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

$Comfortable Home with Private Pool, Central AC, WiFi, and Private Washer\/Dryer$
From $533 per night (USD)
VRBO
Comfortable Home with Private Pool, Central AC, WiFi, and Private Washer\/Dryer
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Flagler Station Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $533 per night (USD)
VRBO
From $398 per night (USD)
Expedia
Waterfront Home with 33-Ft. Dock and Cabana Club Membership with Beach and Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Ninth Street Cabana Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $398 per night (USD)
Expedia
From $213 per night (USD)
VRBO
Waterfront home with private dock, canal views, large terrace & modern kitchen
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
La Isla Bonita Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $213 per night (USD)
VRBO
From $731 per night (USD)
Expedia
Two Master Suites! 35' Boat Dockage! Outdoor Living Space & Summer Kitchen!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
At Sombrero Serenity boaters will appreciate the deep water docking out back with room to accommodate up to a 35 ft. boa ...
From $731 per night (USD)
Expedia
From $391 per night (USD)
VRBO
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 $391 per night (USD)
VRBO
From $621 per night (USD)
VRBO
Keys Cottage with Beach and Dockage! Bayfront Property!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
"Deckhouse" is the perfect beachy cottage for your Keys vacation! It has a full-size kitchen with granite countertops an ...
From $621 per night (USD)
VRBO
From $222 per night (USD)
VRBO
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
Bedrooms:
1
Bathrooms:
2
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 $222 per night (USD)
VRBO
From $430 per night (USD)
Expedia
Heart of Old Town; 2 Bicycles, Grill, High Speed WiFi, 1st Floor, Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Here in Key West we believe in One Human Family where everyone is welcome and treated like family. Our condo has always ...
From $430 per night (USD)
Expedia
From $565 per night (USD)
VRBO
Waterfront Cottage - Beach and Dockage! Open Water Views!
Bedrooms:
1
Bathrooms:
3
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 $565 per night (USD)
VRBO
$\Your own private resort\ - Mockingbird Pointe - Waterfront, pool and dockage$
From $474 per night (USD)
Expedia
\"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 $474 per night (USD)
Expedia
From $291 per night (USD)
VRBO
Nader's Vacation Home
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 $291 per night (USD)
VRBO
From $308 per night (USD)
Expedia
P64 - Spacious 3 bedroom duplex in Key Colony with dockage and Cabana Club...
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 $308 per night (USD)
Expedia
From $112 per night (USD)
VRBO
Great Rates! Remodeled Cozy Waterfront Mobile Home In Key Largo
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Totally remodeled home located at Eagle Dr in quiet Sexton Cove. 5 minutes away from John Pennekamp State Park, great r ...
From $112 per night (USD)
VRBO
From $305 per night (USD)
Expedia
Manatee Bay , Pool table, Jacuzzi, Pool, Kayaks, REDUCED RATES AVAIL NOW<br>
Bedrooms:
5
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 $305 per night (USD)
Expedia
From $284 per night (USD)
VRBO
Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon
Bedrooms:
2
Bathrooms:
3
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 $284 per night (USD)
VRBO
$A Taste Of Vitamin Sea 4bed\/3bath updated single family with pool, dockage &$
From $608 per night (USD)
Expedia
A Taste Of Vitamin Sea 4bed\/3bath updated single family with pool, dockage &
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
STR21-000361 Your vacation awaits at A Taste of Vitamin Sea in desirable Key Colony Beach! Vitamin Sea’s canal fronta ...
From $608 per night (USD)
Expedia
$Henry's Penthouse on the Ocean in Key West - weekly \/ nightly rentals$
From $573 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 $573 per night (USD)
VRBO
$**OLD TOWN OASIS @ THE ANNEX** Oceanside 2BR\/2BA Condo & Pool + LAST KEY SERVICE$
From $978 per night (USD)
Expedia
**OLD TOWN OASIS @ THE ANNEX** Oceanside 2BR\/2BA Condo & Pool + LAST KEY SERVICE
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 $978 per night (USD)
Expedia
From $729 per night (USD)
VRBO
Waterfront home with dock, pool table & private pool - walk to Sombrero Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Anchor House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $729 per night (USD)
VRBO
$3BR\/3BA Sunset Cottage located at The Villages of Hawks Cay$
From $664 per night (USD)
Expedia
3BR\/3BA Sunset Cottage located at The Villages of Hawks Cay
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
In response to COVID-19, our cottage will be disinfected and sanitized professionally prior to all check-ins. Professio ...
From $664 per night (USD)
Expedia
From $1100 per night (USD)
VRBO
Elegant Home with Beach & Dockage! Spectacular Sunsets!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
This elegant home is located on a beautiful 2.5 acre gated beachfront estate with amazing views of our beautiful island ...
From $1100 per night (USD)
VRBO
From $342 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 $342 per night (USD)
Expedia
$~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool\/parking$
From $3409 per night (USD)
VRBO
~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool\/parking
Bedrooms:
5
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 $3409 per night (USD)
VRBO
$Key Largo! Luxurious 2BR\/2BA! Amazing Pool and Large Pool!$
From $328 per night (USD)
Expedia
Key Largo! Luxurious 2BR\/2BA! Amazing Pool and Large Pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Summary: Stunning Condo with Garden View located in Tavernier, Key Largo, Florida. Escape to paradise in this breathtak ...
From $328 per night (USD)
Expedia
$Spectacular Open-Water Sunset Views w\/Boat Slip & Trailer Parking. Pet Friendly!$
From $337 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 $337 per night (USD)
VRBO
From $463 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 $463 per night (USD)
Expedia
From $390 per night (USD)
VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $390 per night (USD)
VRBO
From $508 per night (USD)
Expedia
Craig & Cindy Truman Annex Foundry Townhouse 2 bedrooms 2.5 baths
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Craig & Cindy Truman Annex Foundry Townhouse is a 2 bedroom 2 1/2 bath townhouse in the best location in all of Key West ...
From $508 per night (USD)
Expedia
From $1014 per night (USD)
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 ...
From $1014 per night (USD)
VRBO
From $248 per night (USD)
Expedia
Vacation like a local
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Newly renovated 3 bedroom/ 2 bathroom + loft, corner canal lot. Fully equipped home. Plenty of room for boat and great ...
From $248 per night (USD)
Expedia
From $731 per night (USD)
VRBO
TikiBar,HeatedPool,PriSpa,kayaks,SUP’s,Bikes,BBQ,Fire ring, outside TV, and more
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Experience the ultimate tropical getaway in our enchanting bungalow, boasting 78 consecutive 10/10 guest reviews! Our ho ...
From $731 per night (USD)
VRBO
From $329 per night (USD)
Expedia
COCONUT Adorable cottage in Old Town
Bedrooms:
1
Bathrooms:
2
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 $329 per night (USD)
Expedia
From $222 per night (USD)
VRBO
Ocean Shores Home Key Largo
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Oceanside single family home in one of Key largo most desirable neighborhoods with waterview and private pool. Large lot ...
From $222 per night (USD)
VRBO
From $307 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 $307 per night (USD)
Expedia
$Dog-Friendly Canalfront Home with Dock, Central AC, Fast WiFi, & Washer\/Dryer$
From $509 per night (USD)
VRBO
Dog-Friendly Canalfront Home with Dock, Central AC, Fast WiFi, & Washer\/Dryer
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Relax Inn Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $509 per night (USD)
VRBO
$Snowbird-Friendly Home with Central AC, High-Speed WiFi, and Washer\/Dryer$
From $150 per night (USD)
Expedia
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 $150 per night (USD)
Expedia
From $839 per night (USD)
VRBO
**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 $839 per night (USD)
VRBO
From $701 per night (USD)
Expedia
**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 $701 per night (USD)
Expedia
From $231 per night (USD)
VRBO
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 ...
From $231 per night (USD)
VRBO
From $1121 per night (USD)
Expedia
Sun of a Beach: Luxurious 7-Bedroom Split-Level Home with private pool, hot tub
Bedrooms:
5
Bathrooms:
8
Sleeps:
16
Indulge in the charm of this splendid split-level residence nestled in the heart of the captivating Florida Keys. This d ...
From $1121 per night (USD)
Expedia
From $288 per night (USD)
VRBO
Work remote, or not at all, in paradise at this cozy, beachy condo!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Flexible cancellation policy. Futura Yacht Club is an exclusive private, gated resort community. Not like a hotel, FYC ...
From $288 per night (USD)
VRBO
From $304 per night (USD)
Expedia
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 $304 per night (USD)
Expedia
From $813 per night (USD)
VRBO
136 Mariners Club | 3 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This spectacular 2600 square foot villa boasts a blissful atmosphere and breathtaking view of the harbor and Atlantic Oc ...
From $813 per night (USD)
VRBO
From $1018 per night (USD)
VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Minimum Age: 25 years old Pet Policy: No Pets An ID and credit card for a refundable security deposit will be required. ...
From $1018 per night (USD)
VRBO
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VRBO
Little Casita: Key West Monthly rental Close to Duval - RealKeyWest
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
WELCOME TO LITTLE CASITA! If looking for the perfect couple’s retreat, look no further! This one bedroom, one bath hi ...
Click For Pricing
VRBO
From $318 per night (USD)
Expedia
610 Mariners Club | 1 Bed, 1 Bath
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Sweet studio apartment in coveted Mariners Club on the island of Key Largo. This is a duplex-style, ground floor 1-bedr ...
From $318 per night (USD)
Expedia
$Canal-front Keys escape with amazing view, boat access, firepit, gril, AC, & W\/D$
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VRBO
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 ...
Click For Pricing
VRBO
From $416 per night (USD)
Expedia
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 $416 per night (USD)
Expedia
From $369 per night (USD)
VRBO
Welcome to the Shady Palms - Private Pool - RealKeyWest
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Step into this beautifully restored and redecorated 1933 Key West home. This first-floor home has Bahama shutters throug ...
From $369 per night (USD)
VRBO
From $904 per night (USD)
Expedia
Ocean view home with private pool, hot tub, Cabana club and 40 ft dock for boats
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Ocean's Edge Retreat is a 3 bedroom / 3 bath home with open water views of the Atlantic Ocean and directly on the canal. ...
From $904 per night (USD)
Expedia
From $781 per night (USD)
VRBO
**ENVY OF THE ISLAND @ OLD TOWN** Pristine Home & Pool + LAST KEY SERVICES...
Bedrooms:
7
Bathrooms:
5
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! While Old Tow ...
From $781 per night (USD)
VRBO
From $901 per night (USD)
VRBO
Amazing Stay, Great Location! Bike Rental, Pools, Onsite Bar
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $901 per night (USD)
VRBO
From $459 per night (USD)
VRBO
Luxurious Vacation! Pools, Tiki Bar, Bike Rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $459 per night (USD)
VRBO
$Doc`s Holiday 2bed\/2bath half duplex with Cabana Club$
From $340 per night (USD)
Expedia
Doc`s Holiday 2bed\/2bath half duplex with Cabana Club
Bedrooms:
2
Bathrooms:
3
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 $340 per night (USD)
Expedia
$Angler`s Paradise 2bed\/2bath updated half duplex brand new pool & dockage$
From $412 per night (USD)
VRBO
Angler`s Paradise 2bed\/2bath updated half duplex brand new pool & dockage
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy the Florida Keys in this lovely two bedroom two bath half duplex located minutes away from beautiful Sombrero Beac ...
From $412 per night (USD)
VRBO
From $774 per night (USD)
Expedia
Mariners Club 410 - Oceanview 3 levels!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Trip Advisor Award Winner! Oceanview from all three levels! From your living room or master suite enjoy the expansive ...
From $774 per night (USD)
Expedia
From $483 per night (USD)
VRBO
SOUTHERNMOST SWIM AND SOCIAL CLUB
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Look no further! You've found your home away from home. Where your family and friends can share their own piece of para ...
From $483 per night (USD)
VRBO
From $400 per night (USD)
Expedia
Oceanfront! Oceanfront! Oceanfront!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
License # 24-0123 - Completely Renovated - 2 Bedroom, 2 Bath, condominium unit. Just steps from the elevator on the 5th ...
From $400 per night (USD)
Expedia
$Hyatt Windward Pointe, Key West, Fl. - 2 Bedroom Unit - 1064 sq\/ft$
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Expedia
Hyatt Windward Pointe, Key West, Fl. - 2 Bedroom Unit - 1064 sq\/ft
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
3rd floor (top level accessible by elevator or stairs) Balcony faces the Atlantic Ocean and gardens. 2 bedrooms (large m ...
Click For Pricing
Expedia
From $308 per night (USD)
Expedia
Play & Stay - Marina Front 2br Condo with Picturesque Views!
Bedrooms:
2
Bathrooms:
3
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 $308 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). Centra ...
From $203 per night (USD)
VRBO
$Treasure Cove- 2BDR\/2.5BA | 2 Bed, 2.5 Bath$
From $645 per night (USD)
Expedia
Treasure Cove- 2BDR\/2.5BA | 2 Bed, 2.5 Bath
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
~~7 day minimum~~Experience the famous island city of Key West and stay at the Treasure Cove Townhouse in the private P ...
From $645 per night (USD)
Expedia
From $161 per night (USD)
VRBO
Ground-level getaway with free WiFi, private deck, & shared outdoor pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Louisa's Garden Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $161 per night (USD)
VRBO
From $216 per night (USD)
Expedia
Penthouse view - Futura Yacht Club #604
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Condo #604, 3 Bedrooms, 2.0 Baths, (Sleeps 6) Enjoy penthouse views of the fabulous blue waters of the Atlantic and Flo ...
From $216 per night (USD)
Expedia
From $416 per night (USD)
VRBO
Quiet Lane in the Heart of Old Town, Sleeps 4 + 🐶🐾
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Unbeatable location just 1 block from the iconic Green Parrot Bar and 2 blocks from world famous Duval Street. Blue Heav ...
From $416 per night (USD)
VRBO
From $327 per night (USD)
Expedia
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 $327 per night (USD)
Expedia
From $308 per night (USD)
VRBO
LUXURY VACATION RENTAL CONDO KEY LARGO TOP AMENITIES & VALUE in the FLORIDA KEYS
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Book your stay with us, and ‘we promise you’, you’ll experience a Wonderful Vacation in the Florida Keys. Our home is ...
From $308 per night (USD)
VRBO
$Blue Vacation Home. Ask about a free pontoon boat rental in our off season.\n$
From $572 per night (USD)
VRBO
Blue Vacation Home. Ask about a free pontoon boat rental in our off season.\n
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This vacation home has a spectacular view over Cudjoe Bay to the Atlantic from the upper deck, and from the seats in the ...
From $572 per night (USD)
VRBO
From $416 per night (USD)
VRBO
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 $416 per night (USD)
VRBO
From $556 per night (USD)
Expedia
Waterfront luxury Villa (54) with sunset views and boat slip
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse y ...
From $556 per night (USD)
Expedia
From $720 per night (USD)
VRBO
Waterfront luxury Villa (43) with spectacular sunset views and boat slip
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse y ...
From $720 per night (USD)
VRBO
$A great place to relax, fish, or even work from. 2\/2 , 66 ft$
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Expedia
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
Expedia
From $826 per night (USD)
VRBO
White Vacation Home. Private heated pool, and great view of the Atlantic Ocean.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Kayaks included with the rental. Property has a small floating dock for your boat. We have 2 other homes right next to t ...
From $826 per night (USD)
VRBO
From $585 per night (USD)
Expedia
TROPICAL PROPERTIES VACATION RENTAL - KEY WEST
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
****This property requires a minimum stay of 28 nights in the same calendar month**** ***Brand New Pool with waterfall, ...
From $585 per night (USD)
Expedia
From $581 per night (USD)
VRBO
Waterfront luxury Villa (34) with sunset views and boat slip
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse y ...
From $581 per night (USD)
VRBO
$ISLAND TIME - 5 Bed\/3 Bath OldTown Complex - MONTHLY - Private pool$
From $941 per night (USD)
Expedia
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 $941 per night (USD)
Expedia
From $731 per night (USD)
VRBO
Beautiful Waterfront Gulf of Mexico 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 $731 per night (USD)
VRBO
From $508 per night (USD)
VRBO
Yellow Vacation Home. Ask about a free pontoon boat rental in our slow season.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This vacation home is nestled far off of US 1. Kayaks included in the rental. Rent one or both of our other properties t ...
From $508 per night (USD)
VRBO
From $270 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 $270 per night (USD)
VRBO
From $267 per night (USD)
Expedia
LAMLA's Key Largo's Paradise
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
EXPERIENCE KEY LARGO LIVING 🌇 🏊‍♂️ ⛱ Perfect for a couple's retreat. Enjoy your stay in LAMLA's Key Largo's Para ...
From $267 per night (USD)
Expedia
$Tropical Jewel: Historic Seaport Oldtown - 2BR\/2BA - Pool - RealKeyWest$
From $286 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 $286 per night (USD)
VRBO
$Lazy Tortuga 2bed\/2bath updated half duplex with Cabana Club & dockage$
From $308 per night (USD)
Expedia
Lazy Tortuga 2bed\/2bath updated half duplex with Cabana Club & dockage
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Lazy Tortuga is a ground level luxurious half duplex! This property features 2 bedrooms and 2 bathrooms. The master bedr ...
From $308 per night (USD)
Expedia
From $493 per night (USD)
VRBO
MAJESTIC PARADISE II Luxury living in Truman Annex. Downtown, pool, 2 blks
Bedrooms:
3
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 $493 per night (USD)
VRBO
From $225 per night (USD)
Expedia
COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This beautiful home has 2 bedroom and 2 bath, a large Living/Dining and Kitchen area for entertaining. The Dining area ...
From $225 per night (USD)
Expedia
From $424 per night (USD)
VRBO
2 story condo with panoramic bay views and balconies!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
This is a 1,350sqft 2 bedrooms/3 bath condo with amazing unobstructed Gulf Bay views. Right next to vaca cut, sunrise an ...
From $424 per night (USD)
VRBO
From $543 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 $543 per night (USD)
Expedia
From $1410 per night (USD)
VRBO
Pirate Point, Stunning 5BR, 5BA Home with pool, tiki, doc
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
From the moment you walk up to the covered entryway at Pirate Point, you know you have arrived at your own personal isla ...
From $1410 per night (USD)
VRBO
From $294 per night (USD)
Expedia
Sirena Key Cottage in Venture Out
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
VO365 Sirena Key Cottage 35' Seawall It's a wonderful time to enjoy Paradise! Quick ocean side access to gulf a ...
From $294 per night (USD)
Expedia
From $238 per night (USD)
VRBO
Another Day in Paradise Best Waterfront and Poolside Views.
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Our Moon Bay Luxury Condominium unit # B403, 4th floor, is located directly on the scenic Blackwater Sound near Florida ...
From $238 per night (USD)
VRBO
From $1754 per night (USD)
Expedia
**JASMINE JEWEL @ THE ANNEX** Lush Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Hidden amongs ...
From $1754 per night (USD)
Expedia
From $522 per night (USD)
VRBO
Villa 5087 on Duck Key BOAT SLIP available
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Enjoy the nicest Fully Renovated Villa on Duck Key. Boat slip available for additional $100 a night. Largest boat that ...
From $522 per night (USD)
VRBO
From $605 per night (USD)
Expedia
Kelly's Kabin - Adorable Private Summerland Key Cottage
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Kelly's Kabin is a recently renovated property freshly painted in tropical blues. It's a private home without neighbors ...
From $605 per night (USD)
Expedia
$Key Colony Beach 3\/3 Townhouse - Ocean View$
Click For Pricing
VRBO
Key Colony Beach 3\/3 Townhouse - Ocean View
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Unit is in mint condition, located in prime Key Colony Beach surrounded by spectacular ocean views. All furnishings are ...
Click For Pricing
VRBO
From $374 per night (USD)
Expedia
Paradise in Beautiful Key Largo!! Amazing Views!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your dream vacation awaits you at Kawama Yacht Club! A unique gated townhome community located in the heart of Key Larg ...
From $374 per night (USD)
Expedia
Click For Pricing
VRBO
P20 - 551 8th St in Key Colony Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to the heart of the Florida Keys! Located in the very desirable Key Colony Beach, this 3 bedroom, 3 bath home is ...
Click For Pricing
VRBO
$Getaway in Key West: Tranquil Room w\/ Balcony | Resort w\/ Pool Access$
From $783 per night (USD)
VRBO
Getaway in Key West: Tranquil Room w\/ Balcony | Resort w\/ Pool Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $783 per night (USD)
VRBO
$Old Town Key West Family Retreat | Spacious Room w\/ Balcony | Parking Onsite$
From $851 per night (USD)
VRBO
Old Town Key West Family Retreat | Spacious Room w\/ Balcony | Parking Onsite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $851 per night (USD)
VRBO
From $279 per night (USD)
VRBO
Sugar Cane - Florida Keys tropical retreat. Newly renovated!
Bedrooms:
1
Bathrooms:
2
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 $279 per night (USD)
VRBO
$Absolutely Perfect! Reel Vacation Villa w\/Pool, Dock, Close to Beach w\/Extras!$
From $807 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 $807 per night (USD)
VRBO
Click For Pricing
Expedia
Cozy 2 Bedroom home in Summerland Key
Bedrooms:
1
Bathrooms:
3
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

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