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Stock Island Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
2053 rentals in Stock Island.
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St, vacation rental in Stock Island
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St, vacation rental in Stock Island
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St, vacation rental in Stock Island

Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St

Condo/Apartment
0 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Casa Atlantica: A studio condo on the Atlantic shore of Key West, vacation rental in Stock Island
Casa Atlantica: A studio condo on the Atlantic shore of Key West, vacation rental in Stock Island
Casa Atlantica: A studio condo on the Atlantic shore of Key West, vacation rental in Stock Island

Casa Atlantica: A studio condo on the Atlantic shore of Key West

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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YKNOT CHARTERS,  ON AND OFF DOCK CHARTERS, vacation rental in Stock Island
YKNOT CHARTERS,  ON AND OFF DOCK CHARTERS, vacation rental in Stock Island
YKNOT CHARTERS,  ON AND OFF DOCK CHARTERS, vacation rental in Stock Island

YKNOT CHARTERS, ON AND OFF DOCK CHARTERS

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Duval balcony - street suite, vacation rental in Stock Island
Duval balcony - street suite, vacation rental in Stock Island
Duval balcony - street suite, vacation rental in Stock Island

Duval balcony - street suite

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Key West Classic Yacht Charter, vacation rental in Stock Island
Key West Classic Yacht Charter, vacation rental in Stock Island
Key West Classic Yacht Charter, vacation rental in Stock Island

Key West Classic Yacht Charter

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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CLOSE TO PERFECT at Key West Golf Club - 2/2.5 w/ Private Pool, vacation rental in Stock Island
CLOSE TO PERFECT at Key West Golf Club - 2/2.5 w/ Private Pool, vacation rental in Stock Island
CLOSE TO PERFECT at Key West Golf Club - 2/2.5 w/ Private Pool, vacation rental in Stock Island

CLOSE TO PERFECT at Key West Golf Club - 2/2.5 w/ Private Pool

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Dog-friendly condo with pool & hot tub - walk or bike to beach, vacation rental in Stock Island
Dog-friendly condo with pool & hot tub - walk or bike to beach, vacation rental in Stock Island
Dog-friendly condo with pool & hot tub - walk or bike to beach, vacation rental in Stock Island

Dog-friendly condo with pool & hot tub - walk or bike to beach

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!, vacation rental in Stock Island
ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!, vacation rental in Stock Island
ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!, vacation rental in Stock Island

ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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~FISH CAMP!~ Family friendly, canal front, monthly rental., vacation rental in Stock Island
~FISH CAMP!~ Family friendly, canal front, monthly rental., vacation rental in Stock Island
~FISH CAMP!~ Family friendly, canal front, monthly rental., vacation rental in Stock Island

~FISH CAMP!~ Family friendly, canal front, monthly rental.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Curry House- 2nd Floor w/ Balcony! Room 1, vacation rental in Stock Island
Curry House- 2nd Floor w/ Balcony! Room 1, vacation rental in Stock Island
Curry House- 2nd Floor w/ Balcony! Room 1, vacation rental in Stock Island

Curry House- 2nd Floor w/ Balcony! Room 1

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Waterfront Retreat, Old Town, 7 Nights, Sleeps 2, Hyatt, Swimming Pool, Hot Tub, vacation rental in Stock Island
Waterfront Retreat, Old Town, 7 Nights, Sleeps 2, Hyatt, Swimming Pool, Hot Tub, vacation rental in Stock Island
Waterfront Retreat, Old Town, 7 Nights, Sleeps 2, Hyatt, Swimming Pool, Hot Tub, vacation rental in Stock Island

Waterfront Retreat, Old Town, 7 Nights, Sleeps 2, Hyatt, Swimming Pool, Hot Tub

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Florida Keys outpost, vacation rental in Stock Island
Florida Keys outpost, vacation rental in Stock Island
Florida Keys outpost, vacation rental in Stock Island

Florida Keys outpost

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Ground-level getaway with free WiFi, private deck, & shared outdoor pool, vacation rental in Stock Island
Ground-level getaway with free WiFi, private deck, & shared outdoor pool, vacation rental in Stock Island
Ground-level getaway with free WiFi, private deck, & shared outdoor pool, vacation rental in Stock Island

Ground-level getaway with free WiFi, private deck, & shared outdoor pool

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful Family-Sized Vacation House! 5 minute drive from Most Beautiful Places, vacation rental in Stock Island
Beautiful Family-Sized Vacation House! 5 minute drive from Most Beautiful Places, vacation rental in Stock Island
Beautiful Family-Sized Vacation House! 5 minute drive from Most Beautiful Places, vacation rental in Stock Island

Beautiful Family-Sized Vacation House! 5 minute drive from Most Beautiful Places

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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The Queens Villa, vacation rental in Stock Island
The Queens Villa, vacation rental in Stock Island
The Queens Villa, vacation rental in Stock Island

The Queens Villa

Rental Home
2 bedrooms
4 bathrooms
Sleeps 4
Match: Sleeps
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SOUTHERNMOST SUNSHINE- 4 Bed/3 Bath- Old Town Key West w/ Pool & Parking!, vacation rental in Stock Island
SOUTHERNMOST SUNSHINE- 4 Bed/3 Bath- Old Town Key West w/ Pool & Parking!, vacation rental in Stock Island
SOUTHERNMOST SUNSHINE- 4 Bed/3 Bath- Old Town Key West w/ Pool & Parking!, vacation rental in Stock Island

SOUTHERNMOST SUNSHINE- 4 Bed/3 Bath- Old Town Key West w/ Pool & Parking!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Tranquil tropical retreat with pool, private deck, & W/D - walk to bars/dining, vacation rental in Stock Island
Tranquil tropical retreat with pool, private deck, & W/D - walk to bars/dining, vacation rental in Stock Island
Tranquil tropical retreat with pool, private deck, & W/D - walk to bars/dining, vacation rental in Stock Island

Tranquil tropical retreat with pool, private deck, & W/D - walk to bars/dining

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Shipyard 208-6 2 Bedroom 2 Bathroom in Truman Annex, vacation rental in Stock Island
Shipyard 208-6 2 Bedroom 2 Bathroom in Truman Annex, vacation rental in Stock Island
Shipyard 208-6 2 Bedroom 2 Bathroom in Truman Annex, vacation rental in Stock Island

Shipyard 208-6 2 Bedroom 2 Bathroom in Truman Annex

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Middle Sunset: 3 Bedroom Luxury Condo at Bayfront Suites & Marina, vacation rental in Stock Island
Middle Sunset: 3 Bedroom Luxury Condo at Bayfront Suites & Marina, vacation rental in Stock Island
Middle Sunset: 3 Bedroom Luxury Condo at Bayfront Suites & Marina, vacation rental in Stock Island

Middle Sunset: 3 Bedroom Luxury Condo at Bayfront Suites & Marina

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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A Palm Tree Haven in Key West *Pet Friendly*, vacation rental in Stock Island
A Palm Tree Haven in Key West *Pet Friendly*, vacation rental in Stock Island
A Palm Tree Haven in Key West *Pet Friendly*, vacation rental in Stock Island

A Palm Tree Haven in Key West *Pet Friendly*

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Hyatt Beach House Resort. Key West. 2 Bedroom. 2 Bathroom WEEK  Stay., vacation rental in Stock Island
Hyatt Beach House Resort. Key West. 2 Bedroom. 2 Bathroom WEEK  Stay., vacation rental in Stock Island
Hyatt Beach House Resort. Key West. 2 Bedroom. 2 Bathroom WEEK  Stay., vacation rental in Stock Island

Hyatt Beach House Resort. Key West. 2 Bedroom. 2 Bathroom WEEK Stay.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo in The Meadows!, vacation rental in Stock Island
ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo in The Meadows!, vacation rental in Stock Island
ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo in The Meadows!, vacation rental in Stock Island

ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo in The Meadows!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH, vacation rental in Stock Island
BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH, vacation rental in Stock Island
BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH, vacation rental in Stock Island

BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Price Drop! Oceanfront Resort 2 bedrooms sleeps 6 Hyatt. Check in December 24, vacation rental in Stock Island
Price Drop! Oceanfront Resort 2 bedrooms sleeps 6 Hyatt. Check in December 24, vacation rental in Stock Island
Price Drop! Oceanfront Resort 2 bedrooms sleeps 6 Hyatt. Check in December 24, vacation rental in Stock Island

Price Drop! Oceanfront Resort 2 bedrooms sleeps 6 Hyatt. Check in December 24

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cockadoodle Cottage on Duval, vacation rental in Stock Island
Cockadoodle Cottage on Duval, vacation rental in Stock Island
Cockadoodle Cottage on Duval, vacation rental in Stock Island

Cockadoodle Cottage on Duval

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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ANNIE'S HIDEAWAY at The Truman Annex in Key West, vacation rental in Stock Island
ANNIE'S HIDEAWAY at The Truman Annex in Key West, vacation rental in Stock Island
ANNIE'S HIDEAWAY at The Truman Annex in Key West, vacation rental in Stock Island

ANNIE'S HIDEAWAY at The Truman Annex in Key West

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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~AZUR PALM~ Oceanfront elegance with pools, peace, and a designer interior!, vacation rental in Stock Island
~AZUR PALM~ Oceanfront elegance with pools, peace, and a designer interior!, vacation rental in Stock Island
~AZUR PALM~ Oceanfront elegance with pools, peace, and a designer interior!, vacation rental in Stock Island

~AZUR PALM~ Oceanfront elegance with pools, peace, and a designer interior!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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3 Spacious Units Great For Family Getaways Minutes From The Beach! Cycling!, vacation rental in Stock Island
3 Spacious Units Great For Family Getaways Minutes From The Beach! Cycling!, vacation rental in Stock Island
3 Spacious Units Great For Family Getaways Minutes From The Beach! Cycling!, vacation rental in Stock Island

3 Spacious Units Great For Family Getaways Minutes From The Beach! Cycling!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Sunshine State at Custom House Inn by Brightwild, vacation rental in Stock Island
Sunshine State at Custom House Inn by Brightwild, vacation rental in Stock Island
Sunshine State at Custom House Inn by Brightwild, vacation rental in Stock Island

Sunshine State at Custom House Inn by Brightwild

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Perfect staycation! 4 Spacious Units, On-site Pool, vacation rental in Stock Island
Perfect staycation! 4 Spacious Units, On-site Pool, vacation rental in Stock Island
Perfect staycation! 4 Spacious Units, On-site Pool, vacation rental in Stock Island

Perfect staycation! 4 Spacious Units, On-site Pool

Rental Home
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Key West - President’s Week!, vacation rental in Stock Island
Key West - President’s Week!, vacation rental in Stock Island
Key West - President’s Week!, vacation rental in Stock Island

Key West - President’s Week!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The GUAVA DUFF - Beautiful KW home with space to chill & lots of FREE PARKING!!, vacation rental in Stock Island
The GUAVA DUFF - Beautiful KW home with space to chill & lots of FREE PARKING!!, vacation rental in Stock Island
The GUAVA DUFF - Beautiful KW home with space to chill & lots of FREE PARKING!!, vacation rental in Stock Island

The GUAVA DUFF - Beautiful KW home with space to chill & lots of FREE PARKING!!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Reynolds Paradise- 2BDR/2BA house with Jacuzzi close to Duval Street, vacation rental in Stock Island
Reynolds Paradise- 2BDR/2BA house with Jacuzzi close to Duval Street, vacation rental in Stock Island
Reynolds Paradise- 2BDR/2BA house with Jacuzzi close to Duval Street, vacation rental in Stock Island

Reynolds Paradise- 2BDR/2BA house with Jacuzzi close to Duval Street

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Dream Vacation! Pool, Near the Beach, On-site Pool!, vacation rental in Stock Island
Dream Vacation! Pool, Near the Beach, On-site Pool!, vacation rental in Stock Island
Dream Vacation! Pool, Near the Beach, On-site Pool!, vacation rental in Stock Island

Dream Vacation! Pool, Near the Beach, On-site Pool!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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TUCKED AWAY OFF DUVAL - A contemporary home w/ local color at your door step, vacation rental in Stock Island
TUCKED AWAY OFF DUVAL - A contemporary home w/ local color at your door step, vacation rental in Stock Island
TUCKED AWAY OFF DUVAL - A contemporary home w/ local color at your door step, vacation rental in Stock Island

TUCKED AWAY OFF DUVAL - A contemporary home w/ local color at your door step

Rental Home
4 bedrooms
6 bathrooms
Sleeps 9
Match: Sleeps
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Old Town Classic with plenty of charm, porch swing and parking, vacation rental in Stock Island
Old Town Classic with plenty of charm, porch swing and parking, vacation rental in Stock Island
Old Town Classic with plenty of charm, porch swing and parking, vacation rental in Stock Island

Old Town Classic with plenty of charm, porch swing and parking

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Family Friendly Resort Condo. Private Beach, Great Key West Location!, vacation rental in Stock Island
Family Friendly Resort Condo. Private Beach, Great Key West Location!, vacation rental in Stock Island
Family Friendly Resort Condo. Private Beach, Great Key West Location!, vacation rental in Stock Island

Family Friendly Resort Condo. Private Beach, Great Key West Location!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Mermaids House - Old Town, MONTHLY ! Historic Bahama Conch House, vacation rental in Stock Island
The Mermaids House - Old Town, MONTHLY ! Historic Bahama Conch House, vacation rental in Stock Island
The Mermaids House - Old Town, MONTHLY ! Historic Bahama Conch House, vacation rental in Stock Island

The Mermaids House - Old Town, MONTHLY ! Historic Bahama Conch House

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Traveler's Palm- Sun-filled Studio w/ Pvt Deck!, vacation rental in Stock Island
Traveler's Palm- Sun-filled Studio w/ Pvt Deck!, vacation rental in Stock Island
Traveler's Palm- Sun-filled Studio w/ Pvt Deck!, vacation rental in Stock Island

Traveler's Palm- Sun-filled Studio w/ Pvt Deck!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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PARADISE PLACE:A tastefully decorated space in the heart of Old Town Key West, vacation rental in Stock Island
PARADISE PLACE:A tastefully decorated space in the heart of Old Town Key West, vacation rental in Stock Island
PARADISE PLACE:A tastefully decorated space in the heart of Old Town Key West, vacation rental in Stock Island

PARADISE PLACE:A tastefully decorated space in the heart of Old Town Key West

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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**VILLA ANGELITA * OLD TOWN** Renovated Condo Off Duval + LAST KEY SERVICES..., vacation rental in Stock Island
**VILLA ANGELITA * OLD TOWN** Renovated Condo Off Duval + LAST KEY SERVICES..., vacation rental in Stock Island
**VILLA ANGELITA * OLD TOWN** Renovated Condo Off Duval + LAST KEY SERVICES..., vacation rental in Stock Island

**VILLA ANGELITA * OLD TOWN** Renovated Condo Off Duval + LAST KEY SERVICES...

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Eddie Griffiths Overnight Charters and  Vacation Rentals!!!!!, vacation rental in Stock Island
Eddie Griffiths Overnight Charters and  Vacation Rentals!!!!!, vacation rental in Stock Island
Eddie Griffiths Overnight Charters and  Vacation Rentals!!!!!, vacation rental in Stock Island

Eddie Griffiths Overnight Charters and Vacation Rentals!!!!!

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Truman Annex Private Oasis with pool, vacation rental in Stock Island
Truman Annex Private Oasis with pool, vacation rental in Stock Island
Truman Annex Private Oasis with pool, vacation rental in Stock Island

Truman Annex Private Oasis with pool

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!, vacation rental in Stock Island
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!, vacation rental in Stock Island
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!, vacation rental in Stock Island

SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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PERFECTION...STEPS FROM DUVAL ~, vacation rental in Stock Island
PERFECTION...STEPS FROM DUVAL ~, vacation rental in Stock Island
PERFECTION...STEPS FROM DUVAL ~, vacation rental in Stock Island

PERFECTION...STEPS FROM DUVAL ~

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Dog-friendly suite with pool, hot tub, tennis & full kitchen, vacation rental in Stock Island
Dog-friendly suite with pool, hot tub, tennis & full kitchen, vacation rental in Stock Island
Dog-friendly suite with pool, hot tub, tennis & full kitchen, vacation rental in Stock Island

Dog-friendly suite with pool, hot tub, tennis & full kitchen

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Little Casita:  Key West Monthly rental Close to Duval - RealKeyWest, vacation rental in Stock Island
Little Casita:  Key West Monthly rental Close to Duval - RealKeyWest, vacation rental in Stock Island
Little Casita:  Key West Monthly rental Close to Duval - RealKeyWest, vacation rental in Stock Island

Little Casita: Key West Monthly rental Close to Duval - RealKeyWest

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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**COASTAL LOVING * OLD TOWN** Chic 4BR Home & Pool + LAST KEY SERVICES..., vacation rental in Stock Island
**COASTAL LOVING * OLD TOWN** Chic 4BR Home & Pool + LAST KEY SERVICES..., vacation rental in Stock Island
**COASTAL LOVING * OLD TOWN** Chic 4BR Home & Pool + LAST KEY SERVICES..., vacation rental in Stock Island

**COASTAL LOVING * OLD TOWN** Chic 4BR Home & Pool + LAST KEY SERVICES...

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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1 BLOCK OFF DUVAL!  PRIVATE POOL AND HOT TUB, vacation rental in Stock Island
1 BLOCK OFF DUVAL!  PRIVATE POOL AND HOT TUB, vacation rental in Stock Island
1 BLOCK OFF DUVAL!  PRIVATE POOL AND HOT TUB, vacation rental in Stock Island

1 BLOCK OFF DUVAL! PRIVATE POOL AND HOT TUB

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Perfect staycation! 2 Spacious Units, Minutes from Shopping, Close to Airport, vacation rental in Stock Island
Perfect staycation! 2 Spacious Units, Minutes from Shopping, Close to Airport, vacation rental in Stock Island
Perfect staycation! 2 Spacious Units, Minutes from Shopping, Close to Airport, vacation rental in Stock Island

Perfect staycation! 2 Spacious Units, Minutes from Shopping, Close to Airport

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Showing results 1-50 of 2,053
Frequently Asked Questions about Stock Island