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From $1698 per night (USD)
VRBO
**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)
VRBO
From $315 per night (USD)
Expedia
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)
Expedia
From $396 per night (USD)
VRBO
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)
VRBO
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)
VRBO
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)
VRBO
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)
Expedia
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)
Expedia
From $391 per night (USD)
VRBO
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)
VRBO
From $492 per night (USD)
Expedia
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)
Expedia
From $211 per night (USD)
VRBO
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)
VRBO
From $464 per night (USD)
Expedia
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)
Expedia
From $670 per night (USD)
VRBO
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)
VRBO
From $406 per night (USD)
Expedia
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)
Expedia
From $415 per night (USD)
VRBO
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)
VRBO
From $536 per night (USD)
Expedia
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)
Expedia
From $212 per night (USD)
VRBO
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)
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 Pricing
VRBO
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 Pricing
VRBO
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 $1156 per night (USD)
Expedia
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)
Expedia
From $493 per night (USD)
VRBO
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)
VRBO
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)
VRBO
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)
VRBO
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)
VRBO
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)
VRBO
From $352 per night (USD)
Expedia
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)
Expedia
From $554 per night (USD)
VRBO
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)
VRBO
From $760 per night (USD)
Expedia
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)
Expedia
From $227 per night (USD)
VRBO
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)
VRBO
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)
VRBO
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)
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 Pricing
VRBO
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 Pricing
VRBO
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
From $166 per night (USD)
VRBO
NAUTI HIDEAWAY - 2/2, Slip, Private Ramp, Pool, Trailer Parking, Bait Freezer!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Vehicle parking, trailer parking, the private boat ramp, your slip, and the pool are each, at most 200 ft from the cond ...
From $166 per night (USD)
VRBO
From $492 per night (USD)
Expedia
Sweet Caroline Historic Seaport Key West Home Rental Floor 2
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This fully renovated house is located in the historic seaport with many highly rated restaurants and shops. A quick 5-mi ...
From $492 per night (USD)
Expedia
From $652 per night (USD)
VRBO
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Torchview Lookout – Your Private Waterfront Retreat! Escape to paradise at Torchview Lookout, a secluded 3-b ...
From $652 per night (USD)
VRBO
From $825 per night (USD)
Expedia
**CASA AMARILLA** Old Town Cottage & Pool + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The moment yo ...
From $825 per night (USD)
Expedia
From $572 per night (USD)
VRBO
Copacabana, Overlooking the Gulf!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Overlooking the Gulf of Mexico allows for the great views at this beautiful home. Bring your boat or rent one! The new d ...
From $572 per night (USD)
VRBO
From $437 per night (USD)
Expedia
🌇 Ocean Sunset Views with Pool and Dock 🌇
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautiful two bedroom two bath single family home with pool and spa with dock right on the water! Enjoy the beautiful s ...
From $437 per night (USD)
Expedia
From $584 per night (USD)
VRBO
Oceanside Key Largo Townhome, Private Marina, pools, Tennis and Golf Cart
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Located in the Heart of Key Largo, in a 24 acre private community you will find Kawama Yacht Club which is surrounded by ...
From $584 per night (USD)
VRBO
From $145 per night (USD)
Expedia
Prime Time 2: Charming Canal Front Duplex, Your Gateway to South Pine Channel & Atlantic/Gulf Waters
Bedrooms:
1
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 $145 per night (USD)
Expedia
From $151 per night (USD)
VRBO
Prime Time: A Tropical Paradise on Big Pine Key, Canal Front Duplex, Swift Access to Atlantic & Gulf
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 $151 per night (USD)
VRBO
From $607 per night (USD)
VRBO
Luxurious tropical water-front Heated pool home with Boat Dock and two master .
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Please see the video. This video does not show latest decorations and improvements. Including new tile sunset roof top ...
From $607 per night (USD)
VRBO
From $574 per night (USD)
VRBO
Water front home. 50' Dock w/ Pool & Hot Tub. Just S. of Tavernier Creek
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This beautiful Conch style home was completed in 2019. The house is a 2000 sq ft. 3 bedroom 2 bath home, each of it's 3 ...
From $574 per night (USD)
VRBO
From $307 per night (USD)
Expedia
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy our little peace of paradise! Come and make memories at this laid back and family-friendly waterfront home. Locate ...
From $307 per night (USD)
Expedia
From $289 per night (USD)
VRBO
~Reel Paradise~Beautiful private townhouse in a small gated community.
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $289 per night (USD)
VRBO
From $192 per night (USD)
Expedia
Convenient central Marathon location, canal view.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Cute and super clean! One bedroom and one bath, nicely decorated & furnished. Bedroom has queen bed with topper. Bedroom ...
From $192 per night (USD)
Expedia
From $467 per night (USD)
VRBO
Casa de Sueno
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Summary: Casa de Sueno is a spacious 5-bedroom, 2.5-bath waterfront retreat on Little Torch Key, perfect for up to 10 g ...
From $467 per night (USD)
VRBO
From $428 per night (USD)
Expedia
OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
STEPS TO DUVAL STREET! WALK EVERYWHERE--TO ALL RESTAURANTS, SHOPS AND BARS OF OLD TOWN, KEY WEST!! You wont nee ...
From $428 per night (USD)
Expedia
From $327 per night (USD)
VRBO
Sunbeam Dream 2BR Oceanfront Condo in Florida Keys
Bedrooms:
2
Bathrooms:
1
Sleeps:
6
Summary: Escape to Sunbeam Dream, a beautifully curated two-bedroom, two-bath coastal condo at Ocean Pointe Suites in T ...
From $327 per night (USD)
VRBO
From $962 per night (USD)
Expedia
Conch House - Ocean front with dock and pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
The Conch House is located at mile marker 28.5 on Little Torch Key. You can dock your boat right in your own front yard! ...
From $962 per night (USD)
Expedia
From $250 per night (USD)
VRBO
SEP-DEC SELL-OFF!! OCEANFRONT Lux 1350sf, Great Views &All Amenities of Home!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Rates for remaining available dates in Sep-Dec have just been SLASHED for quick sell-off! Rates are now up to approx. $1 ...
From $250 per night (USD)
VRBO
From $419 per night (USD)
Expedia
OCEANFRONT CONDO w/Lake, 2Kayaks, 2Paddleboards, 2Bikes, Tennis, Boat Ramp
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy a Key Largo adventure in our deluxe oceanfront condo WHICH INCLUDES 2 KAYAKS, 2 PADDLEBOARDS, 2 BIKES, TENNIS RACK ...
From $419 per night (USD)
Expedia
From $583 per night (USD)
VRBO
Blue Paradise 5bed/5bath walking distance to the beach with a private pool
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
License #: Vaca-20-106 Welcome to Blue Paradise: Your Dream Getaway in the Heart of Sombrero! Escape to luxury and com ...
From $583 per night (USD)
VRBO
From $279 per night (USD)
Expedia
Gulf Getaway | Condo w/Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Conveniently situated in the picturesque Truman Annex gated Community, Gulf Getaway is a charming 2 bedroom 2. ...
From $279 per night (USD)
Expedia
From $590 per night (USD)
VRBO
Coral Lagoon Updated Single Family Home with 40' Boat Slip directly behind home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to paradise! The Silly Sailfish is 1 of 8 stand-alone single-family homes within the 25-unit Coral Lagoon commun ...
From $590 per night (USD)
VRBO
Click For Pricing
Expedia
Poolside townhouse in Key West Golf Club
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful 2 bed/2.5 bath townhome in key west golf club. Pool steps away. Gated community. Enjoy everything beautiful Ke ...
Click For Pricing
Expedia
From $524 per night (USD)
VRBO
Newly renovated coastal home; Marina, Pools, Lagoon, Bikes, Tiki’s and More!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy your Florida Keys vacation in this upgraded modern coastal home that is waterfront to a saltwater lagoon. Boater's ...
From $524 per night (USD)
VRBO
From $817 per night (USD)
Expedia
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
• Luxury 2nd & 3rd floor Penthouse • 3 Bedrooms with private porches & 2 1/2 Baths • 2200 square feet of living space • ...
From $817 per night (USD)
Expedia

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