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Florida Keys Rentals

From $263 per night (USD)
VRBO
Ocean Point Retreat ~ Immaculate Ocean Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Private Beach, Fishing Pier, Fish Cleaning Station, Jr. Olympic pool, Spa, Pickleball Court, BBQ grills, nature ...
From $263 per night (USD)
VRBO
From $250 per night (USD)
Expedia
Coo Coo's Nest ~ Key Largo canal front 2/3 with pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Beautiful pool home with dockage in the heart of Key Largo! The Space: Step into the enchanting Coo Coo's Nest ...
From $250 per night (USD)
Expedia
From $350 per night (USD)
VRBO
New pool & Huge master suite! Open water views , 2 stories of wrap around decks
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Captivating views from sunrise to sunset overlooking expansive salt ponds and open water from this newly renovated 2-sto ...
From $350 per night (USD)
VRBO
From $163 per night (USD)
Expedia
New Tiny House RV, Kayak, Beach, Marina, Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Camper RV at Key Largo Kampground and Marina Resort W/ 24 hour security. 1 Queen Bed, 1 Pull out Sofa, Single bed in Lof ...
From $163 per night (USD)
Expedia
From $266 per night (USD)
VRBO
Light, Bright & Nautical Condo - 5 min to Local Attractions [Ocean Pointe 1211]
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy our beautifully designed oceanfront condo in Key Largo, nestled beside a tropical mangrove forest. The condo offer ...
From $266 per night (USD)
VRBO
From $374 per night (USD)
VRBO
Amazing Beach! Near John Pennekamp National Marine Sanctuary, 2 Outdoor Pools!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stretch out and settle into our Resort View Junior Suite, featuring a private bedroom with a king bed and a separate liv ...
From $374 per night (USD)
VRBO
From $483 per night (USD)
VRBO
Ohana Cay 4 bed & 4 bath Unit 906 @Mariners Club - Sleeps 10!!
Bedrooms:
1
Bathrooms:
4
Sleeps:
10
Welcome to our island oasis, Ohana Cay! We would love to welcome you to our recently updated four bedroom/four bathroom ...
From $483 per night (USD)
VRBO
From $293 per night (USD)
VRBO
Vacation home in Paradise
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
AWESOME View of the Bay- from Chickee Hut Dock to Full Roof Top Patio. 2 Story. Large Master Bedroom with Steam Shower. ...
From $293 per night (USD)
VRBO
From $520 per night (USD)
VRBO
**CARIBBEAN CHARM @ THE FOUNDRY** Villa Near Duval & Beach + 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! The sound of ...
From $520 per night (USD)
VRBO
From $538 per night (USD)
Expedia
P03 - Charming 4 bedroom home with pool and dock.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This beautiful home is located in the quiet and very desirable Coco Plum neighborhood, a few minutes' walk to the beach. ...
From $538 per night (USD)
Expedia
From $309 per night (USD)
VRBO
P41 - Beach Front condo with 2 bedrooms, 2 bath, pool and tennis courts!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Condo overlooking the natural beach of Coco Plum. This 2 bedroom, 2 bath congo unit offers 1,280 sq feet of living space ...
From $309 per night (USD)
VRBO
From $456 per night (USD)
Expedia
P78 - Charming beach home just down the road from Sombrero Beach. 3 bedroom 2...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This 3 bedroom, 2 bath single family home is ideally located in the heart of Sombrero Beach and is an easy 7 minute walk ...
From $456 per night (USD)
Expedia
From $456 per night (USD)
VRBO
P27 - Private Beach Access! Pool home with everything you need for an...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This beautiful 3 bedroom, 2 bath home located in the very desirable Key Colony Beach, boasts a large open floor plan, pr ...
From $456 per night (USD)
VRBO
From $269 per night (USD)
Expedia
P29 - Charming 3 bedroom 2 bath duplex with deep water dockage and Cabana...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Key Colony at its most charming! This 3 bedroom, 2 bathroom, half duplex is located in the heart of Marathon in Key Colo ...
From $269 per night (USD)
Expedia
From $442 per night (USD)
VRBO
P67 - New Construction 3 bedroom 4 bath with private pool, dock and beach...
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
This lovely two story duplex offers 3 bedroom, 4 bathrooms and abundant living space on both levels. The lower level off ...
From $442 per night (USD)
VRBO
From $316 per night (USD)
Expedia
P22 - Updated 3 bedroom 2 bath duplex with private pool and deep water dockage.
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This lovely 3 bedroom, 2 bath home located on Sixth Street (The Causeway) and boasts a private fenced yard and private h ...
From $316 per night (USD)
Expedia
From $367 per night (USD)
VRBO
P17 - Charming 3 Bedroom 2 Bath Duplex With Private Pool And Deep Water...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Paradise found in the tropical city of Key Colony Beach! This all ground level home has ease of access inside and out, b ...
From $367 per night (USD)
VRBO
From $321 per night (USD)
Expedia
P42 - Gulf Front condo with 3 bedrooms 2.5 baths, pool and dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located in the beautiful gated community of Indigo Reef! This 3 bedroom, 2 1/2 bath townhouse boasts plent ...
From $321 per night (USD)
Expedia
From $339 per night (USD)
VRBO
P62 - 3 Bedroom 2 bath, private pool and beach membership
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful duplex in Key Colony Beach with private fenced yard and private heat optional pool. Three bedroom, two bath ho ...
From $339 per night (USD)
VRBO
From $651 per night (USD)
Expedia
P12 - Single Family, Direct Ocean Front home with private pool and dockage. 3...
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This 3 bedroom, 2.5 bath home boasts a beautiful open floor plan with "Keys-style" charm and appeal. As an all ground le ...
From $651 per night (USD)
Expedia
From $492 per night (USD)
VRBO
P34 - Beautiful 4 bedroom 2 bath, single family home with private pool and...
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Beautiful and spacious 4 bedroom, 2 bathroom, private pool home in the desirable Key Colony Beach neighborhood located n ...
From $492 per night (USD)
VRBO
Click For Pricing
Expedia
P74 - Direct Ocean Front, 4 bedroom home near 7-Mile Bridge
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This spacious 4 bedroom, 3 bathroom, open waterfront home is located at the south end of Marathon. With this homes ...
Click For Pricing
Expedia
From $331 per night (USD)
VRBO
P51 - 2 bedroom 2 bath, single family pool home with dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This 2 bedroom, 2 bath home has been beautifully updated inside and out. Located oceanside, canal front in Marathon, the ...
From $331 per night (USD)
VRBO
From $960 per night (USD)
Expedia
P05 - 5 bedroom Ocean Front home with Private pool and deep water dockage.
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
This custom designed Mediterranean style home is nothing less than exquisite! Located in very desirable Key Colony Beach ...
From $960 per night (USD)
Expedia
From $621 per night (USD)
VRBO
P28 - Luxury 4 bedroom, single family home with pool and dock in Key Colony...
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This all ground level 4 bedroom, 3 bath, single family home is located in desirable Key Colony Beach. This home offers a ...
From $621 per night (USD)
VRBO
From $274 per night (USD)
Expedia
P21 - Charming 3 bedroom 3.5 bath duplex in Key Colony. Offers deep water...
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This beautiful 3 bedroom, 3.5 bath duplex is located in Key Colony Beach. This home comes with access to The Cabana Club ...
From $274 per night (USD)
Expedia
Click For Pricing
VRBO
P50 - Beautiful 3 bedroom single home with zero entry pool and deep water...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy the Florida Keys in this lovely 3 bedroom 2 bath canal home with private pool, located minutes from Sombrero Beach ...
Click For Pricing
VRBO
From $534 per night (USD)
Expedia
P02 - 5 bed, 3.5 bath home with large private pool in Sombrero Beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
This 5 bedroom, 3-1/2 bath home is located in the Sombrero Beach neighborhood! Beautiful hardwood floors, tall ceilings, ...
From $534 per night (USD)
Expedia
From $423 per night (USD)
VRBO
P53 - Gulf Side 3 bedroom, single family home with pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
3 bedrooms and 2 bathrooms with heat optional pool in the heart of Marathon. Great boating location near the Vaca Cut Br ...
From $423 per night (USD)
VRBO
From $307 per night (USD)
Expedia
P10 - Charming 2 bedroom, 2 bath duplex with private pool and deep water...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This lovely 2 bedroom, 2 bath home is located on the gulf side with immediate Gulf water access and near the Vaca Cut fo ...
From $307 per night (USD)
Expedia
From $317 per night (USD)
VRBO
P72 - Charming 4 bedroom, 2 bath duplex with deep water dockage and Cabana...
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Beautiful 4 Bedroom, 2 bathroom duplex in Key Colony Beach. Key Colony Beach is a small, friendly, walkable island with ...
From $317 per night (USD)
VRBO
From $847 per night (USD)
Expedia
P00 - 4 Bedroom Pool Home overlooking Sombrero Beach!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This beautiful 4 bedroom, 4 bath family home is located in the very desirable area of Sombrero Beach and is directly acr ...
From $847 per night (USD)
Expedia
From $419 per night (USD)
VRBO
By The Sea ~ Islamorada Home with Ocean Views!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Canal front 2/2 with ocean views and relaxing breezes! The Space: This canal front two bedroom two bathroom ho ...
From $419 per night (USD)
VRBO
From $301 per night (USD)
Expedia
Latitude Adjustment: Renovated 2 Bed/2 Bath Half Duplex with Dock Access and
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Latitude Adjustment is a ground-level, updated half duplex featuring 2 bedrooms and 2 bathrooms. The master bedroom offe ...
From $301 per night (USD)
Expedia
From $279 per night (USD)
VRBO
P49 - Charming 2 bedroom, single family home just a short walk to the beach.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This charming all ground level, 2 bedroom, 2 bath home is walking distance to Sombrero Beach. This truly makes you feel ...
From $279 per night (USD)
VRBO
From $507 per night (USD)
Expedia
P43 - Updated 3 bedroom 3 bath home with Pool in the Sombrero Beach Area
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This tropical pool home offers everything you need for a perfect Florida Keys vacation! This home has been completely up ...
From $507 per night (USD)
Expedia
From $616 per night (USD)
VRBO
Big Kahuna: 5BR/4BA, Private Pool, Dock, Beach Proximity & More!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Welcome to the Big Kahuna – an expansive and inviting 5-bedroom, 4-bathroom single-family haven that encapsulates the es ...
From $616 per night (USD)
VRBO
From $481 per night (USD)
Expedia
P33 - Charming 4 bedroom house with pool and a short walk to the beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This charming 4 bedroom, 3 bathroom home has it all! Located in the very desirable neighborhood of Sombrero Beach ...
From $481 per night (USD)
Expedia
From $671 per night (USD)
VRBO
P58 - Gulf Front Luxury 4 bedroom 4 bath with private pool and deep water...
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This beautiful Polynesian style home offers 4 bedrooms, 4 baths, beautifully landscaped grounds and a large, private, he ...
From $671 per night (USD)
VRBO
From $722 per night (USD)
Expedia
Swept Away: 3-Bed/2-Bath Oasis with Open Water Views, Private Pool & Dockage
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
"Swept Away," an exquisite and newly crafted luxury single-family residence boasting three bedrooms and two bathrooms. T ...
From $722 per night (USD)
Expedia
From $510 per night (USD)
VRBO
Fisherman's dream!!, Privacy, Heated Pool,Hot Tub, 50' Dockage, Tiki, pets ok,
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
copy and paste following URL link for a virtual tour of the property........with 360 walk around of the property... ...
From $510 per night (USD)
VRBO
From $5067 per night (USD)
Expedia
**ALL TOGETHER NOW @ OLD TOWN** Three Homes & Pools + LAST KEY SERVICES…
Bedrooms:
14
Bathrooms:
13
Sleeps:
32
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Coordinating ...
From $5067 per night (USD)
Expedia
From $195 per night (USD)
Expedia
*Paradise Found* Key Largo Townhouse w/ Private Boat Slip
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to Key Largo, FL. a destination, not a vacation. Known as the chameleon of the Keys, Key Largo is the preferre ...
From $195 per night (USD)
Expedia
From $714 per night (USD)
Expedia
Fabulous Canal Front Villa, Private Pool in KCB!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
The Blue Turtle Villa, located in Key Colony Beach, in the Marathon area, is a gorgeous, brand new, designer decorated c ...
From $714 per night (USD)
Expedia
From $432 per night (USD)
VRBO
Waterfront luxury Villa (14) with spectacular sunset views and boat slip
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This spacious 3BD, 2.5BA Villa is the perfect blend of comfort and coastal charm. Each bedroom features its own televisi ...
From $432 per night (USD)
VRBO
From $288 per night (USD)
Expedia
Ocean View Condo is a Fisherman's Paradise in Islamorada
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This spacious two bedroom, two bath condominium overlooking the ocean is located on a quiet 12 acre private gated commun ...
From $288 per night (USD)
Expedia
From $1232 per night (USD)
VRBO
**MAYA’S SECRET TREASURE @ DUVAL** Private Pool & Balcony over Duval + LAST KEY
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Walking along ...
From $1232 per night (USD)
VRBO
From $1663 per night (USD)
Expedia
Balcony on Duval - Duval's Duet on Duval
Bedrooms:
2
Bathrooms:
4
Sleeps:
16
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! Duval's ...
From $1663 per night (USD)
Expedia
From $398 per night (USD)
VRBO
Anglers Reef Islamorada - 2:2.5, Marina, Pool, Beach.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
- VR#258 - Saturday check-in. 2 bedroom and 2.5 bath at 117 Anglers Way. Awesome family get-a-away in beautiful Islamor ...
From $398 per night (USD)
VRBO
From $463 per night (USD)
Expedia
Dog-Friendly Home on the Water w/ Dock, Boat Access, Private Pool, & Free WiFi
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Marathon Magic Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $463 per night (USD)
Expedia
From $810 per night (USD)
VRBO
Waterfront Private Home-7 BR, 6 Full BA, Pool, 80' Dock, Parking, Screened Porch
Bedrooms:
6
Bathrooms:
7
Sleeps:
16
Welcome to 'Sombrero Sunset House' located in the heart of Sombrero Beach in Marathon, Florida! This prime waterfront ...
From $810 per night (USD)
VRBO
From $321 per night (USD)
Expedia
Mini lobster available! Open Water View from porch , dock, bikes, kayaks
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
This beautifully furnished, very clean, well-stocked modern house is located in Venture Out, a private residential commu ...
From $321 per night (USD)
Expedia
From $471 per night (USD)
VRBO
122 Mariners Club Key Largo | 2 Bed, 2.5 Bath
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Imagine yourself in this luxury, immaculately maintained two-bedroom, two and one-half bath, 2nd-floor villa with a brea ...
From $471 per night (USD)
VRBO
From $378 per night (USD)
Expedia
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Ocean Pointe Suites in Key Largo is an all-suite resort located directly on the Atlantic Ocean. Our 60 acres in the Flor ...
From $378 per night (USD)
Expedia
Click For Pricing
VRBO
Time share week in a tropical paradise! Jan 31 - Feb 7
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
My loss is your gain. We can't go this year but that means you can! We are unable to visit this year so I'd like to off ...
Click For Pricing
VRBO
From $301 per night (USD)
Expedia
Old Town home a short walk to Duval/Couples Oasis
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Add this listing to your wishlist by clicking the ♥ in the upper right hand corner. This 1 bedroom/1.5 bathroom ...
From $301 per night (USD)
Expedia
From $253 per night (USD)
VRBO
Relaxing island home/Great location/Stylish
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Only 4 short blocks to Duval, this 1 bedroom/1.5 bathroom home is walking distance to your favorite Key West sp ...
From $253 per night (USD)
VRBO
From $761 per night (USD)
Expedia
5 STAR yet low rates. 3 BR + 1 BR cottage, private pool, close to Duval.
Bedrooms:
0
Bathrooms:
4
Sleeps:
8
Our calendar is updated in real time and our rates are accurately displayed. You can book instantly without waiting for ...
From $761 per night (USD)
Expedia
From $723 per night (USD)
VRBO
Oceanfront 4 bedroom House, Pool and Deep Water Pier!!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Wow! Mesmerizing views, outstanding location, directly on the Atlantic Ocean, so close to the Ocean that you can practic ...
From $723 per night (USD)
VRBO
From $488 per night (USD)
Expedia
SPACIOUS 4/3.5 VILLA! INDOOR PICKLEBALL! MOST UPSCALE OCEANFRONT RESORT IN KL!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Ree ...
From $488 per night (USD)
Expedia
From $1762 per night (USD)
VRBO
La Palma Verde 4bed/4 bath with pool and dockage plus 2 kayaks
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Vaca-21-69 Gorgeous Home in the heart of Marathon! Located in a 4-home gated community, La Palma Verde (The Green Palm) ...
From $1762 per night (USD)
VRBO
From $336 per night (USD)
Expedia
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
SULTRY GARDEN SANCTUARY... Steal away from reality and find your way to the quintessential, tropical & adults only Trave ...
From $336 per night (USD)
Expedia
From $352 per night (USD)
VRBO
COCONUT PALM SUITE ~ Adult Only, 1 BR, 1 Ba w/ Kitchen & Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
BOTANICAL MAGIC AWAITS YOU... Only three blocks from all of the fine dining and entertainment of Duval Street, yet tucke ...
From $352 per night (USD)
VRBO
From $422 per night (USD)
Expedia
Charming Islamorada Villa in Gated Anglers Reef – Pool & Kayaks
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
*Boat Slip Available: July 12-25, August 1-9, October 2-9 Keezy Does It – Anglers Reef, Islamorada Escape to paradise ...
From $422 per night (USD)
Expedia
From $576 per night (USD)
VRBO
Beautiful 4 Bedroom/3 Bath Home w/Private Pool,40 ft. Dock near Sombrero Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
New 4 Bedroom/3 Bath Family Home with private pool and 40ft dock near Sombrero Beach, shopping & dining! This spacious ...
From $576 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 $250 per night (USD)
VRBO
Charming 'Boho Breeze' Retreat w/ Pool Access
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Experience crystal clear waters, picturesque beaches, and famous historic sites with a stay at 'Boho Breeze!' This 2-bed ...
From $250 per night (USD)
VRBO
From $336 per night (USD)
Expedia
ROYAL PALM SUITE ~ Adult Only, 1 BR, 1 Ba w/ Kitchen and Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
ESCAPE TO A BOTANICAL HIDEAWAY... Immerse yourself at the charming adults only Travelers Palm Inn with unique suites and ...
From $336 per night (USD)
Expedia
From $580 per night (USD)
VRBO
ISLAND OASIS in the Truman Annex
Bedrooms:
2
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 $580 per night (USD)
VRBO
From $245 per night (USD)
Expedia
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 $245 per night (USD)
Expedia
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 Pricing
VRBO
From $442 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 $442 per night (USD)
Expedia
Click For Pricing
VRBO
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 Pricing
VRBO
Click For Pricing
Expedia
Conch Cottage | 'Old Town' Home w/ Shared Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Escape to this charming Key West cottage, the perfect home base for your island getaway. Whether you relax by t ...
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Expedia
From $435 per night (USD)
VRBO
~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 $435 per night (USD)
VRBO
From $1003 per night (USD)
Expedia
P44 - 4 bed, 3 bath estate home with Southern Charm and private pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This estate style home is breathtaking! Built in beautiful southern tradition, this home does not disappoint with 4 bedr ...
From $1003 per night (USD)
Expedia
From $518 per night (USD)
VRBO
203 Sombrero- 4 Bedroom/3 Bath Attached Villa w/ Private Boat Dock
Bedrooms:
3
Bathrooms:
4
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 $518 per night (USD)
VRBO
From $388 per night (USD)
Expedia
Stay near Jimmy Johnson’s Big Chill – just a 18-min stroll away
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Escape to the stunning shores of Key Largo and experience the ultimate island getaway at our 2-bedroom condo. Nestled ju ...
From $388 per night (USD)
Expedia
From $847 per night (USD)
VRBO
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 $847 per night (USD)
VRBO
From $146 per night (USD)
Expedia
NEW MONTHLY RENTAL, Old Town Duplex, SUMMER DEALS, private backyard, pets welcom
Bedrooms:
2
Bathrooms:
2
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 $146 per night (USD)
Expedia
From $692 per night (USD)
VRBO
Enjoy Old Town Key West in this Beautifully furnished house
Bedrooms:
2
Bathrooms:
2
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 $450 per night (USD)
Expedia
4 Bedroom,4 Bath with private pool and 37 and 1/2 foot boat dock
Bedrooms:
2
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 $450 per night (USD)
Expedia
From $331 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 $331 per night (USD)
VRBO
From $447 per night (USD)
Expedia
Rx: Paradise 2bed/2.5bath updated open water condo with shared pool & dockage
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Indulge in the mesmerizing beauty of colorful sunsets during your vacation in this recently renovated property! Unwind o ...
From $447 per night (USD)
Expedia
From $328 per night (USD)
VRBO
Yellow Room at the Grand Maloney
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 $328 per night (USD)
VRBO
From $334 per night (USD)
Expedia
Blue Room at the Grand Maloney
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 $334 per night (USD)
Expedia
From $422 per night (USD)
VRBO
Green Room at the Grand Maloney
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 $422 per night (USD)
VRBO
From $594 per night (USD)
Expedia
SPECTACULAR Indigo Reef Waterfront Home #41 - Marathon, Florida
Bedrooms:
2
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 $594 per night (USD)
Expedia
From $498 per night (USD)
VRBO
Angler`s Retreat: Updated 3-Bed/2-Bath Home with Dockage
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy the Florida Keys in this beautifully updated 3-bedroom, 2-bath home just minutes from Sombrero Beach! The fully eq ...
From $498 per night (USD)
VRBO
From $443 per night (USD)
Expedia
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks, SUPs, Washer,Dryer!
Bedrooms:
2
Bathrooms:
2
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 $443 per night (USD)
Expedia
From $378 per night (USD)
VRBO
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 $378 per night (USD)
VRBO
From $314 per night (USD)
Expedia
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 $314 per night (USD)
Expedia
From $379 per night (USD)
VRBO
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 $379 per night (USD)
VRBO
From $291 per night (USD)
Expedia
Keys Life at Ocean Pointe, Pool, Jacuzzi, Beach, Gated Resort, Baby Friendly !!
Bedrooms:
1
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 $291 per night (USD)
Expedia
From $575 per night (USD)
VRBO
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 $575 per night (USD)
VRBO
From $172 per night (USD)
Expedia
The Hideaway: Lose Yourself At This Recently Decorated Canal Front Home on Big Torch Key, Dockage!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $172 per night (USD)
Expedia
From $264 per night (USD)
VRBO
Ocean Jewel 1bed/1bath updated condo with pool access, tiki bar & more!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
"Ocean Jewel" is a beautifully decorated one bedroom & one bath condo in a resort style setting with some resort ameniti ...
From $264 per night (USD)
VRBO
From $583 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 $583 per night (USD)
Expedia
From $233 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 $233 per night (USD)
VRBO
From $312 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 $312 per night (USD)
Expedia

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