Florida Keys, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Florida Keys, Florida on RentalSaver.com!

Florida Keys Rentals

From $274 per night (USD)
VRBO
Gulf Pointe Paradise
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Gulf Pointe Paradise is a tranquil townhouse featuring a balcony with sweeping Gulf of Mexico views. Dockage is availabl ...
From $274 per night (USD)
VRBO
From $661 per night (USD)
Expedia
Oceanfront Duplex with Beautiful Beach & Dock for Boat Access - Dogs OK
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The Zane Grey Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $661 per night (USD)
Expedia
From $279 per night (USD)
VRBO
Waterfront home with 24-foot dock, shared pool, & beach access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Key Lime on Fifth Street Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $279 per night (USD)
VRBO
From $345 per night (USD)
Expedia
Waterfront Home with 35-Foot Dock, Bay Views, WiFi, and Shared Pool and Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Tropical Charm Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $345 per night (USD)
Expedia
From $390 per night (USD)
VRBO
Breezy waterfront home with pool, 35-foot dock & cabana club access
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Captain's Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $390 per night (USD)
VRBO
From $268 per night (USD)
Expedia
Dog-Friendly Home with 60-Ft. Dock and Access to Cabana Club and Shared Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Downhome Cabin by the Canal Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply e ...
From $268 per night (USD)
Expedia
From $363 per night (USD)
VRBO
Waterfront Home with 35-Foot Dock and Access to Private Beach and Shared Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Ninth Street Utopia Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $363 per night (USD)
VRBO
From $406 per night (USD)
Expedia
Waterfront home with 35-ft dock & access to Cabana Club pool & beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Canal-side Charisma Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $406 per night (USD)
Expedia
From $646 per night (USD)
VRBO
Waterfront Duplex with Shared Pool & Beach Access, 35-ft Dock
Bedrooms:
7
Bathrooms:
7
Sleeps:
17
Breezy Palms & Tropical Charm Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $646 per night (USD)
VRBO
From $255 per night (USD)
Expedia
Cozy Canal-Front House w/ Free WiFi and Deck - Close to Beaches & State Park
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Anchors Aweigh Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $255 per night (USD)
Expedia
From $837 per night (USD)
VRBO
Oceanfront Paradise w new 365' Dock Huge Tiki and Firepit. Dogs OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Direct Oceanfront Home with plenty of outdoor living space. Huge Tiki Hut with, 50" TV, refrigerator, fire pit area, an ...
From $837 per night (USD)
VRBO
From $408 per night (USD)
Expedia
Waterfront Tiny House w Pool, Beach, and Boat Dock
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Private community with 2 private beach areas, boat ramp, heated swimming pool, beach volleyball, children's area with pl ...
From $408 per night (USD)
Expedia
From $328 per night (USD)
VRBO
Group Therapy | 3 bed, 2 bath home w/ pool, quick ocean access - deep discount for JULY!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your dream escape! This beautifully remodeled 3-bedroom, 2-bathroom pool home on Cudjoe Key's oceanside is th ...
From $328 per night (USD)
VRBO
From $843 per night (USD)
Expedia
One of the very few beach houses with a daily, rental license in the Keys.
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
This is a newly remodeled four bedrooms elegant house. The property located in the heart of Summerland Key. It is the ...
From $843 per night (USD)
Expedia
From $634 per night (USD)
VRBO
Oceanfront Duplex with Spectacular Views, Beach, & Dock
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The Henry Flagler Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $634 per night (USD)
VRBO
From $488 per night (USD)
Expedia
**VILLA CUBANA @ OLD TOWN** Comfy Cottage Near Duval + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This colorful ...
From $488 per night (USD)
Expedia
From $720 per night (USD)
VRBO
W10 - 4 Bedroom Sombrero Isle Beauty on Crystal Lagoon!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This spacious 4-bedroom, 3-bath home is a half a mile from the picturesque Sombrero Beach. Located on Sombrero Is ...
From $720 per night (USD)
VRBO
From $1109 per night (USD)
Expedia
**BRISA FRESCA @ THE ANNEX** Airy Home by Duval & Beach + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! A trip to Key ...
From $1109 per night (USD)
Expedia
From $660 per night (USD)
VRBO
**VILLA OLIVIETTA @ SOLARES HILL** Upscale Home & Pool + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! This ultimate ...
From $660 per night (USD)
VRBO
From $661 per night (USD)
Expedia
**SMOOTH SAILING @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES..
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $661 per night (USD)
Expedia
From $512 per night (USD)
VRBO
**VILLA BAHAMA @ THE ANNEX** 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! VILLA BAHAMA ...
From $512 per night (USD)
VRBO
From $972 per night (USD)
Expedia
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Traveling to ...
From $972 per night (USD)
Expedia
From $3151 per night (USD)
VRBO
**THE ROYAL COMPOUND @ THE ANNEX** Lush Estate & Pool + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Located in th ...
From $3151 per night (USD)
VRBO
From $2703 per night (USD)
Expedia
**SOUTHERNMOST HOSPITALITY VII** 7BR/7BA & Pool + LAST KEY SERVICES...
Bedrooms:
7
Bathrooms:
7
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERNMOST ...
From $2703 per night (USD)
Expedia
From $729 per night (USD)
VRBO
**GULFSIDE VISTAS @ THE ANNEX** Condo & Pool + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! GULFSIDE VIST ...
From $729 per night (USD)
VRBO
From $1674 per night (USD)
Expedia
**STAR OF THE SEAPORT @ OLD TOWN** Huge Home & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For a truly o ...
From $1674 per night (USD)
Expedia
From $694 per night (USD)
VRBO
**CASA OLIVIANA @ SOLARES HILL** Grand Home & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Finally, a la ...
From $694 per night (USD)
VRBO
From $226 per night (USD)
Expedia
Beautiful Modern House in Key Largo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Open layout of the living area, dining room and kitchen. Large, screened patio offers the tropical 'out of doors and fre ...
From $226 per night (USD)
Expedia
From $554 per night (USD)
VRBO
Coral Hammock Poolside Home 3 bdrm 3 bath10 minute drive to Old Town Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Coral Hammock – 3BR/3BA Home with Pool Views in Coral Hammock 3 Bedrooms | 3 Full Bathrooms | Sleeps up to 8 | Backs to ...
From $554 per night (USD)
VRBO
From $503 per night (USD)
Expedia
**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo / Pool + LAST KEY SERVICES
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $503 per night (USD)
Expedia
From $313 per night (USD)
VRBO
**MAISON TROPICALE @ OLD TOWN** Historic Home + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Imagine a tra ...
From $313 per night (USD)
VRBO
From $423 per night (USD)
Expedia
**CASA SUITE CASA @ CASA MARINA** Lush Home / Pool + LAST KEY SERVICE...
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Imagine your ...
From $423 per night (USD)
Expedia
From $2267 per night (USD)
VRBO
**SOUTHERNMOST HOSPITALITY V** 5BR/5BA & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERNMOST ...
From $2267 per night (USD)
VRBO
From $486 per night (USD)
Expedia
Our Nautical Home Key West prime location & amenities. Last minute specials.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $486 per night (USD)
Expedia
From $344 per night (USD)
VRBO
**CAYO CALYPSO @ HIGGS BEACH** Modern Home / Pool + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Upscale islan ...
From $344 per night (USD)
VRBO
From $454 per night (USD)
Expedia
Poolside Breeze a Tropical Retreat has a wrap around Balcony best location
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $454 per night (USD)
Expedia
From $1158 per night (USD)
VRBO
**AMERICANA TROPICALE @ OLD TOWN** Home & Pool by Duval + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For the ultim ...
From $1158 per night (USD)
VRBO
From $632 per night (USD)
Expedia
**SHANG-RI-LA @ THE BEACH** Oceanview Condo / Pool & Tennis + LAST KEY SERVICES.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $632 per night (USD)
Expedia
From $607 per night (USD)
VRBO
**ATLANTIC REFLECTIONS @ THE BEACH** Ocean Penthouse / Pool + LAST KEY SERVICES.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $607 per night (USD)
VRBO
From $2239 per night (USD)
Expedia
**THE IBIS & THE CRANE @ OLD TOWN** Compound Near Duval + LAST KEY SERVICES...
Bedrooms:
7
Bathrooms:
6
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Dreaming of a ...
From $2239 per night (USD)
Expedia
From $397 per night (USD)
VRBO
Botanical Island Delight Key West fantastic discounts for Summer & Fall
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $397 per night (USD)
VRBO
From $436 per night (USD)
Expedia
**SALTWATER HARMONY @ THE ANNEX** Charming Condo & Pool + LAST KEY SERVICES...
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SALTWATER HAR ...
From $436 per night (USD)
Expedia
From $577 per night (USD)
VRBO
Atlantic Paradise Found modern luxury Best pool in Key West fine finishes
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $577 per night (USD)
VRBO
From $418 per night (USD)
Expedia
**LA PETITE PENTHOUSE @ THE ANNEX** Elegant Condo & Pool + LAST KEY SERVICES...
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! LA PETITE PEN ...
From $418 per night (USD)
Expedia
From $2005 per night (USD)
VRBO
**CONCH CASA GRANDE @ THE ANNEX** Home+ Pool near Duval + LAST KEY SERVICES...
Bedrooms:
6
Bathrooms:
5
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! CONCH CASA GR ...
From $2005 per night (USD)
VRBO
From $812 per night (USD)
Expedia
**LA GRANDE REUNION @ OLD TOWN** Estate & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Traveling wit ...
From $812 per night (USD)
Expedia
From $972 per night (USD)
VRBO
**RIVIERA AMERICANA @ THE BEACH** Ocean Views + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $972 per night (USD)
VRBO
From $863 per night (USD)
Expedia
Find Sanity in the Heart of Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Experience the charm of this fantastic Old Town location surrounded by local businesses and restaurants, allowing you to ...
From $863 per night (USD)
Expedia
From $719 per night (USD)
VRBO
**CASITA ANGELITA @ OLD TOWN** Historic Condo by Duval + 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! This Old Town ...
From $719 per night (USD)
VRBO
From $284 per night (USD)
Expedia
**SUNSET DREAMS @ SUNSET MARINA** Condo / Pool & Spa + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SUNSET DREAMS ...
From $284 per night (USD)
Expedia
From $382 per night (USD)
VRBO
Truman Annex Gem • 2BR Condo • Walk to Beach & Bars
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Best Deal in Truman Annex – Céad Míle Fáilte! 2 Bedroom | 1 Bathroom | Sleeps Up to 5 Guests Welcome to Innis-free, ou ...
From $382 per night (USD)
VRBO
From $237 per night (USD)
Expedia
New Listing! Beautiful Canal front , Key Deer and jacuzzi.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
-Remodeling house 3 bedroom and 3 bath. -Please note that there is a 28 minimum rental period for this property. - D ...
From $237 per night (USD)
Expedia
From $709 per night (USD)
VRBO
**PUERTA CORALINA @ OLD TOWN** Cottage Near Duval + LAST KEY SERVICE...
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This precious ...
From $709 per night (USD)
VRBO
From $456 per night (USD)
Expedia
High Tide awaits your next visit upgraded condo close to Smathers Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $456 per night (USD)
Expedia
From $1579 per night (USD)
VRBO
**CASA VICTORIA @ OLD TOWN** Historic 5BR Home & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! CASA VICTORIA ...
From $1579 per night (USD)
VRBO
From $745 per night (USD)
Expedia
**FOLLOW THE SUN @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES..
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $745 per night (USD)
Expedia
From $2111 per night (USD)
VRBO
**NOONA'S MANSION @ THE ANNEX** Grand Home & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
6
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Located in Tr ...
From $2111 per night (USD)
VRBO
From $408 per night (USD)
Expedia
Tranquility by Smathers and 10 minute bike downtown Key West value savings
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $408 per night (USD)
Expedia
From $689 per night (USD)
VRBO
Somewhere on the Beach a dream property all amenities included simply amazing
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $689 per night (USD)
VRBO
$4 Bed 3 Bath Duck Key Sanctuary Villa W\/ Private Pool & 35 Foot Dock - Sleeps 10$
From $1266 per night (USD)
Expedia
4 Bed 3 Bath Duck Key Sanctuary Villa W\/ Private Pool & 35 Foot Dock - Sleeps 10
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
We offer a unique Sanctuary Villa located on the island of Duck Key. This 4 bedroom 3 bath villa sleeps 10 people comfor ...
From $1266 per night (USD)
Expedia
From $507 per night (USD)
VRBO
**THE ARTISTS' MUSE @ LOVE LANE** Immaculate Home & Pool + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! For many, the ...
From $507 per night (USD)
VRBO
From $1911 per night (USD)
Expedia
**DIAMOND GIRL @ THE ANNEX** Elegant Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Seals & Croft ...
From $1911 per night (USD)
Expedia
From $973 per night (USD)
VRBO
**THE SMILING IBIS @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Traveling to ...
From $973 per night (USD)
VRBO
From $405 per night (USD)
Expedia
Waterfront luxury Villa (30) with 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 $405 per night (USD)
Expedia
From $510 per night (USD)
VRBO
**NATURES EDGE @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $510 per night (USD)
VRBO
From $472 per night (USD)
Expedia
**OCTOPUS'S GARDEN @ CORAL HAMMOCK** Spacious Home & Pool + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! OCTOPUS'S GAR ...
From $472 per night (USD)
Expedia
From $510 per night (USD)
VRBO
Frost Free at 1800 Atlantic overlooking Smathers Beach top and the sunrise
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $510 per night (USD)
VRBO
From $469 per night (USD)
Expedia
Top floor Ocean Views, Spacious 2 Bedroom Condo, Views from every room
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $469 per night (USD)
Expedia
From $320 per night (USD)
VRBO
**SUNSET POINT @ SUNSET MARINA** Condo / Pool & Spa + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SUNSET POINT ...
From $320 per night (USD)
VRBO
From $550 per night (USD)
Expedia
**SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & Pool + 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! SEA CAPTAIN'S ...
From $550 per night (USD)
Expedia
From $474 per night (USD)
VRBO
**THE MELLOW MACAW** Cozy Condo Near Duval + LAST KEY SERVICES...
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This colorful ...
From $474 per night (USD)
VRBO
From $478 per night (USD)
Expedia
Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $478 per night (USD)
Expedia
From $702 per night (USD)
VRBO
**NEPTUNE'S PENTHOUSE @ THE BEACH** Oceanfront Condo / Pool + LAST KEY SERVICE.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $702 per night (USD)
VRBO
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Expedia
Best Deals in Duck Key . 2 Bedroom /2 Bath w/40' 'Dock, Trailer Storage Incl,
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
*** This property is completely renovated on the inside and out! We cordially invite you to our property and enjoy the v ...
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Expedia
From $333 per night (USD)
VRBO
Flamingo Nook. Renovated, Private Pool, Canal & Cabana Club Access!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The ultimate Florida Keys getaway! The Flamingo Nook located at Key Colony Beach near Marathon. Privacy is what separate ...
From $333 per night (USD)
VRBO
From $340 per night (USD)
Expedia
**HAVANA HOUSE @ OLD TOWN** Elegant Cottage Near Duval + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Located on So ...
From $340 per night (USD)
Expedia
From $954 per night (USD)
VRBO
**WINDSWEPT PALMS @ THE BEACH** Oceanfront / Pool & Jacuzzi + LAST KEY SERVICE
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $954 per night (USD)
VRBO
From $202 per night (USD)
Expedia
**SUNDRENCHED REFLECTIONS @ SUNSET MARINA** Bayfront Condo + LAST KEY SERVICES..
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SUNDRENCHED R ...
From $202 per night (USD)
Expedia
From $1274 per night (USD)
VRBO
**SWEET HOME ANGELITA @ OLD TOWN** Renovated Home Off Duval + LAST KEY SERVICES
Bedrooms:
4
Bathrooms:
5
Sleeps:
13
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This renovate ...
From $1274 per night (USD)
VRBO
From $858 per night (USD)
Expedia
ROOFTOP PENTHOUSE- | 2 Bed, 1.5 Bath
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The high-end sophisticated Rooftop Penthouse is located directly above the famous Wyland Gallery on Duval Street. Enjoy ...
From $858 per night (USD)
Expedia
From $648 per night (USD)
VRBO
**PROMENADE TO PARADISE @ THE ANNEX** Ocean Condo & Pool + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! If you dream ...
From $648 per night (USD)
VRBO
From $293 per night (USD)
Expedia
Island Therapy
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautiful 2BD/2BA vacation home features open water views and a full size 35' seawall for docking a boat. Amenities incl ...
From $293 per night (USD)
Expedia
From $524 per night (USD)
VRBO
**SOUTHERNMOST PALMS @ THE ANNEX** 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! When you thin ...
From $524 per night (USD)
VRBO
From $303 per night (USD)
Expedia
Stay where you play, On the water w/Boat dock & Trailer parking. Pet friendly!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Stay where you play. The spacious newly refreshed two bedroom vacation rentals are ideal for fishermen and families or ...
From $303 per night (USD)
Expedia
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VRBO
4 BED DUCK KEY VILLA W/ 35FT DOCK BEHIND IT & CABANA CLUB ACCESS
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
WE HAVE JOINED CABANA CLUB IN KEY COLONY BEACH A SHORT DRIVE AWAY WHICH INCLUDES AN OLYMPIC SIZE POOL. TIKI BAR, RESTAUR ...
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VRBO
From $355 per night (USD)
Expedia
Dog-Friendly Sunrise Suites Condo with Pool, Hot Tub & Free Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Cayo Coco Suite 208 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $355 per night (USD)
Expedia
From $262 per night (USD)
VRBO
Dog-friendly home with pool & walk to parks & beach - snowbirds welcome
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Casa Atlantic Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $262 per night (USD)
VRBO
From $411 per night (USD)
Expedia
Bright Condo with Homey Feel, Entertainment & Private Parking - Beach Nearby
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Jasmine Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $411 per night (USD)
Expedia
From $901 per night (USD)
VRBO
Newly-Built, Dog-Friendly Home with Shared Pool - Walk to Beach & Dining
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Cabana Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $901 per night (USD)
VRBO
From $360 per night (USD)
Expedia
Cheery Beach Getaway Near Local Attractions - Pool & Easy Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Shipyard Perch Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $360 per night (USD)
Expedia
From $273 per night (USD)
VRBO
Tropical Getaway with Private Balcony, Shared Pool & Hot Tub - Dogs OK
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Antigua Suite 312 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $273 per night (USD)
VRBO
From $454 per night (USD)
Expedia
Sunny Condo with WiFi, Hot Tub, Pool & Tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sunrise Suites - Big Kahuna Suite 202 Our calendar is updated in real-time & our nightly rates are accurately displayed ...
From $454 per night (USD)
Expedia
From $550 per night (USD)
VRBO
Waterfront Duck Key Villa - Sleeps 6
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautiful and spacious 2 bedroom & 2.5 bathrooms Town house in the one and only Duck Key Florida, Harbor Village. In the ...
From $550 per night (USD)
VRBO
From $446 per night (USD)
Expedia
Dog-friendly condo with pool, hot tub, balcony, central AC, W/D, & fitness room
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Saint Lucia Suite 201 Our calendar is updated in real-time & our nightly rates are accurately displaye ...
From $446 per night (USD)
Expedia
From $346 per night (USD)
VRBO
Stunning, Oceanfront Home with Private Pool & Docks - Dog-Friendly
Bedrooms:
3
Bathrooms:
5
Sleeps:
18
Bay Harbor View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $346 per night (USD)
VRBO
From $692 per night (USD)
Expedia
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Hemingway's View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $692 per night (USD)
Expedia
From $435 per night (USD)
VRBO
Sunrise Suites Condo w/ Balcony, Pool & Hot Tub, Tennis & Covered Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Tahiti Suite 104 Our calendar is updated in real-time & our nightly rates are accurately displayed. Si ...
From $435 per night (USD)
VRBO
From $223 per night (USD)
Expedia
Breezy Florida Home with Shared Pool, Dog & Snowbird-Friendly - Walk to Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Headquarters Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $223 per night (USD)
Expedia
From $371 per night (USD)
VRBO
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Barbados Suite 204 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $371 per night (USD)
VRBO
From $354 per night (USD)
Expedia
Dog-Friendly Cottage with Private Hot Tub & Garden - Great Downtown Location
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Windward Isle Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $354 per night (USD)
Expedia

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