Monroe Area Rentals
- From $593 per night (USD)
VRBO
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w\/ Kitchen and Shared Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
SULTRY GARDEN SANCTUARY... Steal away from reality and find your way to the quintessential, tropical & adults only Trave ...
From $593 per night (USD)VRBO
- From $484 per night (USD)
Expedia
Anglers Dream House; Close To It All - Beach, Pool & Kayaks in Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Keezy Does It at Anglers Reef in Islamorada! A charming, oceanfront gated community in the heart of Islamora ...
From $484 per night (USD)Expedia
- From $686 per night (USD)
VRBO
NEW 4 Bedroom\/3 Bath Home w\/Private Pool,40 ft. Dock near Sombrero Beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Brand New 4 Bedroom/3 Bath Family Home with private pool and 40ft dock near Sombrero Beach, shopping & dining! This spa ...
From $686 per night (USD)VRBO
- From $401 per night (USD)
Expedia
GORGEOUS SEA THEMED 2 STORY HOME W\/ PRIVATE POOL AND BEACH ACCESS
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Beautiful new 2-Story home with balcony patio. Perfect to do some grilling and feel the salt in the air. Home was finali ...
From $401 per night (USD)Expedia
- From $169 per night (USD)
VRBO
Charming 'Boho Breeze' Retreat w\/ Pool Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Experience crystal clear waters, picturesque beaches, and famous historic sites with a stay at 'Boho Breeze!' This 2-bed ...
From $169 per night (USD)VRBO
- From $442 per night (USD)
Expedia
ROYAL PALM SUITE ~ Adult Only, 1 BR, 1 Ba w\/ Kitchen and Shared Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
ESCAPE TO A BOTANICAL HIDEAWAY... Immerse yourself at the charming adults only Travelers Palm Inn with unique suites and ...
From $442 per night (USD)Expedia
- From $548 per night (USD)
VRBO
ISLAND OASIS in the Truman Annex
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Island Oasis @ the Truman Annex is beautifully renovated town home in the historic Foundry. | The living area is the ent ...
From $548 per night (USD)VRBO
- From $437 per night (USD)
Expedia
COCONUT PALM SUITE ~ Adult Only, 1 BR, 1 Ba w\/ Kitchen & Shared Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
BOTANICAL MAGIC AWAITS YOU... Only three blocks from all of the fine dining and entertainment of Duval Street, yet tucke ...
From $437 per night (USD)Expedia
- From $320 per night (USD)
VRBO
Coastal retreat with private balcony, pool, & easy beach access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Ocean Pointe #2210 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $320 per night (USD)VRBO
- Click For Pricing
Expedia
Cozy RV, Ocean Boaters Fish Lodge
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Direct ocean access Camper RV at Key by the Sea. 2 Bedrooms, 1 Queen Bed, 3 Bunks, Full Kitchen and Full Bathroom, Cable ...
Click For PricingExpedia
- Click For Pricing
VRBO
2 Bedroom, Cozy home in sunny Key Largo, FL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Beautifully decorated beach house where you can get away and disconnect for a few days with your family or for a romanti ...
Click For PricingVRBO
- From $671 per night (USD)
Expedia
Waterfront Sunway Lagoon *Huge Private Dock*
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Marathon, home of the best fishing town in the Middle Keys. This home has an incredible 120ft boat dockage, a ...
From $671 per night (USD)Expedia
- From $758 per night (USD)
VRBO
Sea Esta Suite | Pool on Duval
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: - In the middle of Duval Street and walking distance to the Southernmost Point! - Bright & airy two-story townh ...
From $758 per night (USD)VRBO
- From $180 per night (USD)
Expedia
NEW MONTHLY RENTAL, Old Town, Duplex, private backyard, pets welcome
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Sea Monkey and The Mermaid. Our home is a duplex located in Old Town and full of Key West charm. Walk to a ...
From $180 per night (USD)Expedia
- From $151 per night (USD)
VRBO
Conch Cottage, Near Downtown! | Quiet w\/ Shared Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Escape to this cozy Key West Cottage and enjoy all the island has to offer! Whether you plan to stay in or go o ...
From $151 per night (USD)VRBO
- From $995 per night (USD)
Expedia
~The Escape ~ Your own tropical escape on private island!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $995 per night (USD)Expedia
- From $1235 per night (USD)
VRBO
P44 - 4 bed, 3 bath estate home with Southern Charm and private pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
New in our inventory! This estate style home is premier! Built in beautiful southern tradition, this home does not disap ...
From $1235 per night (USD)VRBO
- From $544 per night (USD)
Expedia
203 Sombrero- 4 Bedroom\/3 Bath Attached Villa w\/ Private Boat Dock
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
4 Bedroom 3 Full Bath Attached Villa on the Canal in Marathon, a 15 minute boat ride to the ocean. Private Heated Pool. ...
From $544 per night (USD)Expedia
- From $427 per night (USD)
VRBO
Stay near Jimmy Johnson’s Big Chill – just a 18-min stroll away
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to the stunning shores of Key Largo and experience the ultimate island getaway at our 2-bedroom condo. Nestled ju ...
From $427 per night (USD)VRBO
- From $871 per night (USD)
Expedia
PARADISE FOUND!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Paradise Found at Mariners Club in Key Largo, FL a beautiful spacious 3-story town-home in an exclusive resort located ...
From $871 per night (USD)Expedia
- From $692 per night (USD)
VRBO
Enjoy Old Town Key West in this Beautifully furnished house
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
We recently bought this house because we LOVE Key West! It is a 2 story Key West style house. The bedrooms are upstair ...
From $692 per night (USD)VRBO
- From $486 per night (USD)
Expedia
4 Bedroom,4 Bath with private pool and 37 and 1\/2 foot boat dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This home has 2 levels and is located at 401 9th Street in Key Colony Beach. Private Boat dock that is 37 and half feet ...
From $486 per night (USD)Expedia
- From $305 per night (USD)
VRBO
Newly Renovated! Relax & Explore The Keys In Comfort. We Make It Simple.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Ocean Pointe Suites is a secluded resort overlooking the Atlantic. A great getaway for families or couples. You relax in ...
From $305 per night (USD)VRBO
- From $497 per night (USD)
Expedia
Rx: Paradise 2bed\/2.5bath updated open water condo with shared pool & dockage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
Indulge in the mesmerizing beauty of colorful sunsets during your vacation in this recently renovated property! Unwind o ...
From $497 per night (USD)Expedia
- From $594 per night (USD)
VRBO
Key Colony Beach Waterfront Pool Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Paradise Found...come stay at Casa Sueño Del Mar to experience the Florida Keys in a peacful retreat with luxurious surr ...
From $594 per night (USD)VRBO
- From $360 per night (USD)
Expedia
Yellow Room at Grand Maloney by Brightwild
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $360 per night (USD)Expedia
- From $359 per night (USD)
VRBO
Blue Room at the Grand Maloney by Brightwild
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $359 per night (USD)VRBO
- From $391 per night (USD)
Expedia
Green Room at the Grand Maloney by Brightwild
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $391 per night (USD)Expedia
- From $723 per night (USD)
VRBO
SPECTACULAR Indigo Reef Waterfront Home #41 - Marathon, Florida
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Indigo Reef #41 is the BEST KEPT SECRET in the Florida Keys!! This home is spectacular in every sense of the word and no ...
From $723 per night (USD)VRBO
- From $512 per night (USD)
Expedia
Angler`s Retreat 3bed\/2bath updated single family with dockage
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy the Florida Keys in this stunning 3 bedroom / 2 bath updated single family located minutes away from Sombrero Beac ...
From $512 per night (USD)Expedia
- From $499 per night (USD)
VRBO
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks, SUPs, Washer,Dryer!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come stay with us at VENTURE OUT, a fantastic safe, activity filled community in Cudjoe Key, Fl- only 20 miles north of ...
From $499 per night (USD)VRBO
- From $468 per night (USD)
Expedia
Poolside King Room Steps from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Poolside King Room is a hotel-style room adjacent to the pool. It can sleep up to four persons, two in the king-size ...
From $468 per night (USD)Expedia
- From $417 per night (USD)
VRBO
Poolside Queen Room Steps from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Poolside Queen Room is a hotel-style bedroom and bath unit that offers the amenities of our Key West villas for thos ...
From $417 per night (USD)VRBO
- From $542 per night (USD)
Expedia
One Bedroom Deck Villa Steps from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy a wonderful Key West accommodation. Our One Bedroom Deck Villa features a living room, a separate bedroom with ki ...
From $542 per night (USD)Expedia
- From $517 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 $517 per night (USD)VRBO
- From $740 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 $740 per night (USD)Expedia
- From $259 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 $259 per night (USD)VRBO
- From $257 per night (USD)
Expedia
The Hideaway: Discover and Lose Yourself! Newly Decorated Canal Front Home, Dockage & Dog-Friendly!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to "The Hideaway," a charming canal-front retreat nestled adjacent to a serene nature preserve on Big Torch Key. ...
From $257 per night (USD)Expedia
- From $378 per night (USD)
VRBO
Florida Keys: Ocean Front 3bd 4 ba
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Centrally located on Long Key MM65 this Ocean Front 3 story 1714 sf condo will melt your troubles away. Private beach al ...
From $378 per night (USD)VRBO
- From $656 per night (USD)
Expedia
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 ...
From $656 per night (USD)Expedia
- Click For Pricing
VRBO
Sombrero- Waterfront 4 BR Luxury Pool Home- M#9
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
5 STAR Waterfront Luxury 4BR, Dock, Private Pool. Fresh & Fabulous , best describes this listing. This fantastic luxury ...
Click For PricingVRBO
- From $303 per night (USD)
Expedia
Duval Street Suite on Duval Free Parking and 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 $303 per night (USD)Expedia
- From $399 per night (USD)
VRBO
Duval Street Suite full kitchen, parking, & 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 $399 per night (USD)VRBO
- From $361 per night (USD)
Expedia
Duval Street Suites full kitchen, parking, 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 $361 per night (USD)Expedia
- From $316 per night (USD)
VRBO
Duval Street Suite full kitchen and 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 $316 per night (USD)VRBO
- From $353 per night (USD)
Expedia
Duval Street Suite with full kitchen pool, parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Mile Zero Suite is a one bedroom (queen) 1 bath suite with a sleeper sofa (queen) and kitchen. Overlooking Duv ...
From $353 per night (USD)Expedia
- From $3379 per night (USD)
VRBO
6 BR 6 BA Guesthouse Suites on Duval parking, 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 $3379 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 $614 per night (USD)
VRBO
Waterfront home w\/ gorgeous views from the patio Shared pool, hot tub, & tennis
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Dock of the Bay Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $614 per night (USD)VRBO
- From $592 per night (USD)
Expedia
P60 - 4 bedroom 4 bathroom home with pool and dockage. Amazing outside living...
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
This fabulous 4 bedroom, 4.5 bathroom home was designed and built for comfort and style with extra attention being given ...
From $592 per night (USD)Expedia
- From $986 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 $986 per night (USD)VRBO
- From $392 per night (USD)
Expedia
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)Expedia
- From $181 per night (USD)
VRBO
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 $181 per night (USD)VRBO
- From $239 per night (USD)
Expedia
Key Largo, Calusa, 2 bedroom 1.5 bath with screened in patio
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Calusa resort is a gated community located in Key Largo. Community rests on Buttonwood bay. Guests are sure to enjoy a m ...
From $239 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 $286 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 $286 per night (USD)Expedia
- From $669 per night (USD)
VRBO
Amazing Views in Florida Keys Bayside BAY BREEZES, SUNSETS, SAILBOATS n SEAGULLS
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Make memories that last a lifetime at Anchors Aweigh - experience Bay Breezes, Sunsets, Sailboats n Seagulls with this p ...
From $669 per night (USD)VRBO
- From $361 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 $361 per night (USD)Expedia
- From $587 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 $587 per night (USD)VRBO
- From $589 per night (USD)
Expedia
Poolside Suite | Pool & Parking
- 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 $589 per night (USD)Expedia
- From $382 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 $382 per night (USD)VRBO
- From $174 per night (USD)
Expedia
PARADISE FOUND - ISLAMORADA FLORIDA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
BEAUTIFUL THREE BEDROOM, 2 FULL SIZE BATHROOM VACATION RENTAL IS LOCATED IN THE EXECUTIVE BAY CLUB. BREATHTAKING BAY VI ...
From $174 per night (USD)Expedia
- From $400 per night (USD)
VRBO
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 $400 per night (USD)VRBO
- From $498 per night (USD)
Expedia
The BeachComer ~ Paradise in the Florida Keys!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
** CHECK OUT OUR REVIEWS!..... Come see why The BeachComer is truly "Paradise" in the Keys! ** Thank you for your inter ...
From $498 per night (USD)Expedia
- From $647 per night (USD)
VRBO
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 $647 per night (USD)VRBO
- From $428 per night (USD)
Expedia
*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 $428 per night (USD)Expedia
- From $398 per night (USD)
VRBO
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 $398 per night (USD)VRBO
- From $590 per night (USD)
Expedia
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 $590 per night (USD)Expedia
- From $483 per night (USD)
VRBO
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 $483 per night (USD)VRBO
- From $752 per night (USD)
Expedia
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. *Please be ...
From $752 per night (USD)Expedia
- From $1385 per night (USD)
VRBO
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 $1385 per night (USD)VRBO
- From $456 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 $456 per night (USD)VRBO
- From $197 per night (USD)
VRBO
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 $197 per night (USD)VRBO
- From $276 per night (USD)
Expedia
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 $276 per night (USD)Expedia
- From $867 per night (USD)
VRBO
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 $867 per night (USD)VRBO
- From $666 per night (USD)
Expedia
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 $666 per night (USD)Expedia
- From $1992 per night (USD)
VRBO
**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 $1992 per night (USD)VRBO
- From $390 per night (USD)
Expedia
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 $390 per night (USD)Expedia
- From $418 per night (USD)
VRBO
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 $418 per night (USD)VRBO
- From $536 per night (USD)
Expedia
Pool View & Pvt Balcony | Samana Cay Suite
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Summary: - Welcome to the quiet Sunrise Suites community located on the southeast side of Key West. - Just 1 mile from t ...
From $536 per night (USD)Expedia
- From $604 per night (USD)
VRBO
The Grand Turk | Sunset View & Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: - Welcome to the fun-filled Sunrise Suites complex located on the quiet side of Key West. - Just 1 mile from th ...
From $604 per night (USD)VRBO
- From $295 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
Welcome to The Salty Sailfish, a magnificent canal-front home nestled on Cudjoe Key. With updated furnishings and a comm ...
From $295 per night (USD)Expedia
- From $510 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 $510 per night (USD)VRBO
- From $399 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 $399 per night (USD)Expedia
- From $858 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 set this home apart from all others. This ocean front home is specta ...
From $858 per night (USD)VRBO
- From $160 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 $160 per night (USD)Expedia
- From $1291 per night (USD)
VRBO
5 bedrooms, 8 bath, pool\/spa, bikes, kayaks, game room, elevator, ice machine.
- Bedrooms:
- 8
- Bathrooms:
- 6
- Sleeps:
- 12
Mediterranean-Style Paradise Retreat in Key Colony Beach Escape to luxury at this stunning Mediterranean-style waterfro ...
From $1291 per night (USD)VRBO
- From $454 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 $454 per night (USD)Expedia
- Click For Pricing
VRBO
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 $749 per night (USD)
Expedia
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 $749 per night (USD)Expedia
- From $3414 per night (USD)
VRBO
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 $3414 per night (USD)VRBO
- From $296 per night (USD)
Expedia
Duval Street Suite full kitchen Old Town with 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 $296 per night (USD)Expedia
- From $232 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 $232 per night (USD)VRBO
- From $1051 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 $1051 per night (USD)Expedia
- From $188 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 $188 per night (USD)VRBO
- From $657 per night (USD)
Expedia
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Where the Ocean Meets the Windswept is nothing like . You don't have to spend a fortune to enjoy a spacious, clean and ...
From $657 per night (USD)Expedia
- From $516 per night (USD)
VRBO
Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Caribbean Conch is a fantastic rental with a prime location near the pool. This unit features an extra-large floor plan, ...
From $516 per night (USD)VRBO
- From $530 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 $530 per night (USD)Expedia
- Click For Pricing
VRBO
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 $527 per night (USD)
Expedia
The Trinidad | Pool View & Parking
- 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 t ...
From $527 per night (USD)Expedia