Florida Keys Vacation Rentals & House Rentals - 245 Rentals Available
Florida Keys (245) Filter Cancel
Loading...
Islamorada Florida Vacation Rentals - Townhouse
1 / 24

Islamorada Townhouse
2 BR / 2.5 BA / Sleeps 6 2 6 Min stay varies
Townhouse / 2 Bedrooms / Sleeps 6
2 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
This oceanfront resort is a boutique complex of 52 homes inspired by Native Conch & British West Indies architecture built in 2007. Quaint streets & walking paths wind through this village- styled retreat. Amenities incl...
Marathon Florida Vacation Rentals - Home
1 / 16

Marathon Home
3 BR / 2.5 BA / Sleeps 6 3 6 7 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
High- end Estate overlooking tranquil "Bonefish Flats" in picturesque Marathon. Brand new, Designer decorated with contemporary colors, loads of fine architectural details, Crema Marfil marble, Granite, fine Hardwoo...
(12) Excellent (12 reviews)
Marathon Florida Vacation Rentals - Home
1 / 31

Marathon Home
4 BR / 2 BA / Sleeps 8 4 8 7 night min stay
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN Dolphin Bay is a lush tropical setting offering both quiet and privacy. This spacious four bedroom home is located directly on the Gulf of Mexic...
(1) Excellent (1 review)
Marathon Florida Vacation Rentals - Home
1 / 22

Marathon Home
3 BR / 3 BA / Sleeps 8 3 8 7 night min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Microwave • Washer/Dryer
Seabird Key is a private 10 acre tropical island hideaway located one- half mile offshore Marathon in the heart of the Florida Keys. As our guest, you have the entire Island to yourself, including an exquisite hardwood...
(3) Excellent (3 reviews)
Key West Florida Vacation Rentals - Guesthouse
1 / 3

Key West Guesthouse
2 BR / 2 BA / Sleeps 4 2 4 7 night min stay
Guesthouse / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
Beachfront home located on privately owned Sugarloaf Beach. This gated estate offers 350 feet of private beach and 4 acres of tropical gardens. The gardens have tropical plants and bananas that have been collected from a...
(3) Excellent (3 reviews)
Front View
1 / 29

Islamorada Home
3 BR / 2 BA / Sleeps 6 3 6 30 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Location: Islamorada, Islamorada Area, Florida Keys, Florida, USA Accommodations: House, 3 Bedrooms, 2 Baths , Sleeps 6 122 Nautilus Drive, Islamorada, Florida Keys mile marker 74. 5 bay side, White Marl...
(10) Excellent (10 reviews)
Key West Florida Vacation Rentals - Yacht
1 / 13

Key West Yacht
2 BR / 2 BA / Sleeps 4 2 4 3 night min stay
Yacht / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
Microwave • Washer/Dryer • DVD Player
Make your next Key West vacation on the Lion's Paw, a roomy monohull sailboat located in Key West premier marina resort - the Key West Harbour Marina. Three night to seven day vacation packages have options for half da...
Key West Florida Vacation Rentals - Condo
1 / 21

Key West Condo
2 BR / 2 BA / Sleeps 5 2 5 7 night min stay
Condo / 2 Bedrooms / Sleeps 5
2 bedrooms 2 bathrooms Sleeps 5
High Speed Internet • Dishwasher • Microwave
7 day minimum please Key West Vacation Rental This fully furnished newly updated getaway! It is so close to all the Beach, our pool and the local Key West bars & restaurants and museums just take a short stroll or jum...
(1) Excellent (1 review)
Pool, Spa and Sunshade Area
1 / 24

Key West Condo
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
This is a non- smoking condo (you may smoke on the balcony only) with that "home away from home" comfortable appeal. My condo is reasonably priced and includes 2 bedrooms (1 king in the master suite/1 queen in the guest ...
(55) Excellent (55 reviews)
Marathon Florida Vacation Rentals - Home
1 / 10

Marathon Home
2 BR / 2 BA / Sleeps 6 2 6 7 night min stay
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Marathon Florida Vacation Rental License Castaway is a 2 bedroom 2 bath ocean view waterfront home in Marathon, Florida keys. The home has been extensively remodeled. It is fully furnished and includes a living ro...
(28) Excellent (28 reviews)
Marathon Florida Vacation Rentals - Home
1 / 32

Marathon Home
2 BR / 1 BA / Sleeps 6 2 6 7 night min stay
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 1 bathroom Sleeps 6
High Speed Internet • Dishwasher • Microwave
Escape to your own private tropical island! This Vacation Rental home combines the best of both worlds, a modern, fully furnished, waterfront shore home with all the amenities for your nights and your own private tro...
Marathon Florida Vacation Rentals - Home
1 / 37

Marathon Home
4 BR / 4 BA / Sleeps 10 4 10 7 night min stay
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 4 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
This is a rare 4 bedroom, 4 bath waterfront home near the Vaca Cut on the Gulf of Mexico. This home features a 9x20 foot splash pool, beach sand backyard and kayaks. Bring your own boat or rent one from us for $695/wee...
(3) Excellent (3 reviews)
1 / 7

Key Largo Home
3 BR / 2 BA / Sleeps 6 3 6 3 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Come and relax in our water front property.. The upstairs features 3 bedrooms, 2 full baths and a laundry room. The upstairs also has an enclosed patio where you can sit and enjoy the wonderful views. The downstairs off...
Marathon Florida Vacation Rentals - Home
1 / 16

Marathon Home
5 BR / 3 BA / Sleeps 10 5 10 7 night min stay
Home / 5 Bedrooms / Sleeps 10
5 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Please Call/email For Availability As We Do Not Use The Calendar Shown "margarita On The Gulf" Is A Spacious 5 Bedroom, 4 Bath Home Located On The Gulf Of Mexico. Enjoy Endless Gulf Views As You Relax At This Pr...
(5) Excellent (5 reviews)
Marathon Florida Vacation Rentals - Townhouse
1 / 44

Marathon Townhouse
3 BR / 2.5 BA / Sleeps 6 3 6 No min stay
Townhouse / 3 Bedrooms / Sleeps 6
3 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse yourself in long leisurely days of boating, lounging by the pool and watching spectacular sunsets f...
(20) Excellent (20 reviews)
Marathon Florida Vacation Rentals - Villa
1 / 28

Marathon Villa
8 BR / 5.5 BA / Sleeps 20 8 20 7 night min stay
Villa / 8 Bedrooms / Sleeps 20
8 bedrooms 5.5 bathrooms Sleeps 20
High Speed Internet • Dishwasher • Microwave
Southern Diversion Two is an exclusive private gated estate located in Marathon in the Florida Keys. This sprawling 2 acre private estate is located directly on the Gulf of Mexico featuring 300 feet of open water, deep ...
(5) Excellent (5 reviews)
Key West Florida Vacation Rentals - Cottage
1 / 18

Key West Cottage
4 BR / 3 BA / Sleeps 8 4 8 Min stay varies
Cottage / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Microwave • Washer/Dryer
Daily price varies by season, and length of stay. Range of prices shown above. Private compound right in the heart of old town. 1 minute or less from Schooner Wharf with all the water activities imaginable; Sloppy Joe'...
(12) Excellent (12 reviews)
Key West Florida Vacation Rentals - Townhouse
1 / 20

Key West Townhouse
2 BR / 2 BA / Sleeps 4 2 4 7 night min stay
Townhouse / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
ISLAND WIND: 2 bedroom, 2 bath Bahamian- style townhome, with tin roof and white spindled decks. Snuggle into an oh- so- comfy king bed in the Master bedroom upstairs; bathroom is ensuite. Guest bedroom downstairs...
WOW! This is the view of INCH BEACH oceanside (see our rental between the trees)
1 / 84

Key Colony Beach Home
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"Location, Location, Locaton" And 2 "ocean Beach Memberships" (rare To Find), Keys Ocean Drive Rental Has It All! ! ! Legally Sleeps 6 Max. (including Babies); 1, 314 Sf 1/2 Stilted (not Ground) Duplex; 2 Br, ...
Marathon Florida Vacation Rentals - Home
1 / 21

Marathon Home
4 BR / 5 BA / Sleeps 10 4 10 7 night min stay
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
4 bedroom and 5 full bathrooms private gated home, heated pool, Tiki hut, deep 135ft boat dock, fish cleaning station, bait freezer, gourmet kitchen, 2 full size refrigerator and freezers. Sleeps 10, covered park...
Key West Florida Vacation Rentals - Condo
1 / 42

Key West Condo
2 BR / 2.5 BA / Sleeps 6 2 6 Min stay varies
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"Tee By The Sea" Vacation Rental (we Include 7 Bikes Free For Our Guests! ! ! ) If You Love... Golf, Sport Fishing/boating, Art/theater And Fantastic Live Entertainment... Than You'll Love "tee By The Sea". We're ...
(4) Excellent (4 reviews)
1 / 15

Key Largo Home
4 BR / 2 BA / Sleeps 8 4 8 30 night min stay
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
The City of Key Largo only allows monthly rentals on private houses. No nightly or weekly rentals allowed. Ocean View Pool Hot Tub Dock House, 4 Bedrooms, 2 Baths, Sleeps 8 Oceanview. Fulfill your vision of a tropic...
Marathon Florida Vacation Rentals - Home
1 / 42

Marathon Home
2 BR / 2 BA / Sleeps 6 2 6 7 night min stay
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Microwave • TV (Cable/Satellite)
WHAT IS UNIQUE ABOUT THIS VACATION RENTAL? This vacation rental puts you on your own tropical island in a quiet cove of protected mangroves in the Gulf of Mexico. You stay on a 2 bedroom houseboat that is docked on the ...
(1) Excellent (1 review)
Tavernier Florida Vacation Rentals - Home
1 / 24

Tavernier Home
2 BR / 2 BA / Sleeps 4 2 4 30 night min stay
Home / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
ISLAMORADA MM 91 - Enjoy our beautiful single family home with lots of outdoor seating, including under our very large Tiki Hut! An outdoor lovers paradise! Enjoy stunning sunsets, from our homeowners park directly ...
(1) Excellent (1 review)
Key Largo Florida Vacation Rentals - Home
1 / 34

Key Largo Home
4 BR / 4 BA / Sleeps 14 4 14 30 night min stay
Home / 4 Bedrooms / Sleeps 14
4 bedrooms 4 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
Spectacular Waterfront Ocean side 4/4 3 story home with Pool & 60 Ft Dock Oceanfront home with 2 wrap around balconies and great views. Ocean access with no bridges. Next to John Pennekamp, Jacobs Aquatic Center Wate...
(1) Excellent (1 review)
Marathon Florida Vacation Rentals - Cottage
1 / 15

Marathon Cottage
3 BR / 2 BA / Sleeps 6 3 6 7 night min stay
Cottage / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Please Call/email For Availability As We Do Not Use The Calendar Shown "sunset Bay" Is A 3 Bedroom, 2 Bathroom Home Located On The Clear, Aquamarine Waters Of The Beautiful Gulf Of Mexico. This Beautiful Waterfront...
(3) Excellent (3 reviews)
Islamorada Florida Vacation Rentals - Home
1 / 14

Islamorada Home
4 BR / 2 BA / Sleeps 8 4 8 30 night min stay
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
This is a newly remodeled 4 bedroom 2 bath private home on the ocean side (just 3 houses from the open ocean) with ocean views, pool, tiki hut ice machine and all the comforts of home. This home is perfect for family a...
Key West Florida Vacation Rentals - Villa
1 / 55

Key West Villa
5 BR / 5.5 BA / Sleeps 12 5 12 Min stay varies
Villa / 5 Bedrooms / Sleeps 12
5 bedrooms 5.5 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street with room to park 2 vehicles off- street...
(3) Excellent (3 reviews)
Tavernier Florida Vacation Rentals - Home
1 / 15

Tavernier Home
5 BR / 3 BA / Sleeps 10 5 10 No min stay
Home / 5 Bedrooms / Sleeps 10
5 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
28 Night Minimum Rental - No Exceptions. (i Don't Respond To Inquires Of Less Than 28 Nights. ) September Or October $3500! ! ! A Beautiful, Relaxing 5 Bedroom Home At Harry Harris Beach (mile Marker 92. 5). ...
(2) Excellent (2 reviews)
1 / 10

Islamorada Condo
2 BR / 2 BA / Sleeps 4 2 4 30 night min stay
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
28 Day Minimum Stay Spectacular sunset views over Shell Key and Florida National Everglades Park, sit back every day and watch the glorious water views and peaceful backdrop of mother nature at her best. This 3rd floor...
1  2  3  4  5 
12345
page 1 of 9
LoadingLoading...

Top 10 Activities in Florida Keys

Top 10 Activities in Florida Keys
Whether you prefer swimming, fishing, or sunning, there’s no shortage of things to do in the Florida Keys. Read on for the top 10 activities on these tropical islands.
 

Seven Mile Bridge

To get to the Florida Keys, you’ll have to traverse the Seven Mile Bridge, which is an attraction in its own right. For nearly seven miles, this bridge travels over the ocean, connecting the Middle Keys to the Lower Keys and providing travelers with stunning views.
 

John Pennekamp Coral Reef State Park

John Pennekamp Coral Reef State Park, the first underwater park in the U.S., offers a fascinating look under the surface of the Keys. Snorkel or scuba dive to get up close and personal with the reefs, or book a glass bottom boat tour to gaze from above. The admission fee is $8 per car, and there’s an extra charge for tours.
 

Lignumvitae Key Botanical State Park

Though it’s only accessible by private boat, this secluded island is worth a visit, since it ...

Read more

Three Day Itinerary: Florida Keys

Three Day Itinerary: Florida Keys
The Florida Keys are an island archipelago off of Florida's southeast coast. Though the Keys include more than 1,700 islands, most are unpopulated, and only 43 are connected by bridge. The Keys enjoy warm tropical weather year-round, but are very exposed to hurricanes and tropical cyclones. The best time to visit is between March and May, before hurricane season commences on June 1. Weather permitting, a diverse array of historic and natural highlights await you throughout the year.
 

Day 1: Culture and History in Key West

Begin your visit at one of Key West's most famous sites. Take a 30-minute tour of the Ernest Hemingway Home and Museum, and see where the celebrated author penned many of his great works. Around 40 to 50 six-toed cats also live on the property, exhibiting the same polydactyl trait that distinguished Hemingway's own cat.

Explore more of Key West's history at the Harry S. Truman Little White House. The building originally served as a ...

Read more

About Florida Keys

While all the Florida Keys serve up a high dose of tropical leisure, each has its own personality and flavor. The Florida Keys are a wonderful vacation spot for families in search of a little relaxation or adventure. Enjoy Key Largo’s reputation as the dive capital of the world; Islamorada’s spectacular fishing; Marathon’s family friendly beaches; Big Pine Key and the Lower Keys' slowed pace and natural playground; and the unforgettable Key West, the Southernmost city in the continental U.S. and playground to Presidents, authors, and a number of bon vivants. And each has it's own unique offering of Florida Keys oceanfront vacation rentals to choose from. For families visiting the Florida Keys, vacation rentals by owner offer the maximum amount of space and privacy for the price.

Things to Do

Decide what sorts of fun in the sun you enjoy best and there’s a Key for that. If sports fishing and boating interests you, spend some time on Islamorada and take a dip in the Gulf Stream. If you wonder what inspired one of America’s top writers, don’t miss Key West and the historic Hemingway House. While you’re there, check out the descendants of his famous six-toed cats. No matter which Key you choose, the water is a draw around all of them. The crystalline blue surrounding these islands makes a drive up Highway 1 a spectacular way to spend some time, particularly if you’re in a convertible.

​The Keys have plenty of fun things to do for every activity level. Families who enjoy the outdoors can take advantage of the wide availability of Florida Keys condo rentals and stay right on the beach!
  • Fishing enthusiasts visiting the Florida Keys will be very excited to hear that Islamorada is known as the sport fishing capital of the world, offering a variety of game fish.
  • Water sports are also very popular in the Keys. Hang gliding, parasailing, kayaking, and paddle boarding are great choices for adventurous families.
  • Swimming with dolphins is a unique experience that every tourist of the Florida Keys should try! Through Dolphins Plus in Key Largo, visitors can go on a structured or natural swim with the dolphins or visit the sea lions through the Sea Lion Encounters program. In Islamorada, Theater of the Sea offers a wonderful opportunity to swim with dolphins, sea lions, and rays. Kids will have a blast learning about these delightful creatures.

Climate

The weather is warm for much of the year, but the balmy Caribbean breezes make it comfortable along the beaches even in summer. The highest temp ever recorded in the Keys was 97 F (36 C) back in 1880, but the summer average high is 89 F. Mosquitos like the Keys too, so keep this in mind on your visit. The highest potential for hurricanes in this part of Florida is from August 15-October 15 when waters are warmest, but it’s also a time of some of the most beautiful weather and one of the most affordable times to visit.

Shopping 

While there are shops on all the Keys, Key West provides the largest number of stores and boutiques. From literary memorabilia to craft beer, Key West offers some of the most memorable shopping of these tropical hot spots.

Events

The Keys offer a number of fishing tournaments throughout the year, not only for sport but to keep certain populations under control, especially the pervasive lion fish. Don’t miss the annual Hemingway look-alike contest in July or Key West’s annual Halloween celebration, Fantasy Fest. If you go, leave the kids at home.  

Nightlife

Nightlife or daylife, you’re on Island time here, and there’s always a party to be found, particularly in Key West. When people say “It’s 5:00 somewhere,” that somewhere is the Keys. Just ask Jimmy Buffet who is sometimes spotted in Key West, where he opened his first Margaritaville store in the mid-80s. Most of the hot bars are within walking distance on Duvall Street, making it a favorite of those looking for a party.  

Beaches and Parks

Florida Keys tourists can enjoy a leisurely day at one of the best parks in the nation. These are just a few of the Keys most popular destinations:
  • John Pennekamp Coral Reef State Park is the oldest underwater park in the world. Located in Key Largo, families can explore the 47 campsites located on 67,845 acres, split between land and underwater areas. Nature trails, beaches, kayak and canoe rentals, and glass-bottom boat tours are available.
  • Everglades National Park has many fun activities for families. Kids can become Junior Rangers or go on a wildlife hike.
  • Bahia Honda State Park is known for its beautiful beaches and crystal clear water. Visitors can book a snorkeling tour online and enjoy over an hour of snorkeling in the Looe Key National Marine Sanctuary, where swimmers will explore the gorgeous Elkhorn and Star coral.

Local History

Florida Keys visitors may want to learn a little about the history of these breathtaking islands.
  • Ernest Hemingway Home and Museum is a must for literature enthusiasts. Located in Key West, this historical landmark was Hemingway's home from 1931 to 1939, and the place in which he penned some of his most-loved work.
  • The Florida Keys Eco-Discovery Center is sure to be a hit with the kids. Housing over 6,000 square-feet of interactive exhibits, this museum is a great way to introduce kids to underwater and wildlife ecosystems. And admission is free!
Sightseeing Tours are one of the best ways to learn about the islands. Glass-bottom boat rides, sunset tours, and dinner cruises are all available. Remember to reserve your spot online ahead of time to save on ticket prices.

Fun With Kids

While vacationing in the Florida Keys, rental homes leased by owner are a great choice for families with a few kids who need a little extra space. Some of the top activities for kids are:
  • The Key West Butterfly and Nature Conservatory was voted the #1 attraction in Key West by TripAdvisor and People's Choice Awards. Take a stroll through the conservatory, which houses between 50 and 60 species of plants, waterfalls, colorful birds, and of course--butterflies.
  • The Conch Tour Train is a fun way to see Key West with the kids. In operation since 1958, the 90-minute tour will take you through all of the island's most popular attractions.
  • Tropic Cinema has been named "Best Florida Cinema" by Florida Monthly magazine for four consecutive years. This landmark theater screens Hollywood blockbusters, documentaries, and foreign films.
The Keys are a delightful mix of Old Florida and the Caribbean. They offer the recognizable feel of the U.S. with the laid back approach of the islands. Best of all, you don’t need a passport for this tropical adventure when you stay in one of the many Key West vacation rentals.