Monroe Area Rentals
From $339 per night (USD)VRBO
Archipelago l at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $339 per night (USD)VRBO
From $279 per night (USD)Expedia
Penthouse Apartment Sunsets in Key Largo, Kawama Yacht Club Tower
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy the panoramic view this tropically decorated, fifth-story penthouse unit has to offer of the Atlantic Ocean and th ...
From $279 per night (USD)Expedia
From $809 per night (USD)VRBO
Duck Key Tarpon House 5 Bedroom 3 Baths Duck Key w/45 Dock and Private Pool boat lift available
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Duck Key Tarpon House Exquisite Home on Duck Key with 5 bedrooms and 3 baths with Cabrera Marble Countertops and brand ...
From $809 per night (USD)VRBO
From $843 per night (USD)Expedia
Waterfront 4 Bed Home w/Pool – Marlin Bay
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort fea ...
From $843 per night (USD)Expedia
From $614 per night (USD)VRBO
Vista Marquesa 4/3 Ground Level Home w/ Pool & 50` Dock
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Vaca-23-231 Friday to Friday Booking only( We will not honor any bookings that do not follow the Friday booking unless ...
From $614 per night (USD)VRBO
From $546 per night (USD)Expedia
Waterfront luxury Villa (21) with sunset views and boat slip
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This spacious 3-bedroom, 2.5-bath Villa blends comfort with coastal charm. Each bedroom includes its own TV, and the liv ...
From $546 per night (USD)Expedia
From $805 per night (USD)VRBO
**THE ADMIRAL'S ESTATE** Grand Home & Pool + Last Key White Glove Service...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Like many hig ...
From $805 per night (USD)VRBO
From $298 per night (USD)Expedia
Knee Deep in the Water Somewhere...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The only worry if the tide's reaching your chair! Come on in The waters nice (there's a dock for a 32' boat right out ...
From $298 per night (USD)Expedia
From $725 per night (USD)VRBO
KEY LARGO WEEKLY PARADISE HOUSE RENTAL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Private Gated Community with Direct Ocean Access home. 2 bedroom, 2 bathrooms, comfortably furnished with an open floor ...
From $725 per night (USD)VRBO
From $762 per night (USD)Expedia
Oceanfront 4-Bed 3-Bath home with pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
4 Bedroom, 3 Bathroom, Sleeps 8 Luxurious furnishings and spacious interiors centered around the expansive water views p ...
From $762 per night (USD)Expedia
From $406 per night (USD)VRBO
Pickleball & Pool Vacation at Sombrero Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Come and stay at our beautiful 3 bed/2ba home, with plenty of space to park your vacation water toys (boats, jetskis, et ...
From $406 per night (USD)VRBO
From $442 per night (USD)Expedia
Sky Loft - Steps from Duval Street & Shared Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Experience the best of Key West from Sky Loft, your perfect weekend getaway! Just one block from the iconic Du ...
From $442 per night (USD)Expedia
Click For PricingVRBO
Beautiful Beach Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to our beach house located in the heart of Islamorada. Just a short drive from the best restaurants, bars, state ...
Click For PricingVRBO
From $400 per night (USD)Expedia
Canal Front Retreat with Pool + Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The MAD MAHI is a charming waterfront condo featuring one bedroom (sleeps 4), one bathroom, a full kitchen, and a privat ...
From $400 per night (USD)Expedia
From $2946 per night (USD)VRBO
Takeover at the Grand Maloney
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
Summary: The Grand Maloney Hotel is a boutique hotel located in the heart of downtown Key West. Our signature red brick ...
From $2946 per night (USD)VRBO
From $315 per night (USD)Expedia
Key Colony Beach Paradise
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The property is a 2 bedroom, 2 bath over 1,200 square feet very open floor plan home where you can enjoy this wonderful ...
From $315 per night (USD)Expedia
From $309 per night (USD)VRBO
Key Largo gem on the water with a little slice of heaven!!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
New waterfront CBS home on a beautiful 200 ft wide basin (not a canal) with immediate access to the bay. Mature lands ...
From $309 per night (USD)VRBO
From $412 per night (USD)Expedia
Oceanfront, 2 Bedroom Unit At Ocean Pointe Condominium
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Accommodations: Condominium, 2 Bedroom, 2 Bath (Sleeps 4) This is one of the finest destinations in the Florida Keys. ...
From $412 per night (USD)Expedia
From $245 per night (USD)VRBO
Nice home on Atlantic side of Cudjoe Key!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This home would be the perfect vacation spot for a small family or a group of friends. There are plenty of fun restauran ...
From $245 per night (USD)VRBO
From $476 per night (USD)Expedia
Blue Lagoon at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This cheery property located on Southard Street features three bedrooms, one on the first level and two on on the second ...
From $476 per night (USD)Expedia
From $267 per night (USD)VRBO
Tiki Time! Private Pool~Tiki Hut~Kayak~Grill~Ocean View!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Tiki Time ~ your private paradise in beautiful Marathon, heart of the Florida Keys! This is the perfect place for a fami ...
From $267 per night (USD)VRBO
From $225 per night (USD)Expedia
50’ dock on Vaca Cut, deep wide unlimited dockage.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
One bedroom and one 1/2 baths nicely decorated. Cute and super clean. Tile floors throughout. Kitchen fully equipped. Wi ...
From $225 per night (USD)Expedia
From $379 per night (USD)VRBO
3/2 Waterfront / Private Dock / Cabana Club Pool & Beach / Kayaks / Tiki Hut 🏝.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
**IMPORTANT: RENTAL IS SATURDAY TO SATURDAY ONLY, UNLESS APPROVED BY OWNER** The Starfish House is walking distance to ...
From $379 per night (USD)VRBO
From $1698 per night (USD)Expedia
**BELLE OF THE BEACH @ CASA EAST** Beach House + Last Key White Glove Service...
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Get the gang ...
From $1698 per night (USD)Expedia
From $315 per night (USD)VRBO
Sailor's Sanctuary - A Renovated Condo in Old Town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Renovated ground floor apartment in Truman Annex. Steps from Duval Street! Enjoy all that the beautiful gated community ...
From $315 per night (USD)VRBO
From $396 per night (USD)Expedia
Luxury Condo at Ocean Front Kawama Tower Complex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy your Key Largo stay in a private gated oceanfront community. This 3rd floor 2-bed 2-bath condo boasts approx. 1350 ...
From $396 per night (USD)Expedia
From $2250 per night (USD)VRBO
Historic Old Town Key West - Main House, 4 beds, 1 Sleeper Sofa, Accommodates 8
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
OVERVIEW The 'Main House' is a two-story, four (4) bedroom, one and a half (1.5) bathroom renovated historic home. The ...
From $2250 per night (USD)VRBO
From $417 per night (USD)Expedia
Lock in summer months. For up to date availability 510-381-5000
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
A beautifully appointed home with all the amenities you will need to have an enjoyable vacation. The first thing you wil ...
From $417 per night (USD)Expedia
From $1996 per night (USD)VRBO
Features.Key West Suites Hotel has an outdoor pool and fitness center
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Key West Suites Hotel Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used ...
From $1996 per night (USD)VRBO
From $337 per night (USD)VRBO
Odisa Key Largo Vacation Home with Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Odisa Key Largo Vacation Home! Nestled in the heart of the stunning Port Largo community, this beautiful tw ...
From $337 per night (USD)VRBO
From $551 per night (USD)VRBO
Archipelago at the Truman Annex in Key West
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
This gorgeous townhouse has 4 bedrooms, 4 full Bathrooms, and 2 half bathrooms. It is unique in that it has 2 of everyt ...
From $551 per night (USD)VRBO
From $391 per night (USD)Expedia
Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This property has 2 bedrooms 2 baths and sleeps 6 with all updated appliances furniture.& wifi There are 4 single kayaks ...
From $391 per night (USD)Expedia
From $492 per night (USD)VRBO
Aqua Breeze at the Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This two bedroom condo is located in the Truman Annex, Key West's premier residential community in Harbour Place on the ...
From $492 per night (USD)VRBO
From $211 per night (USD)Expedia
Shady Nook at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This first floor 2 bedroom, 1 bath condo is a blend of Key West charm, modern comfort and unbeatable location! You'll en ...
From $211 per night (USD)Expedia
From $464 per night (USD)VRBO
Royal Poinciana >>WEEKLY RENTAL! Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
WEEKLY RENTAL - This property has the ability to be rented weekly all year long. Nestled in the heart of Old Town Key We ...
From $464 per night (USD)VRBO
From $670 per night (USD)Expedia
A Gulfstream Drift at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Imagine yourself watching the sunset over the ocean from the huge penthouse balcony. This tropical retreat in Paradise h ...
From $670 per night (USD)Expedia
From $406 per night (USD)VRBO
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
ALL NEW RENOVATIONS COMPLETED JUST FOR YOU! A perfect oasis with beautiful views all day, every day. Come enjoy your tim ...
From $406 per night (USD)VRBO
From $415 per night (USD)Expedia
Saltwater Angler at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Large corner unit with three balconies and waterfront sunset view. Oversized living room with plenty of seating includin ...
From $415 per night (USD)Expedia
From $536 per night (USD)VRBO
Island Breezes at the Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
WEEKLY RENTAL - This property has the ability to be rented weekly. This charming second floor condominium features two b ...
From $536 per night (USD)VRBO
From $212 per night (USD)Expedia
A Sanctuary Home at the Key West Golf Club in Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A Sanctuary Home - Stay on the only 18-hole golf club in the Florida Keys and enjoy the lush tropical foliage and resort ...
From $212 per night (USD)Expedia
From $567 per night (USD)VRBO
Waterfront House in the heart of Cudjoe Key.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Breathtaking sunset views! Fully stocked kitchen with all appliances you need for at home cooking. Spacious rooms with d ...
From $567 per night (USD)VRBO
From $337 per night (USD)Expedia
Ascension at the Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stepping through the white picket gate into this town home located in the gated Truman Annex community, in the heart of ...
From $337 per night (USD)Expedia
From $355 per night (USD)VRBO
DANCING PALMS @ The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Come stay at this bright and airy 2 bedroom, 2 full bath town home in the renowned Truman Annex in Old Town. Convenientl ...
From $355 per night (USD)VRBO
From $566 per night (USD)Expedia
4 Bedroom 3 Full Bath Home on Canal in Marathon w/Private 35 foot dock
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
4 Bedroom 3 Full Bath Home on the Canal in Marathon, a 15 minute boat ride to the ocean. Private Heated Pool. Private 35 ...
From $566 per night (USD)Expedia
From $482 per night (USD)VRBO
Ocean Breeze at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Gorgeous open water views from this 2-bedroom, 2.5 bath condominium in Harbour Place in the award-winning Truman Annex! ...
From $482 per night (USD)VRBO
From $360 per night (USD)Expedia
Sago Palm at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $360 per night (USD)Expedia
From $605 per night (USD)VRBO
Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
This modern and beautifully decorated vacation rental is the perfect spot for your next family vacation or couples` geta ...
From $605 per night (USD)VRBO
From $278 per night (USD)Expedia
Dock, Pool, FREE RAMP, Kayaks, Jacuzzi, Amazing Ocean Views Pets are Welcomed!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to this beautiful, newly constructed vacation home in Marathon, Florida. With its modern design and a newly inst ...
From $278 per night (USD)Expedia
From $401 per night (USD)VRBO
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for compute ...
From $401 per night (USD)VRBO
From $327 per night (USD)Expedia
Sunrise Suite with Unobstructed Ocean Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Enjoy the ultimate Florida Keys getaway at Ocean Pointe 4315, a stunning oceanfront condo in Tavernier. Wake u ...
From $327 per night (USD)Expedia
From $513 per night (USD)VRBO
Key largo Kawama Villa N2
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Relax and enjoy our family friendly 3 bedroom/3 bathroom Villa Lago in Key Largo! Salt water swimming lagoon, Pools, the ...
From $513 per night (USD)VRBO
From $334 per night (USD)Expedia
Hidden gem in Key Largo, bunk room, outdoor kitchen, 2 pools, laundry, 2 beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This hidden gem is anything but ordinary! Come enjoy a piece of paradise in Key Largo while you relax in this spacious N ...
From $334 per night (USD)Expedia
From $486 per night (USD)VRBO
Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Boat slip available for additional $100 a night. Ask for availability. This villa boasts breathtaking sunsets, close t ...
From $486 per night (USD)VRBO
From $649 per night (USD)VRBO
Come stay in an amazing house close to everything! Duvall! North Seaport!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
We love this home, and we just know you will too!! A fully renovated conch home with amazing finishes and 3 great bedro ...
From $649 per night (USD)VRBO
From $239 per night (USD)VRBO
New House Paradise Without a Pasport On Atlantic Ocean Deck Sunsets Water Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Brand New Home, Brand New Furniture, Sunset and Ocean Views, Outdoor communal Fire Pits, Outdoor Kitchen, Grill, Possib ...
From $239 per night (USD)VRBO
From $680 per night (USD)Expedia
~ SOLARIS PAIR-A-DISE ~ A garden lover’s dream on a quiet Key West lane.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
THE PROPERTY: If you are looking for that tropical island vibe, look no further! Both sections of this casual home are ...
From $680 per night (USD)Expedia
From $314 per night (USD)VRBO
Waterfront Luxury Home with Private Dock, Pool & Ramp
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
About the property *** CONTACT ME DIRECTLY FOR SPECIAL RATES ON DATES YOU MAY BE INTERESTED IN. ASK FOR TANIA at 786-486 ...
From $314 per night (USD)VRBO
Click For PricingVRBO
Big Pine Latitude Adjustment
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: Welcome to Big Pine Latitude Adjustment, a beautifully remodeled 5-bedroom, 3-bath waterfront retreat for up t ...
Click For PricingVRBO
From $253 per night (USD)VRBO
Camp Mango | 2 bed/2 bath condo w/dockage, pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Camp Mango: 2 bed/2 bath condo w/ boat slip & community pool The Space: Camp Mango is a relaxed, ground-fl ...
From $253 per night (USD)VRBO
From $661 per night (USD)Expedia
Boli Townhouse - Luxury WEEKLY Rental in gated Truman Annex-Saturday to Saturday
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Boli Townhouse is an extraordinary WEEKLY rental property that you will enjoy with only a short walk to Old Town and the ...
From $661 per night (USD)Expedia
From $747 per night (USD)VRBO
**DARLING OF DUVAL @ OLD TOWN** Cottage + Spa + Last Key White Glove Service...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Don't miss an ...
From $747 per night (USD)VRBO
From $471 per night (USD)Expedia
Fish, Swim, Relax, Party - 4bd, 3ba - 75’ Dockage & Private POOL!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
DOWNSTAIRS NOW AVAILABLE! Our 4/3 Beautiful Two Story Home is in Marathon Fl. Located in the middle of the Florida Keys ...
From $471 per night (USD)Expedia
From $273 per night (USD)VRBO
The Garden Villa – Cozy 1BR Ground-Level Half Duplex with Private Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The Garden Villa is a stunning 1bed/1bath unit with its own private pool. This unit has fresh paint, all new furniture a ...
From $273 per night (USD)VRBO
From $404 per night (USD)Expedia
Tropical Breezes is a spacious 3bed/2bath half duplex in desirable Key Colony Beach with dockage & Cabana Club access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Tropical Breezes is a spacious 3bed/2bath beautifully decorated half duplex in desirable Key Colony Beach. There is a br ...
From $404 per night (USD)Expedia
From $1156 per night (USD)VRBO
OCEANFRONT POOL HOUSE WITH 5 BEDROOM 3 BATH, SLEEPS 12 GUESTS.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Breathtaking sunset views from this open water home. Large dock with room for two large boats. Every night a unique su ...
From $1156 per night (USD)VRBO
From $493 per night (USD)Expedia
2405 Ocean Pointe Suites
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This lovely 2-bedroom oceanview condo in Ocean Pointe Resort is a delight! Located on the 4th floor allows the guest to ...
From $493 per night (USD)Expedia
From $219 per night (USD)VRBO
Newly Remodeled Corner House on the Water
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
There’s no better place to experience the laid-back calm of the Florida Keys than this bright and newly-remodeled two-be ...
From $219 per night (USD)VRBO
From $754 per night (USD)Expedia
Two Bedroom Two Bath Balcony Villa Steps from Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Two Bedroom Balcony Villa is a gracious two story Key West rental decorated in a tropical style with a living room, ...
From $754 per night (USD)Expedia
From $822 per night (USD)VRBO
VILLA BELLA - AN EXCEPTIONAL 5/4 ISLAND HOME-Convenient to Old Town
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
29 Night Minimum Stay Required. This beautiful island retreat is secluded away on a quiet Old Town lane and features 5 l ...
From $822 per night (USD)VRBO
From $417 per night (USD)Expedia
Sunshine and Sandbars Waterfront Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Experience the ultimate island getaway at Ocean Pointe 2302, a charming Tavernier condominium. Perfectly situa ...
From $417 per night (USD)Expedia
From $352 per night (USD)VRBO
Beautiful Ocean view with 35' private seawall, 80' Heated Pool, Hottub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Gorgeous stilt home with beautiful ocean views. This Lobstering paradise is just 1 house down from open water on a deep ...
From $352 per night (USD)VRBO
From $554 per night (USD)Expedia
TOWNHOUSE FL KEYS ON ATLANTIC, MARINA, PICKLEBALL, TENNIS, POOLS, BIKES, KAYAKS
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
3 bedrooms and 3 full bathrooms townhome. Full bathroom on each floor and 2 separate living rooms to accommodate large f ...
From $554 per night (USD)Expedia
From $760 per night (USD)VRBO
Two Bedroom Two Bath Poolside Villa Steps from Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We have the perfect accommodation for a family vacation or friends getaway in Old Town Key West, Florida. Our Two-Bedroo ...
From $760 per night (USD)VRBO
From $227 per night (USD)Expedia
Our Happy Place on the BEACH!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Our Happy Place – Your Perfect Beachfront Escape! If you’re looking for a serene getaway just 100 steps from ...
From $227 per night (USD)Expedia
From $397 per night (USD)VRBO
3 Story Waterfront House with a pool and Beautiful Views!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
***NEW POOL***29 DAYS MINIMUM STAY. Bring your boat (20,000 Lbs. boat lift). This is a family-friendly Home. Equipped wi ...
From $397 per night (USD)VRBO
From $345 per night (USD)Expedia
RITA'S PARADISE 37.5' DOCK-ICE MAKER-Cabana Club-TIKI HUT-Screen Porch-Bait Frez
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Perfect home for a Family Gathering, or Extended Family Get Together. Snowbirds welcomed at request dates R ...
From $345 per night (USD)Expedia
From $344 per night (USD)VRBO
Deja Blue Oceanfront Condo- 2 Lanais, Pool + Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Come enjoy a relaxing stay at this peaceful oceanfront condominium in Tavernier. Set on sixty private acres, o ...
From $344 per night (USD)VRBO
From $509 per night (USD)Expedia
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
*ALL NEW AND A PERFECT LOCATION! 35' Seawall *Magnificent newly renovated 2 bedroom 1 bath waterfront home in Cudjoe Key ...
From $509 per night (USD)Expedia
From $278 per night (USD)VRBO
Sea Glass Beach Bungalow in Key Colony Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to Sea Glass Beach Bungalow! What made us first fall in love with the Florida Keys was the captivating blue/gree ...
From $278 per night (USD)VRBO
From $1081 per night (USD)Expedia
Waterfront 4 Bed 4 Bath Home in Key Cove Landings
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $1081 per night (USD)Expedia
From $344 per night (USD)VRBO
Perfect Location+Beautiful Ocean Views+Pool & Bar
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Our spacious and well-appointed condo provides the perfect home away from home. Step onto your private balcony ...
From $344 per night (USD)VRBO
From $336 per night (USD)Expedia
Golf Villa - Indulge Without Overpaying - 2BD/2Bath - Large Open Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Golf Villa, your perfect Key West getaway in the highly sought-after Key West Golf Club neighborhood! Immerse ...
From $336 per night (USD)Expedia
Click For PricingVRBO
Sweet Caroline Historic Seaport Key West Home Rental Floor 1
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The unit located on the first floor has three-dimensional ceilings throughout with indirect LED lighting. The kitchen is ...
Click For PricingVRBO
From $394 per night (USD)Expedia
Paradise Getaway Flamingo Island, Marathon
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
If you want to experience the true meaning of a Florida Keys Island Vacation then look no further than our spacious and ...
From $394 per night (USD)Expedia
From $432 per night (USD)VRBO
Peacock Shores Islamorada - Vacation On The Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The ocean is your front yard at this modern, luxurious townhome hidden away in a small, private seaside community. Enjoy ...
From $432 per night (USD)VRBO
From $551 per night (USD)Expedia
Boaters Delight! Great Location! Fair Price!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
If you are looking for a tropical Keyz experience, you have arrived in paradise at this three bedroom two bathroom home ...
From $551 per night (USD)Expedia
From $213 per night (USD)VRBO
R & K’s Marathon Paradise 2/2 Duplex w/35` Dock & Cabana Club Included
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Vaca-21-501 R & K’s Marathon Paradise 7 Day Minimum Rental Saturday to Saturday booking only Unless prior agent appro ...
From $213 per night (USD)VRBO
From $331 per night (USD)Expedia
Yellow 3 Story Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Brand new oceanside yellow 3 story home located in "Key Largo Ocean Resort". This home has 4 bedrooms which include 3 qu ...
From $331 per night (USD)Expedia
From $328 per night (USD)VRBO
Sea Breeze at 1800 Atlantic
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Sea Breeze at 1800 Atlantic — Your Luxurious Oceanfront Escape in Key West Discover the ultimate blend of co ...
From $328 per night (USD)VRBO
From $456 per night (USD)Expedia
P77 - Sombrero Beach - Pool home offering 3 bedrooms, private pool and deep water dockage!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This updated 3 bedroom, 2 bath single family home is ideally located in the heart of Sombrero Beach and is an easy 7 min ...
From $456 per night (USD)Expedia
From $529 per night (USD)VRBO
NEW POOL ** Waterfront Paradise with Amazing Sunsets on Beach**
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
The house is perfect for those traveling with different age groups, in-laws, teenagers or 2 families. The house is extra ...
From $529 per night (USD)VRBO
From $716 per night (USD)Expedia
203 Mariners Club - This tri-level townhouse boasts 4 bedrooms and 3 baths
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Got gear? If so, then this is the end of your search for the perfect Key Largo vacation rental! Hard-to-find, 4-bedroo ...
From $716 per night (USD)Expedia
From $575 per night (USD)VRBO
P98 - 75ft dock with shore power, 4 bed, 4 bath home w/private pool in Sombrero Beach Neighborhood.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This fabulous 4 bedroom, 4.5 bathroom home was designed and built for comfort and style with extra attention given to ea ...
From $575 per night (USD)VRBO
From $326 per night (USD)Expedia
Breathtaking Ocean views! Owners who care. “Sangria Sunrise”! 10% off charters!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
We would like to cordially invite you to our vacation home, Sangria Sunrise! SangriaSunriseVacations@gmail. com Our co ...
From $326 per night (USD)Expedia
From $249 per night (USD)VRBO
Coastal Charm: 2BR Condo, Patio, Pool Views, Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Coastal Charm, your serene seaside retreat located in Marathon, Florida! This charming condo offers 2 bedroom ...
From $249 per night (USD)VRBO
From $331 per night (USD)Expedia
Bird of Paradise: 3BR Condo, Atlantic Views, Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This charming property offers 3 bedrooms and 2 bathrooms, ideal for families or groups looking to enjoy the beauty and t ...
From $331 per night (USD)Expedia
From $524 per night (USD)VRBO
Caribbean Sunsets: 3BR Home Gulf Views Pool & Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Property Overview: Prime Location: Caribbean Sunsets is nestled in a quiet and picturesque neighborhood, offering breat ...
From $524 per night (USD)VRBO
From $433 per night (USD)Expedia
Oct. Cancellation Deals: 10/17 thru 10/31
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
2026 - New eco-friendly pool resurface completed This ground level waterfront home has received a new face lift. Comple ...
From $433 per night (USD)Expedia
From $588 per night (USD)VRBO
Tropical: 4BR Luxury Home Gulf Views Pool and Dock
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Tropical Sunsets, your tropical oasis in the heart of Marathon, Florida! This stunning 4-bedroom, 3-bathroom ...
From $588 per night (USD)VRBO
From $987 per night (USD)Expedia
Casa Rosa: 4BR/4BA house, pool, near Duval
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Casa Rosa, your tropical sanctuary nestled in the vibrant heart of Key West, Florida. *Saturday-to-Saturday ...
From $987 per night (USD)Expedia