Meadows Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Meadows, Key West, Florida, USA

BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
10.0 (121 Reviews)
2 Bedrooms 6 Guests
Upper Bayview South
FromR20,679 per night
10.0 (1 Review)
4 Bedrooms 8 Guests
Authors of Key West Guest House
FromR5,155 per night
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9.0 (1008 Reviews)
1 Bedroom 2 Guests
Old Town "Eleuthera" 2BR Waterfront Corner Condo
10.0 (33 Reviews)
2 Bedrooms 8 Guests
Aruba - Downtown Waterfront 2x2 Dock & Pool Pet-Friendly
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9.8 (15 Reviews)
2 Bedrooms 8 Guests
Bayview North One
FromR45,850 per night
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New
1 Bedroom 2 Guests
Heron Hideaway
FromR6,306 per night
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9.5 (10 Reviews)
1 Bedroom 4 Guests
The Palms Hotel
FromR6,364 per night
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8.8 (1001 Reviews)
1 Bedroom 2 Guests
Dominica - New Waterfront Condo Pool Dock 2 Bedroom 2 Bathroom
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9.5 (2 Reviews)
1 Bedroom 8 Guests
"Dominica" Key West 2BR Dock, Pool, Pet-Friendly
10.0 (6 Reviews)
2 Bedrooms 8 Guests
Curacao - Large 2x2 Waterfront Condo Great View Pool & Dock
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9.3 (9 Reviews)
2 Bedrooms 8 Guests
Welcome to the Shady Palms - Private Pool - 2 Bdrm, 2.5 baths
10.0 (6 Reviews)
2 Bedrooms 4 Guests
St Croix - Downtown 4x4 Waterfront Penthouse Pool Dock Pet
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9.3 (8 Reviews)
4 Bedrooms 15 Guests
Tropical Hideaway w/Hot Tub + Pool
10.0 (3 Reviews)
1 Bedroom 4 Guests
St John - Downtown Waterfront Penthouse Pool Parking Dock
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9.3 (3 Reviews)
4 Bedrooms 16 Guests
Andros - Spacious 2x2 Waterfront Condo
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9.2 (11 Reviews)
2 Bedrooms 8 Guests
The Margaret Suite | Renovated studio, shared pool
10.0 (1 Review)
1 Bedroom 3 Guests
Eleuthera - 2x2 Fully Updated Old Town Waterfront Corner Condo
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9.1 (18 Reviews)
2 Bedrooms 8 Guests
St Thomas - Waterfront Penthouse sleeps 16 w Pool & Boat Dock
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9.1 (11 Reviews)
4 Bedrooms 16 Guests
Florida - Spacious Updated Waterfront Condo 2x2 Pool Dock
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9.0 (2 Reviews)
2 Bedrooms 8 Guests
Abaco - Large waterfront 2x2 end unit with boat slip
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8.8 (5 Reviews)
2 Bedrooms 8 Guests
Curaçao Key West 2BR Condo w/Pool&Waterfront Dock
9.8 (35 Reviews)
2 Bedrooms 6 Guests
Authors Key West Guesthouse
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8.3 (1330 Reviews)
16 Bedrooms 34 Guests
SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/Pool!
9.8 (9 Reviews)
2 Bedrooms 4 Guests
St Kitts - Downtown Waterfront Penthouse Pool Dock Parking
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8.2 (12 Reviews)
4 Bedrooms 16 Guests
The Elizabeth Suite
FromR5,630 per night
7.0 (1 Review)
1 Bedroom 4 Guests
Florida | Waterfront 2BR/2BA w/Pool + Dock Access
9.6 (42 Reviews)
2 Bedrooms 8 Guests
Upper Sunset North
FromR19,134 per night
4.5 (2 Reviews)
4 Bedrooms 8 Guests
"Abaco" Key West 2/2 End Unit Waterfront+Dockage
9.6 (27 Reviews)
2 Bedrooms 8 Guests
The Fleming Suite
FromR4,730 per night
2.0 (1 Review)
1 Bedroom 4 Guests
Key West Andros 2BR Waterfront, Pool, Dock&Pet OK
9.6 (25 Reviews)
2 Bedrooms 8 Guests
Antigua Retreat- 2BR 2BA waterfront condo w/pool & boat slip
9.4 (147 Reviews)
2 Bedrooms 8 Guests
Downtown Key West 2BR/2BA Pool, Dock, Pet "Aruba"
9.4 (18 Reviews)
2 Bedrooms 6 Guests
Flamingo Retreat-waterfront 2BR 2BA condo w/pool & boat slip
9.2 (106 Reviews)
2 Bedrooms 8 Guests
Waterfront "St. Croix" Penthouse, Pool, Dock, Pet
9.6 (32 Reviews)
4 Bedrooms 15 Guests
Middle Sunset
FromR18,149 per night
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New
3 Bedrooms 6 Guests
Keys Please
FromR2,775 per night
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New
1 Bedroom 6 Guests
Meadows Manor
FromR41,055 per night
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New
4 Bedrooms 8 Guests
Meadows Manor | Elegant Oasis with Private Pool
9.4 (14 Reviews)
4 Bedrooms 8 Guests
Bayview Retreat
FromR34,264 per night
New
4 Bedrooms 10 Guests
Island Chic
FromR30,354 per night
New
3 Bedrooms 8 Guests
Eisenhower Retreat
FromR30,090 per night
New
4 Bedrooms 10 Guests
Seafarer's Refuge
FromR27,122 per night
New
4 Bedrooms 10 Guests
Historic "Old Town" Charm
FromR13,165 per night
New
4 Bedrooms 6 Guests
Upper Sunset South
FromR20,402 per night
New
3 Bedrooms 6 Guests
Sunset North
FromR19,685 per night
New
4 Bedrooms 8 Guests
Upper Bayview North
FromR18,962 per night
New
4 Bedrooms 8 Guests
Boomerang Boathouse - Located in The Meadows
New
4 Bedrooms 8 Guests
Bayview North One
FromR18,962 per night
New
4 Bedrooms 8 Guests
Bayview South 801 Eisenhower Dr. #6
New
4 Bedrooms 8 Guests
The Meadows Retreat
FromR7,411 per night
New
3 Bedrooms 6 Guests
Sunset South
FromR10,999 per night
New
2 Bedrooms 4 Guests

About Meadows Vacation Rentals

With more than 146 Meadows vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Meadows.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Meadows, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Meadows. Places to stay near Meadows are 1142.95 ft² on average, with prices averaging R13,677 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Meadows with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Frequently Asked Questions About Meadows?

What are the top vacation rentals in Meadows?

How many Rentbyowner vacation rentals are available in Meadows?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 146 in the Meadows area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Meadows. 

Nearby Neighborhood (3)

NeighborhoodProperty Count
Old Town Vacation Rentals in Key West, Florida 2155
The Meadows Vacation Rentals in Key West, Florida 105
White Street Gallery District Vacation Rentals in Key West, Florida 4446