim Spa Pool, Kayaks, Walk to Ocean Front Bars & Restaurants!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
**If you’re looking for larger accommodations, please view our home on the same canal, VRBO # 2413494** Enjoy total pri ...
From $284 per night (USD)VRBO
From $389 per night (USD)VRBO
Summer Month's Just Opened Up!!! Canal Front Pool Home in Summerland Key
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Atlantic Chateau, is a beautiful 3 bedroom 2 bath house on Cruikshank Island. Cruikshank Island is a peaceful private is ...
From $389 per night (USD)VRBO
From $420 per night (USD)VRBO
A Cut Above - 5 Star property that lives up to its name
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome TO “A Cut Above”- A 5 Star Property That Lives UP TO Its Name! **** Check Out Our Updated Rates!! **** ...
From $420 per night (USD)VRBO
From $408 per night (USD)Expedia
2 Bedroom 1 Bath Condo at Bayfront Suites & Marina - CLEANING FEE INCLUDED
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $408 per night (USD)Expedia
From $750 per night (USD)VRBO
Waterfront 4 Bed, 4-Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $750 per night (USD)VRBO
From $443 per night (USD)Expedia
~HORSE CONCH~ Amazing location with shared pool and covered balcony!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
THE PROPERTY: Enjoy your stay in the tropics at Horse Conch, part of the highly touted "Queen Conch" complex, which incl ...
From $443 per night (USD)Expedia
From $690 per night (USD)VRBO
AUGUST Opening, Fishermen, Couples, Families, Pool, Cabana Club
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to our beautiful 4bdrm/ 3 full bath waterfront home. Relax and relish the tropical waters that surround you in p ...
From $690 per night (USD)VRBO
From $730 per night (USD)Expedia
Waterfront 4-Bed 3-Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $730 per night (USD)Expedia
Click For PricingVRBO
Exquisite Key Colony Beach Retreat- 420/430 11th Street KCB
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Have you been dreaming of a sun-soaked Florida Keys getaway with ample space for your whole family? Turn those dreams in ...
Click For PricingVRBO
From $282 per night (USD)Expedia
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cottage #13 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. SpaciouQuaint, clean, co ...
From $282 per night (USD)Expedia
From $867 per night (USD)VRBO
Waterfront home in the heart of the fishing capital of the world.
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 14
Forget your worries in this private water front home. This private two family home is ideal of large fishing groups and ...
From $867 per night (USD)VRBO
From $1429 per night (USD)Expedia
Beach House, Waterfront, Sombrero Beach, Florida Keys Rental, Private Pool, Dock
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
New Listing - Family Reunion Large Vacation Rental 6 bedrooms 5 baths steps to Sombrero Beach. 6 bedrooms (5 King size b ...
From $1429 per night (USD)Expedia
From $784 per night (USD)VRBO
Paradise Without A Passport New Home Ocean Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Brand New Home, Brand New Furniture, Sunset and Ocean Views, Outdoor communal Fire Pits, Outdoor Kitchen, Grill, Possibl ...
From $784 per night (USD)VRBO
From $674 per night (USD)Expedia
3-Bedroom 3-Bath Condo at Bayfront Suites & Marina - CLEANING FEE INCLUDED
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $674 per night (USD)Expedia