Monroe Area Rentals
From $286 per night (USD)VRBO
Keys Life at Ocean Pointe, Pool, Jacuzzi, Beach, Gated Resort, Baby Friendly !!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our Romeo & Juliet Suite with 2 Balconies, perfect for family fun and memory-making vacations. The master sui ...
From $286 per night (USD)VRBO
From $618 per night (USD)Expedia
Casa Calypso- Beautiful Tropical 3 KING Beds, 3 baths - 2 miles to beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This house is a 3 bedroom stand alone unit with 2 king bedrooms upstairs with balconies and own bathrooms and the bedroo ...
From $618 per night (USD)Expedia
From $276 per night (USD)VRBO
Ocean Jewel 1bed\/1bath updated condo with pool access, tiki bar & more!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
"Ocean Jewel" is a beautifully decorated one bedroom & one bath condo in a resort style setting with some resort ameniti ...
From $276 per night (USD)VRBO
Click For PricingExpedia
Beachfront Villa - Duck Key
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Beachfront Villa that has recently been renovated. The 2 bedroom 1.5 bath luxury villa is located in the popu ...
Click For PricingExpedia
From $176 per night (USD)VRBO
The Hideaway: Lose Yourself At This Recently Decorated Canal Front Home on Big Torch Key, Dockage!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $176 per night (USD)VRBO
From $550 per night (USD)Expedia
Sombrero Island Breeze 4BD Pool Paradise (M#9)
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Indulge in five-star waterfront luxury at this stunning 4BR, 3BA retreat in one of the Keys' most unique island communit ...
From $550 per night (USD)Expedia
From $358 per night (USD)VRBO
Duval Street Suites on Duval Free Parking and heated Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Cuban Club Suite is a one bedroom (queen) 1 bath suite with a queen murphy bed and kitchen. Overlooking Duval ...
From $358 per night (USD)VRBO
From $398 per night (USD)Expedia
Duval Street Suites full kitchen, free parking, & heated pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Key West Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. In historic O ...
From $398 per night (USD)Expedia
From $255 per night (USD)VRBO
Duval Street Suites full kitchen, free parking, heated pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Paradise Suite is a one bedroom (king bed) 1 bath suite with a murphy bed (queen) and kitchen. In historic Old ...
From $255 per night (USD)VRBO
From $239 per night (USD)Expedia
Duval Street Suites full kitchen and heated pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Little Palm Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. Overlookin ...
From $239 per night (USD)Expedia
From $279 per night (USD)VRBO
Duval Street Suites with full kitchen heated pool, free parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Mile Zero Suite is a one bedroom (queen) 1 bath suite with a sleeper sofa (king) and kitchen. Overlooking Duva ...
From $279 per night (USD)VRBO
From $1970 per night (USD)Expedia
6 BR 6 BA Guesthouse Suites on Duval free parking, private pool
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 24
Summary: This can accommodate 24 people, each apartment has 2 beds. You'll have privacy with 6 individual suites each eq ...
From $1970 per night (USD)Expedia
From $579 per night (USD)VRBO
P60 - 4 bedroom 4 bathroom home with pool and dockage. Amazing outside living...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This fabulous 4 bedroom, 4.5 bathroom home was designed and built for comfort and style! Guests love the different theme ...
From $579 per night (USD)VRBO
From $1045 per night (USD)Expedia
Great deal ! Private pool and dock. Five minute bike ride to Sombrero Beach.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This 3 bedroom and 3.5 bath house has everything you need in order to experience a relaxing and enjoyable vacation at S ...
From $1045 per night (USD)Expedia
From $1016 per night (USD)VRBO
ATLANTIS...Ocean Front Cottage Retreat!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need ...
From $1016 per night (USD)VRBO
From $160 per night (USD)Expedia
MONTHLY RENTAL, Old Town, Duplex, private yard, 2 BR\/2 BA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Sea Monkey and The Mermaid! Our home is a duplex located in Old Town and full of Key West charm. Both unit ...
From $160 per night (USD)Expedia
From $392 per night (USD)VRBO
Sunset Villas: Bayfront Beach Compound<br>**28 Night Min**
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
Sunset Villas is a boutique resort boasting 4 private villas on a Bayfront acre with one of the few swimmable sandy beac ...
From $392 per night (USD)VRBO
From $206 per night (USD)Expedia
Key Largo, Calusa Resort, 2 bedroom 1 bath with screened in patio
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Calusa resort is a gated community located in Key Largo. The resort rests on the peaceful edge of Buttonwood bay. Guests ...
From $206 per night (USD)Expedia
From $526 per night (USD)VRBO
Quiet canal-front 3\/3 Single-Family Home with Private Pool & Cabana Club Access
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Blue Heron House. Enjoy and relax in our ground-level 3 bedroom / 3 bathroom private, single-family home whi ...
From $526 per night (USD)VRBO
From $302 per night (USD)Expedia
Easy Ocean Access House 30' Dock & Pool at Cabana Club
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our Beach House in the prestigious Key Colony Beach. 30 FT dock house in a 90 FT canal with easy access to th ...
From $302 per night (USD)Expedia
From $549 per night (USD)VRBO
Amazing Views in Florida Keys Bayside BAY BREEZES, SUNSETS, SAILBOATS n SEAGULLS
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Make memories lasting a lifetime at Anchors Aweigh - experience Bay Breezes, Sunsets, Sailboats n Seagulls with this per ...
From $549 per night (USD)VRBO
From $403 per night (USD)Expedia
Tropical oasis near all the action with central AC & balcony
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Harbor Villa 7103 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $403 per night (USD)Expedia
From $539 per night (USD)VRBO
115 Mariners Club | 3 Bed, 2.5 Bath
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Key Largo’s coastal setting beckons from inside your marina-front villa as you enter through the front door with a spect ...
From $539 per night (USD)VRBO
From $649 per night (USD)Expedia
Parking & Near Duval - Poolside Suite
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Poolside Suite is the PERFECT vacation home for family and friends looking for a fun-filled getaway in the hear ...
From $649 per night (USD)Expedia
From $418 per night (USD)VRBO
Cozy Home!!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Newly renovated half duplex on a quiet street in Marathon. Conveniently located in the heart of Marathon, on a canal jus ...
From $418 per night (USD)VRBO
From $337 per night (USD)Expedia
AWAY FROM IT ALL @ The Truman Annex
- 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 $337 per night (USD)Expedia
From $566 per night (USD)VRBO
Coral Lagoon #13: Pool, Water Views, Both Gulf & Atlantic Access via Vaca Cut
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
****Please note that the boat slip is currently not available for use as the seawall is under repair, and there may be ...
From $566 per night (USD)VRBO
From $662 per night (USD)Expedia
Galleon Resort beach hotel luxury in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It ...
From $662 per night (USD)Expedia
From $348 per night (USD)VRBO
*New Modern* 3br\/2ba Duplex\/37' Dock\/Cabana\/Kayaks\/Bikes
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Perfectly situated in KCB w/ 37.5 feet of dockage on a wide and pristine canal that leads easy access to both the Ocean ...
From $348 per night (USD)VRBO
From $354 per night (USD)Expedia
Waterfront Sunset View Aqua Villa at Conch Shell @ Mangrove Resort LLC
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
The Conch Shell houseboat has 1 Queen bed, 1 Queen sofa sleeper and 2 Twin beds in the loft. Each houseboat has flat-scr ...
From $354 per night (USD)Expedia
From $483 per night (USD)VRBO
VOTED TRIPADVISOR'S #1 KEY LARGO DESTINATION, KAYAKS, MARINA, POOL TENNIS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Please check out our other properties in Kawama by entering the following property numbers in the section "where do you ...
From $483 per night (USD)VRBO
From $511 per night (USD)Expedia
VOTED TRIPADVISOR'S #1 DESTINATION 5 REMODELED UNITS! KAYAKS, MARINA, TENNIS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Please check out our other properties in Kawama by entering the following property numbers in the section "where do you ...
From $511 per night (USD)Expedia
From $972 per night (USD)VRBO
P18 - Spectacular 4 bedroom home with dockage and oversized private pool in...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This lovely 4 bedroom, 4 bath home is located in the highly desirable area of Key Colony Beach. - Maximum ...
From $972 per night (USD)VRBO
From $1705 per night (USD)Expedia
NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
Seaside Place welcomes guests from all states and follows all cleanliness and safety guidelines. Your safety and comfor ...
From $1705 per night (USD)Expedia
From $581 per night (USD)VRBO
Gorgeous 3\/2 plus loft Islamorada next to Marina, Pool, Dock & Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Townhome with all extras. Keys style with beautiful new furnishings, newly remodeled with three bedrooms plus oversized ...
From $581 per night (USD)VRBO
From $176 per night (USD)Expedia
Enjoy this relaxing beachy house on a canal flowing into sexton cove bay.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy this cozy home with a beautiful water front terrace. Conveniently located close to grocery stores, great restaura ...
From $176 per night (USD)Expedia
From $286 per night (USD)VRBO
Vibrant Family Condo \/ Pool & Ocean Panorama #3
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy vibrant living at our 2-bedroom Colourful Keys Condo, where fun meets relaxation. Boasting pool and ocean views, t ...
From $286 per night (USD)VRBO
From $735 per night (USD)Expedia
P82 - Sombrero Beach - 4 bedroom pool home with dock and private ramp.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Sombrero Beach Sea-clusion awaits our guests! Get ready to create great vacation memories! This spacious 4- ...
From $735 per night (USD)Expedia
From $665 per night (USD)VRBO
3bed vacation ocean side townhome 2pools,marina,lagoon,golf cart,bikes,kayaks
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Family and Friends vacation in mind - beautiful Key Largo townhouse with 2 separate living rooms which that offers a un ...
From $665 per night (USD)VRBO
From $1078 per night (USD)Expedia
**THE ZESTY LIME @ OLD TOWN** Beautifully Restored Home + LAST KEY SERVICES…
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West is k ...
From $1078 per night (USD)Expedia
From $361 per night (USD)VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo w\/ a patio at Mile Marker 0!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 1 bath {queen and ...
From $361 per night (USD)VRBO
From $419 per night (USD)Expedia
Sunsets on the bay at Villa Mia
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Come and enjoy sunsets on the bay at Villa Mia! We created a peaceful retreat for our family and friends to enjoy. It is ...
From $419 per night (USD)Expedia
From $591 per night (USD)VRBO
Balcony, Pool, & Pet Friendly - The Grand Turk
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $591 per night (USD)VRBO
From $286 per night (USD)Expedia
The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock & Dog-Friendly Bliss!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $286 per night (USD)Expedia
From $410 per night (USD)VRBO
Paradise in Key Colony with Cabana Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
This is a fisherman's dream rental. 3/2 half duplex in Key Colony Beach. By water 5 min. to the Atlantic and 15 min. to ...
From $410 per night (USD)VRBO
From $389 per night (USD)Expedia
Reel Paradise I 2bed\/2bath updated half duplex with brand new private pool, deck
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This two bedroom two bath half duplex is recently remodeled and updated with brand new everything! The kitchen & living ...
From $389 per night (USD)Expedia
From $998 per night (USD)VRBO
P87 - New Construction house. 4 bedrooms, open water view - Sombrero Beach home!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Stunning views with premier Sombrero Beach location sets this home apart from all others! This ocean front home is spect ...
From $998 per night (USD)VRBO
From $215 per night (USD)Expedia
Beautiful, sunlit home with pool, tennis court & beach access - near the marina
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Executive Bay Club Condo M-1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $215 per night (USD)Expedia
From $1342 per night (USD)VRBO
5 bedrooms, pool\/spa heated, bikes, kayaks, game room, elevator, deep 75' dock.
- Bedrooms:
- 8
- Bathrooms:
- 6
- Sleeps:
- 12
Mediterranean-Style Paradise Retreat in Key Colony Beach Escape to luxury at this stunning Mediterranean-style waterfron ...
From $1342 per night (USD)VRBO
From $352 per night (USD)Expedia
Waterfront Community in Key Largo, Florida - Moon Bay Condo A210 Sunsets
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Moon Bay, a piece of paradise! It is located on Blackwater Sound in Key Largo, Florida. Unit A210 is an end ...
From $352 per night (USD)Expedia
Click For PricingVRBO
Key Largo Beautiful House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your dream vacation in a gorgeous 3 bedroom, 2 bathroom house, with bay views on one side and a canal view on ...
Click For PricingVRBO
From $242 per night (USD)Expedia
Duval Street Suites full kitchen Old Town with heated pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Key Lime Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and full kitchen complete w ...
From $242 per night (USD)Expedia
From $584 per night (USD)VRBO
Oceanside Kawama Villa R5
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Come experience ultimate relaxation and comfort in this stunning three-story vacation home. On the first floor, you will ...
From $584 per night (USD)VRBO
From $3396 per night (USD)Expedia
BEAUTIFUL SANCTUARY PRIVATE ISLAND CONNECTED BY BRIDGE TO KEY WEST
- Bedrooms:
- 9
- Bathrooms:
- 9
- Sleeps:
- 20
A Castle on an Island On A Privately Owned Key West Island Private Bridge for Cars and Trucks connected to Key West Fr ...
From $3396 per night (USD)Expedia
From $246 per night (USD)VRBO
Relax in Paradise! Enjoy a tropical lifestyle.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Impeccable 42' Luxury RV: One bedroom, loft with 3 beds,1 Bath stylish kitchen and living areas. Welcoming and spacious ...
From $246 per night (USD)VRBO
From $699 per night (USD)Expedia
Luxurious waterfront home with panoramic views, pool, spa, & dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Plein Air Point Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $699 per night (USD)Expedia
From $121 per night (USD)VRBO
Keys Life Cottage ~ Downtown Islamorada Cottage with Pool Access!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to the "Keys Life Cottage!" This beautifully updated and spacious two bedroom, one bath home is tucked away on ...
From $121 per night (USD)VRBO
From $492 per night (USD)Expedia
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $492 per night (USD)Expedia
From $530 per night (USD)VRBO
Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $530 per night (USD)VRBO
From $518 per night (USD)Expedia
Key Largo Vacation Rental with Dock Slip and Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This centrally located boater's paradise is the perfect place to relax. Walk to restaurants, cook in kitchen or grill do ...
From $518 per night (USD)Expedia
Click For PricingVRBO
Close enough to Bike Ride to Mallory Square,far away to sleep during FantasyFest
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Coconut Mallory Resort and marina has multiple amenities including two pools, hot tubs, open air restaurant and bar, mar ...
Click For PricingVRBO
From $598 per night (USD)Expedia
Balcony, Pool, & Pet Friendly - The Trinidad
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $598 per night (USD)Expedia
From $313 per night (USD)VRBO
Coral Club Condo - Your Slice of Paradise in the Sombrero Beach Neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Coral Club Condo is your tropical haven in the serene Sombrero Beach Neighborhood, just a brief 10-minute walk from the ...
From $313 per night (USD)VRBO
From $392 per night (USD)Expedia
P11 - Charming 2 bedroom 2 bath duplex with private pool and dock -...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This lovely 2 bedroom, 2 bath home is located on the gulfside with immediate Gulf water access and near the Vaca Cut for ...
From $392 per night (USD)Expedia
From $689 per night (USD)VRBO
335 Mariners Club Key Largo | 3 Bed, 2.5 Bath
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Infinite horizons...from this third floor, luxury, three-bedroom, two and one-half bath villa! A peaceful, relaxing get ...
From $689 per night (USD)VRBO
From $717 per night (USD)Expedia
Beautiful Oceanside Mariner's 3 Bedroom Townhome
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Best vacation rental to explore the Florida keys. Marina Villa 210 (3b/3b) with Marina and ocean views. Escape to pa ...
From $717 per night (USD)Expedia
From $1121 per night (USD)VRBO
Waterfront, 100ft Boat Dock, Kayaks, Paddle boards, Bikes, Private Pool, Sunsets
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Coco Plum on the Bay, your private waterfront single family home in Marathon, FL. You will enjoy a spacious ...
From $1121 per night (USD)VRBO
From $300 per night (USD)Expedia
RV Camper in the heart of Key Largo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
A beautiful RV camper right in the middle of paradise. A beautiful ambiance with such friendly neighbors. You wake up an ...
From $300 per night (USD)Expedia
From $321 per night (USD)VRBO
Rent a Piece of Paradise, Best Location on the Island!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Rent a piece of paradise right in the heart of beautiful Old Town Key West. Walking distance to all major attraction (r ...
From $321 per night (USD)VRBO
From $1105 per night (USD)Expedia
W09 - New Luxury Property! Breathtaking 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 $1105 per night (USD)Expedia
From $396 per night (USD)VRBO
**TIDEWATER VIEWS @ VENTURE OUT** 2BR\/2BA Cottage + 35’ Private Slip | 80’ Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! TIDEWATER VIE ...
From $396 per night (USD)VRBO
From $274 per night (USD)Expedia
Tropical Getaway in Paradise.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
3 Nite Minimum Stay! **7 day minimum for Lobster Fest, July 22-Aug. 13. ** This bright, freshly decorated, modern 2 bedr ...
From $274 per night (USD)Expedia
From $651 per night (USD)VRBO
Beautiful 4 Bedroom, 3 Bath, Spacious Pool\/SPA Home with 200' wide Canal.
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 10
Welcome to Casa del Cielo. Enjoy breathtaking views of the Gulf and Ocean from this beautiful canal front home. Bring y ...
From $651 per night (USD)VRBO
From $381 per night (USD)Expedia
Little Island Pearl
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Have you been dreaming of a get away in the Florida Keys in Key Colony Beach. A little piece of heaven with a brand ne ...
From $381 per night (USD)Expedia
From $354 per night (USD)VRBO
B-105 Moon Bay | 3 Bed, 2.5 Bath
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
7-night minimum stay requirement. Lovely bayside townhouse with 2 bedrooms, 1 1/2 baths on the main floor and a studio ...
From $354 per night (USD)VRBO
From $563 per night (USD)Expedia
Great Location , Great Vibes, Great Pool
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
Quiet, secluded Keys house with a pool. Ideal for larger groups of friends and family's. Equal distance to Marathon an ...
From $563 per night (USD)Expedia
From $397 per night (USD)VRBO
The Palms...A beautiful space in the perfect place.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The perfect space in the perfect place. A quiet oasis on the 2nd floor nestled amongst palm trees in the shipyard secti ...
From $397 per night (USD)VRBO
From $412 per night (USD)Expedia
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful home overlooking the Atlantic Ocean is part of the Sunrise Beach Resort, an exclusive gated community bui ...
From $412 per night (USD)Expedia
From $531 per night (USD)VRBO
Key Largo Ocean Shore Villa 1 with pool & boat slip
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Located in the heart of the Florida Keys, this one-of-a-kind vacation rental offers the perfect combination of luxury an ...
From $531 per night (USD)VRBO
From $428 per night (USD)Expedia
TA Beach, Pool, Marina, family friendly, Kitchen, Jacuzzi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This listing is for a TROPICAL ISLAND villa, at Cocoplum Beach and Tennis Club and Marina, which is one of the 2 villas ...
From $428 per night (USD)Expedia
From $670 per night (USD)VRBO
A BANANA REPUBLIC in Old Town Key West
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
A Banana Republic Gem. This Old Town house may be the nicest property in Key West. Totally redone and professionally dec ...
From $670 per night (USD)VRBO
From $427 per night (USD)Expedia
Waterfront Bliss! Marina Access, Pool, Tiki Bar & Dining – Spring Break!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
THE DAPPER DOLPHIN, an updated coastal-themed 1-bedroom, 1-bathroom condo, is the perfect getaway, accommodating up to 4 ...
From $427 per night (USD)Expedia
From $389 per night (USD)VRBO
**DANCE OF THE BUTTERFLIES @ SOUTHERNMOST** New Home & Pool + LAST KEY SERVICES.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! For a month i ...
From $389 per night (USD)VRBO
From $539 per night (USD)Expedia
207 Mariners Club Key Largo | 3 Bed, 3 Bath
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Perfectly located along the picture perfect marina front overlooking the beautifully landscaped gardens of Mariners Club ...
From $539 per night (USD)Expedia
From $718 per night (USD)VRBO
611 Mariners Club Key Largo | 4 Bed, 4 Bath
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This luxury Key Largo vacation townhome rental (Unit 611) is a 4 bedroom/4 bath unit. Ideal accommodations for the Flori ...
From $718 per night (USD)VRBO
From $977 per night (USD)Expedia
**THE TOASTED COCONUT @ OLD TOWN** Fully Restored + Pool + LAST KEY SERVICES…
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Throughout Ke ...
From $977 per night (USD)Expedia
From $407 per night (USD)VRBO
P63 - Beautiful, waterfront Key Colony Duplex. Short walk to the Cabana Beach...
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful duplex home in Key Colony Beach. Key Colony Beach is a small, friendly, walkable island with easy access to lo ...
From $407 per night (USD)VRBO
From $735 per night (USD)Expedia
M12 - Beautiful house in Key Colony offering 4 bedrooms, pool and dockage!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This 4 bedroom, 3 bathroom home in the heart of the Florida Keys is located in the very desirable Key Colony Beach and w ...
From $735 per night (USD)Expedia
From $278 per night (USD)VRBO
M18 - Spacious 3 bedroom, 2 bath Gulf side condo!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spacious 3 bedroom, 2 bathroom, second floor condo, with split floor plan. Large screened wrap around porc ...
From $278 per night (USD)VRBO
From $265 per night (USD)Expedia
M123 - Cabana Beach Duplex! Premier location across the street from Cabana...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This comfy, cozy 2 bedroom, 2 bathroom duplex is ideally located in the heart of the Keys in Key Colony Beach. ...
From $265 per night (USD)Expedia
From $590 per night (USD)VRBO
Luxury and Lovely Water Front House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
If you're looking for a low-key vacation, Big Pine Key is the place for you. In Big Pine Key, about 100 miles south of M ...
From $590 per night (USD)VRBO
From $350 per night (USD)Expedia
Florida keys Waterfront,Forever Summer
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
MINIMUM STAY OF 28 DAYS REQUIERED BY THE COUNTY.Booking from the 1st of the month. Waterfront house with heated pool. Lo ...
From $350 per night (USD)Expedia
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Fully Furnished Condo
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Large Living Room with water view. Park you boat at the private Boat Dock. Swim in the heated Pool. Grill you fresh cau ...
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Fully Furnished Condo
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Large Living Room with water view. Park you boat at the private Boat Dock. Swim in the heated Pool. Grill you fresh cau ...
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Fully Furnished Condo
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Large Living Room with water view. Park you boat at the private Boat Dock. Swim in the heated Pool. Grill you fresh cau ...
Click For PricingVRBO
Click For PricingExpedia
Fully Furnished Condo
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Large Living Room with water view. Park you boat at the private Boat Dock. Swim in the heated Pool. Grill you fresh cau ...
Click For PricingExpedia
Click For PricingVRBO
Fully Furnished Condo
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Large living room with water view and deck. Deck off Master Bedroom overlooking the Adams cut waterway and pool. Relax ...
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From $379 per night (USD)Expedia
Water front property with bar, tennis, market place, and restaurants close by.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Comfortable home with 2 bedrooms and a bath on both upper level and lower level. Great for fishing and kayaking, has a d ...
From $379 per night (USD)Expedia
![Boaters Delight [Ocean Pointe 5301]](https://media.vrbo.com/lodging/61000000/60260000/60255900/60255808/93a2f410.jpg?impolicy=ccrop&w=350&h=233&q=medium)
From $315 per night (USD)VRBO
Boaters Delight [Ocean Pointe 5301]
- 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 oc ...
From $315 per night (USD)VRBO
From $569 per night (USD)Expedia
Balcony, Pool, & Pet Friendly - The Barbados
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to the quiet Sunrise Suites community located on the southeast side of Key West. Just 1 mile from the b ...
From $569 per night (USD)Expedia