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Saddlebunch Keys Vacation Rentals

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Saddlebunch Keys vacation rentals

A cozy room with a brown leather sofa, a white table, and a ceiling fan.

1. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (373 reviews)
"Best stop over before going to Key west. We enjoyed here a lot, parking our trailer was never a problem."
United States
Daisybel
$251 nightly
The price is $283
Sep 30 - Oct 1
Total with taxes and fees
Old Wooden Bridge Resort and Marina
A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

2. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (198 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
$242 nightly
The price is $272
Oct 2 - Oct 3
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
Exterior

3. Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (3 reviews)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
$260 nightly
The price is $292
Oct 5 - Oct 6
Total with taxes and fees
Island View 1BR Residence With Balcony
A resort pool area with lounge chairs and palm trees, surrounded by resort buildings.

4. 47ft Viking Yacht · 2 Pools · Perry Marina · Key West

47ft Viking Yacht · 2 Pools · Perry Marina · Key West
Stock Island
7.6 out of 10, Good, (42 reviews)
"Great set up!!!"
United States
Benjamin
$367 nightly
The price is $408
Sep 30 - Oct 1
Total with taxes and fees
47ft Viking Yacht · 2 Pools · Perry Marina · Key West
A hot tub with a view of a marina and boats during sunset.

5. Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (62 reviews)
"Great would definitely stay again "
United States
Zach C.
$361 nightly
The price is $401
Sep 30 - Oct 1
Total with taxes and fees
Living the Dream Key West Style
A waterfront property with a covered porch, a boat dock, and a clear sky.

6. SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (112 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
$366 nightly
The price is $407
Sep 30 - Oct 1
Total with taxes and fees
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A beach with lounge chairs, palm trees, and a water body.

7. Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.6 out of 10, Exceptional, (33 reviews)
"Pool was great! Just far enough from Duval street to get away and relax if needed or jump in the car and head down for live music! "
United States
Brent H.
$507 nightly
The price is $563
Sep 30 - Oct 1
Total with taxes and fees
Grand Marina Suite - Poolside & Waterfront Condo
A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

8. SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (97 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
$366 nightly
The price is $407
Sep 30 - Oct 1
Total with taxes and fees
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A clear swimming pool surrounded by palm trees and lounge chairs.

9. Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (39 reviews)
"Great to stay. Good places to eat close by."
United States
Robert B.
Paradise found
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

10. Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
Stock Island
9.6 out of 10, Exceptional, (136 reviews)
"I can't say enough about how wonderful this property is or the host."
United States
Linda
$464 nightly
The price is $515
Sep 30 - Oct 1
Total with taxes and fees
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A modern kitchen with granite countertops, stainless steel appliances, and light-colored cabinetry.

11. Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (128 reviews)
"Very nice place. Centrally located near good restaurants, markets, etc.. Pet friendly which worked for us. Nice long walking trail behind cottage."
United States
John B.
$454 nightly
The price is $504
Oct 3 - Oct 4
Total with taxes and fees
Kelly's Kabin - Adorable Private Summerland Key Cottage
A two-story building with a blue exterior, white railings, and a staircase leading to the upper floor.

12. Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
9.8 out of 10, Exceptional, (6 reviews)
"Property was perfectly located and very clean and comfortable."
United States
Kiara
$520 nightly
The price is $577
Sep 30 - Oct 1
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

13. Resort View 2BR Residence

Resort View 2BR Residence
2.0 star property
Key West
$444 nightly
The price is $500
Oct 7 - Oct 8
Total with taxes and fees
Resort View 2BR Residence
A wide sandy beach with palm trees and a clear sky.

14. Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Key West
9.0 out of 10, Wonderful, (49 reviews)
"Great place for our 1 night in key west "
United States
Thadd W.
$366 nightly
The price is $407
Sep 30 - Oct 1
Total with taxes and fees
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

15. Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Cudjoe Key
9.4 out of 10, Exceptional, (18 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
$457 nightly
The price is $507
Sep 30 - Oct 1
Total with taxes and fees
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
A wooden boardwalk leading to a hotel with a green roof, surrounded by palm trees and a water feature.

16. The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
Key West
10.0 out of 10, Exceptional, (35 reviews)
"Very nice clean place. Had a minor problem with the beds after checking in but property manager was quick to respond and correct issue. Would stay here again. "
United States
Teri K.
$446 nightly
The price is $496
Sep 30 - Oct 1
Total with taxes and fees
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
A covered outdoor seating area with white chairs and tables, overlooking turquoise waters and distant islands.

17. Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Cudjoe Key
9.8 out of 10, Exceptional, (148 reviews)
"Everything was exactly as described and we could not be happier. The community that this house is in is very pleasant as well"
United States
Jaret R.
$671 nightly
The price is $746
Sep 30 - Oct 1
Total with taxes and fees
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Pool

18. Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Cudjoe Key
8.8 out of 10, Excellent, (11 reviews)
"We loved our stayed and booked again for next year. Its in our price range, plenty of space and we were all so comfortable. Its our favorite house we have rented in the area and hope to be able to continue to enjoy it years to come. "
United States
Alisa M.
$468 nightly
The price is $520
Sep 30 - Oct 1
Total with taxes and fees
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
A wooden boardwalk leading to a hotel with a green roof, surrounded by lush greenery and palm trees.

19. The Salt Cay | Updated! Stunning Sunset View, Pool

The Salt Cay | Updated! Stunning Sunset View, Pool
Key West
9.6 out of 10, Exceptional, (59 reviews)
"Everything was amazing! My family and I enjoyed every part of our stay; 10 out of 10 would recommend :)"
United States
Rebecca H.
$446 nightly
The price is $496
Sep 30 - Oct 1
Total with taxes and fees
The Salt Cay | Updated! Stunning Sunset View, Pool
Property Overview

20. Aquaria House at Lunara Bay

Aquaria House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (46 reviews)
"Loved the property and the location!! It was perfect for me and the family. Short commute to everything we needed and wanted. I can't wait to go back for the next visit!!"
United States
Chris H.
$1,313 nightly
The price is $1,457
Sep 30 - Oct 1
Total with taxes and fees
Aquaria House at Lunara Bay
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Saddlebunch Keys Hotel Reviews

Hampton Inn Key West FL

Hampton Inn Key West FL

10/10 Excellent
"n"
Luis 1-night trip
Posted 1 hour ago
Hampton Inn Key West FL

Find out more about Saddlebunch Keys

Everything you need to know about Saddlebunch Keys vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Saddlebunch Keys vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

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Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $262 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

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